Microcionamides A and B, Bioactive Peptides from the Philippine Sponge Clathria (Thalysias) abietina

Microcionamides A (1) and B (2) have been isolated from the Philippine marine sponge Clathria (Thalysias) abietina. These new linear peptides are cyclized via a cystine moiety and have their C-terminus blocked by a 2-phenylethylenamine group. Their total structures, including absolute stereochemistr...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-06, Vol.69 (12), p.4170-4176
Main Authors: Davis, Rohan A, Mangalindan, Gina C, Bojo, Zenaida P, Antemano, Rowena R, Rodriguez, Nell O, Concepcion, Gisela P, Samson, Shiela C, de Guzman, Dennis, Cruz, Lourdes J, Tasdemir, Deniz, Harper, Mary Kay, Feng, Xidong, Carter, Guy T, Ireland, Chris M
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - toxicity
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - toxicity
Apoptosis
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Cell Line, Tumor
Chemistry
Exact sciences and technology
Female
Fundamental and applied biological sciences. Psychology
Humans
Methods. Procedures. Technologies
Mycobacterium tuberculosis - drug effects
Organic chemistry
Peptides
Peptides - chemistry
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - toxicity
Philippines
Porifera - chemistry
Preparations and properties
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Summary:Microcionamides A (1) and B (2) have been isolated from the Philippine marine sponge Clathria (Thalysias) abietina. These new linear peptides are cyclized via a cystine moiety and have their C-terminus blocked by a 2-phenylethylenamine group. Their total structures, including absolute stereochemistry, were determined by a combination of spectral and chemical methods. Compound 1 was shown to slowly isomerize about the C-36/C-37 double bond when stored in DMSO. Microcionamides A (1) and B (2) exhibited significant cytotoxicity against the human breast tumor cells lines MCF-7 and SKBR-3 and displayed inhibitory activity against Mycobacterium tuberculosis H37Ra.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo040129h