Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)

doi:10.1007/s13659-015-0065-3

Abstract

Abstract: A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC-MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene(1), 9-hydroxysilphiperfol-6-en-13-oic acid(2), 2-hydroxysilphiperfol-6-en-13-oic acid(3) and 15-hydroxysilphiperfol-6-en-13-oic acid(4). For compounds 2-4 we propose the trivial names rickinic acids A-C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu),(+)-ramulosin and aeleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.

Key words: Hypoxylon, Xylariaceae, Natural products, Secondary metabolites, Structure elucidation

摘要： A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC-MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene(1), 9-hydroxysilphiperfol-6-en-13-oic acid(2), 2-hydroxysilphiperfol-6-en-13-oic acid(3) and 15-hydroxysilphiperfol-6-en-13-oic acid(4). For compounds 2-4 we propose the trivial names rickinic acids A-C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu),(+)-ramulosin and aeleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.

关键词: Hypoxylon, Xylariaceae, Natural products, Secondary metabolites, Structure elucidation

Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler. Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)[J]. Natural Products and Bioprospecting, 2015, 5(3): 167-173.

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