Minutissamides A鈥揇, Antiproliferative Cyclic Decapeptides from the Cultured Cyanobacterium Anabaena minutissima

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• 作者：Hahk-Soo Kang ; Aleksej Krunic ; Qi Shen ; Steven M. Swanson ; Jimmy Orjala
• 刊名：Journal of Natural Products
• 出版年：2011
• 出版时间：July 22, 2011
• 年：2011
• 卷：74
• 期：7
• 页码：1597-1605
• 全文大小：861K
• 年卷期：v.74,no.7(July 22, 2011)
• ISSN：1520-6025

文摘

Four cyclic decapeptides, minutissamides A鈥揇 (1鈥?b>4), were isolated from the cultured cyanobacterium Anabaena minutissima (UTEX 1613). The planar structures were determined using various spectroscopic techniques including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the 伪-amino acid residues were assigned using Marfey鈥檚 method after acid hydrolysis. The absolute configuration of a 尾-amino acid residue was assigned by a combination of the advanced Marfey鈥檚 method, J-based configurational analysis, and ROE spectroscopic analysis. The structures of minutissamides A鈥揇 (1鈥?b>4) were characterized by the presence of three nonstandard 伪-amino acid residues (two 伪,尾-dehydro-伪-aminobutyric acids and one N-methylated Asn) and one 尾-amino acid residue (2-hydroxy-3-amino-4-methyldodecanoic acid or 2-hydroxy-3-amino-4-methylhexadecanoic acid). Minutissamides A鈥揇 (1鈥?b>4) exhibited antiproliferative activity against the HT-29 human colon cancer cell line with IC₅₀ values of 2.0, 20.0, 11.8, and 22.7 渭M, respectively.