- Email: [email protected]
Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels. And their chemotaxonomic significance
Biochemical Systematics and Ecology 85 (2019) 43–45
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels. And their chemotaxonomic significance
T
Liguo Yanga,∗, Yingjie Zhangb, Shuangxi Meib, Zhaoyun Zhub a b
College of Traditional Mongolian Medicine and Pharmacy, Inner Mongolia University for Nationalities, Tongliao, 028000, China Yunnan Institute of Materia Medica, Kunming, 650111, China
ARTICLE INFO
ABSTRACT
Keywords: Aconitum brachypodum Diels. Diterpenoid alkaloids Chemotaxonomy
From the roots of Aconitum brachypodum Diels., twelve diterpenoid alkaloids, such as bullatine H (1), 16, 17dihydroxylepenine (2), N-ethyl-1α-hydroxydictizine (3), bullatine A (4), lepenine (5), 12-epi-napelline (6), songoramine (7), aconine (8), N-deethyldeoxyaconitine (9), aconitine (10), N-deethyl-3-acetylaconitine (11) and N-deethylaconitine (12) were isolated and identified. Structure elucidation of these compounds was performed on the basis of NMR spectroscopic data. Compounds 2, 3, 6, 7, 9 and 12 were obtained from this species for the first time. Chemotaxonomic significance of these compounds is described herein.
1. Subject and source
(2.7 kg) was dissolved in 2% H2SO4 and then filtrated. The acidic solution was alkalized to pH 9–10 with 25% aqueous NH4OH and extracted with CHCl3 to give crude alkaloids (230 g) after the solvent was evaporated under vacuum. The crude alkaloids were subjected to silica gel column chromatography with CHCl3/MeOH (100:1 to 1:1) to obtain seven fractions (X1-X7), which were combined according to TLC analysis. Fraction X1-X6 were further chromatographed on silica gel column using gradient elution with petroleum ether-acetone-diethylamine and then purified through Sephadex LH-20 (CHCl3–MeOH = 1 : 1) to yield compound 1 (12 mg), 2 (21 mg), 3 (17 mg), 4 (210 mg), 5 (23 mg), 6 (19 mg), 7 (11 mg), 8 (26 mg), 9 (13 mg), 10 (56 mg), 11 (31 mg) and 12 (29 mg), respectively. The structures of compounds 1–12 were identified on the basis of spectroscopic data (1H and 13C NMR, MS). Their structures were elucidated as bullatine H (1) (Yang et al., 2016b), 16, 17-dihydroxylepenine (2) (Zhang et al., 2005), N-ethyl-1α-hydroxydictizine (3) (Kolak et al., 2006), bullatine A (4) (Feng et al., 2003), lepenine (5) (Wang et al., 2013), 12-epi-napelline (6) (Chen et al., 1987), songoramine (7) (Fuente et al., 1988), aconine (8) (Pelletier et al., 1979), Ndeethyldeoxyaconitine (9) (Wang et al., 2011), aconitine (10) (Wang et al., 2010), N-deethyl-3-acetylaconitine (11) (Feng et al., 2003) and N-deethylaconitine (12) (Yin et al., 2014) (Fig. 1).
Aconitum L. (Ranunculaceae) contains about 350 species distributed in the temperate regions of the Northern Hemisphere (Li et al., 2012). About 160 species are found in China, most of which are distributed in southwestern China, particularly the Hengduan Mountains region (Hao et al., 2013). The dried roots of Aconitum brachypodum Diels. is one of the most important Chinese traditional herbs, named “Xueshangyizhihao” in Chinese, which has long been used in Yi medicine to treat rheumatism and pains (Luo et al., 2008). The roots of A. brachypodum Diels. (12.0 kg) were collected from Dongchuan, Yunnan Province, China in November 2014, and identified by Professor Bin Qiu of Yunnan Institute of Materia Medica. A voucher specimen (1512-XSYZH-001) has been deposited in the herbarium of Yunnan Institute of Materia Medica. 2. Previous work Previous phytochemical investigations of the roots of A. brachypodum Diels. showed the presence of alkaloids (Shen et al., 2010a, 2010b; Wang et al., 2013, 2014; Yang et al., 2016b), triterpenoids (Wang et al., 2013, 2014) and steroids (Wang et al., 2013, 2014). 3. Present study The roots of Aconitum brachypodum Diels. (12 kg) were powdered and percolated with 90% EtOH at room temperature (72 L × 48 h × 3). The combined extracts were concentrated under vacuum. The residue
∗
4. Chemotaxonomic significance In the present study, five denudatine-type C20-diterpenoid alkaloids (1–5), two napelline-type C20-diterpenoid alkaloids (6 and 7) and five
Corresponding author. E-mail address: [email protected] (L. Yang).
https://doi.org/10.1016/j.bse.2019.05.004 Received 9 April 2019; Received in revised form 6 May 2019; Accepted 11 May 2019 Available online 17 May 2019 0305-1978/ © 2019 Elsevier Ltd. All rights reserved.
Biochemical Systematics and Ecology 85 (2019) 43–45
L. Yang, et al.
Fig. 1. Chemical structures of compounds 1–12 isolated from the roots of Aconitum brachypodum.
Fig. 2. A plausible biogenetic relationships between denudatines, napellines and aconitines. Table 1 Diterpenoid alkaloids isolated from the species of series Brachypoda. Species
Diterpenoid alkaloids
Reference
A. anthoroideum DC.
Anthoroidine A-J, condelphine, talatisamine, hetidine hydrochloride, trifolidasine E, atisinium chloride, tadzhaconinie, hetisine, hetisinone, nominine, aconicarmicharcutinium hydrochloride Aconine, N-deethyldeoxyaconitine, aconitine, N-deethyl-3-acetylaconitine, N-deethylaconitine, secokaraconitine, talatisamine, bullatine B, senbusine C, mesaconitine, hypaconitine, N (4)-butanoneflavaconitine, brachyaconitine A-D, bullatine A and H, 16,17-dihydroxylepenine, N-ethyl-1α-hydroxydictizine, lepenine, 12-epi-napelline, songorine, N (19)-en-denudatine Twenty-nine hetisine-type C20-diterpenoid alkaloids, five atisine-type C20-diterpenoid alkaloids and six aconitine-type C19-diterpenoid alkaloids Aconitine, 3-acetylaconitine, deoxyaconitine, dehydronapelline, 12-acetyllucidusculine, 1-epinapelline, 12epinapelline, 1-demethylhapaconitine, napelline, lucidusculine, flavaconitine, benzoylaconine, neoline, 3deoxyaconine-8-linoleate, songorine, aconine-8-linoleate Hypaconitine, penduline, pseudaconitine Aconitine, neoline, 3-acetylaconitine, 3-deoxyaconitine, 15-hydroxyneoline, 8-acetyl-15-hydroxyneoline, 14benzoyl-8-O-methylaconine, benzoylaconine, N-deethyl-3-acetylaxonitine, N-deethyldeoxyaconitine, secoaconitine Aconitine, benzoylaconine, benzoyldeoxyaconine, deoxyaconitine, polyschistine A-D
Zhang (2014)
A. brachypodum Diels.
A. coreanum (Levl.) Rapaics A. flavum Hand.-Mazz. A. ludlowii Exell A. pendulum Busch A. polyschistum Hand.-Mazz.
aconitine-type C19-diterpenoid alkaloids (8–12) were isolated from the roots of A. brachypodum. A plausible biogenetic relationships between denudatine-type C20-diterpenoid alkaloids, napelline-type C20-diterpenoid alkaloids and aconitine-type C19-diterpenoid alkaloids is proposed in Fig. 2 (Xiao et al., 2006). Among the isolated alkaloids, compound 1 is the first example with 11, 13-dioxygenated denudatine-type C20-diterpenoid alkaloid, which could be utilized to distinguish Aconitum brachypodum from related species. In addition, compounds 2, 3, 6, 7, 9 and 12 were obtained from this species for the first time. A. brachypodum belongs to series Brachypoda, which occupies an intermediate position in subgenus Aconitum. In this study, the
Yang et al. (2016a)
Meng et al. (2013) Chen et al., 1987; Li et al., 1997 Fan et al. (2000) Wang et al., 2010; Wang et al., 2011 Wang and Lao, 1985; Wang and Lao, 1988
coexistence of denudatine-type and napelline-type C20-diterpenoid alkaloids, and aconitine-type C19-diterpenoid alkaloids as major components supported the intermediate position of A. brachypodum. Series Brachypoda contains 10 species, A. anthoroideum DC., A. brachypodum Diels., A. chilienshanicum W. T. Wang, A. coreanum (Levl.) Rapaics, A. flavum Hand.-Mazz., A. glabrisepalum W. T. Wang, A. ludlowii Exell, A. pendulum Busch, A. polyschistum Hand.-Mazz. and A. sessiliflorum (Finet et Gagnep.) Hand.-Mazz. (Li et al., 2001). Up to now, seven species of series Brachypoda, including A. anthoroideum, A. brachypodum, A. coreanum, A. flavum, A. ludlowii, A. pendulum and A. polyschistum, were investigated on their chemical ingredients (Table 1). As shown in 44
Biochemical Systematics and Ecology 85 (2019) 43–45
L. Yang, et al.
Table 1, the presence of aconitine-type C19-diterpenoid alkaloids as major components in A. brachypodum, A. flavum, A. ludlowii, A. pendulum and A. polyschistum, revealed they are closely related species (Hao et al., 2013). However, A. anthoroideum and A. coreanum contain mainly the C20-diterpenoid alkaloids, therefore, it is reasonable to segregate A. anthoroideum and A. coreanum from series Brachypoda, which was also supported by the result of comparative anatomical studies (Li et al., 1991). The data form this study and those from earlier studies imply that diterpenoid alkaloids could serve as chemotaxonomic markers of species in series Brachypoda, but more research is needed to conform this.
Li, H., Yang, J., Tian, Y., 1997. Studies on the alkaloids of the flower, stem, leaf of yellow monkshood (Aconitum flavum). Chin. Tradit. Herb. Drugs 28, 265–266. Li, L., Yuichi, K., 2001. Flora of China. Science Press, Beijing, China. Li, M., Feng, Y., Xiao, P., 1991. Comparative anatomical studies on Chinese medicinal plants of the genus Aconitum. Acta Phytotaxon. Sin. 29, 97–112. Li, Y., Meng, Y., Shen, S., Wang, Y., 2012. Karyological studies of Aconitum brachypodum and related species. Cytologia 77, 491–498. Luo, H., Wang, H., Huang, X., Wang, Y., 2008. Preparation and in vitro evaluation of compound Aconitum brachypodum patches. Chin. J. Pharm. 39, 662–665. Meng, X., Yang, C., Liu, J., Wang, H., 2013. Aconitum coreanum: chemical components and their pharmacological actions. Prog. Pharmaceut. Sci. 37, 390–395. Pelletier, S., Mody, N., Sawhney, R., 1979. 13C nuclear magnetic resonance spectra of some C19-diterpenoid alkaloids and their derivatives. Can. J. Chem. 57, 1652–1655. Shen, Y., Zuo, A., Jiang, Z., Zhang, X., Wang, H., Chen, J., 2010a. Two new diterpenoid alkaloids from Aconitum brachypodum. Bull. Korean Chem. Soc. 31, 3301–3303. Shen, Y., Zuo, A., Jiang, Z., Zhang, X., Wang, H., Chen, J., 2010b. Four new nor-diterpenoid alkaloids from Aconitum brachypodum. Helv. Chim. Acta 93, 863–869. Wang, H., Lao, A., 1985. The structure of polyschistine A, B, C: three new diterpenoid alkaloids from Aconitum polyschistum Hand-Mazz. Heterocycles 23, 803–807. Wang, H., Lao, A., 1988. Studies on the alkaloids from Aconitum polyschistum handmazz. Heterocycles 27, 1615–1621. Wang, H., Zuo, A., Sun, Y., Rao, G., 2013. Chemical constituents of Aconitum brachypodum from Dongchuan area. China J. Chin. Mater. Med. 38, 4324–4328. Wang, H., Zuo, A., Sun, Y., Rao, G., 2014. Chemical constituents from aerial part of Aconitum brachypodum. J. Chin. Med. Mater. 37, 1391–1395. Wang, Y., Zeng, C., Yao, Z., Zhang, J., Zhang, Y., Zhang, F., 2010. Diterpene alkaloids from roots and processed products of Aconitum pendulum. Chin. Tradit. Herb. Drugs 41, 347–351. Wang, Y., Zhang, J., Zeng, C., Yao, Z., Zhang, Y., 2011. Three new C19-diterpenoid alkaloids from Aconitum pendulum. Phytochem. Lett. 4, 166–169. Xiao, P., Wang, F., Gao, F., Yan, L., Chen, D., Liu, Y., 2006. A pharmacophylogenetic study of Aconitum L. (Ranunculaceae) from China. Acta Phytotaxon. Sin. 44, 1–46. Yang, L., Xia, W., Tang, M., Cui, R., 2016a. Research progress on chemical constituents and pharmacological activities of Aconitum brachypodum. J. Yunnan Univ. Tradit. Chin. Med. 39, 95–97. Yang, L., Zhang, Y., Xie, J., Xia, W., Zhang, H., Tang, M., Mei, S., Cui, T., Wang, J., Zhu, Z., 2016b. Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels. J. Asian Nat. Prod. Res. 18, 908–912. Yin, T., Cai, L., Zhou, H., Zhu, X., Chen, Y., Ding, Z., 2014. A new C19-diterpenoid alkaloid from the roots of Aconitum duclouxii. Nat. Prod. Res. 28, 1649–1654. Zhang, F., Peng, S., Liao, X., Yu, K., Ding, L., 2005. Three new diterpene alkaloids from the roots of Aconitum nagarum var. lasiandrum. Planta Med. 71, 1073–1076. Zhang, J., 2014. Biological Activity of Five Specific Traditional Chinese Medicines “Cao Wu” in Xinjiang. Southwest Jiaotong University Doctor Degree Dissertation.
Acknowledgements This work was financially supported by the grants from the Training Program for Science and Technology Talents of Yunnan Province (No. 2014HA001, Program 1512), a grant from Youth Project of Applied Basic Research Program of Yunnan Provincial Science and Technology Department (No. 201501YH00073), and a grant from the Doctoral Scientific Research Foundation of Inner Mongolia University for Nationalities (No. BS464). References Chen, Z., Lao, A., Wang, H., Hong, S., 1987. Studies on the active principles from Aconitum flavum Hand-Mazz. The structures of five new dierpenoid alkaloids. Heterocycles 26, 1455–1460. Fan, Z., Chen, R., Jiang, S., 2000. Chemical composition of Aconitum ludlowii Exell. Tibet Science and Technology 7, 64–65. Feng, F., Liu, W., Chen, Y., Ye, W., Liu, J., Zhao, S., 2003. Chemical studies on Aconitum kirinense nakai. J. China Pharm. Univ. 34, 17–20. Fuente, G., Reina, M., Valencia, E., Rodriguez-Ojeda, A., 1988. The diterpenoid alkaloids from Aconitum napellus. Heterocycles 27, 1109–1113. Hao, D., Gu, X., Xiao, P., Xu, L., Peng, Y., 2013. Recent advances in the chemical and biological studies of Aconitum pharmaceutical resources. J. Chin. Pharm. Sci. 22, 209–221. Kolak, U., Öztürk, M., Özgökçe, F., Ulubelen, A., 2006. Norditerpene alkaloids from Delphinium linearilobum and antioxidant activity. Phytochemistry 67, 2170–2175.
45
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels. And their chemotaxonomic significance
T
Liguo Yanga,∗, Yingjie Zhangb, Shuangxi Meib, Zhaoyun Zhub a b
College of Traditional Mongolian Medicine and Pharmacy, Inner Mongolia University for Nationalities, Tongliao, 028000, China Yunnan Institute of Materia Medica, Kunming, 650111, China
ARTICLE INFO
ABSTRACT
Keywords: Aconitum brachypodum Diels. Diterpenoid alkaloids Chemotaxonomy
From the roots of Aconitum brachypodum Diels., twelve diterpenoid alkaloids, such as bullatine H (1), 16, 17dihydroxylepenine (2), N-ethyl-1α-hydroxydictizine (3), bullatine A (4), lepenine (5), 12-epi-napelline (6), songoramine (7), aconine (8), N-deethyldeoxyaconitine (9), aconitine (10), N-deethyl-3-acetylaconitine (11) and N-deethylaconitine (12) were isolated and identified. Structure elucidation of these compounds was performed on the basis of NMR spectroscopic data. Compounds 2, 3, 6, 7, 9 and 12 were obtained from this species for the first time. Chemotaxonomic significance of these compounds is described herein.
1. Subject and source
(2.7 kg) was dissolved in 2% H2SO4 and then filtrated. The acidic solution was alkalized to pH 9–10 with 25% aqueous NH4OH and extracted with CHCl3 to give crude alkaloids (230 g) after the solvent was evaporated under vacuum. The crude alkaloids were subjected to silica gel column chromatography with CHCl3/MeOH (100:1 to 1:1) to obtain seven fractions (X1-X7), which were combined according to TLC analysis. Fraction X1-X6 were further chromatographed on silica gel column using gradient elution with petroleum ether-acetone-diethylamine and then purified through Sephadex LH-20 (CHCl3–MeOH = 1 : 1) to yield compound 1 (12 mg), 2 (21 mg), 3 (17 mg), 4 (210 mg), 5 (23 mg), 6 (19 mg), 7 (11 mg), 8 (26 mg), 9 (13 mg), 10 (56 mg), 11 (31 mg) and 12 (29 mg), respectively. The structures of compounds 1–12 were identified on the basis of spectroscopic data (1H and 13C NMR, MS). Their structures were elucidated as bullatine H (1) (Yang et al., 2016b), 16, 17-dihydroxylepenine (2) (Zhang et al., 2005), N-ethyl-1α-hydroxydictizine (3) (Kolak et al., 2006), bullatine A (4) (Feng et al., 2003), lepenine (5) (Wang et al., 2013), 12-epi-napelline (6) (Chen et al., 1987), songoramine (7) (Fuente et al., 1988), aconine (8) (Pelletier et al., 1979), Ndeethyldeoxyaconitine (9) (Wang et al., 2011), aconitine (10) (Wang et al., 2010), N-deethyl-3-acetylaconitine (11) (Feng et al., 2003) and N-deethylaconitine (12) (Yin et al., 2014) (Fig. 1).
Aconitum L. (Ranunculaceae) contains about 350 species distributed in the temperate regions of the Northern Hemisphere (Li et al., 2012). About 160 species are found in China, most of which are distributed in southwestern China, particularly the Hengduan Mountains region (Hao et al., 2013). The dried roots of Aconitum brachypodum Diels. is one of the most important Chinese traditional herbs, named “Xueshangyizhihao” in Chinese, which has long been used in Yi medicine to treat rheumatism and pains (Luo et al., 2008). The roots of A. brachypodum Diels. (12.0 kg) were collected from Dongchuan, Yunnan Province, China in November 2014, and identified by Professor Bin Qiu of Yunnan Institute of Materia Medica. A voucher specimen (1512-XSYZH-001) has been deposited in the herbarium of Yunnan Institute of Materia Medica. 2. Previous work Previous phytochemical investigations of the roots of A. brachypodum Diels. showed the presence of alkaloids (Shen et al., 2010a, 2010b; Wang et al., 2013, 2014; Yang et al., 2016b), triterpenoids (Wang et al., 2013, 2014) and steroids (Wang et al., 2013, 2014). 3. Present study The roots of Aconitum brachypodum Diels. (12 kg) were powdered and percolated with 90% EtOH at room temperature (72 L × 48 h × 3). The combined extracts were concentrated under vacuum. The residue
∗
4. Chemotaxonomic significance In the present study, five denudatine-type C20-diterpenoid alkaloids (1–5), two napelline-type C20-diterpenoid alkaloids (6 and 7) and five
Corresponding author. E-mail address: [email protected] (L. Yang).
https://doi.org/10.1016/j.bse.2019.05.004 Received 9 April 2019; Received in revised form 6 May 2019; Accepted 11 May 2019 Available online 17 May 2019 0305-1978/ © 2019 Elsevier Ltd. All rights reserved.
Biochemical Systematics and Ecology 85 (2019) 43–45
L. Yang, et al.
Fig. 1. Chemical structures of compounds 1–12 isolated from the roots of Aconitum brachypodum.
Fig. 2. A plausible biogenetic relationships between denudatines, napellines and aconitines. Table 1 Diterpenoid alkaloids isolated from the species of series Brachypoda. Species
Diterpenoid alkaloids
Reference
A. anthoroideum DC.
Anthoroidine A-J, condelphine, talatisamine, hetidine hydrochloride, trifolidasine E, atisinium chloride, tadzhaconinie, hetisine, hetisinone, nominine, aconicarmicharcutinium hydrochloride Aconine, N-deethyldeoxyaconitine, aconitine, N-deethyl-3-acetylaconitine, N-deethylaconitine, secokaraconitine, talatisamine, bullatine B, senbusine C, mesaconitine, hypaconitine, N (4)-butanoneflavaconitine, brachyaconitine A-D, bullatine A and H, 16,17-dihydroxylepenine, N-ethyl-1α-hydroxydictizine, lepenine, 12-epi-napelline, songorine, N (19)-en-denudatine Twenty-nine hetisine-type C20-diterpenoid alkaloids, five atisine-type C20-diterpenoid alkaloids and six aconitine-type C19-diterpenoid alkaloids Aconitine, 3-acetylaconitine, deoxyaconitine, dehydronapelline, 12-acetyllucidusculine, 1-epinapelline, 12epinapelline, 1-demethylhapaconitine, napelline, lucidusculine, flavaconitine, benzoylaconine, neoline, 3deoxyaconine-8-linoleate, songorine, aconine-8-linoleate Hypaconitine, penduline, pseudaconitine Aconitine, neoline, 3-acetylaconitine, 3-deoxyaconitine, 15-hydroxyneoline, 8-acetyl-15-hydroxyneoline, 14benzoyl-8-O-methylaconine, benzoylaconine, N-deethyl-3-acetylaxonitine, N-deethyldeoxyaconitine, secoaconitine Aconitine, benzoylaconine, benzoyldeoxyaconine, deoxyaconitine, polyschistine A-D
Zhang (2014)
A. brachypodum Diels.
A. coreanum (Levl.) Rapaics A. flavum Hand.-Mazz. A. ludlowii Exell A. pendulum Busch A. polyschistum Hand.-Mazz.
aconitine-type C19-diterpenoid alkaloids (8–12) were isolated from the roots of A. brachypodum. A plausible biogenetic relationships between denudatine-type C20-diterpenoid alkaloids, napelline-type C20-diterpenoid alkaloids and aconitine-type C19-diterpenoid alkaloids is proposed in Fig. 2 (Xiao et al., 2006). Among the isolated alkaloids, compound 1 is the first example with 11, 13-dioxygenated denudatine-type C20-diterpenoid alkaloid, which could be utilized to distinguish Aconitum brachypodum from related species. In addition, compounds 2, 3, 6, 7, 9 and 12 were obtained from this species for the first time. A. brachypodum belongs to series Brachypoda, which occupies an intermediate position in subgenus Aconitum. In this study, the
Yang et al. (2016a)
Meng et al. (2013) Chen et al., 1987; Li et al., 1997 Fan et al. (2000) Wang et al., 2010; Wang et al., 2011 Wang and Lao, 1985; Wang and Lao, 1988
coexistence of denudatine-type and napelline-type C20-diterpenoid alkaloids, and aconitine-type C19-diterpenoid alkaloids as major components supported the intermediate position of A. brachypodum. Series Brachypoda contains 10 species, A. anthoroideum DC., A. brachypodum Diels., A. chilienshanicum W. T. Wang, A. coreanum (Levl.) Rapaics, A. flavum Hand.-Mazz., A. glabrisepalum W. T. Wang, A. ludlowii Exell, A. pendulum Busch, A. polyschistum Hand.-Mazz. and A. sessiliflorum (Finet et Gagnep.) Hand.-Mazz. (Li et al., 2001). Up to now, seven species of series Brachypoda, including A. anthoroideum, A. brachypodum, A. coreanum, A. flavum, A. ludlowii, A. pendulum and A. polyschistum, were investigated on their chemical ingredients (Table 1). As shown in 44
Biochemical Systematics and Ecology 85 (2019) 43–45
L. Yang, et al.
Table 1, the presence of aconitine-type C19-diterpenoid alkaloids as major components in A. brachypodum, A. flavum, A. ludlowii, A. pendulum and A. polyschistum, revealed they are closely related species (Hao et al., 2013). However, A. anthoroideum and A. coreanum contain mainly the C20-diterpenoid alkaloids, therefore, it is reasonable to segregate A. anthoroideum and A. coreanum from series Brachypoda, which was also supported by the result of comparative anatomical studies (Li et al., 1991). The data form this study and those from earlier studies imply that diterpenoid alkaloids could serve as chemotaxonomic markers of species in series Brachypoda, but more research is needed to conform this.
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