The preparation and bioactivities of (-)-isovelleral.
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.
Jonassohn
M
M
Department of Organic Chemistry 2, Lund University, Sweden.
Hjertberg
R
R
Anke
H
H
Dekermendjian
K
K
Szallasi
A
A
Thines
E
E
Witt
R
R
Sterner
O
O
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
D000890:Anti-Infective Agents; D001552:Benzazepines; D000081223:Polycyclic Sesquiterpenes; D017447:Receptors, Dopamine D1; D011955:Receptors, Drug; D012717:Sesquiterpenes; C089286:isovelleral