Phoriospongin A and B: two new nematocidal depsipeptides from the Australian marine sponges Phoriospongia sp. and Callyspongia bilamellata.
Bioassay-directed fractionation of two southern Australian sponges, Phoriospongia sp. and Callyspongia bilamellata, yielded two new nematocidal depsipeptides, identified as phoriospongins A (1) and B (2). The structures of the phoriospongins were determined by detailed spectroscopic analysis and comparison with the previously reported sponge depsipeptide cyclolithistide A (3), as well as ESIMS and HPLC analysis of acid hydrolysates. It is noteworthy that the unique and yet structurally related metabolites 1-3 are found in sponges spanning three taxonomic orders, Poescilosclerida, Haplosclerida, and Lithistida.
Capon
Robert J
RJ
School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. r.capon@unimelb.edu.au
Ford
Joanne
J
Lacey
Ernest
E
Gill
Jennifer H
JH
Heiland
Kirstin
K
Friedel
Thomas
T
D000596:Amino Acids / Q000032:analysis; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D002851:Chromatography, High Pressure Liquid; D047630:Depsipeptides; D006868:Hydrolysis; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D014633:Valine / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000596:Amino Acids; D000969:Antinematodal Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C455782:phoriospongin A; C455783:phoriospongin B; D014633:Valine