来自茎点霉属真菌SANK 13899的新型肌醇磷酸神经酰胺合酶抑制剂多球壳菌素。II. 结构解析。

Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. II. Structural elucidation.

作者信息

Aoyagi Azusa, Yano Tatsuya, Kozuma Shiho, Takatsu Toshio

机构信息

Core Technology Research Laboratories, Sankyo Co., Ltd., Hiromachi, Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 2007 Feb;60(2):143-52. doi: 10.1038/ja.2007.14.

DOI:10.1038/ja.2007.14

PMID:17420565

Abstract

Pleofungins (formerly called F-15078) A, B, C and D, novel depsipeptide antifungal antibiotics, were found in a mycelium extract of the producing fungus, Phoma sp. SANK 13899. The structures of pleofungins A, B, C and D were elucidated mainly by various NMR studies. The absolute configurations of the amino acids and N-methyl amino acids of pleofungin A constituents in the hydrolysate were determined by the application of advanced Marfey's method in combination with gas chromatography/mass spectrometry analysis of their silylation products with N-methyl-N-(tert-butylsilyl)trifluoroacetamide. Two alpha-hydroxy acid constituents, alpha-hydroxyisocaproic acid and alpha-hydroxyisovaleric acid, were isolated from the hydrolysate and their stereochemistries were determined by their specific rotations.

摘要

从产生真菌茎点霉属SANK 13899的菌丝体提取物中发现了新型缩肽类抗真菌抗生素多球霉素A、B、C和D（以前称为F - 15078）。多球霉素A、B、C和D的结构主要通过各种核磁共振研究得以阐明。通过先进的马尔费方法结合其与N - 甲基 - N -（叔丁基硅烷基）三氟乙酰胺的硅烷化产物的气相色谱/质谱分析，确定了水解产物中多球霉素A成分的氨基酸和N - 甲基氨基酸的绝对构型。从水解产物中分离出两种α - 羟基酸成分，α - 羟基异己酸和α - 羟基异戊酸，并通过它们的比旋光度确定了它们的立体化学结构。