- Email: [email protected]
Chemical constituents from Euphorbia stracheyi Boiss
Biochemical Systematics and Ecology 84 (2019) 52–54
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Chemical constituents from Euphorbia stracheyi Boiss a,b
a
c
a
d
a
Tie Liu , Qian Liang , Xin-Min Zhang , Xiao-Min Su , Jian-Chun Qin , Gen-Qian Li , Wen-Hui Xua,∗
T
a
Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Ministry of Education, Southwest Forestry University, Kunming, 650224, PR China The First People's Hospital of Zunyi, Zunyi, 563002, PR China c Key Laboratory of Forest Disaster Warning and Control of Yunnan Province, Southwest Forestry University, Kunming, 650224, PR China d College of Plant Science, Jilin University, Changchun, 130062, PR China b
ARTICLE INFO
ABSTRACT
Keywords: Euphorbia stracheyi boiss. Diterpenes Coumarins Chemotaxonomy
The chemical investigation of whole plants Euphorbia stracheyi Boiss. led to the isolation of 14 compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14). Their structures were elucidated by extensive spectroscopic analyses and by comparison with the literature. Compounds 1–6, and 8–12 were firstly isolated from E. stracheyi, while compounds 6, and 9 were isolated from Euphorbia genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.
1. Subject and source The genus Euphorbia belongs to Euphorbiaceae family and contains more than 2000 species, which are widely distributed throughout tropical and temperate regions of the world (Shi et al., 2008a,; Vasas and Hohmann, 2014). There are approximately 70 species grown in China (Liang et al., 2014). Euphorbia stracheyi Boiss is a perennial herb mainly located in alpine meadow. Its roots have been used as a traditional Chinese medicine to treat haemostasis, analgesia and muscular regeneration (Liu et al., 2017). In the present study, the whole parts of E. stracheyi were collected in Shangri-la, Yunnan Province, China, in June 2013, and identified by Prof. Fan Du (School of Forestry, Southwest Forestry University, Kunming 650224, China). A voucher specimen (No.130604) was deposited in the Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Southwest Forestry University, Kunming City, Yunnan Province, China. 2. Previous work Extensive chemical studies on Euphorbia genus have resulted in the isolation of a large number of structurally diverse compounds, including diterpenoids, sesquiterpenes, triterpenoid, steroids and flavonoids. Diterpenoids are considered as the major characteristic secondary metabolites and taxonomic markers of Euphorbia genus (Shi et al., 2008a,; Vasas and Hohmann, 2014; Li et al., 2015). Previous phytochemical studies on E. stracheyi led to the isolation of
∗
diterpenoids, sesquiterpenes, flavonoids, ionones, steroids, aliphatic alcohol, glycosides and phenolic compounds (Yang et al., 2014b; Liu et al., 2017; Zhang et al., 2012b; Ma et al., 2012). 3. Present study Powdered, air-dried whole parts of E. stracheyi (6.3 kg) were exhaustively extracted with 95% EtOH (40 L × 3) at room temperature for 72 h. The extraction was evaporated to dryness in vacuo. The residue (1100 g) was suspended in H2O and then partitioned with petroleum ether and EtOAc respectively. The EtOAc layer was evaporated to dryness and the resultant residue (117.0 g) was subjected to silica gel liquid column chromatography using stepwise gradient elution CHCl3MeOH (200:1 → 3:1, v/v) to afford 13 pooled fractions A-M according to TLC. Fraction A (6.1 g) was purified on silica gel column eluted with CHCl3-acetone (40:1 → 2:1, v/v) and C18 reversed-phase column with MeOH-H2O (5:5 → 19:1, v/v) to afford 1 (14.2 mg), 2 (7.0 mg), 3 (39.6 mg), 4 (16.5 mg), 5 (77.5 mg) and 12 (49.0 mg). Fraction B (12.4 g) was decolorized on MCI gel eluted with MeOH-H2O (9:1, v/v), then purified on silica gel column eluted with CHCl3-acetone (40:1 → 2:1, v/v) and C18 reversed-phase column with MeOH-H2O (6:4 → 9:1, v/v) to give 9 (5.0 mg), and 10 (63.0 mg). Fraction C (3.7 g) was further purified on a C18 reversed-phase column eluted with MeOH-H2O (5:5 → 19:1, v/v) to yield 11 (10 mg) and 4 subfractions (C1-C4). Fraction C2 was subjected to C18 Semi-HPLC column (Agilent ZORBAX SB-C18 column, 250 × 9.4 mm, 5 μm) (52% MeOH-H2O, at a flow rate
Corresponding author. E-mail address: [email protected] (W.-H. Xu).
https://doi.org/10.1016/j.bse.2019.04.006 Received 21 February 2019; Received in revised form 25 March 2019; Accepted 6 April 2019 0305-1978/ © 2019 Elsevier Ltd. All rights reserved.
Biochemical Systematics and Ecology 84 (2019) 52–54
T. Liu, et al.
Fig. 1. Structures of compounds 1–14.
of 4 mL/min) to afford 8 (16.5 mg). Fraction C3 was chromatographed on a semipreparative C18 reversed phase HPLC column (Agilent ZORBAX SB-C18 column, 250 × 9.4 mm, 5 μm), using 59% MeOH-H2O, at a flow rate of 4 mL/min, to obtain 7 (12.1 mg). Compounds 13 (64.0 mg) and 14 (21.0 mg) were obtained by C18 column eluted with MeOH-H2O (4:6 → 9:1, v/v) from fraction D (4.4 g). The petroleum ether extract (248.0 g) was performed on silica gel column eluted with petroleum ether-acetone (100:1 → 1:1, v/v) to yield 8 pooled fractions 1–8. Fraction 2 (33.7 g) was decolorized on MCI gel eluted with MeOHH2O (9:1, v/v), then purified on silica gel column eluted with CHCl3MeOH (100:1 → 2:1, v/v) and C18 reversed-phase column with MeOHH2O (6:4 → 9:1, v/v) to obtain 6 (15.0 mg). The structures of the isolated compounds were elucidated on the basis of spectroscopic data and by comparison of these data with literature (Fig. 1). Their structures were identified as jolkinol A (1) (Valente et al., 2004; Uemura et al., 1976), jolkinol A’ (2) (Valente et al., 2004; Adolf et al., 1984), ent-(16R)-16,17-dihydroxykauran-3one (3) (Zhang et al., 2012a), ent-16α,17-dihydroxyatisan-3-one (4) (Wang et al., 2004), ent-3β,16-dihydroxyiso-pimar-7-ene-2,15-dione (5) (Yang et al., 2014a), 3β,15-dihydroxy-labd-8(17)-ene (6) (David et al., 1998), phorbol-13-actate (7) (Zhang et al., 2012c), ingenol (8) (Giovanni et al., 1999), boscialin (9) (Pauli et al., 1990), scopoletin (10) (Wu et al., 2012), esculetin (11) (Shi et al., 2008b), 6,7-dimethoxycoumarin (12) (Wu et al., 2001), methyl gallate (13) (An et al., 2007), and ethyl gallate (14) (Mehla et al., 2011).
1984; Giovanni et al., 1999, 1–2, 8), E. yinshanica S.Q.Zhou & G.H.Liu (Zhang et al., 2012a, 3), E. wallichii Hook.f. (Wang et al., 2004, 4), E. tibetica Boiss. (Yang et al., 2014a, 5), and E. tangutica Prokh. (Zhang et al., 2012c, 7). These results show that E. stracheyi shares similar diterpene compounds with these seven species of Euphorbia. However, the profile of specific diterpenes differ among these species and the presence of compound 6 in E. stracheyi differentiates it from the other species. This suggests that it could be potential chemotaxonomic marker to differentiate E. stracheyi from other species of Euphorbia. Monoterpenes are very rarely reported from species of Euphorbia. In the present study, the monoterpene boscialin (9), is reported for the first time from the genus Euphorbia. This finding provides new information on the chemistry for E. stracheyi. The occurrence of boscialin (9) suggests that it may be used to distinguish E. stracheyi from other species of Euphorbia. Coumarins and phenols are all minor constituents in the genus Euphorbia (Shi et al., 2008a). Coumarins (10–12) were previously isolated from E. schimperi C. Presl (Abdel-Monem et al., 2008, 10), E. hirta Linn. (Wu et al., 2012, 10, 12), E. supina Rafin (An et al., 2007, 10), E. petiolata Banks & Soland (Nazemiyeh et al., 2010, 11), and E. lathyris L. (Masamoto et al., 2003, 11), while phenols (13–14) were previously obtained from E. supina Rafin (An et al., 2007, 13), E. tibetica Boiss. (Yang et al., 2014a, 13, 14). The present results show chemotaxonomic relationships between E. stracheyi and these six species of Euphorbia, which are further supported by the isolation of the diterpenes (1–2, 8) from E. lathyris L. (Adolf et al., 1984; Giovanni et al., 1999) and the diterpene (5) from E. tibetica Boiss (Yang et al., 2014a). In conclusion, the results of this study increase our knowledge about the chemical diversity of E. stracheyi. The chemical constituents of E. stracheyi reported in this study are generally consistent with the previous reports on the genus Euphorbia. Labdane diterpene (6) and monoterpene (9) have not been previously reported from the genus Euphorbia. Therefore, compounds 6 and 9 could serve as chemotaxonomic markers to differentiate E. stracheyi from other species of Euphorbia. Further phytochemical investigations on the genus Euphorbia should be undertaken to strengthen our knowledge about the role these groups of compounds have in differentiating among the species of Euphorbia.
4. Chemotaxonomic significance Present study reports on the isolation of fourteen compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14) from the whole plants E. stracheyi (Fig. 1). To the best of our knowledge, this is the first report of compounds 1–6, and 8–12 from E. stracheyi, this is also the first report of compounds 6, and 9 from a species of Euphorbia. Chemical investigations of the Euphorbia genus have shown that diterpenoids with lathyrane, ent-atisane, ent-kaurane, ent-isopimarane, tigliane, ingenane skeletons are the common characteristic secondary metabolites in the genus (Shi et al., 2008a,; Vasas and Hohmann, 2014). In present study, eight diterpenes (1-8), including two lathyranes (1–2), one ent-kaurane (3), one ent-atisane (4), one ent-isopimarane (5), one labdane (6) one tigliane (7), and one ingenane (8) were isolated from E. stracheyi. All of them, except for 6, have been discovered from other species of Euphorbia, such as E. jolkinii Boiss. (Uemura et al., 1976, 1), E. pubescens Vahl (Valente et al., 2004, 1–2), E. lathyris L. (Adolf et al.,
Acknowledgments This work was financially supported by the National Natural Science Foundation of China (21362035 and 31160075), and Joint Scientific and Technological Research Project (Study on Antibacterial Active 53
Biochemical Systematics and Ecology 84 (2019) 52–54
T. Liu, et al.
Components from Streptomyces sp. FHS 2–3: 2017) by Zunyi Science and Technology Bureau and The First People's Hospital of Zunyi.
Biotech. Bioch. 67, 631–634. Mehla, K., Balwani, S., Kulshreshtha, A., Nandiet, D., Jaisankar, P., Ghosh, B., 2011. J. Ethnopharmacol. 137, 1345–1352. Nazemiyeh, H., Kazemi, E.M., Zare, K., Jodari, M., Nahar, L., Sarker, S.D., 2010. J. Nat. Med. 64, 187–190. Pauli, N., Séquin, U., Walter, A., 1990. Helv. Chim. Acta 73, 578–582. Shi, Q.W., Su, X.H., Kiyota, H., 2008a. Chem. Rev. 108, 4295–4327. Shi, S.Y., Zhou, C.X., Xu, Y., Tao, Q.F., Bai, H., Lu, F.S., Lin, W.Y., Chen, H.Y., Zheng, W., Wang, L.W., Wu, Y.H., Zeng, S., Huang, K.X., Zhao, Y., Li, X.K., Qu, J., 2008b. China J. Chin. Mater. Med. 33, 1147–1157. Uemura, D., Nobuhara, K., Nakayama, Y., Shizuri, Y., Hirata, Y., 1976. Tetrahedron Lett. 17, 4593–4596. Valente, C., Pedro, M., Ascenso, J.R., Abreu, P.M., Nascimento, M.S.J., Ferreira, M.J.U., 2004. Planta Med. 70, 244–249. Vasas, A., Hohmann, J., 2014. Chem. Rev. 114, 8579–8612. Wang, H., Zhang, X.F., Ma, Y.B., Cai, X.H., Wu, D.G., Luo, X.D., 2004. Chin. Tradit. Herb. Drugs 35, 611–614. Wu, S.H., Luo, X.D., Ma, Y.B., Hao, X.J., Zhou, J., Wu, D.G., 2001. J. Asian Nat. Prod. Res. 3, 95–102. Wu, Y., Qu, W., Geng, D., Liang, J.Y., Luo, Y.L., 2012. Chin. J. Nat. Med. 10, 40–42. Yang, D.S., He, Q.X., Yang, Y.P., Liu, K.C., Li, X.L., 2014a. Chin. J. Nat. Med. 12, 38–42. Yang, D.S., Peng, W.B., Li, Z.L., Wang, X., Wei, J.G., He, Q.X., Yang, Y.P., Liu, K.C., Li, X.L., 2014b. Fitoterapia 97, 211–218. Zhang, B.Y., Wang, H., Luo, X.D., Du, Z.Z., Shen, J.W., Wu, H.F., Zhang, X.F., 2012a. Helv. Chim. Acta 95, 1672–1679. Zhang, B.Y., Wang, H., Luo, X.D., Du, Z.Z., Shen, J.W., Zeng, L.F., Zhang, X.F., 2012b. Chin. Tradit. Herb. Drugs 43, 1496–1498. Zhang, B.Y., Wang, H., Luo, X.D., Du, Z.Z., Wu, H.F., Shen, J.W., Zhang, X.F., 2012c. Nat. Prod. Res. 26, 2309–2315.
Appendix A. Supplementary data Supplementary data to this article can be found online at https:// doi.org/10.1016/j.bse.2019.04.006. References Abdel-Monem, A.R., Abdelsattar, E., Harraz, F.M., Petereit, F., 2008. Record Nat. Prod. 2, 39–45. Adolf, W., Hecker, E., Becker, H., 1984. Planta Med. 50, 259–261. An, R.B., Kwon, J.W., Kwon, T.O., Chung, W.T., Lee, H.S., Kim, Y.C., 2007. Korean J. Pharmacogn. 38, 291–295. David, J.P., David, J.M., Yang, S.W., Cordell, G.A., 1998. Phytochemistry 50, 443–447. Giovanni, A., Gian, C.T., Giancarlo, C., Giovanni, P., Jasmin, J., 1999. J. Nat. Prod. 62, 76–79. Li, E.T., Liu, K.H., Zang, M.H., Zhang, X.L., Jiang, H.Q., Zhou, H.L., Wang, D.Y., Liu, J.G., Hu, Y.L., Wu, Y., 2015. Biochem. Syst. Ecol. 62, 204–207. Liang, X., Liu, Z.G., Cao, Y.F., Meng, D.L., Hua, H.M., 2014. Biochem. Syst. Ecol. 57, 345–349. Liu, T., Liang, Q., Xiong, N.N., Dai, L.F., Wang, J.M., Ji, X.H., Xu, W.H., 2017. Nat. Prod. Res. 31, 233–238. Ma, Z.K., Dai, Y., Zhang, B.B., Liao, Z.X., 2012. Northwest Pharm. J. 27, 1–4. Masamoto, Y., Ando, H., Murata, Y., Shimoishi, Y., Tada, M., Takahata, K., 2003. Biosci.
54
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Chemical constituents from Euphorbia stracheyi Boiss a,b
a
c
a
d
a
Tie Liu , Qian Liang , Xin-Min Zhang , Xiao-Min Su , Jian-Chun Qin , Gen-Qian Li , Wen-Hui Xua,∗
T
a
Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Ministry of Education, Southwest Forestry University, Kunming, 650224, PR China The First People's Hospital of Zunyi, Zunyi, 563002, PR China c Key Laboratory of Forest Disaster Warning and Control of Yunnan Province, Southwest Forestry University, Kunming, 650224, PR China d College of Plant Science, Jilin University, Changchun, 130062, PR China b
ARTICLE INFO
ABSTRACT
Keywords: Euphorbia stracheyi boiss. Diterpenes Coumarins Chemotaxonomy
The chemical investigation of whole plants Euphorbia stracheyi Boiss. led to the isolation of 14 compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14). Their structures were elucidated by extensive spectroscopic analyses and by comparison with the literature. Compounds 1–6, and 8–12 were firstly isolated from E. stracheyi, while compounds 6, and 9 were isolated from Euphorbia genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.
1. Subject and source The genus Euphorbia belongs to Euphorbiaceae family and contains more than 2000 species, which are widely distributed throughout tropical and temperate regions of the world (Shi et al., 2008a,; Vasas and Hohmann, 2014). There are approximately 70 species grown in China (Liang et al., 2014). Euphorbia stracheyi Boiss is a perennial herb mainly located in alpine meadow. Its roots have been used as a traditional Chinese medicine to treat haemostasis, analgesia and muscular regeneration (Liu et al., 2017). In the present study, the whole parts of E. stracheyi were collected in Shangri-la, Yunnan Province, China, in June 2013, and identified by Prof. Fan Du (School of Forestry, Southwest Forestry University, Kunming 650224, China). A voucher specimen (No.130604) was deposited in the Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Southwest Forestry University, Kunming City, Yunnan Province, China. 2. Previous work Extensive chemical studies on Euphorbia genus have resulted in the isolation of a large number of structurally diverse compounds, including diterpenoids, sesquiterpenes, triterpenoid, steroids and flavonoids. Diterpenoids are considered as the major characteristic secondary metabolites and taxonomic markers of Euphorbia genus (Shi et al., 2008a,; Vasas and Hohmann, 2014; Li et al., 2015). Previous phytochemical studies on E. stracheyi led to the isolation of
∗
diterpenoids, sesquiterpenes, flavonoids, ionones, steroids, aliphatic alcohol, glycosides and phenolic compounds (Yang et al., 2014b; Liu et al., 2017; Zhang et al., 2012b; Ma et al., 2012). 3. Present study Powdered, air-dried whole parts of E. stracheyi (6.3 kg) were exhaustively extracted with 95% EtOH (40 L × 3) at room temperature for 72 h. The extraction was evaporated to dryness in vacuo. The residue (1100 g) was suspended in H2O and then partitioned with petroleum ether and EtOAc respectively. The EtOAc layer was evaporated to dryness and the resultant residue (117.0 g) was subjected to silica gel liquid column chromatography using stepwise gradient elution CHCl3MeOH (200:1 → 3:1, v/v) to afford 13 pooled fractions A-M according to TLC. Fraction A (6.1 g) was purified on silica gel column eluted with CHCl3-acetone (40:1 → 2:1, v/v) and C18 reversed-phase column with MeOH-H2O (5:5 → 19:1, v/v) to afford 1 (14.2 mg), 2 (7.0 mg), 3 (39.6 mg), 4 (16.5 mg), 5 (77.5 mg) and 12 (49.0 mg). Fraction B (12.4 g) was decolorized on MCI gel eluted with MeOH-H2O (9:1, v/v), then purified on silica gel column eluted with CHCl3-acetone (40:1 → 2:1, v/v) and C18 reversed-phase column with MeOH-H2O (6:4 → 9:1, v/v) to give 9 (5.0 mg), and 10 (63.0 mg). Fraction C (3.7 g) was further purified on a C18 reversed-phase column eluted with MeOH-H2O (5:5 → 19:1, v/v) to yield 11 (10 mg) and 4 subfractions (C1-C4). Fraction C2 was subjected to C18 Semi-HPLC column (Agilent ZORBAX SB-C18 column, 250 × 9.4 mm, 5 μm) (52% MeOH-H2O, at a flow rate
Corresponding author. E-mail address: [email protected] (W.-H. Xu).
https://doi.org/10.1016/j.bse.2019.04.006 Received 21 February 2019; Received in revised form 25 March 2019; Accepted 6 April 2019 0305-1978/ © 2019 Elsevier Ltd. All rights reserved.
Biochemical Systematics and Ecology 84 (2019) 52–54
T. Liu, et al.
Fig. 1. Structures of compounds 1–14.
of 4 mL/min) to afford 8 (16.5 mg). Fraction C3 was chromatographed on a semipreparative C18 reversed phase HPLC column (Agilent ZORBAX SB-C18 column, 250 × 9.4 mm, 5 μm), using 59% MeOH-H2O, at a flow rate of 4 mL/min, to obtain 7 (12.1 mg). Compounds 13 (64.0 mg) and 14 (21.0 mg) were obtained by C18 column eluted with MeOH-H2O (4:6 → 9:1, v/v) from fraction D (4.4 g). The petroleum ether extract (248.0 g) was performed on silica gel column eluted with petroleum ether-acetone (100:1 → 1:1, v/v) to yield 8 pooled fractions 1–8. Fraction 2 (33.7 g) was decolorized on MCI gel eluted with MeOHH2O (9:1, v/v), then purified on silica gel column eluted with CHCl3MeOH (100:1 → 2:1, v/v) and C18 reversed-phase column with MeOHH2O (6:4 → 9:1, v/v) to obtain 6 (15.0 mg). The structures of the isolated compounds were elucidated on the basis of spectroscopic data and by comparison of these data with literature (Fig. 1). Their structures were identified as jolkinol A (1) (Valente et al., 2004; Uemura et al., 1976), jolkinol A’ (2) (Valente et al., 2004; Adolf et al., 1984), ent-(16R)-16,17-dihydroxykauran-3one (3) (Zhang et al., 2012a), ent-16α,17-dihydroxyatisan-3-one (4) (Wang et al., 2004), ent-3β,16-dihydroxyiso-pimar-7-ene-2,15-dione (5) (Yang et al., 2014a), 3β,15-dihydroxy-labd-8(17)-ene (6) (David et al., 1998), phorbol-13-actate (7) (Zhang et al., 2012c), ingenol (8) (Giovanni et al., 1999), boscialin (9) (Pauli et al., 1990), scopoletin (10) (Wu et al., 2012), esculetin (11) (Shi et al., 2008b), 6,7-dimethoxycoumarin (12) (Wu et al., 2001), methyl gallate (13) (An et al., 2007), and ethyl gallate (14) (Mehla et al., 2011).
1984; Giovanni et al., 1999, 1–2, 8), E. yinshanica S.Q.Zhou & G.H.Liu (Zhang et al., 2012a, 3), E. wallichii Hook.f. (Wang et al., 2004, 4), E. tibetica Boiss. (Yang et al., 2014a, 5), and E. tangutica Prokh. (Zhang et al., 2012c, 7). These results show that E. stracheyi shares similar diterpene compounds with these seven species of Euphorbia. However, the profile of specific diterpenes differ among these species and the presence of compound 6 in E. stracheyi differentiates it from the other species. This suggests that it could be potential chemotaxonomic marker to differentiate E. stracheyi from other species of Euphorbia. Monoterpenes are very rarely reported from species of Euphorbia. In the present study, the monoterpene boscialin (9), is reported for the first time from the genus Euphorbia. This finding provides new information on the chemistry for E. stracheyi. The occurrence of boscialin (9) suggests that it may be used to distinguish E. stracheyi from other species of Euphorbia. Coumarins and phenols are all minor constituents in the genus Euphorbia (Shi et al., 2008a). Coumarins (10–12) were previously isolated from E. schimperi C. Presl (Abdel-Monem et al., 2008, 10), E. hirta Linn. (Wu et al., 2012, 10, 12), E. supina Rafin (An et al., 2007, 10), E. petiolata Banks & Soland (Nazemiyeh et al., 2010, 11), and E. lathyris L. (Masamoto et al., 2003, 11), while phenols (13–14) were previously obtained from E. supina Rafin (An et al., 2007, 13), E. tibetica Boiss. (Yang et al., 2014a, 13, 14). The present results show chemotaxonomic relationships between E. stracheyi and these six species of Euphorbia, which are further supported by the isolation of the diterpenes (1–2, 8) from E. lathyris L. (Adolf et al., 1984; Giovanni et al., 1999) and the diterpene (5) from E. tibetica Boiss (Yang et al., 2014a). In conclusion, the results of this study increase our knowledge about the chemical diversity of E. stracheyi. The chemical constituents of E. stracheyi reported in this study are generally consistent with the previous reports on the genus Euphorbia. Labdane diterpene (6) and monoterpene (9) have not been previously reported from the genus Euphorbia. Therefore, compounds 6 and 9 could serve as chemotaxonomic markers to differentiate E. stracheyi from other species of Euphorbia. Further phytochemical investigations on the genus Euphorbia should be undertaken to strengthen our knowledge about the role these groups of compounds have in differentiating among the species of Euphorbia.
4. Chemotaxonomic significance Present study reports on the isolation of fourteen compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14) from the whole plants E. stracheyi (Fig. 1). To the best of our knowledge, this is the first report of compounds 1–6, and 8–12 from E. stracheyi, this is also the first report of compounds 6, and 9 from a species of Euphorbia. Chemical investigations of the Euphorbia genus have shown that diterpenoids with lathyrane, ent-atisane, ent-kaurane, ent-isopimarane, tigliane, ingenane skeletons are the common characteristic secondary metabolites in the genus (Shi et al., 2008a,; Vasas and Hohmann, 2014). In present study, eight diterpenes (1-8), including two lathyranes (1–2), one ent-kaurane (3), one ent-atisane (4), one ent-isopimarane (5), one labdane (6) one tigliane (7), and one ingenane (8) were isolated from E. stracheyi. All of them, except for 6, have been discovered from other species of Euphorbia, such as E. jolkinii Boiss. (Uemura et al., 1976, 1), E. pubescens Vahl (Valente et al., 2004, 1–2), E. lathyris L. (Adolf et al.,
Acknowledgments This work was financially supported by the National Natural Science Foundation of China (21362035 and 31160075), and Joint Scientific and Technological Research Project (Study on Antibacterial Active 53
Biochemical Systematics and Ecology 84 (2019) 52–54
T. Liu, et al.
Components from Streptomyces sp. FHS 2–3: 2017) by Zunyi Science and Technology Bureau and The First People's Hospital of Zunyi.
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