Antitermite activity of beta-caryophyllene epoxide and episulfide.

Caryophyllene-6,7-epoxide and caryophyllene-6,7-episulfide can be easily synthesized from beta-caryophyllene by autoxidation or episulfidation. The bioactivities of beta-caryophyllene and its derivatives were investigated against the subterranean termite Reticulitermes speratus Kolbe. The antifeedant, feeding, and termiticidal activities of each compound were tested using no-choice, dual-choice, and non-contact methods.

Antifungal abietane-type diterpenes from the cones of Taxodium distichum Rich.

The chemical composition of Taxodium distichum cones and the antifungal activities of twelve diterpenoids against two wood decay fungi, Trametes versicolor (white-rot) and Fomitopsis palustris (brown-rot) were examined. The chemical composition of the major extractive fraction, the n-C(6)H(14) extract, was evaluated and its antifungal properties were identified. Twelve diterpenoids including ten abietane-type components were isolated from the n-C(6)H(14) extract: 6,7-dehydroferruginol (1), ferruginol (2), 6,7-dehydroroyleanone (3), sandaracopimaric acid (4), taxodione (5), taxodal (6), taxodone (7), sugiol (8), xanthoperol (9), salvinolone (10), 5,6-dehydrosugiol (11), and 14-deoxycoleon U (12).

Bioactivity of latifolin and its derivatives against termites and fungi.

Latifolin (1) and its derivatives were investigated with the aim of confirming the correlation between bioactivity (antitermite and antifungal activity) and chemical structure. Termite mortality in response to the derivatives 2'-O-methyllatifolin (2), latifolin dimethyl ether (4), and latifolin diacetate (5) increased 2-fold compared to compound 1. The mortality rate from 5-O-methyllatifolin (3) was not different from 1.

Antitermitic activities of abietane-type diterpenes from Taxodium distichum cones.

Eight known abietane-type diterpenes were isolated from the weak acidic fraction of the n-hexane extract from cones of Taxodium distichum, one of the extant, living fossil conifers. They were identified as 6,7-dehydroroyleanone (1), taxodal (2), taxodione (3), salvinolone (4), 14-deoxycoleon U (5), 5,6-dehydrosugiol (6), sandaracopimaric acid (7), and xanthoperol (8). The structures of these compounds were determined by comparison of NMR spectral data with published data.

Three lanostane triterpenoids, aeruginosols A, B and C, from the fruiting bodies of Stropharia aeruginosa.

Phytochemical analysis of the MeOH extract of the fruiting bodies of Stropharia aeruginosa resulted in the isolation of three lanostane triterpenoids, aeruginosols A, B and C. The structures of the new compounds were determined by spectroscopic analysis. The biological activities of aeruginosols A, B and C were examined by bioassay with lettuce seedling.

Isolation and structure elucidation of neofusapyrone from a marine-derived Fusarium species, and structural revision of fusapyrone and deoxyfusapyrone.

Three polyketides containing a pyrone ring, neofusapyrone, fusapyrone, and deoxyfusapyrone, were isolated from the marine-derived fungus Fusarium sp. FH-146. Their structures were determined by extensive ID- and 2D-NMR and MS spectral analyses.

Three lanostane triterpenoids from the fruiting bodies of Stropharia aeruginosa.

Three new lanostane triterpenoids, aeruginosic acid derivatives, were isolated from the fruiting bodies of Stropharia aeruginosa and their structures were determined on the basis of spectral data.

Three oxygenated cyclohexenone derivatives produced by an endophytic fungus.

Three cyclohexenone derivatives, (4S,5S,6S)-5,6-epoxy-4-hydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (1), (4R,5R)-4,5-dihydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (2), and (4R,5S,6R)-4,5,6-trihydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (3), were isolated from unpolished rice fermented with an xylariaceous endophytic fungus (strain YUA-026). The structures of three compounds were established on the basis of spectroscopic analyses and chemical conversion. The minimum inhibitory concentrations of 1 and 3 were 100 microg/ml and 400 microg/ml against Staphylococcus aureus, 100 microg/ml and 200 microg/ml against Pseudomonas aeruginosa, and 200 microg/ml and >400 microg/ml against Candida albicans, respectively.