Salvinorins J from Salvia divinorum: mutarotation in the neoclerodane system.
A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia divinorum. A leaf surface extraction method was used on S. divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including the new salvinorins J (2) and 14 known analogues. Salvinorins J (2) represent an example of a neoclerodane hemiacetal (lactol) susceptible to mutarotation with the formation of an equilibrium mixture of C-17 epimers.
Kutrzeba
Lukasz M
LM
Department of Pharmacognosy, University of Mississippi, University, Mississippi 38677-1848, USA.
Ferreira
Daneel
D
Zjawiony
Jordan K
JK
D045785:Diterpenes, Clerodane / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D027544:Salvia / Q000737:chemistry*; D013237:Stereoisomerism
D045785:Diterpenes, Clerodane; C544048:salvinorin J; C090499:salvinorin A