The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp

R J Capon; C Skene; E H Liu; E Lacey; J H Gill; K Heiland; T Friedel

doi:10.1021/jo0106750

The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp

J Org Chem. 2001 Nov 16;66(23):7765-9. doi: 10.1021/jo0106750.

Authors

R J Capon¹, C Skene, E H Liu, E Lacey, J H Gill, K Heiland, T Friedel

Affiliation

¹ School of Chemistry, University of Melbourne, Parkville, Victoria 3010, Australia. [email protected]

PMID: 11701034
DOI: 10.1021/jo0106750

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / isolation & purification*
Alkenes / pharmacology
Animals
Antinematodal Agents / chemical synthesis*
Antinematodal Agents / isolation & purification*
Antinematodal Agents / pharmacology
Haemonchus / drug effects
Haemonchus / growth & development
Nuclear Magnetic Resonance, Biomolecular
Porifera / chemistry*
Structure-Activity Relationship
Thiocyanates / chemical synthesis*
Thiocyanates / isolation & purification*
Thiocyanates / pharmacokinetics
Thiocyanates / pharmacology

Substances

Alkenes
Antinematodal Agents
Thiocyanates
thiocyanatin A
thiocyanatin B