Cheimical constituents of Psilocybe samuiensis

Abstract

Mycelia and fermentation broth of hallucinogenic mushroom Psilocybe samuiensis a new species of Psilocybe mushroom found on buffalo dung from Samui island, Surat Thani province, Thailand were investigated. Two novel sesquiterpenoid compounds, ent-2,3-secoaromadendrane-2,10,12-triol (1) and ent-2,3-secoaromadendrane-2-methoxy-10,12-diol (2) were isolated from the extract of fermentation broth. Additionally compound 2 was synthesized by treatment of 1 with methanol and p-toluenesulfonic acid. The structure of both compounds were established by spectroscopic data (IR, MS and 1D and 2D NMR techniques including COSY, HSQC, HMBC and NOESY) and X-ray crystallographic data. Compound 1 was tested for cytotoxic activity against various human tumor cell lines including SW620 (colon), BT474 (breast), KATO-3 (gastric), HEP-G2 (hepatoma) and CHAGO (lung) and antimicrobial activity towards 5 microorganisms consisting of Bacillus subtilis, Staphyllococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans. The results showed that compound 1 was inactive against all of those tumor cell lines and those five microorganisms.