Antitumor sterols from the mycelia of Cordyceps sinensis.
Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-glucopyranoside and 22-dihydroergosteryl-3-O-beta-D-glucopyranoside were also isolated. The structures of hitherto unknown sterols were established by 1D and 2D NMR spectroscopic techniques with the former synthesized in order to confirm the identity of the sugar moiety by chemical correlation. The glycosylated form of ergosterol peroxide was found to be a greater inhibitor to the proliferation of K562, Jurkat, WM-1341, HL-60 and RPMI-8226 tumor cell lines by 10 to 40% at 10 micrograms/ml than its previously identified aglycone, 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-ol.
Bok
J W
JW
Department of Botany, University of British Columbia, Vancouver, Canada.
Lermer
L
L
Chilton
J
J
Klingeman
H G
HG
Towers
G H
GH
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification*; D002775:Cholestadienols / Q000737:chemistry / Q000302:isolation & purification*; D002776:Cholestanes; D005658:Fungi / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D013055:Spectrophotometry, Infrared
C121077:5,6-epoxy-24-methylcholesta-7,22-dien-3-ol; C121076:5,8-epidioxy-24-methyl-cholesta-6,22-dien-3-glucopyranoside; D000972:Antineoplastic Agents, Phytogenic; D002775:Cholestadienols; D002776:Cholestanes; D012503:Saponins