Dysideaprolines A-F and barbaleucamides A-B, novel polychlorinated compounds from a Dysidea species.
Chemical investigation of a marine sponge, Dysidea sp., collected at Bararin Island, Philippines, has afforded the novel metabolites 1-6, proline-derived analogues of dysidenin (7). We have termed compounds 1-6 dysideaprolines A-F, respectively. Also isolated were compounds 8 and 9, structural analogues of barbamide (10), a metabolite originally isolated from the cyanobacterium Lyngbya majuscula. We have termed these novel compounds barbaleucamides A (8) and B (9). It is most probable that the compounds presented here are actually derived from a symbiotic cyanobacterium found in close association with the Dysidea sp. Structure elucidation of the isolated metabolites involved high-field 2D NMR spectroscopy including (1)H-(1)H COSY, HSQC, and HMBC.
Harrigan
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GG
Pharmacia Corporation, 700 Chesterfield Parkway North, Chesterfield, MO 63198, USA. george.g.harrigan@pharmacia.com
Goetz
G H
GH
Luesch
H
H
Yang
S
S
Likos
J
J
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010679:Philippines; D011161:Porifera / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D021241:Spectrometry, Mass, Electrospray Ionization; D013844:Thiazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D013844:Thiazoles; C438070:barbaleucamide A; C438071:barbaleucamide B; C063771:dysidenin; D011392:Proline