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

2.50
Hdl Handle:
http://hdl.handle.net/10033/558285
Title:
Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae).
Authors:
Surup, Frank; Kuhnert, Eric; Liscinskij, Elena; Stadler, Marc ( 0000-0002-7284-8671 )
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.
Affiliation:
Helmholtz Centre for Infection Research, Inhoffenstraße 7, 38124 Braunschweig, Germany.
Citation:
Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae). 2015: Nat Prod Bioprospect
Journal:
Natural products and bioprospecting
Issue Date:
16-Jun-2015
URI:
http://hdl.handle.net/10033/558285
DOI:
10.1007/s13659-015-0065-3
PubMed ID:
26077652
Type:
Article
ISSN:
2192-2195
Appears in Collections:
publications of the department of microbial drugs (MWIS)

Full metadata record

DC FieldValue Language
dc.contributor.authorSurup, Franken
dc.contributor.authorKuhnert, Ericen
dc.contributor.authorLiscinskij, Elenaen
dc.contributor.authorStadler, Marcen
dc.date.accessioned2015-06-19T11:22:49Zen
dc.date.available2015-06-19T11:22:49Zen
dc.date.issued2015-06-16en
dc.identifier.citationSilphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae). 2015: Nat Prod Bioprospecten
dc.identifier.issn2192-2195en
dc.identifier.pmid26077652en
dc.identifier.doi10.1007/s13659-015-0065-3en
dc.identifier.urihttp://hdl.handle.net/10033/558285en
dc.description.abstractA 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.en
dc.languageENGen
dc.titleSilphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae).en
dc.typeArticleen
dc.contributor.departmentHelmholtz Centre for Infection Research, Inhoffenstraße 7, 38124 Braunschweig, Germany.en
dc.identifier.journalNatural products and bioprospectingen

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