Frenolicins C鈥揋, Pyranonaphthoquinones from Streptomyces sp. RM-4-15

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• 作者：Xiachang Wang ; Khaled A. Shaaban ; Sherif I. Elshahawi ; Larissa V. Ponomareva ; Manjula Sunkara ; Yinan Zhang ; Gregory C. Copley ; James C. Hower ; Andrew J. Morris ; Madan K. Kharel ; Jon S. Thorson
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：August 23, 2013
• 年：2013
• 卷：76
• 期：8
• 页码：1441-1447
• 全文大小：300K
• 年卷期：v.76,no.8(August 23, 2013)
• ISSN：1520-6025

文摘

Appalachian active coal fire sites were selected for the isolation of bacterial strains belonging to the class actinobacteria. A comparison of high-resolution electrospray ionization mass spectrometry (HRESIMS) and ultraviolet (UV) absorption profiles from isolate extracts to natural product databases suggested Streptomyces sp. RM-4-15 to produce unique metabolites. Four new pyranonaphthoquinones, frenolicins C鈥揊 (1鈥?b>4), along with three known analogues, frenolicin (6), frenolicin B (7), and UCF76-A (8), were isolated from the fermentation of this strain. An additional new analogue, frenolicin G (5), along with two known compounds, deoxyfrenolicin (9) and UCF 13 (10), were isolated from the fermentation supplied with 18 mg/L of scandium chloride, the first example, to the best of our knowledge, wherein scandium chloride supplementation led to the confirmed production of new bacterial secondary metabolites. Structures 1鈥?b>5 were elucidated on the basis of spectral analysis and chemical modification. While frenolicins are best known for their anticoccidial activity, the current study revealed compounds 6鈥?b>9 to exhibit moderate cytotoxicity against the human lung carcinoma cell line (A549) and thereby extends the anticancer SAR for this privileged scaffold.