Nematocidal thiocyanatins from a southern Australian marine sponge Oceanapia sp.
Investigations of a southern Australian marine sponge, Oceanapia sp., have yielded two new beta methyl branched bisthiocyanates, thiocyanatins D1 (3a) and D(2) (3b), along with two new thiocarbamate thiocyanates, thiocyanatins E1 (4a) and E2 (4b). The new thiocyanatins belong to a rare class of bioactive marine metabolite previously only represented by thiocyanatins A-C (1, 2a/b). Structures were assigned on the basis of detailed spectroscopic analysis, with comparisons to the known bisthiocyanate thiocyanatin A (1) and synthetic model compounds (5-7). The thiocyanatins exhibit potent nematocidal activity, and preliminary structure-activity relationship investigations have confirmed key characteristics of the thiocyanatin pharmacophore.
Capon
Robert J
RJ
Centre for Molecular Biodiversity, Institute for Molecular Biosciences, University of Queensland, St. Lucia, Queensland 4072, Australia. r.capon@imb.uq.edu.au
Skene
Colin
C
Liu
Edward Hsiang-Te
EH
Lacey
Ernest
E
Gill
Jennifer H
JH
Heiland
Kirstin
K
Friedel
Thomas
T
D000475:Alkenes / Q000737:chemistry; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013861:Thiocyanates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000475:Alkenes; D000969:Antinematodal Agents; D013861:Thiocyanates; C444280:thiocyanatin A; C444279:thiocyanatin B; C492306:thiocyanatin D1; C492307:thiocyanatin D2