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The isolation and structure elucidation of four cytotoxic aromatic triterpenes [1-4] along with three known quinoid triterpenes [5-7] from the South American medicinal plants Maytenus ilicifolia and M. chuchuhuasca are described. The structures of these aromatic triterpenes contained aromatized A rings and C-6 oxygenated B rings, and were elucidated by 1H- and 13C-nmr spectroscopic studies and by X-ray crystallographic analysis of 3.

The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.

Seven new neo-clerodane diterpenes, salvidivins A (2), B, (3), C (4), and D (5), salvinorins H (6) and I (7), and divinatorin [corrected] F (8), along with eight known neo-clerodane diterpenes, salvinorins A (1)-F, divinatorins A and B, and seven other constituents, were isolated from the hallucinogenic sage Salvia divinorum. The structures of 1-7 were elucidated on the basis of 2D NMR spectroscopic studies.

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Structures of four triterpene dimers, cangorosins, isolated from Maytenus ilicifolia Mart., were previously reported to consist of two triterpene units joined by an ether bond formed between the two A rings. On the basis of detailed studies of their chemical and spectroscopic data, including inverse-detected 2D-NMR data, and comparisons with other known triterpene dimers, the structures of the cangorosins have been revised to triterpene dimers linked by two ether bridges between the two A rings for cangorosin B and between the A and the B rings for the cangorosin A series (cangorosin A, isocangorosin A, and 6‘,7‘-dihydroisocangorosin A).

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Psilocybe argentipes is a hallucinogenic mushroom. The present study examined the effects of P. argentipes on marble-burying behavior, which is considered an animal model of obsessive-compulsive disorder. P. argentipes significantly inhibited marble-burying behavior without affecting locomotor activity as compared with the same dose of authentic psilocybin. These findings suggest that P. argentipes would be efficient in clinical obsessive-compulsive disorder therapy.