title: Microcionamides A and B, bioactive peptides from the philippine sponge Clathria (Thalysias) abietina.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
authors.forename: Rohan A
authors.initials: RA
authors.lastname: Davis
authors.forename: Gina C
authors.initials: GC
authors.lastname: Mangalindan
authors.forename: Zenaida P
authors.initials: ZP
authors.lastname: Bojo
authors.forename: Rowena R
authors.initials: RR
authors.lastname: Antemano
authors.forename: Nell O
authors.initials: NO
authors.lastname: Rodriguez
authors.forename: Gisela P
authors.initials: GP
authors.lastname: Concepcion
authors.forename: Shiela C
authors.initials: SC
authors.lastname: Samson
authors.forename: Dennis
authors.initials: D
authors.lastname: de Guzman
authors.forename: Lourdes J
authors.initials: LJ
authors.lastname: Cruz
authors.forename: Deniz
authors.initials: D
authors.lastname: Tasdemir
authors.forename: Mary Kay
authors.initials: MK
authors.lastname: Harper
authors.forename: Xidong
authors.initials: X
authors.lastname: Feng
authors.forename: Guy T
authors.initials: GT
authors.lastname: Carter
authors.forename: Chris M
authors.initials: CM
authors.lastname: Ireland
mesh_terms: 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*
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D010455:Peptides; D010456:Peptides, Cyclic; C488616:microcionamide A; C488615:microcionamide B