尼安法胺A，一种从巴布亚新几内亚海洋海绵赫氏尼安海绵中提取的新型抗HIV缩肽。

Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.

作者信息

Oku Naoya, Gustafson Kirk R, Cartner Laura K, Wilson Jennifer A, Shigematsu Nobuharu, Hess Sonja, Pannell Lewis K, Boyd Michael R, McMahon James B

机构信息

Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.

出版信息

J Nat Prod. 2004 Aug;67(8):1407-11. doi: 10.1021/np040003f.

DOI:10.1021/np040003f

PMID:15332865

Abstract

A new HIV-inhibitory cyclic depsipeptide, neamphamide A (2), was isolated from a Papua New Guinea collection of the marine sponge Neamphius huxleyi. Its structure was established through interpretation of spectroscopic data and by acid hydrolysis, derivatization of the free amino acids, and LC-MS analysis of the derivatives. Neamphamide A (2) contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethylheptanoic acid moiety. The amino acid constituents were identified as L-Leu, L-NMeGln, D-Arg, D- and L-Asn, two residues of D-allo-Thr, L-homoproline, (3S,4R)-3,4-dimethyl-L-glutamine, beta-methoxytyrosine, and 4-amino-7-guanidino-2,3-dihydroxyheptanoic acid. In a cell-based XTT assay, 2 exhibited potent cytoprotective activity against HIV-1 infection with an EC50 of approximately 28 nM.

摘要

从巴布亚新几内亚采集的海洋海绵赫氏近指海绵（Neamphius huxleyi）中分离出一种新的具有HIV抑制活性的环缩肽——近指酰胺A（2）。通过光谱数据解析、酸水解、游离氨基酸衍生化以及衍生物的液相色谱-质谱分析确定了其结构。近指酰胺A（2）含有11个氨基酸残基以及一个酰胺连接的3-羟基-2,4,6-三甲基庚酸部分。氨基酸成分鉴定为L-亮氨酸、L-N-甲基谷氨酰胺、D-精氨酸、D-和L-天冬酰胺、两个D-别苏氨酸残基、L-高脯氨酸、(3S,4R)-3,4-二甲基-L-谷氨酰胺、β-甲氧基酪氨酸以及4-氨基-7-胍基-2,3-二羟基庚酸。在基于细胞的XTT试验中，2对HIV-1感染表现出强大的细胞保护活性，半数有效浓度（EC50）约为28 nM。