Abiesatrines A-J: anti-inflammatory and antitumor triterpenoids from Abies georgei Orr.
A novel spiro-lanostane (abiesatrine A, 1) was isolated from the aerial parts of Abies georgei together with 9 new (abiesatrines B-J, 2-10) and 10 known triterpenes (11-20). The new structures were established by the extensive analysis of their spectroscopic data. The configuration of 1, featuring a unique spirolactone formed by C-13 and C-23 via oxygen-bridge, was confirmed by X-ray crystallography, and its biopathway was tentatively proposed. Among these isolates, compound 16 showed the strongest inhibitory activity against LPS-induced NO production in RAW264.7 macrophages (IC(50) = 8.9 microg mL(-1)). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC(50) values of 9.3 and 7.6 microg mL(-1), respectively. Preliminary structure-activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.
Yang
Xian-Wen
XW
Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai, 200433, China.
Li
Su-Mei
SM
Wu
Liang
L
Li
Yong-Li
YL
Feng
Lin
L
Shen
Yun-Heng
YH
Tian
Jun-Mian
JM
Tang
Jian
J
Wang
Ning
N
Liu
Yonghong
Y
Zhang
Wei-Dong
WD
D028202:Abies / Q000737:chemistry*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000737:chemistry; D008264:Macrophages / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D013141:Spiro Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000893:Anti-Inflammatory Agents; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D013141:Spiro Compounds; D007810:Lanosterol