title: The preparation and bioactivities of (-)-isovelleral.
abstract: The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor.
authors.affiliation: Department of Organic Chemistry 2, Lund University, Sweden.
authors.forename: M
authors.initials: M
authors.lastname: Jonassohn
authors.forename: R
authors.initials: R
authors.lastname: Hjertberg
authors.forename: H
authors.initials: H
authors.lastname: Anke
authors.forename: K
authors.initials: K
authors.lastname: Dekermendjian
authors.forename: A
authors.initials: A
authors.lastname: Szallasi
authors.forename: E
authors.initials: E
authors.lastname: Thines
authors.forename: R
authors.initials: R
authors.lastname: Witt
authors.forename: O
authors.initials: O
authors.lastname: Sterner
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D001552:Benzazepines / Q000378:metabolism; D001667:Binding, Competitive; D006801:Humans; D008297:Male; D000081223:Polycyclic Sesquiterpenes; D051381:Rats; D017208:Rats, Wistar; D017447:Receptors, Dopamine D1 / Q000378:metabolism; D011955:Receptors, Drug / Q000378:metabolism; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D001552:Benzazepines; D000081223:Polycyclic Sesquiterpenes; D017447:Receptors, Dopamine D1; D011955:Receptors, Drug; D012717:Sesquiterpenes; C089286:isovelleral