The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp.
Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agent.
Capon
R J
RJ
School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. r.capon@unimelb.edu.au
Skene
C
C
Liu
E H
EH
Lacey
E
E
Gill
J H
JH
Heiland
K
K
Friedel
T
T
D000475:Alkenes / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000969:Antinematodal Agents / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D006189:Haemonchus / Q000187:drug effects / Q000254:growth & development; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013861:Thiocyanates / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000493:pharmacokinetics / Q000494:pharmacology
D000475:Alkenes; D000969:Antinematodal Agents; D013861:Thiocyanates; C444280:thiocyanatin A; C444279:thiocyanatin B