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The genus Amoora: A phytochemical and pharmacological review
Fitoterapia 137 (2019) 104269
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Fitoterapia journal homepage: www.elsevier.com/locate/fitote
Review
The genus Amoora: A phytochemical and pharmacological review Wen-Hui Xu, Xiao-Min Su, Chao Wang, Fan Du, Qian Liang
⁎
T
Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Ministry of Education, Southwest Forestry University, Kunming 650224, PR China
ARTICLE INFO
ABSTRACT
Keywords: Amoora species Phytochemistry Pharmacological activities Terpenoids Limonoids
The genus Amoora belongs to the Meliaceae family comprising approximately 25–30 species. Many Amoora species have been used as folk medicines for the treatment of many diseases. This review focuses on diverse chemical constituents from Amoora species as well as significant pharmacological activities. Up to now, a total of 140 compounds including eight sesquiterpenoids, twenty-six diterpenoids, forty-two triterpenoids, twenty-two limonoids, seven steroids, seven alkaloids, seven rocaglamide derivatives, four flavonoids, four glycosides, two coumarins, nine phenols, and two organic acids and esters were reported from Amoora species. Triterpenoids are characteristic components for Amoora species. The extracts and chemical constituents of Amoora species exhibit a broad spectrum of pharmacological activities including cytotoxic, anti-inflammatory, antibacterial and antifungal activity. The present review may provide useful evidence for reasonable utilization of Amoora species as folk medicines and further research in drug discovery.
1. Introduction
2. Traditional uses
The genus Amoora belongs to the Meliaceae family comprised about 25–30 species. The plants of this genus are economically important timber tree, usually distributed in the tropical and subtropical regions of asia, mostly in China, India, Malaysia and Bangladesh. Eight species and one variant are found in China [1–4]. Species of this genus are important ornamental ecological plants, which provide useful timber for building purposes. Several Amoora species have been used as folk medicines in southeast Asia for the treatment of many diseases such as diarrhea, inflammation, spleen and liver and cardiac diseases [1–4]. As the characteristic constituents of the Meliaceae family for structurally diverse and biologically significant limonoids have attracted increasing research attentions [5]. In recent years, more and more bioactive chemical constituents have been found to validate the folk medicinal usages from many Amoora species. However, up to now no complete review has been published. In present review, we summarizes systematically their phytochemistry and pharmacological activities of genus Amoora reported in the literature as retrieved from Web of Science, SciFinder, PubMed, CNKI, and Google Scholar, up until May 2019 for the first time, with aim of providing the scientific clue for further studies and reasonable utilization.
Plants of Amoora genus have been extensively used as important timber tree, which also are cultivated as ornamental ecological plants. Some Amoora species have been used as traditional medicine to treat dysentery, laxative, skin, cardiac diseases in several countries for a long period [6–13]. The stem barks of A. tsangii, known as “Tie luo” in China, are mainly used as a vermicide in folklore medicine [4]. Among Amoora species, A.tsangii, A.dasyclada, A.rohituka, A.cucullata, and A.tetrapetala have been reported in traditional medicine as important folk herb. A summary of their local names, geographical distribution, and traditional uses were presented in Table 1.
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3. Chemical constituents Up to now 140 compounds (except volatile constituents) have been reported from nine Amoora species (A.tsangii, A.dasyclada, A.rohituka, A.cucullata, A.tetrapetala, A.yunnanensis, A.stellato-squamosa, A.ouangliensis, and A.cucullata) including eight sesquiterpenoids (1–8), twenty-six diterpenoids (9–34), forty-two triterpenoids (35–76), twenty-two limonoids (77–98), seven steroids (99–105), seven alkaloids (106–112), seven rocaglamide derivatives (113–119), four fla-
Corresponding author. E-mail address: [email protected] (Q. Liang).
https://doi.org/10.1016/j.fitote.2019.104269 Received 18 June 2019; Received in revised form 14 July 2019; Accepted 14 July 2019 Available online 16 July 2019 0367-326X/ © 2019 Elsevier B.V. All rights reserved.
Fitoterapia 137 (2019) 104269
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Table 1 Traditional uses of the genus Amoora. Species
Local names
Distribution
Traditional uses
A. tsangii
Tie luo (Chinese)
Hainan Island of China
A. dasyclada
Hong luo, Cu zhi ya mo, (Chinese)
Yunnan, Hainan of China
Vermicide (stem barks) [4], kill lice (stem barks) [6], the volatile oil from the leaves exhibited antimicrobial, antitumor activities [7]. Insecticide (twigs) [2].
Amoor,Latmi, bekak, garotai (Bengali) Si ban ya mo (Chinese)
Bangladesh
A. rohituka A. cucullata A. tetrapetala
Bangladesh, India, Sri Lanka, Malaysia, Indonesia
India, Malaysia, China
Laxative, anthelmintic and cure ulcers (seeds) [8], anticancer, antimicrobial, antiinflammatory and hepatoprotective (various parts of the plant) [9], treatment for tumours, spleen and liver diseases, abdominal complaints (barks) [8,10]. Treatment of marrow, diarrhea (fruits) [11], treatment of inflammation, antibacterial, dysentery, skin, cardiac diseases (leaves) [12] . Insecticide and repellent (stem barks) [13].
Fig. 1. Sesquiterpenoids from the genus Amoora.
vonoids (120−123), four glycosides (124–127), two coumarins (128–129), nine phenols (130–138), and two organic acids and esters (139–140). Terpenoids are the predominant secondary metabolite constituents in the genus, chiefly triterpenoids, which may belong to the dammarane, tirucallane, cycloartane, taraxerane, oleanane, lupane, and hopane skeletal types. Their structures, names, corresponding sources, biological activities and references are collected in Figs. 1-11 and Tables 2–21.
diterpenoids with a double band between C-8 and C-17 position (29–33) and only one kaurane diterpenoid (34) [12]. 3.3. Triterpenoids Extensive phytochemical investigations on Amoora species afforded forty-two triterpenoids (35–76) including fourteen dammaranes (35–48), eight tirucallanes (49–56), nine cycloartanes (57–65), four taraxeranes (66–69), four oleananes (70–73), two lupanes (74–75), and one hopane triterpenoid (76) (Figs. 36 and Tables 6–12). Four new dammaranes (35–38) and eight known ones (39–46) were isolated from the bark of A. yunnanensis. Among them, dammaranes (36–37) possessed a chlorine atom attached to C-23 [18,19]. From the leaves and twigs of A. tsangii, two new 29-nor-cycloartanes (58–59), two dammaranes (47–48), five cycloartanes (60–64), and two lupanes (74–75) were reported [7]. Tirucallanes (49–56) were isolated from A. dasyclada stems and A. tetrapetala by different research group [13,20–23]. Among them, compound 49 contained an epoxide group between C-24 and C-25 [20]. Investigations on the the twigs of A.dasyclada afforded taraxeranes (66–68) [22]. Oleananes (70–73) were obtained from A. yunnanensis, A. ouangtliensi, and A. rohituka [10,14,17,24]. Only one hopane triterpenoid (76) was isolated from the branches of A. tetrapetala [13]. It was noted that compounds (41,4647,65) also were obtained from the leaves and twigs of A.ouangliensis [19].
3.1. Sesquiterpenoids To date, eight sesquiterpenoids (1–8) were isolated from Amoora species (Fig. 1 and Table 2). They were divided into guaianes (1–3), cadinane (4), aromadendrane (5), oppositane (6), eudesmane (7), and isodaucane (8). Phytochemical investigations on the bark of A. yunnanensis afforded a guaiane (1) [14]. Two new 6,7-epoxy guaiane sesquiterpenoids (2–3) were isolated from the stem bark of A. rohituka [9]. Investigation of the twigs and leaves of A. tsangii led to the isolation of four known sesquiterpenoids with different skeleton (4–7) [4]. A sodaucane (8) was obtained from the branches of A. tetrapetala [13]. 3.2. Diterpenoids A total of twenty-six diterpenoids (9–34) including eight clerodanes (9–16), seventeen labdanes (17–33), and one kaurane diterpenoid (34) were ioslated from Amoora species (Fig. 2 and Tables 3–5). Eight neoclerodanes (9–16) and twelve labdane diterpenoids (17–28) were isolated from A.stellato-squamosa and A.ouangliensis by Liu's group [15–17]. Investigations on leaves of A. cucullata afforded five labdane
3.4. Limonoids Twenty-two limonoids (77–98) were isolated from Amoora species
2
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Fig. 2. Clerodane, labdane, and kaurane diterpenoids from the genus Amoora.
(Fig. 7 and Table 13). Phytochemical investigations on the twigs and leaves of A. tsangii afforded seven new limonoids (77–83) and two known ones (84–85) [4]. From the stem bark of A. rohituka, amoorinin (86), a ring B,D-seco limonoid, was isolated [25]. Twelve rare lactambearing limonoids (87–98) were isolated from the twigs and leaves of A. tsangii [6]. It was noted that compounds (77–82, 84–85, 87–98) belonged to ring A, B-seco limonoids, while compound (83) was a ring B-seco limonoid.
(Fig. 9 and Table 15). Rohitukine (106) was isolated from the leaves and stems of A. rohituka, which was the first alkaloid from the Meliaceae [26]. One new alkaloid (107) with a rare five-membered cyclic amide moiety and known one (108) were reported from the leaves of A. cucullata [12]. A new putrescine bisamide, cucullamide (109), also was isolated from the leaves of A. cucullata [27]. From the leaves and twigs of A. ouangliensis, three known amides (110−112) were obtanied [19]. 3.7. Rocaglamide derivatives
3.5. Steroids
Rocaglamide derivatives possessed cyclopenta[b]tetrahydrobenzofuran skeleton, which included a favonoid unit and a cinnamic acid amide moiety. Seven rocaglamide derivatives (113–119) were isolated from Amoora species (Fig. 10 and Table 16). Two new rocaglamide derivatives (113–114) and five known ones (115–119) were isolated from the fruits of A. cucullata,while compounds (113–114) also were obtained from the leaves of A. cucullata [11,12]. Sine rocaglamide derivatives were found exclusively in Aglaia species (Meliaceae) as a significant chemotaxonomic marker, Amoora cucullata now have been assigned to Aglaia genus as Aglaia cucullata in the PLANT LIST reasonably from chemotaxonomic viewpoint [30].
Seven steroids (99–105) were isolated from Amoora species (Fig. 8 and Table 14). Two new sterols (99–100) and two known ones (101−102) were obtained by the bark of A. yunnanensis [14]. β-sitosterol (103) was isolated from A. dasyclada and A. stellato-squamos, while known sterol (104) was isolated from A. ouangtliensis and A. dasyclada [17,20,22]. Investigation on the branches of A. tetrapetala led to the isolation of sterol (105) [13]. 3.6. Alkaloids Seven alkaloids (106–112) were isolated from Amoora species
3
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Fig. 3. Dammarane triterpenoids from the genus Amoora.
Fig. 4. Tirucallane triterpenoids from the genus Amoora.
3.8. Flavonoids
[17,22], while compound (127) was isolated from A. rohituka [29].
Four flavonoids, (+)-catechin (120) from A. ouangtliensis [17], chrysin (121) and apigenin (122) from A. cucullata [27], and lichenxanthone (123) from A. tetrapetala were isolated from Amoora species [13] (Fig. 10 and Table 17).
3.10. Coumarins Two coumarins, scopoletin (128) from A. stellato-squamosa and A. dasyclada [17,22]. and 8-hydroxy-6-methoxy-3-pentylisocoumarin (129) from A. tetrapetala were reported from Amoora genus [13] (Fig. 11 and Table 19).
3.9. Glycosides Four glycosides (124–127) have been identified in the genus Amoora (Fig. 10 and Table 18). Two flavonoid glycosides, compound (124) from A. rohituka, and compound (125) from A. cucullata were reported [27,28]. Two steroidal glycosides, daucosterol (126) were obtained from A. stellato-squamosa, A.ouangliensis,and A.dasyclada
3.11. Phenols Nine phenols (130–138) were reported from Amoora species (Fig. 11 and Table 20). From the leaves and stems of A. rohituka have yielded noreugenin (130) and eugenin(131) [26]. Seven phenols
4
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Fig. 5. Cycloartane triterpenoids from the genus Amoora.
Fig. 6. Taraxerane, oleanane, lupane, and hopane triterpenoids from the genus Amoora.
(131–137) were isolated from the branches of A. tetrapetala [13], while compound (138) was obtained from the leaves and twigs of A.ouangliensis [19].
vivo antitumor effect in mice treated with 10 or 20 mg of extract per kg mean survival time was 21 or 25.5 days with % ILS of 10.5 or 34.2, respectively and in vitro cytotoxic activities with an IC50 value of 9 μg/ mL for the Dalton's lymphoma ascites tumor cells [31]. The cytotoxic activities of the methanol extracts of A.cucullata and A.rohituka from Bangladesh were evaluated by the brine shrimp lethality bioassay, which exhibited significant toxicity to brine shrimps (LC50, 5.16, and 5.95 μg/mL, respectively) [32]. The cytotoxcity of the n-hexane, ethyl acetate and methanol extracts of A.cucullata against Artemia salina showed LC50 of 17.18, 7.943 and 0.549 μg/mL, respectively [33]. A.rohituka and A.chittagonga, fractionated with petroleum ether, dichloromethane, and ethanol, were explored for their cytotoxic activities against two breast cancer cell lines (MCF-7 and HTB-126) and three pancreatic cancer cell lines (Panc-1, Mia-Paca2, and Capan1) using the MTT and label-free photonic crystal biosensor assay, only the CH2Cl2 extract of A.chittagonga exhibited significant cytotoxicity to all five cancer cell lines with IC50 values in the range 30–65 μg/mL [3]. Cytotoxic activities of A.cucullata using brine shrimp lethality bioassay were reported with LC50 value 10, 2.301 and 7.28 μg/mL in bark and 1.308,
3.12. Organic acids and esters Unsaturated fatty acid ester (139) was isolated from the seeds of A. rohituka [8], while the branches of A. tetrapetala yielded organic acid (140) [13] (Fig. 11 and Table 21). 4. Pharmacological activities The extracts and chemical constituents of Amoora species exert a wide range of pharmacological activities, primarily involved in cytotoxic, anti-inflammatory, antibacterial, and antifungal activities. 4.1. Cytotoxic activity The ethyl acetate extracts of stem bark from A. rohituka showed in 5
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Fig. 7. Limonoids from the genus Amoora.
1.94 and 2.14 μg/mL in leaf extracts of petroleum ether, chloroform and methanol respectively [34]. The volatile oil from the leaves of A. tsangii displayed cytotoxic activity against SPCA-1 and BEL-7402 cell lines with IC50 values of 11.20, and 35.52 μg/mL, respectively [35]. Three tirucallane triterpenoids (52–54) from A.dasyclada [22], one clerodane diterpenoid (14) from A. stellato-squamosa [16], and three labdane diterpenoids (26–28) from A. ouangliensis showed cytotoxic activities [16], among them, compund 26 displayed significant cytotoxicity against AGZY 83-a (IC50, 21.52 μM) and SMMC-7721 (IC50, 28.47 μM) cell lines [16]. Eleven triterpenes (47–48, 58–64, and 74–75) from A. tsangii were valuated for the cytotoxicity against HT1080, TE, and A549 cell lines by the CCK8 assay [7]. Cycloartanes (58–64) displayed significant cytotoxic activities with IC50 values
Fig. 8. Sterols from the genus Amoora.
6
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Fig. 9. Alkaloids from the genus Amoora.
Fig. 10. Rocaglamide derivatives, flavonoids and glycosids from the genus Amoora.
ranging from 2.56 to 19.05 μM. Among these triterpenes, mooratsanol A (58) exhibited the most potent cytotoxic activities with IC50 values ranging from 2.56 to 5.10 μM [7]. Amooranin (72) from A.rohituka exhibited the cytotoxcity against MCF-7 (IC50, 2.3 μg/mL) and HeLa cell lines (IC50, 3.4 μg/mL) [24]. Aphanin (73) from A. rohituka were found to display antiproliferative effects, cause G0-G1 cell cycle arrest, inhibit K-Ras G12D mutant activity [10]. Rocaglamide derivatives (113–119) were isolated from the fruits of A.cucullata, which were found to display potent cytotoxic activities against KB, BC, and NCI-H187 cell lines with ED50 values in the range 0.0000028–0.3 μg/mL [11].
with Indomethacin as standard at dose 10 mg/kg p.o. [36]. Compounds (41, 46, 65, and 110) from A. ouangliensis exhibited anti-inflammatory activity on LPS-induced NO production in RAW264.7 [19]. Five limonoids (87–88, 90, and 94–95) from A. tsangii were evaluated the NF-κB inhibitory activities using a luciferase-based NF-κB reporter gene assay. Among these compounds, amooramide I (95) significantly inhibited the TNFα-induced NF-κB luciferase activity by 64% at a concentration of 10 μM, while the other four compounds were inactive [6].
4.2. Anti-inflammatory activity
The petrol ether, dichloromethane and methanol extracts of A. rohituka were found to display antibacterial activity using disc diffusion method and antifungal activity by the poisoned food technique [37].
4.3. Antibacterial and antifungal activity
The alcoholic extract of A. rohituka showed anti-inflammatory effect 7
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Fig. 11. Coumarins, phenols and fatty acids from the genus Amoora.
Table 2 Sesquiterpenoids from the genus Amoora. No.
Compound name
Occurrence
1 2
6-Guaiene-4α, 10α-diol 6β,7β-Epoxyguai-4-en-3-one
A. yunnanensis bark A. rohituka stem bark
3 4 5 6
6β,7β-epoxy-4β,5-dihydroxyguaiane 10-Hydroxy-15-oxo-α-cadinol 11β-Hydroxy-1β,8α-aromadendrene octahydro-4-Hydroxy-3α-methyl-7-methylene-α(1-methylethyl)-1H-indene-1-methanol eudesm-4(15)-ene-1β,6α-diol 10-Oxo-isodauc-3-en-15-al
A. A. A. A.
7 8
Biological activity
rohituka stem bark tsangii twigs and leaves tsangii twigs and leaves tsangii twigs and leaves
A. tsangii twigs and leaves A. tetrapetala branches
Inactive for HIV-inhibitory and cytotoxic activity at 50 mg/mL, antibacterial activity against Escherichia coli with a zone of inhibition of 10.5 mm at a dose of 50 mg/disc. Inactive for HIV-inhibitory and cytotoxic activity at 50 mg/mL.
Inactive against acetylcholinesterase
Ref [14] [9] [4] [4] [4] [4] [4] [13]
Table 3 Clerodane diterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
9 10
Methyl (13E)-2-oxoneocleroda-3,13-dien-15-oate (13E)-2-oxoneocleroda-3,13-dien-15-ol
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
11
(3α,4β,13E)-Neoclerod-13-ene-3,4,15-triol
12 13 14
(3α,4β,13E)-4-Ethoxyneoclerod-13-ene-3,15-diol Neoclerod-14-en-3α,4β,13S-triol (3α,4β,14RS)-Neoclerod-13(16)-ene-3,4,14,15tetrol (13E)-Neocleroda-3,13-diene-15,18-diol (13S)-2-Oxoneocleroda-3,14-dien-13-ol
A. A. A. A. A. A. A. A.
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines Cytotoxic against AGZY 83-a (IC50,50.10 uM), and SMMC-7721(IC50,40.67 uM)
[15,16] [15] [16] [15] [16] [15] [16] [15,16]
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
[15,16] [15,16]
15 16
stellato-squamosa twigs stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs
A. stellato-squamosa twigs A. stellato-squamosa twigs
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
8
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Table 4 Labdane diterpenoids from the genus Amoora. No.
Compound Name
Occurrence
17 18 19
8(17),13(E)-Labdadien-15,19-dioic acid Methyl8(17),13(E)-labdadien-19-oic acid-15-oate 15-Hydroxy-8(17),13(E)-labdadien-19-oic acid
20 21 22 23 24 25 26 27 28 29 30 31 32 33
15-Acetoxy-8(17),13(E)-labdadi-en-19-oic acid 8(17),13(E)-labdadien-19-oic acid-15-al 8(17),13(E)-labdadien-15, 19-diol 19-Hydroxy-8(17),13(E)-labdadien-15-al 19-Hydroxy-8(17),13(Z)-labdadien-15-al 8(17),13(Z)-labdadien-19- oicacid-15-al 5(10),14-ent-Halimadien-3β,13S-diol 8(17),12(E),14-Labdatrien-19-oic acid 6-O-acetyl-austroinulin 2β-Hydroxylabda-8(17),13(16),14-triene 2α-Hydroxylabda-8(17),13(16),14-triene ent-13-epi-manool ent-2β-hydroxymanool 2β,15-Dihydroxy-ent-labda-8(17),13E-diene
A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A.
Biological Activity
stellato-squamosa twigs stellato-squamosa twigs stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks cucullata leaves cucullata leaves cucullata leaves cucullata leaves cucullata leaves
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
Cytotoxic against AGZY 83-a (IC50,21.52 uM), and SMMC-7721(IC50,28.47 uM) Cytotoxic against AGZY 83-a (IC50,86.59 uM) Cytotoxic against AGZY 83-a (IC50,69.61 uM), and SMMC-7721(IC50,56.38 uM) No activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells Activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells
Compound name
Occurrence
Biological activity
Ref
34
kaur-15-en-17ol
A. cucullata leaves
No activity in overcoming TRAIL resistance in AGS cells
[12]
[17] [17] [17] [16] [17] [17] [17] [17] [17] [17] [16] [16] [16] [12] [12] [12] [12] [12]
The methanol extracts of A. chittagonga exhibited antibacterial and antifungal activity against a wide variety of gram positive and gram negative bacteria and fungi at a concentration of 400 μg/disc using disc diffusion method [38]. The antimicrobial activity of ethyl acetate and methanol extracts of A.cucullata against 13 bacteria and 3 fungal strains showed moderate to strong activity [33]. The methanol and chloroform extracts of bark from A. ruhituka showed significant antibacterial activity against gram negative bacteria [39]. The ethyl acetate and methanol bark extracts of A. cucullata displayed moderate to strong
Table 5 Kaurane diterpenoids from the genus Amoora. No.
Ref
Table 6 Dammarane triterpenoids from the genus Amoora. No.
Compound Name
Occurrence
35 36 37 38 39 40 41
20S,24-Epoxy-24,25-dihydroxydammar-3-one 20S,23R,24R-23-Chloro-20,24-epoxy-dammarane-3α,24,25-triol 3-acetate 20S,23R,24S-23-Chloro-20,24-epoxy-dammarane-3α,24,25-triol 3-acetate 20S,24-Epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid 3-Acetylcabraleadiol Cabraleadiol Cabralea-hydroxylactone
42 43 44 45 46
Ocotillone Cabraleone 24,25-Dihydroxy-dammar-20-en-3-one Shoreic acid 20S,24-Epoxy-25,26,27-trisnor,24-oxo−3,4-secodammar-4(28)-en-3-oic acid
47
Cabralealactone
A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis bark A. yunnanensis barks A. ouangliensis leaves,twigs A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. ouangliensis leaves,twigs A. tsangii leaves and twigs A. ouangliensis leaves,twigs
48
Cabralea-hydroxy-lactone acetate
A. tsangii leaves and twigs
9
Biological Activity
Anti-inflammatory activityon LPS -induced NO production in RAW264.7
Anti-inflammatory activity on LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,50.93 uM), TE (IC50,61.21uM), and A549 (IC50, > 100 uM) No antiinflammatory activityon LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,49.99 uM), TE (IC50,51.77 uM), A549 (IC50,40.39 uM)
Ref [18] [18] [18] [18] [18] [18] [18] [19] [18] [18] [18] [18] [18] [19] [7] [19] [7]
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Table 7 Tirucallane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
49 50 51
A. dasyclada stems A. dasyclada stems A. dasyclada stems
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
[20] [21,22] [21]
A. dasyclada twigs
Cytotoxic against SMMC-7721(IC50,0.171 uM)
[22]
53 54
24,25-Epoxy-tirucall-7-ene-3,23-dione 3-Oxo-24, 25, 26, 27-tetranortirucall-7-ene-23(21)-lactone 3α-Hydroxy-24, 25, 26, 27-tetranortirucall-7-ene-23(21)lactone 3α-Acetoxy-24,25,26,27-tetranortirucalla-7-ene-23(21)lactone 3α,21β,25-Trioltirucalla-21,24-epoxy-23-one 21β,25-Dioltirucalla-21,24-epoxy-3,23-dione
A. dasyclada twigs A. dasyclada twigs
[22,23] [22,23]
55 56
22ξ-Hydroxytirucalla-7,24-dien-3,3-dione Dymacrin D
A. tetrapetala branches A. tetrapetala branches
Cytotoxic against AGZY 83-a (IC50,0.065 uM) Cytotoxic against AGZY 83-a (IC50,0.050 uM), and SMMC7721(IC50,0.018 uM) Inactive against acetylcholinesterase Inactive against acetylcholinesterase
52
[13] [13]
Table 8 Cycloartane triterpenoids from the genus Amoora. No. Compound name
Occurrence
Biological activity
Ref
57
A. cucullata leaves
No activity in overcoming TRAIL resistance in AGS cells
[12]
A. A. A. A.
tsangii tsangii tsangii tsangii
Cytotoxic Cytotoxic Cytotoxic Cytotoxic
[7] [7] [7] [7]
A. A. A. A. A.
tsangii leaves, twigs touangliensis leaves,twigs tsangii leaves, twigs tsangii leaves, twigs touangliensis leaves,twigs
62
(24S)-21,24,25,28-tetrahydroxycycloartane3-one Amooratsanol A Amooratsanol B (24S)-25-Methoxycycloartane-3β, 24-diol 4a, 14-Dimethyl-9,19-cyclocholestan-3β,24diol (24R)-Cycloartane-3β,24,25-triol
63 64 65
(24R)-28,29-Dinor-cycloartane-3β,24,25-triol 29-Nor-cycloartan-23-ene-3β,25-diol 24(R)-19-Cyclolanost-3-one-24,25-diol
58 59 60 61
leaves, leaves, leaves, leaves,
twigs twigs twigs twigs
Compound name
Occurrence
Biological activity
66 67 68 69
Taraxerone Taraxerol Taraxerol acetate 11α,12α-Epoxy-14taraxeren-3-one
A. dasyclada twigs A. dasyclada twigs A. dasyclada twigs A. yunnanensis barks
HT1080 HT1080 HT1080 HT1080
(IC50,2.61 (IC50,6.88 (IC50,4.93 (IC50,3.42
uM), uM), uM), uM),
TE TE TE TE
(IC50,5.10 uM), and A549 (IC50,2.56 uM) (IC50,19.05 uM), and A549 (IC50,8.66 uM) (IC50,12.92 uM), and A549 (IC50,7.41 uM) (IC50,10.68 uM), and A549 (IC50,2.92 uM)
Cytotoxic against HT1080 (IC50,5.32 uM), TE (IC50,6.90 uM), and A549 (IC50,5.38 uM) No anti-inflammatory activityon LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,12.82 uM), TE (IC50,14.60 uM), and A549 (IC50,8.53 uM) Cytotoxic against HT1080 (IC50,10.62uM), TE (IC50,14.35 uM), and A549 (IC50,7.62 uM) Anti-inflammatory activityon LPS -induced NO production in RAW264.7
[7] [7] [7] [7] [19]
antibacterial activity against 1 gram-positive bacteria and 6 gram-negative bacteria strains [34]. The volatile oils of leaf and fruit from A. rohitzrka showed significant antimicrobial activity against Escherlcbla coli, Micrococcus flavoroscus, Listeria monocytogenes N and Candida albicans [40]. The volatile oil of the leaves from A. tsangii showed strong inhibitory activities against Escherichia coli [35].
Table 9 Taraxerane triterpenoids from the genus Amoora. No.
against against against against
Ref [22] [22] [22] [14]
4.4. Other activities The petroleum ether, dichloromethane and methanol extracts of A. rohituka demonstrated good laxative potential at 400, 250 and 400 mg/
Table 10 Oleanane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
70 71
β-Amyrone β-Amyrin
72 73
Amooranin Aphanin
A. A. A. A. A.
yunnanensis barks yunnanensis barks ouangtliensi barks rohituka stems, barks rohituka stems
Biological activity
Ref
Cytotoxic against MCF-7 (IC50,2.3μg/mL), HeLa (IC50, 3.4μg/mL) Inhibition K-Ras mutant activity and STAT3 in pancreatic carcinoma cells
[14] [14] [17] [24] [10]
Table 11 Lupane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
74 75
lupenone lupeol
A. tsangii leaves, twigs A. tsangii leaves, twigs
Cytotoxic against HT1080 (IC50, > 100 uM), TE (IC50, > 100 uM), A549 (IC50, > 100 uM) Cytotoxic against HT1080 (IC50,103.36 uM), TE (IC50,85.94 uM), A549 (IC50,59.81 uM)
[7] [7]
10
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W.-H. Xu, et al.
kg respectively [41], while the alcohol extract of A. rohituka possessed hepatoprotective effect [42]. The methanol extract of A.rohituka also showed antioxidant activities. The IC50 value of the DPPH, ABTS, H2O2 and metal chelation are 73 μg/mL, 73 μg/mL, 103 μg/mL and 101 μg/ mL respectively [43]. Compounds (31,107,113–114) from A. cucullata demonstrated TRAIL resistance-overcoming activity, among which compound 113 displayed the most potent activity and enhanced TRAILinduced apoptosis in TRAIL-resistant human gastric adenocarcinoma
Table 12 Hopane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
76
zeorin
A. tetrapetala branches
Inactive against acetylcholinesterase
[13]
Table 13 Limonoids from the genus Amoora. No.
Compound name
Occurrence
77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95
Amotsangin A Amotsangin B Amotsangin C Amotsangin D Amotsangin E Amotsangin F Amotsangin G DM-3 DM-4 Amoorinin Amooramide A Amooramide B Amooramide C Amooramide D Amooramide E Amooramide F Amooramide G Amooramide H Amooramide I Amooramide J Amooramide K Amooramide L
A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A.
96 97 98
Biological activity
tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves rohituka stem barks tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves
Ref
Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM
Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inhibition on TNFα- induced NF-κB activity by 64% at a concentration of 10 μM, No cytotoxic activity against HepG2 cell line at 10 μM
[4] [4] [4] [4] [4] [4] [4] [4] [4] [25] [6] [6] [6] [6] [6] [6] [6] [6] [6] [6] [6]
Table 14 Steroids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
99 100 101 102 103
3β,7α,16β-Trihydroxy-stigmast-5,22-diene 3β,7α,16β-t-Rihydroxy –stigmast-5-ene Ergosta-5,24(28)-dien-3β,7α-diol Ergosta-5,24(28)-dien-3β,7β,16β-triol β-Sitosterol
A. A. A. A. A. A.
yunnanensis barks yunnanensis barks yunnanensis barks yunnanensis barks dasyclada stems dasyclada twigs
[14] [14] [14] [14] [20] [22]
104
Stigmast-5-en-3β,7α-diol
105
α-Spinasterol
A. A. A. A.
stellato-squamos twigs ouangtliensis barks dasyclada twigs tetrapetala branches
[17] [17] [22] [13]
Inactive against acetylcholinesterase
Ref
Table 15 Alkaloids from the genus Amoora. No.
Compound name
Occurrence
106 107 108 109 110 111 112
Rohitukine Hydroxytigloyl-1,4-butanediamidecyclofoveoglin Dasyclamide Cucullamide Aurantiamide acetate Benzenepropanamide Xylogranatinin
A. A. A. A. A. A. A.
Biological activity
rohituka leaves, stems cucullata leaves cucullata leaves cucullata leaves ouangliensis leaves,twigs ouangliensis leaves,twigs ouangliensis leaves,twigs
11
Activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells Anti-inflammatory activityon LPS -induced NO production in RAW264.7 No anti-inflammatory activityon LPS -induced NO production in RAW264.7 No anti-inflammatory activityon LPS -induced NO production in RAW264.7
Ref [26] [12] [12] [27] [19] [19] [19]
Fitoterapia 137 (2019) 104269
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Table 16 Rocaglamide derivatives from the genus Amoora. No.
Compound name
Occurrence
113
1-O-Formylrocagloic acid
114
3′-Hydroxyrocagloic acid
115 116 117 118 119
Rocaglaol Rocagloic acid 3-Hydroxymethylrocaglate 1-O-Formylmethyl rocaglate Methylrocaglate
A. A. A. A. A. A. A. A. A.
cucullata cucullata cucullata cucullata cucullata cucullata cucullata cucullata cucullata
fruits leaves fruits leaves fruits fruits fruits fruits fruits
Biological activity
Ref
Cytotoxic against KB (ED50,0.002 μg/mL, BC (ED50,0.06 μg/mL), and NCI-H187(ED50,0.019 μg/mL); Activity in overcoming TRAIL resistance in AGS cells Cytotoxic against KB (ED50,0.005 μg/mL, BC (ED50,0.002 μg/mL), and NCI-H187(ED50,0.0000028 μg/mL); Activity in overcoming TRAIL resistance in AGS cells Cytotoxic against KB (ED50,0.1 μg/mL, BC (ED50,0.08 μg/mL), and NCI-H187(ED50,0.000031 μg/mL) Cytotoxic against KB (ED50, > 50 μg/mL, BC (ED50, > 50 μg/mL), and NCI-H187(ED50,0.000036 μg/mL) Cytotoxic against KB (ED50, > 50 μg/mL, BC (ED50, > 50μg/mL), and NCI-H187(ED50,0.0019 μg/mL) Cytotoxic against KB (ED50,0.3 μg/mL, BC (ED50,0.07 μg/mL), and NCI-H187(ED50,0.00073 μg/mL) Cytotoxic against KB (ED50,0.02 μg/mL, BC (ED50,0.002 μg/mL), and NCI-H187(ED50,0.000037 μg/mL)
[11] [12] [11] [12] [11] [11] [11] [11] [11]
(AGS) cells [12]. Phenol (135) from A. tetrapetala showed inhibitory activity against acetylcholinesterase with inhibitory rate 20.36% [13].
Table 17 Flavonoids from the genus Amoora. No.
Compound name
Occurrence
120
(+)-Catechin
121 122 123
Chrysin Apigenin Lichenxanthone
A. ouangtliensis barks A. cucullata leaves A. cucullata leaves A. tetrapetala branches
Biological activity
Ref
5. Conclusions
[17]
Inactive against acetylcholinesterase
The genus of Amoora possessed chemical constituents with diverse structural types, exhibited extensive pharmacological activities. Therefore, Amoora species seem to have great potential as a promising ethnopharmacological plant source. Up to now, phytochemical investigations on Amoora species afforded a total of 140 different compounds, which may provide useful evidence for their reasonable
[27] [27] [13]
Table 18 Glycosids from the genus Amoora. No.
Compound name
Occurrence
124
8-C-Methyl-5,7,3′,4′-tetrahydroxy -flavone-3-O-β-D-xylopyranoside Kaempferol-3-O-β-D-glucopyranoside Daucosterol
A. rohituka roots
[28]
A. A. A. A. A.
[27] [17] [17] [22] [29]
125 126 127
Stigmasta-5,24(28)-dien-3B-O-β-Dglucopyranosyl-α- L-rhamnopyranoside
Biological activity
cucullata leaves stellato-squamosa twigs ouangliensis barks dasyclada twigs rohituka seeds
Ref
Table 19 Coumarins from the genus Amoora. No.
Compound name
Occurrence
128
Scopoletin
129
8-hydroxy-6-methoxy-3-pentylisocoumarin
A. stellato-squamosa twigs A. dasyclada twigs A. tetrapetala branches
Biological activity
Ref
Inactive against acetylcholinesterase
[17] [22] [13]
Table 20 Phenols from the genus Amoora. No.
Compound name
Occurrence
130 131 132 133 134 135 136 137 138
Noreugenin Eugenin (+)-ent-Ficusol 3-Methoxy-4-hydroxybenzoate Vanillin Methyl 2,4-hydroxy-3,6-dimethylbenzoate Methyl 2-hydroxy-4-methoxy-6-propylbenzoate Methyl 2,4-dihydroxy-6-methylbenzoate 3,5-Dimethoxy-4-hydroxybenzaldehyde
A. A. A. A. A. A. A. A. A.
rohituka leaves, stems rohituka leaves, stems tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches ouangliensis leaves,twigs
12
Biological activity
Ref
Inactive against acetylcholinesterase Inactive against acetylcholinesterase Inactive against acetylcholinesterase Inhibitory activity against acetylcholinesterase Inactive against acetylcholinesterase Inactive against acetylcholinesterase No anti-inflammatory activityon LPS -induced NO production in RAW264.7
[26] [26] [13] [13] [13] [13] [13] [13] [19]
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Table 21 Fatty acids from the genus Amoora. No.
Compound name
Occurrence
139
7-Keto-octadec-cis11-enoic acid Methyl hydrogen succinate
A. rohituka seeds A. tetrapetala branches
140
Biological activity
constituents from Amoora tetrapetala, Nat. Prod. Res. Dev. 27 (2015) 562–566. [14] X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, The chemical constituents of Amoora yunnanensis, Acta Bot. Sin. 43 (2001) 426–430. [15] S.M. Yang, S.H. Wu, X.D. Qin, X.D. Luo, D.G. Wu, Neoclerodane diterpenes from Amoora stellato-squamosa, Helv. Chim. Acta. 87 (2004) 1279–1286. [16] S.-M. Yang, D.-G. Wu, X.-K. Liu, Anticancer activity of diterpenoids from Amoora ouangliensis and Amoora stellato-squamosa, Z. Naturforsch. C 65 (2010) 39–42. [17] S.-M. Yang, D.-G. Wu, X.-K. Liu, D.-Y. Zhu, Chemical constituentsfrom Amoora ouangliensis and Amoora stellato-squamosa, Nat. Prod. Res. Dev. 20 (2008) 1000–1004. [18] X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, Dammarane triterpenoids from Amoora yunnanensis, Heterocycles 53 (2000) 2795–2802. [19] J.-F. Li, Y.-K. Xu, Constituents from the leaves and twigs of Amoora ouangliensis and their anti-inflammatory activities, Nat. Prod. Res. Dev. 30 (2018) 1361–1366. [20] H. Wang, X. Zhang, S. Yang, X. Luo, A new triterpenoid from Amoora dasyclada, Acta Bot. Sin. 46 (2004) 1256–1260. [21] S.-M. Yang, Y.-B. Ma, X.-D. Luo, S.-H. Wu, D.-G. Wu, Two new tetranortriterpenoids from Amoora dasyclada, Chin. Chem. Lett. 15 (2004) 1187–1190. [22] S.-M. Yang, Q.-S. Song, C. Qing, D.-G. Wu, X.-K. Liu, Anticancer activity of tirucallane triterpenoids from Amoora dasyclada, Z. Naturforsch. C 61 (2006) 193–195. [23] S.-M. Yang, L. Ding, S.-H. Wu, Y.-B. Ma, X.-D. Luo, D.-G. Wu, Two new tirucallane triterpenes with six-membered hemiacetal from Amoora dasyclada, Z. Naturforsch. B. 59 (2004) 1067–1069. [24] T. Rabi, D. Karunagaran, M.K. Nair, V.N. Bhattathiri, Cytotoxic activity of amooranin and its derivatives, Phytother. Res. 16 (2002) S84–S86. [25] V.K. Agnihotri, S.D. Srivastava, S.K. Srivastava, A new limonoid, amoorinin, from the stem bark of Amoora rohituka, Planta Med. 53 (1987) 298–299. [26] A.D. Harmon, U. Weiss, J. Silverton, The structure of rohitukine, the main alkaloid of Amoor arohituka (Syn. Aphanamixis polystachya) (meliaceae), Tetrahedron Lett. 20 (1979) 721–724. [27] M.S. Abdelfattah, K. Toume, F. Ahmed, S.K. Sadhu, M. Ishibashi, Cucullamide, a new putrescine bisamide from Amoora cucullata, Chem. Pharm. Bull. 58 (2010) 1116–1118. [28] S.A. Jain, S.K. Srivastava, 8-C-methyl-quercetin-3-O-β/−D-xylopyranoside, a new flavone glycoside from the roots of Amoora rohituka, J. Nat. Prod. 48 (1985) 299–301. [29] S. Bhatt, V. Saxena, S. Nigam, A new saponin from seeds of Amoora rohituka, Phytochemistry 20 (1981) 1749–1750. [30] L. Pan, J.L. Woodard, D.M. Lucas, J.R. Fuchs, A.D. Kinghorn, Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species, Nat. Prod. Rep. 31 (2014) 924–939. [31] T. Rabi, R. Gupta, Antitumor and cytotoxic investigation of Amoora rohituka, Int. J. Pharmacogn. 33 (1995) 359–361. [32] M.S. Rahman, B. Begum, R. Chowdhury, K.M. Rahman, M.A. Rashid, Preliminary cytotoxicity screening of some medicinal plants of Bangladesh, Dhaka Univ. J. Pharm. Sci. 7 (2008) 47–52. [33] M.S. Rahman, M.A. Rashid, Preliminary antimicrobial and cytotoxic activities of Amoora cucullata extractives, Orient Pharm Exp Med 9 (2009) 182–185. [34] R. Pervin, S. Afrin, F. Sabrin, U. Salma Zohora, M. Shahedur Rahman, K. Didarul Islam, M. Morsaline Billah, Antioxidant, antibacterial and brine shrimp lethality bioassay of Amoora cucullata, a mangrove plant, J. Young Pharm. 8 (2015) 33–38. [35] D. Zhuang, Y. Wang, G. Chen, J. Wang, L. Liu, J. Tang, Q. Shang, W. Zhao, W. Chen, Chemical components, bioactivities of the volatile oil from the leaves of Amoora tsangii (Merr.), Sci. Tec. Food Ind. 34 (2013) 115–117. [36] R. Yadav, V. Kashaw, Evaluation of anti-inflammatory activity of alcoholic, hydroalcoholic and aqueous extract of Amoora Rohituka and Soymida Febrifuga in albino rats, Asian J. Pharm. Pharmacol. 4 (2018) 908–913. [37] R. Chowdhury, C.M. Hasan, M.A. Rashid, Antimicrobial activity of Toona ciliata and Amoora rohituka, Fitoterapia 74 (2003) 155–158. [38] M.S. Rahman, M.Z. Rahman, M.A. Wahab, R. Chowdhury, M.A. Rashid, Antimicrobial activity of some indigenous plants of Bangladesh, Dhaka Univ. J. Pharm. Sci. 7 (2008) 23–26. [39] M.K. Umesh, C.B. Sanjeevkumar, R. Londonkar, Phytochemical and antibacterial evaluation of various extracts of Amoora ruhituka bark, Int. Lett. Nat. Sci. 39 (2015) 68–72. [40] E.A. Aboutabl, F.S. El-Sakhawy, M.M. Fathy, R.M.A. Megid, Composition and antimicrobial activity of the leaf and fruit oils from Amoora rohituka Wigth. et Arn, J. Essent. Oil Res. 12 (2011) 635–638. [41] R. Chowdhury, R. Rashid, Effect of the crude extracts of Amoora rohituka stem bark on gastrointestinal transit in mice, Indian J. Pharm. 35 (2003) 304–307. [42] M. Gole, S. Dasgupta, R. Sur, J. Ghosal, Hepatoprotective effect of Amoora rohituka, Int. J. Pharmacogn. 35 (1997) 318–322. [43] M.K. Umesh, C.B. Sanjeevkumar, R.L. Londonkar, Evaluation of phenolics content and in vitro antioxidant activities of methanolic extract of Amoora rohituka bark, Int. J. Curr. Microbiol. App. Sci. 5 (2016) 225–235.
Ref [8]
Inactive against acetylcholinesterase
[13]
utilization. However, majority of its species' chemical constituents remain unknown, which restrict their utilization and development. Further phytochemical investigations on Amoora species remain to be exploited and studied. Although the crude extracts of Amoora species and their chemical constituents were found to possess extensive pharmacological activities, many chemical constituents have never been pharmacologically tested. Moreover, most studies so far have mainly conducted in vitro bioassays. Comprehensive investigations on the genus Amoora should be fully strengthened to clarify their chemical constituents and pharmacological effects as well as their relationships between the species in the near future. The current review may provide helpful evidence for reasonable utilization of Amoora species as folk medicines and further research in drug discovery. Declaration of Competing Interests There is no conflict of interest. Funding This work were supported by the National Science Foundation of China (NSFC) (No. 21362035 and No. 31160075), the Initial Foundation of Scientific Research for the introduction of talents from Southwest Forestry University for Wen-Hui Xu (No. 20130916). References [1] Editorial Committee of Flora of China, Flora of China, vol. 43, Science Press, Beijing, 1994, pp. 80–87. [2] Yunnan Institute of Botany, Flora of YunNan, 1 Science Press, Beijing, 1977, pp. 231–237. [3] L.L. Chan, S. George, I. Ahmad, S.L. Gosangari, A. Abbasi, B.T. Cunningham, K.L. Watkin, Cytotoxicity effects of Amoora rohituka and chittagonga on breast and pancreatic Cancer cells, Evid. Based Compl. Alt. 2011 (2011) 860605. [4] H.-D. Chen, S.-P. Yang, S.-G. Liao, B. Zhang, Y. Wu, J.-M. Yue, Limonoids and sesquiterpenoids from Amoora tsangii, J. Nat. Prod. 71 (2008) 93–97. [5] Q.G. Tan, X.D. Luo, Meliaceous limonoids: chemistry and biological activities, Chem. Rev. 111 (2011) 7437–7522. [6] G.Y. Zhu, G. Chen, L. Liu, L.P. Bai, Z.H. Jiang, C-17 lactam-bearing limonoids from the twigs and leaves of Amoora tsangii, J. Nat. Prod. 77 (2014) 983–989. [7] Y.-Y. Ma, D.-G. Zhao, Y. Li, J.-J. Chen, J. Zeng, Q.-Q. Zhao, K. Gao, Cytotoxic triterpenes with diverse skeletons from Amoora tsangii, Phytochem. Lett. 15 (2016) 251–255. [8] C. Daulatabad, S.A. Jamkhandi, A keto fatty acid from Amoora rohituka seed oil, Phytochemistry 46 (1997) 155–156. [9] R. Chowdhury, C.M. Hasan, M.A. Rashid, Guaiane sesquiterpenes from Amoora rohituka, Phytochemistry 62 (2003) 1213–1216. [10] T. Rabi, C.V. Catapano, Aphanin, a triterpenoid from Amoora rohituka inhibits K-Ras mutant activity and STAT3 in pancreatic carcinoma cells, Tumour Biol. 37 (2016) 12455–12464. [11] P. Chumkaew, S. Kato, K. Chantrapromma, Potent cytotoxic rocaglamide derivatives from the fruits of Amoora cucullata, Chem. Pharm. Bull. 54 (2006) 1344–1346. [12] F. Ahmed, K. Toume, S.K. Sadhu, T. Ohtsuki, M.A. Arai, M. Ishibashi, Constituents of Amoora cucullata with TRAIL resistance-overcoming activity, Org. Biomol. Chem. 8 (2010) 3696–3703. [13] C.-N. Mi, W.-L. Mei, W.-J. Zuo, C.-H. Cai, H. Wang, S.-P. Li, H.-F. Dai, Chemical
13
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Review
The genus Amoora: A phytochemical and pharmacological review Wen-Hui Xu, Xiao-Min Su, Chao Wang, Fan Du, Qian Liang
⁎
T
Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Ministry of Education, Southwest Forestry University, Kunming 650224, PR China
ARTICLE INFO
ABSTRACT
Keywords: Amoora species Phytochemistry Pharmacological activities Terpenoids Limonoids
The genus Amoora belongs to the Meliaceae family comprising approximately 25–30 species. Many Amoora species have been used as folk medicines for the treatment of many diseases. This review focuses on diverse chemical constituents from Amoora species as well as significant pharmacological activities. Up to now, a total of 140 compounds including eight sesquiterpenoids, twenty-six diterpenoids, forty-two triterpenoids, twenty-two limonoids, seven steroids, seven alkaloids, seven rocaglamide derivatives, four flavonoids, four glycosides, two coumarins, nine phenols, and two organic acids and esters were reported from Amoora species. Triterpenoids are characteristic components for Amoora species. The extracts and chemical constituents of Amoora species exhibit a broad spectrum of pharmacological activities including cytotoxic, anti-inflammatory, antibacterial and antifungal activity. The present review may provide useful evidence for reasonable utilization of Amoora species as folk medicines and further research in drug discovery.
1. Introduction
2. Traditional uses
The genus Amoora belongs to the Meliaceae family comprised about 25–30 species. The plants of this genus are economically important timber tree, usually distributed in the tropical and subtropical regions of asia, mostly in China, India, Malaysia and Bangladesh. Eight species and one variant are found in China [1–4]. Species of this genus are important ornamental ecological plants, which provide useful timber for building purposes. Several Amoora species have been used as folk medicines in southeast Asia for the treatment of many diseases such as diarrhea, inflammation, spleen and liver and cardiac diseases [1–4]. As the characteristic constituents of the Meliaceae family for structurally diverse and biologically significant limonoids have attracted increasing research attentions [5]. In recent years, more and more bioactive chemical constituents have been found to validate the folk medicinal usages from many Amoora species. However, up to now no complete review has been published. In present review, we summarizes systematically their phytochemistry and pharmacological activities of genus Amoora reported in the literature as retrieved from Web of Science, SciFinder, PubMed, CNKI, and Google Scholar, up until May 2019 for the first time, with aim of providing the scientific clue for further studies and reasonable utilization.
Plants of Amoora genus have been extensively used as important timber tree, which also are cultivated as ornamental ecological plants. Some Amoora species have been used as traditional medicine to treat dysentery, laxative, skin, cardiac diseases in several countries for a long period [6–13]. The stem barks of A. tsangii, known as “Tie luo” in China, are mainly used as a vermicide in folklore medicine [4]. Among Amoora species, A.tsangii, A.dasyclada, A.rohituka, A.cucullata, and A.tetrapetala have been reported in traditional medicine as important folk herb. A summary of their local names, geographical distribution, and traditional uses were presented in Table 1.
⁎
3. Chemical constituents Up to now 140 compounds (except volatile constituents) have been reported from nine Amoora species (A.tsangii, A.dasyclada, A.rohituka, A.cucullata, A.tetrapetala, A.yunnanensis, A.stellato-squamosa, A.ouangliensis, and A.cucullata) including eight sesquiterpenoids (1–8), twenty-six diterpenoids (9–34), forty-two triterpenoids (35–76), twenty-two limonoids (77–98), seven steroids (99–105), seven alkaloids (106–112), seven rocaglamide derivatives (113–119), four fla-
Corresponding author. E-mail address: [email protected] (Q. Liang).
https://doi.org/10.1016/j.fitote.2019.104269 Received 18 June 2019; Received in revised form 14 July 2019; Accepted 14 July 2019 Available online 16 July 2019 0367-326X/ © 2019 Elsevier B.V. All rights reserved.
Fitoterapia 137 (2019) 104269
W.-H. Xu, et al.
Table 1 Traditional uses of the genus Amoora. Species
Local names
Distribution
Traditional uses
A. tsangii
Tie luo (Chinese)
Hainan Island of China
A. dasyclada
Hong luo, Cu zhi ya mo, (Chinese)
Yunnan, Hainan of China
Vermicide (stem barks) [4], kill lice (stem barks) [6], the volatile oil from the leaves exhibited antimicrobial, antitumor activities [7]. Insecticide (twigs) [2].
Amoor,Latmi, bekak, garotai (Bengali) Si ban ya mo (Chinese)
Bangladesh
A. rohituka A. cucullata A. tetrapetala
Bangladesh, India, Sri Lanka, Malaysia, Indonesia
India, Malaysia, China
Laxative, anthelmintic and cure ulcers (seeds) [8], anticancer, antimicrobial, antiinflammatory and hepatoprotective (various parts of the plant) [9], treatment for tumours, spleen and liver diseases, abdominal complaints (barks) [8,10]. Treatment of marrow, diarrhea (fruits) [11], treatment of inflammation, antibacterial, dysentery, skin, cardiac diseases (leaves) [12] . Insecticide and repellent (stem barks) [13].
Fig. 1. Sesquiterpenoids from the genus Amoora.
vonoids (120−123), four glycosides (124–127), two coumarins (128–129), nine phenols (130–138), and two organic acids and esters (139–140). Terpenoids are the predominant secondary metabolite constituents in the genus, chiefly triterpenoids, which may belong to the dammarane, tirucallane, cycloartane, taraxerane, oleanane, lupane, and hopane skeletal types. Their structures, names, corresponding sources, biological activities and references are collected in Figs. 1-11 and Tables 2–21.
diterpenoids with a double band between C-8 and C-17 position (29–33) and only one kaurane diterpenoid (34) [12]. 3.3. Triterpenoids Extensive phytochemical investigations on Amoora species afforded forty-two triterpenoids (35–76) including fourteen dammaranes (35–48), eight tirucallanes (49–56), nine cycloartanes (57–65), four taraxeranes (66–69), four oleananes (70–73), two lupanes (74–75), and one hopane triterpenoid (76) (Figs. 36 and Tables 6–12). Four new dammaranes (35–38) and eight known ones (39–46) were isolated from the bark of A. yunnanensis. Among them, dammaranes (36–37) possessed a chlorine atom attached to C-23 [18,19]. From the leaves and twigs of A. tsangii, two new 29-nor-cycloartanes (58–59), two dammaranes (47–48), five cycloartanes (60–64), and two lupanes (74–75) were reported [7]. Tirucallanes (49–56) were isolated from A. dasyclada stems and A. tetrapetala by different research group [13,20–23]. Among them, compound 49 contained an epoxide group between C-24 and C-25 [20]. Investigations on the the twigs of A.dasyclada afforded taraxeranes (66–68) [22]. Oleananes (70–73) were obtained from A. yunnanensis, A. ouangtliensi, and A. rohituka [10,14,17,24]. Only one hopane triterpenoid (76) was isolated from the branches of A. tetrapetala [13]. It was noted that compounds (41,4647,65) also were obtained from the leaves and twigs of A.ouangliensis [19].
3.1. Sesquiterpenoids To date, eight sesquiterpenoids (1–8) were isolated from Amoora species (Fig. 1 and Table 2). They were divided into guaianes (1–3), cadinane (4), aromadendrane (5), oppositane (6), eudesmane (7), and isodaucane (8). Phytochemical investigations on the bark of A. yunnanensis afforded a guaiane (1) [14]. Two new 6,7-epoxy guaiane sesquiterpenoids (2–3) were isolated from the stem bark of A. rohituka [9]. Investigation of the twigs and leaves of A. tsangii led to the isolation of four known sesquiterpenoids with different skeleton (4–7) [4]. A sodaucane (8) was obtained from the branches of A. tetrapetala [13]. 3.2. Diterpenoids A total of twenty-six diterpenoids (9–34) including eight clerodanes (9–16), seventeen labdanes (17–33), and one kaurane diterpenoid (34) were ioslated from Amoora species (Fig. 2 and Tables 3–5). Eight neoclerodanes (9–16) and twelve labdane diterpenoids (17–28) were isolated from A.stellato-squamosa and A.ouangliensis by Liu's group [15–17]. Investigations on leaves of A. cucullata afforded five labdane
3.4. Limonoids Twenty-two limonoids (77–98) were isolated from Amoora species
2
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Fig. 2. Clerodane, labdane, and kaurane diterpenoids from the genus Amoora.
(Fig. 7 and Table 13). Phytochemical investigations on the twigs and leaves of A. tsangii afforded seven new limonoids (77–83) and two known ones (84–85) [4]. From the stem bark of A. rohituka, amoorinin (86), a ring B,D-seco limonoid, was isolated [25]. Twelve rare lactambearing limonoids (87–98) were isolated from the twigs and leaves of A. tsangii [6]. It was noted that compounds (77–82, 84–85, 87–98) belonged to ring A, B-seco limonoids, while compound (83) was a ring B-seco limonoid.
(Fig. 9 and Table 15). Rohitukine (106) was isolated from the leaves and stems of A. rohituka, which was the first alkaloid from the Meliaceae [26]. One new alkaloid (107) with a rare five-membered cyclic amide moiety and known one (108) were reported from the leaves of A. cucullata [12]. A new putrescine bisamide, cucullamide (109), also was isolated from the leaves of A. cucullata [27]. From the leaves and twigs of A. ouangliensis, three known amides (110−112) were obtanied [19]. 3.7. Rocaglamide derivatives
3.5. Steroids
Rocaglamide derivatives possessed cyclopenta[b]tetrahydrobenzofuran skeleton, which included a favonoid unit and a cinnamic acid amide moiety. Seven rocaglamide derivatives (113–119) were isolated from Amoora species (Fig. 10 and Table 16). Two new rocaglamide derivatives (113–114) and five known ones (115–119) were isolated from the fruits of A. cucullata,while compounds (113–114) also were obtained from the leaves of A. cucullata [11,12]. Sine rocaglamide derivatives were found exclusively in Aglaia species (Meliaceae) as a significant chemotaxonomic marker, Amoora cucullata now have been assigned to Aglaia genus as Aglaia cucullata in the PLANT LIST reasonably from chemotaxonomic viewpoint [30].
Seven steroids (99–105) were isolated from Amoora species (Fig. 8 and Table 14). Two new sterols (99–100) and two known ones (101−102) were obtained by the bark of A. yunnanensis [14]. β-sitosterol (103) was isolated from A. dasyclada and A. stellato-squamos, while known sterol (104) was isolated from A. ouangtliensis and A. dasyclada [17,20,22]. Investigation on the branches of A. tetrapetala led to the isolation of sterol (105) [13]. 3.6. Alkaloids Seven alkaloids (106–112) were isolated from Amoora species
3
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Fig. 3. Dammarane triterpenoids from the genus Amoora.
Fig. 4. Tirucallane triterpenoids from the genus Amoora.
3.8. Flavonoids
[17,22], while compound (127) was isolated from A. rohituka [29].
Four flavonoids, (+)-catechin (120) from A. ouangtliensis [17], chrysin (121) and apigenin (122) from A. cucullata [27], and lichenxanthone (123) from A. tetrapetala were isolated from Amoora species [13] (Fig. 10 and Table 17).
3.10. Coumarins Two coumarins, scopoletin (128) from A. stellato-squamosa and A. dasyclada [17,22]. and 8-hydroxy-6-methoxy-3-pentylisocoumarin (129) from A. tetrapetala were reported from Amoora genus [13] (Fig. 11 and Table 19).
3.9. Glycosides Four glycosides (124–127) have been identified in the genus Amoora (Fig. 10 and Table 18). Two flavonoid glycosides, compound (124) from A. rohituka, and compound (125) from A. cucullata were reported [27,28]. Two steroidal glycosides, daucosterol (126) were obtained from A. stellato-squamosa, A.ouangliensis,and A.dasyclada
3.11. Phenols Nine phenols (130–138) were reported from Amoora species (Fig. 11 and Table 20). From the leaves and stems of A. rohituka have yielded noreugenin (130) and eugenin(131) [26]. Seven phenols
4
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Fig. 5. Cycloartane triterpenoids from the genus Amoora.
Fig. 6. Taraxerane, oleanane, lupane, and hopane triterpenoids from the genus Amoora.
(131–137) were isolated from the branches of A. tetrapetala [13], while compound (138) was obtained from the leaves and twigs of A.ouangliensis [19].
vivo antitumor effect in mice treated with 10 or 20 mg of extract per kg mean survival time was 21 or 25.5 days with % ILS of 10.5 or 34.2, respectively and in vitro cytotoxic activities with an IC50 value of 9 μg/ mL for the Dalton's lymphoma ascites tumor cells [31]. The cytotoxic activities of the methanol extracts of A.cucullata and A.rohituka from Bangladesh were evaluated by the brine shrimp lethality bioassay, which exhibited significant toxicity to brine shrimps (LC50, 5.16, and 5.95 μg/mL, respectively) [32]. The cytotoxcity of the n-hexane, ethyl acetate and methanol extracts of A.cucullata against Artemia salina showed LC50 of 17.18, 7.943 and 0.549 μg/mL, respectively [33]. A.rohituka and A.chittagonga, fractionated with petroleum ether, dichloromethane, and ethanol, were explored for their cytotoxic activities against two breast cancer cell lines (MCF-7 and HTB-126) and three pancreatic cancer cell lines (Panc-1, Mia-Paca2, and Capan1) using the MTT and label-free photonic crystal biosensor assay, only the CH2Cl2 extract of A.chittagonga exhibited significant cytotoxicity to all five cancer cell lines with IC50 values in the range 30–65 μg/mL [3]. Cytotoxic activities of A.cucullata using brine shrimp lethality bioassay were reported with LC50 value 10, 2.301 and 7.28 μg/mL in bark and 1.308,
3.12. Organic acids and esters Unsaturated fatty acid ester (139) was isolated from the seeds of A. rohituka [8], while the branches of A. tetrapetala yielded organic acid (140) [13] (Fig. 11 and Table 21). 4. Pharmacological activities The extracts and chemical constituents of Amoora species exert a wide range of pharmacological activities, primarily involved in cytotoxic, anti-inflammatory, antibacterial, and antifungal activities. 4.1. Cytotoxic activity The ethyl acetate extracts of stem bark from A. rohituka showed in 5
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Fig. 7. Limonoids from the genus Amoora.
1.94 and 2.14 μg/mL in leaf extracts of petroleum ether, chloroform and methanol respectively [34]. The volatile oil from the leaves of A. tsangii displayed cytotoxic activity against SPCA-1 and BEL-7402 cell lines with IC50 values of 11.20, and 35.52 μg/mL, respectively [35]. Three tirucallane triterpenoids (52–54) from A.dasyclada [22], one clerodane diterpenoid (14) from A. stellato-squamosa [16], and three labdane diterpenoids (26–28) from A. ouangliensis showed cytotoxic activities [16], among them, compund 26 displayed significant cytotoxicity against AGZY 83-a (IC50, 21.52 μM) and SMMC-7721 (IC50, 28.47 μM) cell lines [16]. Eleven triterpenes (47–48, 58–64, and 74–75) from A. tsangii were valuated for the cytotoxicity against HT1080, TE, and A549 cell lines by the CCK8 assay [7]. Cycloartanes (58–64) displayed significant cytotoxic activities with IC50 values
Fig. 8. Sterols from the genus Amoora.
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Fig. 9. Alkaloids from the genus Amoora.
Fig. 10. Rocaglamide derivatives, flavonoids and glycosids from the genus Amoora.
ranging from 2.56 to 19.05 μM. Among these triterpenes, mooratsanol A (58) exhibited the most potent cytotoxic activities with IC50 values ranging from 2.56 to 5.10 μM [7]. Amooranin (72) from A.rohituka exhibited the cytotoxcity against MCF-7 (IC50, 2.3 μg/mL) and HeLa cell lines (IC50, 3.4 μg/mL) [24]. Aphanin (73) from A. rohituka were found to display antiproliferative effects, cause G0-G1 cell cycle arrest, inhibit K-Ras G12D mutant activity [10]. Rocaglamide derivatives (113–119) were isolated from the fruits of A.cucullata, which were found to display potent cytotoxic activities against KB, BC, and NCI-H187 cell lines with ED50 values in the range 0.0000028–0.3 μg/mL [11].
with Indomethacin as standard at dose 10 mg/kg p.o. [36]. Compounds (41, 46, 65, and 110) from A. ouangliensis exhibited anti-inflammatory activity on LPS-induced NO production in RAW264.7 [19]. Five limonoids (87–88, 90, and 94–95) from A. tsangii were evaluated the NF-κB inhibitory activities using a luciferase-based NF-κB reporter gene assay. Among these compounds, amooramide I (95) significantly inhibited the TNFα-induced NF-κB luciferase activity by 64% at a concentration of 10 μM, while the other four compounds were inactive [6].
4.2. Anti-inflammatory activity
The petrol ether, dichloromethane and methanol extracts of A. rohituka were found to display antibacterial activity using disc diffusion method and antifungal activity by the poisoned food technique [37].
4.3. Antibacterial and antifungal activity
The alcoholic extract of A. rohituka showed anti-inflammatory effect 7
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Fig. 11. Coumarins, phenols and fatty acids from the genus Amoora.
Table 2 Sesquiterpenoids from the genus Amoora. No.
Compound name
Occurrence
1 2
6-Guaiene-4α, 10α-diol 6β,7β-Epoxyguai-4-en-3-one
A. yunnanensis bark A. rohituka stem bark
3 4 5 6
6β,7β-epoxy-4β,5-dihydroxyguaiane 10-Hydroxy-15-oxo-α-cadinol 11β-Hydroxy-1β,8α-aromadendrene octahydro-4-Hydroxy-3α-methyl-7-methylene-α(1-methylethyl)-1H-indene-1-methanol eudesm-4(15)-ene-1β,6α-diol 10-Oxo-isodauc-3-en-15-al
A. A. A. A.
7 8
Biological activity
rohituka stem bark tsangii twigs and leaves tsangii twigs and leaves tsangii twigs and leaves
A. tsangii twigs and leaves A. tetrapetala branches
Inactive for HIV-inhibitory and cytotoxic activity at 50 mg/mL, antibacterial activity against Escherichia coli with a zone of inhibition of 10.5 mm at a dose of 50 mg/disc. Inactive for HIV-inhibitory and cytotoxic activity at 50 mg/mL.
Inactive against acetylcholinesterase
Ref [14] [9] [4] [4] [4] [4] [4] [13]
Table 3 Clerodane diterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
9 10
Methyl (13E)-2-oxoneocleroda-3,13-dien-15-oate (13E)-2-oxoneocleroda-3,13-dien-15-ol
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
11
(3α,4β,13E)-Neoclerod-13-ene-3,4,15-triol
12 13 14
(3α,4β,13E)-4-Ethoxyneoclerod-13-ene-3,15-diol Neoclerod-14-en-3α,4β,13S-triol (3α,4β,14RS)-Neoclerod-13(16)-ene-3,4,14,15tetrol (13E)-Neocleroda-3,13-diene-15,18-diol (13S)-2-Oxoneocleroda-3,14-dien-13-ol
A. A. A. A. A. A. A. A.
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines Cytotoxic against AGZY 83-a (IC50,50.10 uM), and SMMC-7721(IC50,40.67 uM)
[15,16] [15] [16] [15] [16] [15] [16] [15,16]
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
[15,16] [15,16]
15 16
stellato-squamosa twigs stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs
A. stellato-squamosa twigs A. stellato-squamosa twigs
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
8
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Table 4 Labdane diterpenoids from the genus Amoora. No.
Compound Name
Occurrence
17 18 19
8(17),13(E)-Labdadien-15,19-dioic acid Methyl8(17),13(E)-labdadien-19-oic acid-15-oate 15-Hydroxy-8(17),13(E)-labdadien-19-oic acid
20 21 22 23 24 25 26 27 28 29 30 31 32 33
15-Acetoxy-8(17),13(E)-labdadi-en-19-oic acid 8(17),13(E)-labdadien-19-oic acid-15-al 8(17),13(E)-labdadien-15, 19-diol 19-Hydroxy-8(17),13(E)-labdadien-15-al 19-Hydroxy-8(17),13(Z)-labdadien-15-al 8(17),13(Z)-labdadien-19- oicacid-15-al 5(10),14-ent-Halimadien-3β,13S-diol 8(17),12(E),14-Labdatrien-19-oic acid 6-O-acetyl-austroinulin 2β-Hydroxylabda-8(17),13(16),14-triene 2α-Hydroxylabda-8(17),13(16),14-triene ent-13-epi-manool ent-2β-hydroxymanool 2β,15-Dihydroxy-ent-labda-8(17),13E-diene
A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A.
Biological Activity
stellato-squamosa twigs stellato-squamosa twigs stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks stellato-squamosa twigs ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks ouangliensis barks cucullata leaves cucullata leaves cucullata leaves cucullata leaves cucullata leaves
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
Cytotoxic against AGZY 83-a (IC50,21.52 uM), and SMMC-7721(IC50,28.47 uM) Cytotoxic against AGZY 83-a (IC50,86.59 uM) Cytotoxic against AGZY 83-a (IC50,69.61 uM), and SMMC-7721(IC50,56.38 uM) No activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells Activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells
Compound name
Occurrence
Biological activity
Ref
34
kaur-15-en-17ol
A. cucullata leaves
No activity in overcoming TRAIL resistance in AGS cells
[12]
[17] [17] [17] [16] [17] [17] [17] [17] [17] [17] [16] [16] [16] [12] [12] [12] [12] [12]
The methanol extracts of A. chittagonga exhibited antibacterial and antifungal activity against a wide variety of gram positive and gram negative bacteria and fungi at a concentration of 400 μg/disc using disc diffusion method [38]. The antimicrobial activity of ethyl acetate and methanol extracts of A.cucullata against 13 bacteria and 3 fungal strains showed moderate to strong activity [33]. The methanol and chloroform extracts of bark from A. ruhituka showed significant antibacterial activity against gram negative bacteria [39]. The ethyl acetate and methanol bark extracts of A. cucullata displayed moderate to strong
Table 5 Kaurane diterpenoids from the genus Amoora. No.
Ref
Table 6 Dammarane triterpenoids from the genus Amoora. No.
Compound Name
Occurrence
35 36 37 38 39 40 41
20S,24-Epoxy-24,25-dihydroxydammar-3-one 20S,23R,24R-23-Chloro-20,24-epoxy-dammarane-3α,24,25-triol 3-acetate 20S,23R,24S-23-Chloro-20,24-epoxy-dammarane-3α,24,25-triol 3-acetate 20S,24-Epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid 3-Acetylcabraleadiol Cabraleadiol Cabralea-hydroxylactone
42 43 44 45 46
Ocotillone Cabraleone 24,25-Dihydroxy-dammar-20-en-3-one Shoreic acid 20S,24-Epoxy-25,26,27-trisnor,24-oxo−3,4-secodammar-4(28)-en-3-oic acid
47
Cabralealactone
A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis bark A. yunnanensis barks A. ouangliensis leaves,twigs A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. yunnanensis barks A. ouangliensis leaves,twigs A. tsangii leaves and twigs A. ouangliensis leaves,twigs
48
Cabralea-hydroxy-lactone acetate
A. tsangii leaves and twigs
9
Biological Activity
Anti-inflammatory activityon LPS -induced NO production in RAW264.7
Anti-inflammatory activity on LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,50.93 uM), TE (IC50,61.21uM), and A549 (IC50, > 100 uM) No antiinflammatory activityon LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,49.99 uM), TE (IC50,51.77 uM), A549 (IC50,40.39 uM)
Ref [18] [18] [18] [18] [18] [18] [18] [19] [18] [18] [18] [18] [18] [19] [7] [19] [7]
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Table 7 Tirucallane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
49 50 51
A. dasyclada stems A. dasyclada stems A. dasyclada stems
No cytotoxic activity against AGZY 83-a, and SMMC-7721 cell lines
[20] [21,22] [21]
A. dasyclada twigs
Cytotoxic against SMMC-7721(IC50,0.171 uM)
[22]
53 54
24,25-Epoxy-tirucall-7-ene-3,23-dione 3-Oxo-24, 25, 26, 27-tetranortirucall-7-ene-23(21)-lactone 3α-Hydroxy-24, 25, 26, 27-tetranortirucall-7-ene-23(21)lactone 3α-Acetoxy-24,25,26,27-tetranortirucalla-7-ene-23(21)lactone 3α,21β,25-Trioltirucalla-21,24-epoxy-23-one 21β,25-Dioltirucalla-21,24-epoxy-3,23-dione
A. dasyclada twigs A. dasyclada twigs
[22,23] [22,23]
55 56
22ξ-Hydroxytirucalla-7,24-dien-3,3-dione Dymacrin D
A. tetrapetala branches A. tetrapetala branches
Cytotoxic against AGZY 83-a (IC50,0.065 uM) Cytotoxic against AGZY 83-a (IC50,0.050 uM), and SMMC7721(IC50,0.018 uM) Inactive against acetylcholinesterase Inactive against acetylcholinesterase
52
[13] [13]
Table 8 Cycloartane triterpenoids from the genus Amoora. No. Compound name
Occurrence
Biological activity
Ref
57
A. cucullata leaves
No activity in overcoming TRAIL resistance in AGS cells
[12]
A. A. A. A.
tsangii tsangii tsangii tsangii
Cytotoxic Cytotoxic Cytotoxic Cytotoxic
[7] [7] [7] [7]
A. A. A. A. A.
tsangii leaves, twigs touangliensis leaves,twigs tsangii leaves, twigs tsangii leaves, twigs touangliensis leaves,twigs
62
(24S)-21,24,25,28-tetrahydroxycycloartane3-one Amooratsanol A Amooratsanol B (24S)-25-Methoxycycloartane-3β, 24-diol 4a, 14-Dimethyl-9,19-cyclocholestan-3β,24diol (24R)-Cycloartane-3β,24,25-triol
63 64 65
(24R)-28,29-Dinor-cycloartane-3β,24,25-triol 29-Nor-cycloartan-23-ene-3β,25-diol 24(R)-19-Cyclolanost-3-one-24,25-diol
58 59 60 61
leaves, leaves, leaves, leaves,
twigs twigs twigs twigs
Compound name
Occurrence
Biological activity
66 67 68 69
Taraxerone Taraxerol Taraxerol acetate 11α,12α-Epoxy-14taraxeren-3-one
A. dasyclada twigs A. dasyclada twigs A. dasyclada twigs A. yunnanensis barks
HT1080 HT1080 HT1080 HT1080
(IC50,2.61 (IC50,6.88 (IC50,4.93 (IC50,3.42
uM), uM), uM), uM),
TE TE TE TE
(IC50,5.10 uM), and A549 (IC50,2.56 uM) (IC50,19.05 uM), and A549 (IC50,8.66 uM) (IC50,12.92 uM), and A549 (IC50,7.41 uM) (IC50,10.68 uM), and A549 (IC50,2.92 uM)
Cytotoxic against HT1080 (IC50,5.32 uM), TE (IC50,6.90 uM), and A549 (IC50,5.38 uM) No anti-inflammatory activityon LPS -induced NO production in RAW264.7 Cytotoxic against HT1080 (IC50,12.82 uM), TE (IC50,14.60 uM), and A549 (IC50,8.53 uM) Cytotoxic against HT1080 (IC50,10.62uM), TE (IC50,14.35 uM), and A549 (IC50,7.62 uM) Anti-inflammatory activityon LPS -induced NO production in RAW264.7
[7] [7] [7] [7] [19]
antibacterial activity against 1 gram-positive bacteria and 6 gram-negative bacteria strains [34]. The volatile oils of leaf and fruit from A. rohitzrka showed significant antimicrobial activity against Escherlcbla coli, Micrococcus flavoroscus, Listeria monocytogenes N and Candida albicans [40]. The volatile oil of the leaves from A. tsangii showed strong inhibitory activities against Escherichia coli [35].
Table 9 Taraxerane triterpenoids from the genus Amoora. No.
against against against against
Ref [22] [22] [22] [14]
4.4. Other activities The petroleum ether, dichloromethane and methanol extracts of A. rohituka demonstrated good laxative potential at 400, 250 and 400 mg/
Table 10 Oleanane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
70 71
β-Amyrone β-Amyrin
72 73
Amooranin Aphanin
A. A. A. A. A.
yunnanensis barks yunnanensis barks ouangtliensi barks rohituka stems, barks rohituka stems
Biological activity
Ref
Cytotoxic against MCF-7 (IC50,2.3μg/mL), HeLa (IC50, 3.4μg/mL) Inhibition K-Ras mutant activity and STAT3 in pancreatic carcinoma cells
[14] [14] [17] [24] [10]
Table 11 Lupane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
74 75
lupenone lupeol
A. tsangii leaves, twigs A. tsangii leaves, twigs
Cytotoxic against HT1080 (IC50, > 100 uM), TE (IC50, > 100 uM), A549 (IC50, > 100 uM) Cytotoxic against HT1080 (IC50,103.36 uM), TE (IC50,85.94 uM), A549 (IC50,59.81 uM)
[7] [7]
10
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kg respectively [41], while the alcohol extract of A. rohituka possessed hepatoprotective effect [42]. The methanol extract of A.rohituka also showed antioxidant activities. The IC50 value of the DPPH, ABTS, H2O2 and metal chelation are 73 μg/mL, 73 μg/mL, 103 μg/mL and 101 μg/ mL respectively [43]. Compounds (31,107,113–114) from A. cucullata demonstrated TRAIL resistance-overcoming activity, among which compound 113 displayed the most potent activity and enhanced TRAILinduced apoptosis in TRAIL-resistant human gastric adenocarcinoma
Table 12 Hopane triterpenoids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
Ref
76
zeorin
A. tetrapetala branches
Inactive against acetylcholinesterase
[13]
Table 13 Limonoids from the genus Amoora. No.
Compound name
Occurrence
77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95
Amotsangin A Amotsangin B Amotsangin C Amotsangin D Amotsangin E Amotsangin F Amotsangin G DM-3 DM-4 Amoorinin Amooramide A Amooramide B Amooramide C Amooramide D Amooramide E Amooramide F Amooramide G Amooramide H Amooramide I Amooramide J Amooramide K Amooramide L
A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A. A.
96 97 98
Biological activity
tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves rohituka stem barks tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves tsangii twigs, leaves
Ref
Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM
Inactive for TNFα- induced NF-κB activity, No cytotoxic activity against HepG2 cell line at 10 μM Inhibition on TNFα- induced NF-κB activity by 64% at a concentration of 10 μM, No cytotoxic activity against HepG2 cell line at 10 μM
[4] [4] [4] [4] [4] [4] [4] [4] [4] [25] [6] [6] [6] [6] [6] [6] [6] [6] [6] [6] [6]
Table 14 Steroids from the genus Amoora. No.
Compound name
Occurrence
Biological activity
99 100 101 102 103
3β,7α,16β-Trihydroxy-stigmast-5,22-diene 3β,7α,16β-t-Rihydroxy –stigmast-5-ene Ergosta-5,24(28)-dien-3β,7α-diol Ergosta-5,24(28)-dien-3β,7β,16β-triol β-Sitosterol
A. A. A. A. A. A.
yunnanensis barks yunnanensis barks yunnanensis barks yunnanensis barks dasyclada stems dasyclada twigs
[14] [14] [14] [14] [20] [22]
104
Stigmast-5-en-3β,7α-diol
105
α-Spinasterol
A. A. A. A.
stellato-squamos twigs ouangtliensis barks dasyclada twigs tetrapetala branches
[17] [17] [22] [13]
Inactive against acetylcholinesterase
Ref
Table 15 Alkaloids from the genus Amoora. No.
Compound name
Occurrence
106 107 108 109 110 111 112
Rohitukine Hydroxytigloyl-1,4-butanediamidecyclofoveoglin Dasyclamide Cucullamide Aurantiamide acetate Benzenepropanamide Xylogranatinin
A. A. A. A. A. A. A.
Biological activity
rohituka leaves, stems cucullata leaves cucullata leaves cucullata leaves ouangliensis leaves,twigs ouangliensis leaves,twigs ouangliensis leaves,twigs
11
Activity in overcoming TRAIL resistance in AGS cells No activity in overcoming TRAIL resistance in AGS cells Anti-inflammatory activityon LPS -induced NO production in RAW264.7 No anti-inflammatory activityon LPS -induced NO production in RAW264.7 No anti-inflammatory activityon LPS -induced NO production in RAW264.7
Ref [26] [12] [12] [27] [19] [19] [19]
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Table 16 Rocaglamide derivatives from the genus Amoora. No.
Compound name
Occurrence
113
1-O-Formylrocagloic acid
114
3′-Hydroxyrocagloic acid
115 116 117 118 119
Rocaglaol Rocagloic acid 3-Hydroxymethylrocaglate 1-O-Formylmethyl rocaglate Methylrocaglate
A. A. A. A. A. A. A. A. A.
cucullata cucullata cucullata cucullata cucullata cucullata cucullata cucullata cucullata
fruits leaves fruits leaves fruits fruits fruits fruits fruits
Biological activity
Ref
Cytotoxic against KB (ED50,0.002 μg/mL, BC (ED50,0.06 μg/mL), and NCI-H187(ED50,0.019 μg/mL); Activity in overcoming TRAIL resistance in AGS cells Cytotoxic against KB (ED50,0.005 μg/mL, BC (ED50,0.002 μg/mL), and NCI-H187(ED50,0.0000028 μg/mL); Activity in overcoming TRAIL resistance in AGS cells Cytotoxic against KB (ED50,0.1 μg/mL, BC (ED50,0.08 μg/mL), and NCI-H187(ED50,0.000031 μg/mL) Cytotoxic against KB (ED50, > 50 μg/mL, BC (ED50, > 50 μg/mL), and NCI-H187(ED50,0.000036 μg/mL) Cytotoxic against KB (ED50, > 50 μg/mL, BC (ED50, > 50μg/mL), and NCI-H187(ED50,0.0019 μg/mL) Cytotoxic against KB (ED50,0.3 μg/mL, BC (ED50,0.07 μg/mL), and NCI-H187(ED50,0.00073 μg/mL) Cytotoxic against KB (ED50,0.02 μg/mL, BC (ED50,0.002 μg/mL), and NCI-H187(ED50,0.000037 μg/mL)
[11] [12] [11] [12] [11] [11] [11] [11] [11]
(AGS) cells [12]. Phenol (135) from A. tetrapetala showed inhibitory activity against acetylcholinesterase with inhibitory rate 20.36% [13].
Table 17 Flavonoids from the genus Amoora. No.
Compound name
Occurrence
120
(+)-Catechin
121 122 123
Chrysin Apigenin Lichenxanthone
A. ouangtliensis barks A. cucullata leaves A. cucullata leaves A. tetrapetala branches
Biological activity
Ref
5. Conclusions
[17]
Inactive against acetylcholinesterase
The genus of Amoora possessed chemical constituents with diverse structural types, exhibited extensive pharmacological activities. Therefore, Amoora species seem to have great potential as a promising ethnopharmacological plant source. Up to now, phytochemical investigations on Amoora species afforded a total of 140 different compounds, which may provide useful evidence for their reasonable
[27] [27] [13]
Table 18 Glycosids from the genus Amoora. No.
Compound name
Occurrence
124
8-C-Methyl-5,7,3′,4′-tetrahydroxy -flavone-3-O-β-D-xylopyranoside Kaempferol-3-O-β-D-glucopyranoside Daucosterol
A. rohituka roots
[28]
A. A. A. A. A.
[27] [17] [17] [22] [29]
125 126 127
Stigmasta-5,24(28)-dien-3B-O-β-Dglucopyranosyl-α- L-rhamnopyranoside
Biological activity
cucullata leaves stellato-squamosa twigs ouangliensis barks dasyclada twigs rohituka seeds
Ref
Table 19 Coumarins from the genus Amoora. No.
Compound name
Occurrence
128
Scopoletin
129
8-hydroxy-6-methoxy-3-pentylisocoumarin
A. stellato-squamosa twigs A. dasyclada twigs A. tetrapetala branches
Biological activity
Ref
Inactive against acetylcholinesterase
[17] [22] [13]
Table 20 Phenols from the genus Amoora. No.
Compound name
Occurrence
130 131 132 133 134 135 136 137 138
Noreugenin Eugenin (+)-ent-Ficusol 3-Methoxy-4-hydroxybenzoate Vanillin Methyl 2,4-hydroxy-3,6-dimethylbenzoate Methyl 2-hydroxy-4-methoxy-6-propylbenzoate Methyl 2,4-dihydroxy-6-methylbenzoate 3,5-Dimethoxy-4-hydroxybenzaldehyde
A. A. A. A. A. A. A. A. A.
rohituka leaves, stems rohituka leaves, stems tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches tetrapetala branches ouangliensis leaves,twigs
12
Biological activity
Ref
Inactive against acetylcholinesterase Inactive against acetylcholinesterase Inactive against acetylcholinesterase Inhibitory activity against acetylcholinesterase Inactive against acetylcholinesterase Inactive against acetylcholinesterase No anti-inflammatory activityon LPS -induced NO production in RAW264.7
[26] [26] [13] [13] [13] [13] [13] [13] [19]
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Table 21 Fatty acids from the genus Amoora. No.
Compound name
Occurrence
139
7-Keto-octadec-cis11-enoic acid Methyl hydrogen succinate
A. rohituka seeds A. tetrapetala branches
140
Biological activity
constituents from Amoora tetrapetala, Nat. Prod. Res. Dev. 27 (2015) 562–566. [14] X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, The chemical constituents of Amoora yunnanensis, Acta Bot. Sin. 43 (2001) 426–430. [15] S.M. Yang, S.H. Wu, X.D. Qin, X.D. Luo, D.G. Wu, Neoclerodane diterpenes from Amoora stellato-squamosa, Helv. Chim. Acta. 87 (2004) 1279–1286. [16] S.-M. Yang, D.-G. Wu, X.-K. Liu, Anticancer activity of diterpenoids from Amoora ouangliensis and Amoora stellato-squamosa, Z. Naturforsch. C 65 (2010) 39–42. [17] S.-M. Yang, D.-G. Wu, X.-K. Liu, D.-Y. Zhu, Chemical constituentsfrom Amoora ouangliensis and Amoora stellato-squamosa, Nat. Prod. Res. Dev. 20 (2008) 1000–1004. [18] X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, Dammarane triterpenoids from Amoora yunnanensis, Heterocycles 53 (2000) 2795–2802. [19] J.-F. Li, Y.-K. Xu, Constituents from the leaves and twigs of Amoora ouangliensis and their anti-inflammatory activities, Nat. Prod. Res. Dev. 30 (2018) 1361–1366. [20] H. Wang, X. Zhang, S. Yang, X. Luo, A new triterpenoid from Amoora dasyclada, Acta Bot. Sin. 46 (2004) 1256–1260. [21] S.-M. Yang, Y.-B. Ma, X.-D. Luo, S.-H. Wu, D.-G. Wu, Two new tetranortriterpenoids from Amoora dasyclada, Chin. Chem. Lett. 15 (2004) 1187–1190. [22] S.-M. Yang, Q.-S. Song, C. Qing, D.-G. Wu, X.-K. Liu, Anticancer activity of tirucallane triterpenoids from Amoora dasyclada, Z. Naturforsch. C 61 (2006) 193–195. [23] S.-M. Yang, L. Ding, S.-H. Wu, Y.-B. Ma, X.-D. Luo, D.-G. Wu, Two new tirucallane triterpenes with six-membered hemiacetal from Amoora dasyclada, Z. Naturforsch. B. 59 (2004) 1067–1069. [24] T. Rabi, D. Karunagaran, M.K. Nair, V.N. Bhattathiri, Cytotoxic activity of amooranin and its derivatives, Phytother. Res. 16 (2002) S84–S86. [25] V.K. Agnihotri, S.D. Srivastava, S.K. Srivastava, A new limonoid, amoorinin, from the stem bark of Amoora rohituka, Planta Med. 53 (1987) 298–299. [26] A.D. Harmon, U. Weiss, J. Silverton, The structure of rohitukine, the main alkaloid of Amoor arohituka (Syn. Aphanamixis polystachya) (meliaceae), Tetrahedron Lett. 20 (1979) 721–724. [27] M.S. Abdelfattah, K. Toume, F. Ahmed, S.K. Sadhu, M. Ishibashi, Cucullamide, a new putrescine bisamide from Amoora cucullata, Chem. Pharm. Bull. 58 (2010) 1116–1118. [28] S.A. Jain, S.K. Srivastava, 8-C-methyl-quercetin-3-O-β/−D-xylopyranoside, a new flavone glycoside from the roots of Amoora rohituka, J. Nat. Prod. 48 (1985) 299–301. [29] S. Bhatt, V. Saxena, S. Nigam, A new saponin from seeds of Amoora rohituka, Phytochemistry 20 (1981) 1749–1750. [30] L. Pan, J.L. Woodard, D.M. Lucas, J.R. Fuchs, A.D. Kinghorn, Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species, Nat. Prod. Rep. 31 (2014) 924–939. [31] T. Rabi, R. Gupta, Antitumor and cytotoxic investigation of Amoora rohituka, Int. J. Pharmacogn. 33 (1995) 359–361. [32] M.S. Rahman, B. Begum, R. Chowdhury, K.M. Rahman, M.A. Rashid, Preliminary cytotoxicity screening of some medicinal plants of Bangladesh, Dhaka Univ. J. Pharm. Sci. 7 (2008) 47–52. [33] M.S. Rahman, M.A. Rashid, Preliminary antimicrobial and cytotoxic activities of Amoora cucullata extractives, Orient Pharm Exp Med 9 (2009) 182–185. [34] R. Pervin, S. Afrin, F. Sabrin, U. Salma Zohora, M. Shahedur Rahman, K. Didarul Islam, M. Morsaline Billah, Antioxidant, antibacterial and brine shrimp lethality bioassay of Amoora cucullata, a mangrove plant, J. Young Pharm. 8 (2015) 33–38. [35] D. Zhuang, Y. Wang, G. Chen, J. Wang, L. Liu, J. Tang, Q. Shang, W. Zhao, W. Chen, Chemical components, bioactivities of the volatile oil from the leaves of Amoora tsangii (Merr.), Sci. Tec. Food Ind. 34 (2013) 115–117. [36] R. Yadav, V. Kashaw, Evaluation of anti-inflammatory activity of alcoholic, hydroalcoholic and aqueous extract of Amoora Rohituka and Soymida Febrifuga in albino rats, Asian J. Pharm. Pharmacol. 4 (2018) 908–913. [37] R. Chowdhury, C.M. Hasan, M.A. Rashid, Antimicrobial activity of Toona ciliata and Amoora rohituka, Fitoterapia 74 (2003) 155–158. [38] M.S. Rahman, M.Z. Rahman, M.A. Wahab, R. Chowdhury, M.A. Rashid, Antimicrobial activity of some indigenous plants of Bangladesh, Dhaka Univ. J. Pharm. Sci. 7 (2008) 23–26. [39] M.K. Umesh, C.B. Sanjeevkumar, R. Londonkar, Phytochemical and antibacterial evaluation of various extracts of Amoora ruhituka bark, Int. Lett. Nat. Sci. 39 (2015) 68–72. [40] E.A. Aboutabl, F.S. El-Sakhawy, M.M. Fathy, R.M.A. Megid, Composition and antimicrobial activity of the leaf and fruit oils from Amoora rohituka Wigth. et Arn, J. Essent. Oil Res. 12 (2011) 635–638. [41] R. Chowdhury, R. Rashid, Effect of the crude extracts of Amoora rohituka stem bark on gastrointestinal transit in mice, Indian J. Pharm. 35 (2003) 304–307. [42] M. Gole, S. Dasgupta, R. Sur, J. Ghosal, Hepatoprotective effect of Amoora rohituka, Int. J. Pharmacogn. 35 (1997) 318–322. [43] M.K. Umesh, C.B. Sanjeevkumar, R.L. Londonkar, Evaluation of phenolics content and in vitro antioxidant activities of methanolic extract of Amoora rohituka bark, Int. J. Curr. Microbiol. App. Sci. 5 (2016) 225–235.
Ref [8]
Inactive against acetylcholinesterase
[13]
utilization. However, majority of its species' chemical constituents remain unknown, which restrict their utilization and development. Further phytochemical investigations on Amoora species remain to be exploited and studied. Although the crude extracts of Amoora species and their chemical constituents were found to possess extensive pharmacological activities, many chemical constituents have never been pharmacologically tested. Moreover, most studies so far have mainly conducted in vitro bioassays. Comprehensive investigations on the genus Amoora should be fully strengthened to clarify their chemical constituents and pharmacological effects as well as their relationships between the species in the near future. The current review may provide helpful evidence for reasonable utilization of Amoora species as folk medicines and further research in drug discovery. Declaration of Competing Interests There is no conflict of interest. Funding This work were supported by the National Science Foundation of China (NSFC) (No. 21362035 and No. 31160075), the Initial Foundation of Scientific Research for the introduction of talents from Southwest Forestry University for Wen-Hui Xu (No. 20130916). References [1] Editorial Committee of Flora of China, Flora of China, vol. 43, Science Press, Beijing, 1994, pp. 80–87. [2] Yunnan Institute of Botany, Flora of YunNan, 1 Science Press, Beijing, 1977, pp. 231–237. [3] L.L. Chan, S. George, I. Ahmad, S.L. Gosangari, A. Abbasi, B.T. Cunningham, K.L. Watkin, Cytotoxicity effects of Amoora rohituka and chittagonga on breast and pancreatic Cancer cells, Evid. Based Compl. Alt. 2011 (2011) 860605. [4] H.-D. Chen, S.-P. Yang, S.-G. Liao, B. Zhang, Y. Wu, J.-M. Yue, Limonoids and sesquiterpenoids from Amoora tsangii, J. Nat. Prod. 71 (2008) 93–97. [5] Q.G. Tan, X.D. Luo, Meliaceous limonoids: chemistry and biological activities, Chem. Rev. 111 (2011) 7437–7522. [6] G.Y. Zhu, G. Chen, L. Liu, L.P. Bai, Z.H. Jiang, C-17 lactam-bearing limonoids from the twigs and leaves of Amoora tsangii, J. Nat. Prod. 77 (2014) 983–989. [7] Y.-Y. Ma, D.-G. Zhao, Y. Li, J.-J. Chen, J. Zeng, Q.-Q. Zhao, K. Gao, Cytotoxic triterpenes with diverse skeletons from Amoora tsangii, Phytochem. Lett. 15 (2016) 251–255. [8] C. Daulatabad, S.A. Jamkhandi, A keto fatty acid from Amoora rohituka seed oil, Phytochemistry 46 (1997) 155–156. [9] R. Chowdhury, C.M. Hasan, M.A. Rashid, Guaiane sesquiterpenes from Amoora rohituka, Phytochemistry 62 (2003) 1213–1216. [10] T. Rabi, C.V. Catapano, Aphanin, a triterpenoid from Amoora rohituka inhibits K-Ras mutant activity and STAT3 in pancreatic carcinoma cells, Tumour Biol. 37 (2016) 12455–12464. [11] P. Chumkaew, S. Kato, K. Chantrapromma, Potent cytotoxic rocaglamide derivatives from the fruits of Amoora cucullata, Chem. Pharm. Bull. 54 (2006) 1344–1346. [12] F. Ahmed, K. Toume, S.K. Sadhu, T. Ohtsuki, M.A. Arai, M. Ishibashi, Constituents of Amoora cucullata with TRAIL resistance-overcoming activity, Org. Biomol. Chem. 8 (2010) 3696–3703. [13] C.-N. Mi, W.-L. Mei, W.-J. Zuo, C.-H. Cai, H. Wang, S.-P. Li, H.-F. Dai, Chemical
13