Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae).
dc.contributor.author | Surup, Frank | |
dc.contributor.author | Kuhnert, Eric | |
dc.contributor.author | Liscinskij, Elena | |
dc.contributor.author | Stadler, Marc | |
dc.date.accessioned | 2015-06-19T11:22:49Z | en |
dc.date.available | 2015-06-19T11:22:49Z | en |
dc.date.issued | 2015-06-16 | en |
dc.identifier.citation | Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae). 2015: Nat Prod Bioprospect | en |
dc.identifier.issn | 2192-2195 | en |
dc.identifier.pmid | 26077652 | en |
dc.identifier.doi | 10.1007/s13659-015-0065-3 | en |
dc.identifier.uri | http://hdl.handle.net/10033/558285 | en |
dc.description.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 α-eleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported. | |
dc.language | ENG | en |
dc.title | Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae). | en |
dc.type | Article | en |
dc.contributor.department | Helmholtz Centre for Infection Research, Inhoffenstraße 7, 38124 Braunschweig, Germany. | en |
dc.identifier.journal | Natural products and bioprospecting | en |
refterms.dateFOA | 2018-06-13T00:27:45Z | |
html.description.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 α-eleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported. |