title: The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp.
abstract: 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.
authors.affiliation: School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. r.capon@unimelb.edu.au
authors.forename: R J
authors.initials: RJ
authors.lastname: Capon
authors.forename: C
authors.initials: C
authors.lastname: Skene
authors.forename: E H
authors.initials: EH
authors.lastname: Liu
authors.forename: E
authors.initials: E
authors.lastname: Lacey
authors.forename: J H
authors.initials: JH
authors.lastname: Gill
authors.forename: K
authors.initials: K
authors.lastname: Heiland
authors.forename: T
authors.initials: T
authors.lastname: Friedel
mesh_terms: 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
chemical_list: D000475:Alkenes; D000969:Antinematodal Agents; D013861:Thiocyanates; C444280:thiocyanatin A; C444279:thiocyanatin B