Sparassis crispa (SC), known as Hanabiratake in Japanese, is an edible mushroom with various medicinal properties. We isolated 3 novel phthalides, designated hanabiratakelide A (1), B (2), and C (3), from the SC fruit body. In this investigation, 3 known phthalides (4-6), ubiquinone-9, and 2 known unsaturated fatty acids were also isolated. Their structures were elucidated primarily through extensive NMR experiments. The isolated compounds 1-6 were tested for their anti-oxidant activity. The in vitro superoxide dismutase-like activity of the 3 hanabiratakelides was stronger than that of vitamin C. The compounds also exerted inhibitory effects on lipopolysaccharide-stimulated nitric oxide and prostaglandin E2 production by a murine macrophage cell line, RAW264. In addition, the growth of the colon cancer cell lines Caco-2 and colon-26 was significantly inhibited by treatment with the 3 hanabiratakelides. In vivo, the frequency of azoxymethane-induced aberrant crypt foci was reduced in SC-fed F344/N rats compared to rats fed a standard diet. In conclusion, 3 novel phthalides, hanabiratakelides, derived from SC were shown to possess anti-oxidant, anti-inflammatory, and anti-tumor activity.

From Cladonia rangiferina were isolated two novel abietane diterpenoids, hanagokenols A (1) and B (2). Also in this investigation, four known abitetane diterpenoids (3-6), four known labdane diterpenoids (7-10), one known isopimarane diterpenoid (11), and six known aromatic compounds were isolated. These structures were elucidated primarily through extensive NMR experiments. Hanagokenol A (1) was a unique abietane diterpene having an ether linkage between C-6 and C-18 of sugiol. Hanagokenol B (2) is also a unique secoabietane diterpene, having g g-lactone which occurred by cleavage and subsequently oxidation between C-6/C-7 of 12-hydroxydehydroabietinol. Furthermore, all the isolated compounds (1-17) were tested for the antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).

A new aromatic derivative, 5-(3,4-dihydroxyphenyl)-3-methylcyclohex-2-enone (1), and three known compounds, peltigerine, solorinine, and phenyl butanoid, were isolated from the MeOH extract of the lichen Peltigera dolichorrhiza (Peltigeraceae). Their structures were determined by 1D and 2D nuclear magnetic resonance and mass spectroscopy analysis.

isolation, structure elucidation and antimicrobial activity of the unique abietane diterpenes hanagokenol A (I) and B (II).]. -(YOSHIKAWA*, K.; KOKUDO, N.; TANAKA, M.; NAKANO, T.; SHIBATA, H.; ARAGAKI, N.; HIGUCHI, T.; HASHIMOTO, T.; Chem. Pharm. Bull. 56 (2008) 1, 89-92; Fac. Pharm. Sci.,

During the search for secondary metabolites with antiproliferative activity, six new lanostane triterpenoids, tyrosamic acids A-F (1-6) together with ten known compounds (7-16), were isolated from the fruiting body of Tyromyces sambuceus. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation and the structure of 3 was further confirmed by single-crystal X-ray data analyses. All lanostane triterpenoids (1-16) possesses a carboxy group at C-20 position and their strength of antiproliferative activity was affected by the presence or absence of a hydroxy group at C-15 position and at the side chain. Four of the compounds (1, 6, 10, 14) showed antiproliferative activities against human cancer cell lines with IC 50 values of 16.8-48.3 M (HL-60).