title: Botryane, noreudesmane and abietane terpenoids from the ascomycete Hypoxylon rickii.
abstract: In the course of our screening for new bioactive natural products, a culture of Hypoxylon rickii, a xylariaceous ascomycete collected from the Caribbean island Martinique, was identified as extraordinary prolific producer of secondary metabolites. Ten metabolites of terpenoid origin were isolated from submerged cultures of this species by preparative HPLC. Their structures were elucidated using spectral techniques including 2D NMR and HRESIMS. Three of the compounds were elucidated as new botryanes (1-3) along with three known ones, i.e. (3aS)-3a,5,5,8-tetramethyl-3,3a,4,5-tetrahydro-1H-cyclopenta[de]isochromen-1-one (4), (3aS,8R)-3a,5,5,8-tetramethyl-3,3a,4,5,7,8-hexahydro-1H-cyclopenta[de]isochromen-1-one (5) and botryenanol (6). Further three new sesquiterpenoids featured a 14-noreudesmane-type skeleton and were named hypoxylan A-C (7-9); the diterpenoid rickitin A (10) contains an abietane-type backbone. Compounds 1, 2, 3, 7, and 10 showed cytotoxic effects against murine cells.
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Eric
authors.initials: E
authors.lastname: Kuhnert
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Surup
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Vincent
authors.initials: V
authors.lastname: Wiebach
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Steffen
authors.initials: S
authors.lastname: Bernecker
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Stadler
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013729:Terpenes / Q000302:isolation & purification / Q000378:metabolism; D014900:West Indies; D013098:Xylariales / Q000737:chemistry*
chemical_list: D045784:Abietanes; D013729:Terpenes
keywords: Abietane; Ascomycetes; Biodiversity; Botryane; Endophytes; Eudesmane; Hypoxylon; Secondary metabolites; Structure elucidation; Terpenes; Terpenoids; Xylariaceae; Xylariales