Cytotoxic veraguamides, alkynyl bromide-containing cyclic depsipeptides from the marine cyanobacterium cf. Oscillatoria margaritifera.

Abstract

A family of cancer cell cytotoxic cyclodepsipeptides, veraguamides A-C (1-3) and H-L (4-8), were isolated from a collection of cf. Oscillatoria margaritifera obtained from the Coiba National Park, Panama, as part of the Panama International Cooperative Biodiversity Group program. The planar structure of veraguamide A (1) was deduced by 2D NMR spectroscopy and mass spectrometry, whereas the structures of 2-8 were mainly determined by a combination of 1H NMR and MS2/MS3 techniques. These new compounds are analogous to the mollusk-derived kulomo'opunalide natural products, with two of the veraguamides (C and H) containing the same terminal alkyne moiety. However, four veraguamides, A, B, K, and L, also feature an alkynyl bromide, a functionality that has been previously observed in only one other marine natural product, jamaicamide A. Veraguamide A showed potent cytotoxicity to the H-460 human lung cancer cell line (LD50=141 nM).

• Authors: Emily Mevers, Wei-Ting Liu, Niclas Engene, Hosein Mohimani, Tara Byrum, Pavel A Pevzner, Pieter C Dorrestein, Carmenza Spadafora, William H Gerwick
• Journal: Journal of natural products (J Nat Prod) Vol. 74 Issue 5 Pg. 928-36 (May 27 2011) ISSN: 1520-6025 [Electronic] United States
• PMID: 21488639 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Depsipeptides
• Lipopeptides
• Pyrrolidinones
• jamaicamide A
• veraguamide A

Topics

• Amides (chemistry, isolation & purification)
• Depsipeptides (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Lipopeptides (chemistry, isolation & purification)
• Marine Biology
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Oscillatoria (chemistry)
• Panama
• Pyrrolidinones (chemistry, isolation & purification)