Abiesatrines A-J: Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

Xian Wen Yang; Su Mei Li; Liang Wu; Yong Li Li; Lin Feng; Yun Heng Shen; Jun Mian Tian; Jian Tang; Ning Wang; Yonghong Liu; Wei Dong Zhang

doi:10.1039/c001885f

Abiesatrines A-J: Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

Xian Wen Yang
, Su Mei Li
, Liang Wu
, Yong Li Li
, Lin Feng
, Yun Heng Shen
, Jun Mian Tian
, Jian Tang
, Ning Wang
, Yonghong Liu
, Wei Dong Zhang^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer-review

60 Citations (Scopus)

Abstract

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 (IC₅₀ = 8.9 μg mL^-1). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC₅₀ values of 9.3 and 7.6 μg mL^-1, respectively. Preliminary structure-activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.

Original language	English
Pages (from-to)	2609-2616
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	11
DOIs	https://doi.org/10.1039/c001885f
Publication status	Published - 2010

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title = "Abiesatrines A-J: Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr",

abstract = "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 (IC50 = 8.9 μg mL-1). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC50 values of 9.3 and 7.6 μg mL-1, respectively. Preliminary structure-activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.",

author = "Yang, \{Xian Wen\} and Li, \{Su Mei\} and Liang Wu and Li, \{Yong Li\} and Lin Feng and Shen, \{Yun Heng\} and Tian, \{Jun Mian\} and Jian Tang and Ning Wang and Yonghong Liu and Zhang, \{Wei Dong\}",

year = "2010",

doi = "10.1039/c001885f",

language = "English",

volume = "8",

pages = "2609--2616",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Abiesatrines A-J

T2 - Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

AU - Yang, Xian Wen

AU - Li, Su Mei

AU - Wu, Liang

AU - Li, Yong Li

AU - Feng, Lin

AU - Shen, Yun Heng

AU - Tian, Jun Mian

AU - Tang, Jian

AU - Wang, Ning

AU - Liu, Yonghong

AU - Zhang, Wei Dong

PY - 2010

Y1 - 2010

N2 - 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 (IC50 = 8.9 μg mL-1). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC50 values of 9.3 and 7.6 μg mL-1, respectively. Preliminary structure-activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.

AB - 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 (IC50 = 8.9 μg mL-1). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC50 values of 9.3 and 7.6 μg mL-1, respectively. Preliminary structure-activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.

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DO - 10.1039/c001885f

M3 - Article

C2 - 20372737

AN - SCOPUS:77952656566

SN - 1477-0520

VL - 8

SP - 2609

EP - 2616

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Abiesatrines A-J: Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

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