小叶臭黄皮的化学成分研究

doi:10.3969/j.issn.0253-2417.2016.01.018

林产化学与工业 ›› 2016, Vol. 36 ›› Issue (1): 127-134.doi: 10.3969/j.issn.0253-2417.2016.01.018

小叶臭黄皮的化学成分研究

彭文文¹, 刘欣媛², 曾广智³, 谭宁华³

1. 江西农业大学江西省天然产物与功能食品重点实验室, 江西南昌 330045;
2. 江西农业大学学校医院, 江西南昌 330045;
3. 中国科学院昆明植物研究所;植物化学与西部植物资源持续利用国家重点实验室, 云南昆明 650201

收稿日期:2015-01-13 出版日期:2016-02-25 发布日期:2016-03-18
作者简介:彭文文(1977-),男,陕西西安人,讲师,博士,主要从事植物化学及生物活性研究;E-mail:pengwenwen123@sina.com。
基金资助:
江西省博士后科研基金(06292023);江西农业大学博士科研启动基金项目(09004507)

Chemical Constituents from Clausena excavata Burm. F.

PENG Wen-wen¹, LIU Xin-yuan², ZENG Guang-zhi³, TAN Ning-hua³

1. Jiangxi Key Laboratory of Natural Products and Functional Food, Jiangxi Agricultural University, Nanchang 330045, China;
2. Hospital, Jiangxi Agricultural University, Nanchang 330045, China;
3. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

Received:2015-01-13 Online:2016-02-25 Published:2016-03-18

摘要/Abstract

摘要： 从小叶臭黄皮(Clausena excavata Burm F.)的茎和叶中分离得到10个单萜基香豆素,分别鉴定为7-((E)-3'-甲基-4'-(8'-羰基-7',9'-烯-呋喃)-2'-烯)-香豆素(1)、7-((E)-3'-甲基-4'-(7'-甲基-8'-羰基-6'-烯-呋喃)-2'-烯)-香豆素(2)、7-((E)-3'-甲基-4'-(7'-甲基-6'-亚甲基-8'-羰基-呋喃)-2'-烯)-香豆素(3)、7-((E)-3'-甲基-4'-(9'-羟基-8'-羰基-6'-烯-呋喃)-2'-烯)-香豆素(4)、7-(3'-甲基-4'-(7'-甲基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(5)、7-(3'-甲基-4'-(9'-羟基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(6)、7-(3'-甲基-4'-(7'-甲基-7'-羟基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(7)、7-(3'-甲基-4'-(7'-甲基-8'-羰基-呋喃)-2',3'-环氧丁烷)-香豆素(8)、5'-羟基葡萄内酯(9)和7-((E)-7'-羟基-3',7'-二甲基-2',5'-二烯)-香豆素(10), 2个四降三萜,鉴定为11β-羟基-1α-乙酰基黄柏酮(11)、11β-羟基黄柏酮(12)和1个木脂素,鉴定为(-)-丁香脂素(13)。其中化合物11和13为首次从该植物中分离得到。测定了化合物1、2、3、11和12对癌细胞株A549、Hela和BGC-823的细胞毒活性,及其对白色念珠菌(Candida albicans)、金黄色葡萄球菌(Staphylococcus aureus)的抑菌活性。结果显示,化合物1对Hela和A549均有细胞毒活性,其半数抑制质量浓度(IC₅₀)值分别为11.26和13.55 mg/L,化合物3对BGC-823有细胞毒活性,其IC₅₀值为16.65 mg/L,5个化合物对白色念珠菌和金黄色葡萄球菌均没有抗菌活性。

关键词: 小叶臭黄皮, 单萜基香豆素, 四降三萜, 木脂素

Abstract: Ten O-terpenoidal coumarins excavarin (1), excavatin D (2), excavatin G (3), excavatin E (4), excavatin K (5), excavatin L (6), excavacoumarin B (7), excavacoumarin A (8), anisocoumarin H (9) and 7-((E)-7'-hydroxy-3', 7'-dimethylocta-2', 5'-dienyloxy)-coumarin (10), two tetranortriterpenoids claemargine E (11), zapoterin (12), one lignanoid (-)-syringaresinol (13) were isolated from the leaves and barks of Clausena excavata Burm.F.(Rutaceae).Compounds 11 and 13 are isolated from this plant for the first time.Compounds 1, 2, 3, 11 and 12 were tested for their cytotoxicities against A549, Hela and BGC-823 cancer cell lines, and antimicrobial activities against Candida albicans and Staphylococcus aureus.The results showed that compound 1 exhibited cytotoxicity against Hela and A549 with the IC₅₀ values of 11.26 and 13.55 mg/L, and compound 3 against BGC-823 with the IC₅₀ value of 16.65 mg/L. Compounds 1, 2, 3, 11, 12 didn't exhibit antimicrobial activities against Candida albicans and Staphylococcus aureaus.

Key words: Clausena excavata Burm. F., O-terpenoidal coumarins, tetranortriterpenoids, lignanoid

中图分类号:

TQ35

彭文文, 刘欣媛, 曾广智, 谭宁华. 小叶臭黄皮的化学成分研究[J]. 林产化学与工业, 2016, 36(1): 127-134.

PENG Wen-wen, LIU Xin-yuan, ZENG Guang-zhi, TAN Ning-hua. Chemical Constituents from Clausena excavata Burm. F.[J]. Chemistry and Industry of Forest Products, 2016, 36(1): 127-134.

参考文献

[1] 中国科学院昆明植物研究所.云南植物志(第六卷):种子植物[M].北京:科学出版社,1995:759. Kunming Plant Research Institute,Chinese Academy of sciences.Yunnan Plant Annals (Sixth Volume):Seed Plant[M].Beijing:Science and Technology Publishing,1995:759.
[2] HE Hong-ping,ZHANG Jian-xin,SHEN Yue-mao,et al.Tetranortriterpenoids from Clausena excavata[J].Helvetica Chimica Acta,2002,85(2):671-677.
[3] ITO C,ITOIGAWA M,KATSUNO S,et al.Chemical constituents of Clausena excavata:Isolation and structure elucidation of novel furanone-coumarins with inhibitory effects for tumor-promotion[J].Journal of Natural Products,2000,63(9):1218-1224.
[4] PENG Wen-wen,ZHENG Yu-qing,CHEN Yi-shan,et al.Coumarins from roots of Clausena excavata[J].Journal of Asian Natural Products Research,2013,15(3):215-220.
[5] PENG Wen-wen,ZENG Guang-zhi,SONG Wei-wu,et al.A new cytotoxic carbazole alkaloid and two new other alkaloids from Clausena excavata[J].Chemistry & Biodiversity,2013,10(7):1317-1321.
[6] 彭文文,宋卫武,黄茂波,等.小叶臭黄皮中单萜和倍半萜类成分研究[J].中国中药杂志,2014,39(9):1620-1624. PENG Wen-wen,SONG Wei-wu,HUANG Mao-bo,et al.Monoterpenes and sesquiterpenes from Clausena excavata[J].China Journal of Chinese Materia Medica,2014,39(9):1620-1624.
[7] 彭文文,宋卫武,黄茂波,等.小叶臭黄皮中12个苯环衍生物(英文)[J].药学学报,2014,49(12):1689-1693. PENG Wen-wen,SONG Wei-wu,HUANG Mao-bo,et al.Twelve benzene derivatives from Clausena excavata[J].Acta Pharmaceutica Sinica,2014,49(12):1689-1693.
[8] HE Wen-jun,CHU Hong-biao,ZHANG Yu-mei,et al.Antimicrobial,cytotoxic lignans and terpenoids from the twigs of Pseudolarix kaempferi[J].Planta Medica,2011,77(17):1924-1931.
[9] KUMAR R,SAHA A,SAHA D.A new antifungal coumarin from Clausena excavata[J].Fitoterapia,2012,83(1):230-233.
[10] THUY T T,RIPPERGER H,PORZEL A,et al.Coumarins,limonoids and an alkaloid from Clausena excavata[J].Phytochemistry,1999,52(3):511-516.
[11] WANG Yun-song,HUANG Rong,LI Ning-zhong,et al.Coumarins from Clausena anisum-olens Merr[J].Bioscience Biotechnology and Biochemistry,2010,74(7):1483-1484.
[12] TAKEMURA Y,NAKAMURA K,HIRUSAWA T,et al.Four new furanone-coumarins from Clausena excavata[J].Chemical & Pharmaceutical Bulletin,2000,48(4):582-584.
[13] HE Hong-ping,SHEN Yue-mao,ZUO Guo-ying,et al.Two new O-terpenoidal coumarins,excavacoumarin A and B from Clausena excavata[J].Chinese Chemical Letters,2000,11(6):539-542.
[14] NGADJUI B T,AYAFOR J F,SONDENGAM B L,et al.Prenylated coumarins from the leaves of Clausena anisata[J].Journal of Natural Products,1989,52(2):243-247.
[15] CHANG C T,DOONG S L,TSAI I L,et al.Coumarins and anti-HBV constituents from Zanthoxylum schinifolium[J].Phytochemistry,1997,45(7):1419-1422.
[16] MIN B K,HYUN D G,JEONG S Y,et al.A new cytotoxic coumarin,7-[(E)-3',7'-dimethyl-6'-oxo-2',7'-octadienyl] oxy coumarin,from the leaves of Zanthoxylum schinifolium[J].Archives of Pharmacal Research,2011,34(5):723-726.
[17] RASHID M A,GRAY A I,WATERMAN P G,et al.Coumarins from Phebalium tuberculosum ssp.megaphyllum and Phebalium filifolium[J].Journal of Natural Products,1992,55(7):851-858.
[18] XIA Hong-min,LI Chuang-jun,YANG Jing-zhi,et al.A,D-seco-limonoids from the stems of Clausena emarginata[J].Journal of Natural Products,2014,77(4):784-791.
[19] NGADJUI B T,AYAFOR J F,SONDENGAM B L,et al.Prenylated coumarins from the leaves of Clauaena anisata[J].Journal of Natural Products,1989,52(2):243-247.
[20] OUYANG M A,WEIN Y S,ZHANG Z K,et al.Inhibitory activity against tobacco mosaic virus(TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var.roxburghian[J].Journal of Agricultural and Food Chemistry,2007,55(16):6460-6465.

小叶臭黄皮的化学成分研究

Chemical Constituents from Clausena excavata Burm. F.

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