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脂溶性脂肽 A-D:来自喜马拉雅冷生境真菌长枝木霉的细胞毒性脂肽。

Lipovelutibols A-D: Cytotoxic Lipopeptaibols from the Himalayan Cold Habitat Fungus Trichoderma velutinum.

机构信息

Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine , Canal Road, Jammu 180 001, India.

Department of Biotechnology, Faculty of Sciences, Shri Mata Vaishno Devi University , Katra, Jammu and Kashmir 182320, India.

出版信息

J Nat Prod. 2018 Feb 23;81(2):219-226. doi: 10.1021/acs.jnatprod.6b00873. Epub 2018 Jan 26.

DOI:10.1021/acs.jnatprod.6b00873
PMID:29373791
Abstract

Four novel lipovelutibols A (1), B (2), C (3), and D (4) containing six amino acid residues with leucinol at the C-terminus and a fatty acyl moiety (n-octanoyl) at its N-terminus were isolated from the psychrotrophic fungus Trichoderma velutinum collected from the Himalayan cold habitat. The structures (1-4) were determined by NMR and MS/MS, and the stereochemistry of amino acids by Marfey's method. Lipopeptaibols 2 and 4 were found to contain d-isovaline, a nonproteinogenic amino acid, but lacked α-aminoisobutyric acid, characteristic of peptaibols. Cytotoxic activity of 2 and 4 was observed against HL-60, LS180, MDA-MB-231, and A549 cancer cell lines.

摘要

从喜马拉雅寒冷生境中分离到的嗜冷真菌长枝木霉中分离得到了 4 种新型脂肽化合物 lipovelutibols A(1)、B(2)、C(3)和 D(4),它们都含有 6 个氨基酸残基,C 末端为亮氨酰,N 末端为脂肪酰基(正辛酰基)。通过 NMR 和 MS/MS 确定了它们的结构(1-4),并通过 Marfey 法确定了氨基酸的立体化学。发现脂肽化合物 2 和 4 含有非蛋白氨基酸 d-异缬氨酸,但缺乏特征性的肽类氨基酸 α-氨基异丁酸。化合物 2 和 4 对 HL-60、LS180、MDA-MB-231 和 A549 癌细胞系具有细胞毒性活性。

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