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 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 H(37)Ra.
Davis
Rohan A
RA
Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
Mangalindan
Gina C
GC
Bojo
Zenaida P
ZP
Antemano
Rowena R
RR
Rodriguez
Nell O
NO
Concepcion
Gisela P
GP
Samson
Shiela C
SC
de Guzman
Dennis
D
Cruz
Lourdes J
LJ
Tasdemir
Deniz
D
Harper
Mary Kay
MK
Feng
Xidong
X
Carter
Guy T
GT
Ireland
Chris M
CM
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D017209:Apoptosis; D045744:Cell Line, Tumor; D005260:Female; D006801:Humans; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D010679:Philippines; D011161:Porifera / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D010455:Peptides; D010456:Peptides, Cyclic; C488616:microcionamide A; C488615:microcionamide B