蜘蛛香化学成分及其抗肿瘤活性
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摘要
目的研究蜘蛛香Valeriana jatamansi Jones的化学成分及其抗肿瘤活性。方法蜘蛛香95%乙醇提取物采用硅胶、Sephadex LH-20、ODS、制备薄层色谱和半制备型高效液相色谱进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。磺酰罗丹明B(SRB)法进行抗肿瘤活性筛选。结果从中分离得到5个化合物,分别鉴定为(3S,4S,5S,7S,8S,9S)-3,8-ethoxy-7-dihydroxy-4,8-dimethylperhydrocyclopenta-[c]pyran(1)、desoxidodidrovaltrate(2)、valtral C(3)、8-hydroxyl-pathouli alcohol(4)、3, 4-二甲氧基肉桂醛(5)。化合物2～3对胃癌MGC803和肝癌HepG2增殖均显示一定的抑制活性,其IC_(50)分别为4.28、1.90μmol/L和4.96、2.54μmol/L。结论化合物5为首次从该属植物中分离得到,化合物2～3有较强的抗肿瘤活性。
AIM To study the chemical constituents from Valeriana jatamansi Jones and their antitumor activities. METHODS The 95% ethanol extract from V. jatamansi was isolated and purified by silica, Sephadex LH-20, ODS, preparative TLC and semipreparative HPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.Antitumor activities were measured by SRB method.RESULTS Five compounds were isolated and identified as(3S,4S,5S,7S,8S,9S)-3,8-ethoxy-7-dihydroxy-4,8-dimethylperhydrocyclopenta-[c]pyran(1), desoxidodidrovaltrate(2), valtral C(3), 8-hydroxyl-pathouli alcohol(4), 3, 4-dimethoxycinnamaldehyde(5). Compounds 2-3 had certain inhibitory effects on MGC803 and HepG2 with IC_(50) values of 4.28, 1.90 μmol/L and 4.96, 2.54 μmol/L. CONCLUSION Compound 5 is isolated from genus valerianacene for the first time. Compounds 2-3 possess some extent antitumor activities.
AIM To study the chemical constituents from Valeriana jatamansi Jones and their antitumor activities. METHODS The 95% ethanol extract from V. jatamansi was isolated and purified by silica, Sephadex LH-20, ODS, preparative TLC and semipreparative HPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.Antitumor activities were measured by SRB method.RESULTS Five compounds were isolated and identified as(3S,4S,5S,7S,8S,9S)-3,8-ethoxy-7-dihydroxy-4,8-dimethylperhydrocyclopenta-[c]pyran(1), desoxidodidrovaltrate(2), valtral C(3), 8-hydroxyl-pathouli alcohol(4), 3, 4-dimethoxycinnamaldehyde(5). Compounds 2-3 had certain inhibitory effects on MGC803 and HepG2 with IC_(50) values of 4.28, 1.90 μmol/L and 4.96, 2.54 μmol/L. CONCLUSION Compound 5 is isolated from genus valerianacene for the first time. Compounds 2-3 possess some extent antitumor activities.
引文
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[12] 兰明, 张占平, 林玉, 等. 蜘蛛香提取物对人结肠癌SW480细胞增殖抑制及抗转移作用[J].中华中医药学刊, 2015, 33(2):293-295.
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[15] Lin S, Fu P, Chen T, et al. Minor valepotriates from Valeriana jatamansi and their cytotoxicity against metastatic prostate cancer cells[J]. Planta Med, 2015, 81(1): 56-61.
[16] Wang S J, Qiu X Q, Zhu J Y, et al. Two new iridoids from the root and rhizome of Valeriana jatamansi Jones[J]. Helv Chim Acta, 2014, 97(5): 722-726.
[17] 陈冲. 蜘蛛香总环烯醚萜类成分急性毒性及长期毒性安全性评价研究[D].成都: 西南交通大学, 2015:11-53.
[18] 张书勤, 薛存宽, 何学斌, 等. 缬草环烯醚萜酯抗小鼠移植肿瘤的作用[J].中国医院药学杂志, 2010,12(30):1008-1010.
[2] 黄宝康, 郑汉臣, 张巧艳, 等. 缬草和蜘蛛香的资源分布及民族药用调查[J]. 中国野生植物资源, 2006, 25(1): 12-15.
[3] Vidyalakshmi K S, Rajamanikam G V. An iridoid with anticancer activity from the sepals of Mussaenda ‘dona aurora’[J]. Indian J Chem, 2009, 48(7): 1019-1022.
[4] Lin S, Chen T, Liu X H, et al. Iridoids and lignans from Valeriana jatamansi[J]. J Nat Prod, 2010, 73(4): 632-638.
[5] Xu J, Guo P, Guo Y Q, et al. Iridoids from the roots of Valeriana jatamansi and their biological activities[J]. Nat Prod Res,2012, 26(21): 1996-2001.
[6] Lin S, Chen T, Fu P, et al. Three decomposition products of valepotriates from Valeriana jatamansi and their cytotoxic activity[J]. J Asian Nat Prod Res,2015, 17(5): 455-461.
[7] 施金钹, 李萍, 高增平, 等. 蜘蛛香的化学成分研究[J]. 西北药学杂志, 2016, 31(3): 225-227.
[8] Olstein R, Stephenson E F M. The synthesis of methoxy- and hydroxy-substituted cinnamaldehydes and their corresponding epoxides.Ⅱ. the epoxides[J]. Aust J Chem, 1979, 32:1595-1600.
[9] Bounthanh C, Bergmann C, Beck J P, et al. Valepotriates, a new class of cytotoxic and antitumor agents[J]. Planta Med, 1981, 41(1):21 -28.
[10] Bounthanh C, Beck J P, Haag-Berrurier M, et al. Effects of two monoterpene esters, valtrate and didrovaltrate, isolated from Valeriana wallichii, on the ultrastructure of hepatoma cells in culture[J]. Phytother Res, 1993,7(2):124-127.
[11] 叶建明. 缬草波春诱导胃癌细胞凋亡机制的研究[D].武汉: 华中科技大学, 2004:8-53.
[12] 兰明, 张占平, 林玉, 等. 蜘蛛香提取物对人结肠癌SW480细胞增殖抑制及抗转移作用[J].中华中医药学刊, 2015, 33(2):293-295.
[13] 张振学, 姚新生. 药用植物缬草的化学研究进展[J].中国药物化学杂志, 2000,10(3): 226-230.
[14] Zhang Z X, Dou D Q, Liu K, et al. Studies on the chemical constituents of Valeriana fauriei Briq[J]. J Asian Nat Prod Res, 2006, 8(5): 397-400.
[15] Lin S, Fu P, Chen T, et al. Minor valepotriates from Valeriana jatamansi and their cytotoxicity against metastatic prostate cancer cells[J]. Planta Med, 2015, 81(1): 56-61.
[16] Wang S J, Qiu X Q, Zhu J Y, et al. Two new iridoids from the root and rhizome of Valeriana jatamansi Jones[J]. Helv Chim Acta, 2014, 97(5): 722-726.
[17] 陈冲. 蜘蛛香总环烯醚萜类成分急性毒性及长期毒性安全性评价研究[D].成都: 西南交通大学, 2015:11-53.
[18] 张书勤, 薛存宽, 何学斌, 等. 缬草环烯醚萜酯抗小鼠移植肿瘤的作用[J].中国医院药学杂志, 2010,12(30):1008-1010.