Laxaphycins B5 and B6 from the cultured cyanobacterium UIC 10484

Two laxaphycin type-B cyclic dodecapeptides, laxaphycins B5 and B6, were obtained from UIC 10484, a freshwater cf. Phormidium sp. Analysis using the 16S rRNA sequence found UIC 10484 to clade with UIC 10045, a known laxaphycin type-A and -B producer, and MS/MS analysis revealed the presence of two n...

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Bibliographic Details
Published in:Journal of antibiotics 2020-08, Vol.73 (8), p.526-533
Main Authors: Sullivan, Peter, Krunic, Aleksej, Burdette, Joanna E., Orjala, Jimmy
Format: Article
Language:English
Subjects:
101/58
631/67
639/638/309
82/16
Amino acids
Amino Acids - genetics
Bacteriology
Biomedical and Life Sciences
Bioorganic Chemistry
Breast cancer
Breast Neoplasms - drug therapy
Cancer
Cell Line, Tumor
Cyanobacteria - chemistry
Cyanobacteria - genetics
Female
Fresh Water
Humans
Life Sciences
Magnetic Resonance Spectroscopy - methods
Medicinal Chemistry
Melanoma
Melanoma - drug therapy
Metabolites
Microbiology
Organic Chemistry
Ovarian cancer
Ovarian Neoplasms - drug therapy
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
RNA, Ribosomal, 16S - genetics
Special Feature: Article
Tandem Mass Spectrometry - methods
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Summary:Two laxaphycin type-B cyclic dodecapeptides, laxaphycins B5 and B6, were obtained from UIC 10484, a freshwater cf. Phormidium sp. Analysis using the 16S rRNA sequence found UIC 10484 to clade with UIC 10045, a known laxaphycin type-A and -B producer, and MS/MS analysis revealed the presence of two novel laxaphycin type-B compounds. The structures of the metabolites were elucidated using 2D NMR and MS/MS. The absolute configurations of the amino acids were determined by advanced Marfey’s analysis. Both metabolites were evaluated against the same three cancer cell lines. The IC 50 of both laxaphycins B5 and B6 was near 1 μM against breast cancer MDA-MB-231, melanoma MDA-MB-435, and ovarian cancer OVCAR3 cell lines.
ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-020-0301-x