Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities

Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities
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冷杉倍半萜类化合物和三萜类化合物及其生物活性

DOI:
10.1016/j.phytochem.2011.11.011
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发表时间:
2012-02-01
期刊:
影响因子:
3.8
通讯作者:
Zhang, Wei-Dong
Zhang, Wei-Dong
中科院分区:
生物学2区
文献类型:
--
作者:
Xia, Jia-Han;Zhang, Shou-De;Zhang, Wei-Dong

文献摘要

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从全叶冷杉中分离得到6个未见报道的萜类化合物和11个已知的萜类化合物。通过对其一维和二维核磁共振波谱数据的详细分析,确定了六个化合物的结构为两个不常见的双没食烷倍半萜,三个去甲三萜和一个3,4-二次三萜。此外,通过电子圆二色谱计算和分子轨道分析确定了一种双倍半萜类化合物的绝对构型,即阿比斯奎因A对RAW264.7巨噬细胞产生一氧化氮(NO)的抑制作用最强,IC50值为113.1 mU M。Lanosta-7,9(11),24-Trien-26-OIC酸对COLO-205,LOVO和QGY-7703肿瘤细胞显示出较强的细胞毒活性,IC50值分别为0.9mU M,4.2mU M和2.0mU M。(23R,25R)-3,4-Seco-9βH-Lanosta-4(28),7-二烯-26,23-内酯-3-酸对A549细胞有明显的抑制作用(IC_(50)=14.7µM)。(C)2011爱思唯尔有限公司。保留所有权利。
Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC50 value of 113.1 mu M. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC50 values of 0.9, 4.2, and 2.0 mu M, respectively. (23R,25R)-3,4-seco-9 beta H-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC50 = 14.7 mu M). (C) 2011 Elsevier Ltd. All rights reserved.