来自欧洲防风草的镰叶芹醇（9Z-十七碳-1,9-二烯-4,6-二炔-3-醇）的绝对构型。

Absolute configuration of falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca sativa.

作者信息

Corell Mireia, Sheehy Emile, Evans Paul, Brunton Nigel, Valverde Juan

机构信息

Department of Agroforestry Sciences, School of Technical Agricultural Engineering, University of Seville, Ctra de Utrera, C.P. 41013, Spain.

出版信息

Nat Prod Commun. 2013 Aug;8(8):1123-6.

PMID:24079184

Abstract

Falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol; (1) is a polyacetylene commonly found in several plant families. The absolute configuration of naturally occurring 1 is not clear and contradictory results have been reported in the literature. Determination of the absolute configuration of 1 from Pastinaca sativa L. was carried out. Isolation of 95% pure 1 was performed via successive fractionation and preparative-HPLC. A racemic mixture comprised of 3R-1 and 3S-1 was synthesized in order to confirm the absolute configuration of the isolated natural product using chiral HPLC. Based on a combination of chiral HPLC and specific rotation, 1 present in P. saliva was found to have a 3R absolute configuration (i.e. (3R, 9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol).

摘要

镰叶芹醇（9Z-十七碳-1,9-二烯-4,6-二炔-3-醇；(1)）是一种常见于多个植物科的聚乙炔。天然存在的(1)的绝对构型尚不清楚，文献中报道了相互矛盾的结果。对来自欧洲防风草（Pastinaca sativa L.）的(1)的绝对构型进行了测定。通过连续分馏和制备型高效液相色谱法分离出了纯度为95%的(1)。合成了由3R-(1)和3S-(1)组成的外消旋混合物，以便使用手性高效液相色谱法确认分离出的天然产物的绝对构型。基于手性高效液相色谱法和比旋度的综合分析，发现欧洲防风草中存在的(1)具有3R绝对构型（即(3R, 9Z)-十七碳-1,9-二烯-4,6-二炔-3-醇）。