A note from Daniel Siebert: "Divinorin C" is now known as salvinorin C. This work has been elaborated further in:
Salvinorin C, a New Neoclerodane Diterpene from a Bioactive Fraction of the Hallucinogenic Mexican Mint Salvia divinorum.
by L.J. Vald├ęs III, et al. Organic Letters (2001)


"Divinorin C," a New Neoclerodane Diterpene
from a Bioactive TLC Fraction of Salvia divinorum

Lab notes from the desk of Leander J. Valdés III

The Salvia divinorum Research and Information Center
(Received October 25, 2000)

During our research on S. divinorum, salvinorin A was first isolated from a single pharmacologically active preparative TLC band. Differences in potency between the purified diterpene and the original TLC fraction led us to surmise that the latter possibly contained other strongly bioactive compounds which co-chromatographed with salvinorin A during the separation. On changing solvent systems, we found that this "single" TLC band actually consisted of two diterpenes, with salvinorin A as the major component and a new one (1) (tentatively called divinorin C) as the minor one. Even though we estimated that divinorin C comprised only about 10% of the pharmacologically active TLC fraction (the rest being salvinorin A), the fraction was significantly more potent than an equivalent amount of salvinorin A alone. However, since the testing was done using mice, it cannot be stated unequivocally that the new compound is active in humans. The new terpenoid is a diacetate. There is an acetoxy function where salvinorin A has a ketone and a double bond between Carbon-3 and Carbon-4. The compound tended to decompose during the isolation procedure. The attached figure gives the proton nmr assignments, including coupling constants. We also found trace amounts of both possible monoacetates and the diol during our work.

Part of this material was presented at the 20th annual MALTO Meeting in Monroe, LA, May 16-18, 1993.

Involved in this research were: Leander J. Valdés III, Hui-Ming Chang, Dan Visger, and Masato Koreeda.


dvcb.gif - 33849 Bytes

(1)