title: Isolation and X-ray structure analysis of citreohybridonol from marine-derived Penicillium atrovenetum.
abstract: The anti-neuroinflammatory meroterpenoid citreohybridonol was isolated for the first time from a sponge-derived fungus Penicillium atrovenetum. In this study, in addition to isolation and structure featuring, its unambiguous absolute configuration was determined exclusively by single crystal X-ray diffraction. The C-17-keto tautomer was clearly observed in X-ray analysis. The substance crystallises in the monoclinic space group P21with a = 10.7496(5) Å, b = 14.3286(7) Å, c = 17.4909(8) Å, β = 103.235(2)°, V = 2622.5(2) Å3, Z = 2, Dcalcd= 1.280 g/cm3. The chirality of the asymmetric carbon atoms was as follows: C3 (S), C5 (R), C6 (S), C8 (S), C9 (R), C10 (R), C13 (R), C14 (R).
authors.affiliation: a Institute of Pharmaceutical Biology and Biotechnology , Heinrich-Heine University , Düsseldorf , Germany.|b Faculty of Fisheries , İzmir Katip Çelebi University , İzmir , Turkey.
authors.forename: Ferhat Can
authors.initials: FC
authors.lastname: Özkaya
authors.affiliation: a Institute of Pharmaceutical Biology and Biotechnology , Heinrich-Heine University , Düsseldorf , Germany.|c Faculty of Pharmacy, Department of Pharmacognosy , Mansoura University , Mansoura , Egypt.
authors.forename: Weaam
authors.initials: W
authors.lastname: Ebrahim
authors.affiliation: d Institute of Inorganic and Structural Chemistry , Heinrich-Heine University , Düsseldorf , Germany.
authors.forename: Maximilian
authors.initials: M
authors.lastname: Klopotowski
authors.affiliation: a Institute of Pharmaceutical Biology and Biotechnology , Heinrich-Heine University , Düsseldorf , Germany.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Liu
authors.affiliation: d Institute of Inorganic and Structural Chemistry , Heinrich-Heine University , Düsseldorf , Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Janiak
authors.affiliation: a Institute of Pharmaceutical Biology and Biotechnology , Heinrich-Heine University , Düsseldorf , Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
mesh_terms: D000730:Androstadienes / Q000737:chemistry* / Q000302:isolation & purification*; D059001:Aquatic Organisms; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000730:Androstadienes; C000607874:citreohybridonol
keywords: Citreohybridonol; X-ray; absolute configuration; marine-derived fungi