Activity guided fractionations led to the isolation of two antitumor compounds 5a,8a-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-β-D-glucopyranoside and 22-dihydroergosteryl-3-O-β-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 mg/ml than its previously identified aglycone, 5a,8a-epidioxy-24(R)-methylcholesta-6,22-dien-3β-ol
antitumor activity, Cordyceps sinensis, steroidal glycosides, Cordyceps sinenis
NCBI PubMed ID: 10423860Publication DOI: 10.1016/s0031-9422(99)00128-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Botany, University of British Columbia, Vancouver, Canada, North American Reishi, Gibsons, British Columbia, Canada, Department of Medicine, Terry Fox Laboratory, University of British Columbia, Vancouver, Canada, North American Reishi, Gibsons, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, FTIR, extraction, optical rotation measurement, CC, HMBC, antitumor activity assay, HMQC, APT, HRMS