Evanno Laurent, Jossang Akino, Nguyen-Pouplin Julie, Delaroche Diane, Herson Patrick, Seuleiman Mannan, Bodo Bernard, Nay Bastien
Laboratoire de Chimie et Biochimie des Substances Naturelles, Muséum National d'Histoire Naturelle, CNRS, Paris, France.
Planta Med. 2008 Jun;74(8):870-2. doi: 10.1055/s-2008-1074546. Epub 2008 Jun 3.
Harringtonolide (= hainanolide) is a complex polycyclic fused norditerpene isolated from CEPHALOTAXUS HARRINGTONIA var. DRUPACEA. In spite of its appealing biological properties - we measured an IC (50) of 43 nM on KB cells and a significant antifungal activity - its absolute configuration has not yet been firmly established. This was done herein using X-ray anomalous scattering after bromination of the tropone ring, unambiguously giving the stereochemistry 5 R,6 R,7 S,13 S,14 S,15 R,16 R. Detailed IN VITRO biological measurements are provided.
三尖杉酯碱（=海南粗榧内酯）是从粗榧（CEPHALOTAXUS HARRINGTONIA var. DRUPACEA）中分离得到的一种复杂的多环稠合降二萜。尽管它具有吸引人的生物学特性——我们测得其对KB细胞的半数抑制浓度（IC50）为43 nM，且具有显著的抗真菌活性——但其绝对构型尚未完全确定。本文通过对卓酚酮环进行溴化后利用X射线异常散射确定了其绝对构型，明确给出了立体化学结构为5R，6R，7S，13S，14S，15R，16R。文中还提供了详细的体外生物学测量数据。
