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来自一种与海洋海绵相关的微杆菌物种的糖甘油脂的生产与结构解析

Production and structure elucidation of glycoglycerolipids from a marine sponge-associated microbacterium species.

作者信息

Wicke C, Hüners M, Wray V, Nimtz M, Bilitewski U, Lang S

机构信息

Institut für Biochemie und Biotechnologie, Technische Universität Braunschweig, Abt. Biotechnologie, Spielmannstrasse 7, D-38106 Braunschweig, Germany.

出版信息

J Nat Prod. 2000 May;63(5):621-6. doi: 10.1021/np990313b.

DOI:10.1021/np990313b
PMID:10843572
Abstract

The bacterium Microbacterium sp., isolated from the sponge Halichondria panicea, produced four unusual cell-associated glycoglycerolipids and one diphosphatidylglycerol when grown on marine broth and on artificial seawater media. The lipids were isolated by chromatography on silica columns and their structures elucidated using a combination of multidimensional NMR and MS techniques. The main compound was 1-O-acyl-3-[alpha-glucopyranosyl-(1-3)-(6-O-acyl-alpha-mannopyranosyl )]glycerol (GGL.2) with 14-methyl-hexadecanoic acid and 12-methyl-tetradecanoic acid positioned at C-6 of the mannose unit and at the glycerol moiety. Glycolipid production was correlated with growth and reached a maximum value of 200 mg/L when grown on artificial seawater medium with 20 g/L glucose. The main compound decreased the surface tension of water down to 33 mN/m and the interfacial tension of the water/n-hexadecane system down to 5 mN/m. In addition to this good surface-active behavior, the main glycoglycerolipid showed antitumor activities.

摘要

从海绵Halichondria panicea中分离出的微杆菌属细菌,在海洋肉汤和人工海水培养基上生长时,产生了四种不同寻常的细胞相关糖甘油脂和一种双磷脂酰甘油。这些脂质通过硅胶柱色谱法分离,并使用多维核磁共振和质谱技术相结合的方法阐明了它们的结构。主要化合物是1-O-酰基-3-[α-D-吡喃葡萄糖基-(1→3)-(6-O-酰基-α-D-吡喃甘露糖基)]甘油(GGL.2),其中14-甲基十六烷酸和12-甲基十四烷酸分别位于甘露糖单元的C-6位和甘油部分。糖脂的产生与生长相关,在含有20 g/L葡萄糖的人工海水培养基上生长时,糖脂产量最高可达200 mg/L。主要化合物可将水的表面张力降低至33 mN/m,并将水/正十六烷体系的界面张力降低至5 mN/m。除了这种良好的表面活性行为外,主要糖甘油脂还具有抗肿瘤活性。

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