京大戟中松烷、贝壳杉烷和拉伯烷二萜的化学成分及其抗肿瘤活性。

Pimarane, abietane, and labdane diterpenoids from Euphorbia pekinensis Rupr. and their anti-tumor activities.

机构信息

Key Laboratory of Shaanxi Administration of Traditional Chinese Medicine for TCM Compatibility, and Shaanxi Key Laboratory of New Drugs and Chinese Medicine Foundation Research, and State Key Laboratory of Research & Development of Characteristic Qin Medicine Resources (Cultivation), and Shaanxi Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Shaanxi University of Chinese Medicine, Xi'an, 712046, China.

Center of Natural Product WuXi AppTec (Tianjin) Co., Ltd., Tianjin, 300457, China.

出版信息

Phytochemistry. 2022 May;197:113113. doi: 10.1016/j.phytochem.2022.113113. Epub 2022 Feb 16.

DOI:10.1016/j.phytochem.2022.113113

PMID:35182782

Abstract

Chemical investigation of the roots of Euphorbia pekinensis Rupr. led to the isolation of five undescribed labdane diterpenoids "(4S, 5S, 9R, 10S, 13R)-18-O-galloyl-labda-8(17), 14(15)-dien-13-ol; (4S, 5S, 9R, 10S, 13R)-13-hydroxy-labda-8(17), 14(15)-dien-18-one; (4S, 5S, 9R, 10S, 13R)-18-O-acetyl-labda-8(17), 14(15)-dien-13-ol; (4S, 5S, 9R, 10S)-labda-8(17), 13(16), 14(15)-trien-18-ol; (5R, 6R, 9R, 10S, 13R)-labda-8(17), 14(15)-dien-6,13-diol", two undescribed pimarane diterpenoids "(2R, 5S, 9R, 10S, 12R, 13R)-2,12-dihydroxy-isopimara-7,15-dien-3-one; (5S, 9R, 10S, 12R, 13R)-2, 12-dihydroxy-isopimara-1, 7, 15-trien-3-one)", together with nine known diterpenoids, including three pimarane-type "(3β,11α,13α)-3,11-dihydroxypimara-7,15-diene-2,12-dione; (11R, 12S)-2,11,12-trihydroxy-ent-isopimara-1,7,15-trien-3-one; isopimara-7,15-dien-3β-ol)", five abietane-type "helioscopinolide A-C; helioscopinolide E; helioscopinolide I″, and one lathyrane-type "jolkinol B". The structures of these compounds were elucidated by analysis of HRESIMS, 1D NMR, 2D NMR, and X-ray diffraction. These sixteen compounds were evaluated for cytotoxic activity in vitro against three human cancer cell lines, U-937, LOVO, and K-562. Jolkinol B exhibited IC of 3.60 μM and 8.44 μM against U-937 and LOVO cell lines, (4S, 5S, 9R, 10S, 13R)-18-O-galloyl-labda-8(17), 14(15)-dien-13-ol displayed IC of 5.92 μM against U-937 cell lines, isopimara-7,15-dien-3β-ol showed IC of 0.87 μM against K-562 cell lines.

摘要

从北京大戟根部分离得到五个未被描述的贝壳杉烷二萜

(4S, 5S, 9R, 10S, 13R)-18-O- 没食子酰基-贝壳杉-8(17), 14(15)-二烯-13-醇；(4S, 5S, 9R, 10S, 13R)-13- 羟基贝壳杉-8(17), 14(15)-二烯-18-酮；(4S, 5S, 9R, 10S, 13R)-18-O- 乙酰基贝壳杉-8(17), 14(15)-二烯-13-醇；(4S, 5S, 9R, 10S)-贝壳杉-8(17), 13(16), 14(15)-三烯-18-醇；(5R, 6R, 9R, 10S, 13R)-贝壳杉-8(17), 14(15)-二烯-6,13-二醇，两个未被描述的松香烷二萜：(2R, 5S, 9R, 10S, 12R, 13R)-2,12- 二羟基异松烷-7,15-二烯-3-酮；(5S, 9R, 10S, 12R, 13R)-2,12- 二羟基异松烷-1,7,15-三烯-3-酮"，以及九个已知的二萜类化合物，包括三个松香烷型：(3β,11α,13α)-3,11- 二羟基松香烷-7,15-二烯-2,12-二酮；(11R, 12S)-2,11,12- 三羟基-对映-异松烷-1,7,15-三烯-3-酮；异松烷-7,15-二烯-3β-醇"，五个枞烷型：海松醇 A-C；海松醇 E；海松醇 I"，和一个拉坦烷型：乔可林 B。这些化合物的结构通过分析 HRESIMS、1D NMR、2D NMR 和 X 射线衍射来阐明。对这些十六种化合物进行了体外对三种人类癌细胞系 U-937、LOVO 和 K-562 的细胞毒性活性评价。乔可林 B 对 U-937 和 LOVO 细胞系的 IC 为 3.60 μM 和 8.44 μM，(4S, 5S, 9R, 10S, 13R)-18-O- 没食子酰基贝壳杉-8(17), 14(15)-二烯-13-醇对 U-937 细胞系的 IC 为 5.92 μM，异松烷-7,15-二烯-3β-醇对 K-562 细胞系的 IC 为 0.87 μM。