Venturicidin C, a new 20-membered macrolide produced by Streptomyces sp. TS-2-2.

Abstract

Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo(D)-trans-4-OH-Pro-(D)-Phe, cyclo(D)-Pro-(D)-Phe and N-(2-phenylethyl)-acetamide were also isolated and identified. The structure of the new macrolide 1 was elucidated by the cumulative analyses of NMR spectroscopy and HR-MS data. Complete NMR assignments for the known venturicidins A (2) and B (3) are also provided, for the first time, in this report. Venturicidins A-C did not inhibit the proliferation of A549 lung cancer cell line but all displayed potent antifungal activity.

• Authors: Khaled A Shaaban, Shanteri Singh, Sherif I Elshahawi, Xiachang Wang, Larissa V Ponomareva, Manjula Sunkara, Gregory C Copley, James C Hower, Andrew J Morris, Madan K Kharel, Jon S Thorson
• Journal: The Journal of antibiotics (J Antibiot (Tokyo)) Vol. 67 Issue 3 Pg. 223-30 (Mar 2014) ISSN: 1881-1469 [Electronic] England
• PMID: 24252813 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Antifungal Agents
• Macrolides
• Peptides, Cyclic
• venturamide A
• venturamide B
• venturicidin C

Topics

• Antifungal Agents (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Humans
• Lung Neoplasms (drug therapy, pathology)
• Macrolides (chemistry, isolation & purification, pharmacology)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry (methods)
• Peptides, Cyclic (chemistry, isolation & purification, pharmacology)
• Streptomyces (metabolism)