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J. Antibiot. 58(12): 828831, 2005
THE JOURNAL OF
NOTE
ANTIBIOTICS
A New Cytotoxic Lanostane Triterpenoid from the Basidiomycete Hebeloma versipelle
Hong-Jun Shao, Chen Qing, Fei Wang, Yan-Li Zhang, Du-Qiang Luo, Ji-Kai Liu
Received: July 28, 2005 / Accepted: December 5, 2005 Japan Antibiotics Research Association
Abstract A new cytotoxic lanostane triterpenoid, 24(E)-3b -hydroxylanosta-8,24-dien-26-al-21-oic acid (1), was isolated from the fruiting bodies of the mushroom Hebeloma versipelle. The structure was elucidated on the basis of spectroscopic studies including 2D NMR experiments. Compound 1 moderately inhibited the growth of several tumor cell lines (IC50 10 25.0m g/ml).
Keywords lanostane triterpenoid, Hebeloma versipelle, basidiomycete, cytotoxicity
Introduction
The fungi of the genus Hebeloma belonging to the family Cortinariaceae (Basidiomycetes) comprise many inedible or toxic species, but a few species were investigated with respect to their secondary metabolites. From H. crustulinirm and H. sinapizans, a cytotoxic triterpene has been isolated [1], and several new lanostane-type triterpene esters have also been found in H. spoliatum and H. senescens [2 4], and fourteen neurotoxic cucurbitane-type glycosides have been obtained from the poisonous mushroom H. vinosophyilurn [5 7]. Besides triterpenoids a few new caryophyllenes, 6,7-seco-caryophyllenes and related sesquiterpenoids were isolated from the liquid cultures of H. longicaudum [8 10]. As a part of our studies on biologically active substances from higher fungi in Yunnan Province, China [11 16], the fruiting bodies of the mushroom H. versipelle were investigated. In this report, we described the isolation, structural elucidation and
cytotoxic activity of a new lanostanoid, namely, 24(E)-3b -hydroxylanosta-8,24-dien-26-al-21-oic acid (Fig. 1).
Materials and Methods
General
Melting point was obtained on an XRC-1 micro-melting point apparatus and uncorrected. Optical rotations were measured on a Horiba SEPA-300 polarimeter. IR spectra were obtained on a Tensor 27 with KBr pellets. UV spectra were recorded on a Shimadzu UV-2401PC spectrophotometer. NMR spectra were recorded on Bruker DRX-500 spectrometer in C5D5N solvent. EI-MS was recorded with a VG Autospec-3000 spectrometer and
HRESI-MS was recorded with an API QSTAR Pulsar 1 spectrometer.
Silica gel (200 300 mesh, Qingdao Marine Chemical Inc., China) and Sephadex LH-20 (Amersham Biosciences, Sweden) were used for column chromatography. Fractions were monitored by TLC and spots were visualized by heating silica gel plates sprayed with 10% H2SO4 in ethanol.
Mushroom Material
The fresh fruiting bodies...