肉穗爵床中新的稠合六环生物碱骨架——肉穗醇的绝对构型

Absolute configuration of myrobotinol, new fused-hexacyclic alkaloid skeleton from Myrioneuron nutans.

作者信息

Pham Van Cuong, Jossang Akino, Sévenet Thierry, Nguyen Van Hung, Bodo Bernard

机构信息

Laboratoire de Chimie et Biochimie des Substances Naturelles-CNRS, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75005 Paris, France.

出版信息

J Org Chem. 2007 Dec 7;72(25):9826-9. doi: 10.1021/jo7017203. Epub 2007 Nov 14.

DOI:10.1021/jo7017203

PMID:17999527

Abstract

Myrobotinol (1) was isolated from the leaves of Myrioneuron nutans (Rubiaceae) and its structure determined from spectral data, including mass spectrometry and 2D NMR. This compound presents a new hexacyclic alkaloid skeleton including a 1,3-oxazine and aminal functionality. The absolute configuration of myrobotinol was established by using Mosher's method. A plausible biosynthetic pathway starting from L-lysine via Delta-piperideine was proposed for this hexacyclic alkaloid.

摘要

肉果柯楠醇（1）是从肉果柯楠（茜草科）的叶子中分离得到的，其结构通过光谱数据（包括质谱和二维核磁共振）确定。该化合物呈现出一种新的六环生物碱骨架，包括一个1,3-恶嗪和氨基醛官能团。肉果柯楠醇的绝对构型通过使用莫舍尔方法确定。针对这种六环生物碱，提出了一条从L-赖氨酸经Δ-哌啶碱开始的合理生物合成途径。