The Salvia divinorum Research and Information Center - Shroomery

loliolide
LITERATURE CITED
1. L.J. Valdes III, J.L. Diaz, and A.G. Paul, J. Ethnopharmacology, 7, 287 (1983).
2. L.J. Valdes III, W.M. Butler, G.M. Hatfield, A.G. Paul,and M. Koreeda, J. Org. Chem., 49, 4716
(1984).
3. R. Hodges and A.L. Porte, Tetrahedron, 20, 1463 (1964).
4. T. Wada, Chem. Pharm. Bull., 13, 43 (1965).
5. G.R. Pettit, C.L. Herald, R.H. Ode, P. Brown, D.J. Gust, and C. Michel, J. Nat. Prod, 43, 753.
6. S. Isoe, S.B. Hyeon, S. Katsumura, and T. Sakan,Tetrahedron Lett., 2517 (1972).
7. H. Cadosch and C.E. Eugster, Helv. Chim. Acta., 57, 1466 (1974).
8. A.L. Okunade, and D.F. Wiemer, J. Nat. Prod, 48, 472 (1985).
EXPERIMENTAL DETAILS OF LOLIOLIDE ISOLATION
GENERAL EXPERIMENTAL PROCEDURES
Salvia divinorum was grown at the author's home and at the Matthaei Botanical Gardens. Voucher
specimens have been deposited at the University Herbarium. Air-dried leaves (3.4 kg) were finely ground
and extracted with ether using a Soxhlet apparatus. The ethereal extract was dried in vacuo and
partitioned between water and ethyl acetate. The organic fraction weighed 112 g after drying. Preliminary
separations of the organic fraction were accomplished by using gradient-elution flash column
chromatography (2) on 10 g portions of the fraction (5 x 15 cm columns of silica gel 60, 230-400 mesh)
with hexane/EtOAC as the solvent system. Further purifications were performed using gradient-elution
flash column chromatography on 2.5 x 15 cm columns of silica gel 60 (230-400 mesh) with
hexane/EtOAC and CH 2 Cl 2 /MeOH solvent systems. Preparative hplc separations were performed using a
Waters Liquid Chromatograph system (Models U6K injector, M45 solvent delivery system, R400
differential refractometer, and 440 absorbance detector) attached to a microporasil P/N 27477 S/N
column (fitted with a C-18 Corasil prefilter) and Houston OmniScribe B-5000 chart recorder.
Melting points were taken uncorrected on a Thermolyne HP-12615 melting point apparatus. Infrared
spectra were recorded on a Nicolet Model 60SX GC/FTIR Spectrometer as potassium bromide (KBr)
discs. Chemical ionization (NH 3 gas) mass spectra were taken with a Finnigan Model 4023 GC/MS
spectrometer. Nuclear magnetic resonance spectra were obtained on a Bruker WM360 spectrometer (360
MHz for 1 H and 90.56 MHz for 13 C) in CDCl 3 and all chemical shifts are reported in parts per 1 million
relative to internal tetramethylsilane. Ultraviolet spectra were taken using a Beckman Model 25
Spectrophotometer. Optical rotations were determined on a Perkin-Elmer 241 polarimeter using a quartz
cell of 10 cm length and 1 ml volume.
LOLIOLIDE (1). Preparative HPLC (hexane/Et2O 1:1) of a 57 mg fraction of S. divinorum extract led to
isolation of 15 mg of 1 mp 154-155°C (recrystallized from hexane/Et2O). 1H NMR δ1.276 (3H, s, 1 β -
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