Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium Lyngbya bouillonii from Guam

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• 作者：Susan Matthew ; Lilibeth A. Salvador ; Peter J. Schupp ; Valerie J. Paul ; Hendrik Luesch
• 刊名：Journal of Natural Products
• 出版年：2010
• 出版时间：September 24, 2010
• 年：2010
• 卷：73
• 期：9
• 页码：1544-1552
• 全文大小：219K
• 年卷期：v.73,no.9(September 24, 2010)
• ISSN：1520-6025

文摘

Collections of the marine cyanobacterium Lyngbya bouillonii from shallow patch reefs in Apra Harbor, Guam, afforded three hitherto undescribed analogues of the glycosidic macrolide lyngbyaloside, namely, 2-epi-lyngbyaloside (1) and the regioisomeric 18E- and 18Z-lyngbyalosides C (2 and 3). Concurrently we discovered two new analogues of the cytoskeletal actin-disrupting lyngbyabellins, 27-deoxylyngbyabellin A (4) and lyngbyabellin J (5), a novel macrolide of the laingolide family, laingolide B (6), and a linear modified peptide, lyngbyapeptin D (7), along with known lyngbyabellins A and B, lyngbyapeptin A, and lyngbyaloside. The structures of 1−7 were elucidated by a combination of NMR spectroscopic and mass spectrometric analysis. Compounds 1−6 were either brominated (1−3) or chlorinated (4−6), consistent with halogenation being a hallmark of many marine natural products. All extracts derived from these L. bouillonii collections were highly cytotoxic due to the presence of apratoxin A or apratoxin C. Compounds 1−5 showed weak to moderate cytotoxicity to HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cells.