来自黑山的纽曼耳草两个亚种的愈创木内酯。

Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro.

作者信息

Djordjević Iris, Vajs Vlatka, Bulatović Vanja, Menković Nebojsa, Tesević Vele, Macura Slobodan, Janaćković Pedja, Milosavljević Slobodan

机构信息

Faculty for Veterinary Medicine, University of Belgrade, Bulevar JA 18, 11000 Belgrade, Serbia and Montenegro.

出版信息

Phytochemistry. 2004 Aug;65(16):2337-45. doi: 10.1016/j.phytochem.2004.07.014.

DOI:10.1016/j.phytochem.2004.07.014

PMID:15381005

Abstract

Quantitative (1)H NMR measurements revealed delta(11(13)) sesquiterpene gamma-lactones as the main constituents ( >or= 1% per weight of dried plant material) in the crude extracts of the aerial parts of Amphoricarpos neumayeri ssp. neumayeri and ssp. murbeckii from mountains Orjen and Visitor (Montenegro), respectively. Preparative silica gel chromatography afforded thirteen guai-11(13)-en-12,6alpha-olides, named amphoricarpolides (1-13), with the same relative (1alphaH,4betaH,5alphaH,7betaH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3beta,15-dioxygenation pattern. The only exception was 1 (3-deoxyamphoricarpolide), containing a single oxygen substituent (15-OH). Eight of them exhibited an additional oxygen substituent, 9beta-OH (5 and 6), 2alpha-OH (8-12), or 2alpha-OAc (13). Compound 7 was epoxydated at 10alpha(14)-position, whereas the remaining lactones contained a 10(14) double bond.

摘要

定量¹H NMR测量结果显示，δ(11(13))倍半萜γ-内酯是来自黑山奥尔詹山和维斯托山的neumayeri亚种neumayeri和murbeckii亚种地上部分粗提物中的主要成分（按干燥植物材料重量计≥1%）。制备型硅胶柱色谱法得到了13种愈创木-11(13)-烯-12,6α-内酯，命名为amphoricarpolides（1 - 13），其基本骨架具有相同的相对（1αH,4βH,5αH,7βH）构型。内酯2 - 13的共同结构特征是3β,15 - 二氧代模式。唯一的例外是1（3 - 脱氧amphoricarpolide），含有单个氧取代基（15 - OH）。其中8个具有额外的氧取代基，9β - OH（5和6）、2α - OH（8 - 12）或2α - OAc（13）。化合物7在10α(14)位环氧化，而其余内酯含有10(14)双键。