title: Herbarone, a rearranged heptaketide derivative from the sea hare associated fungus Torula herbarum.
abstract: Herbarone (1), a novel heptaketide with a tetrahydro-5,9-methanobenzo[8]annulen-10(5H)-one skeleton, together with the new ent-astropaquinones B (2) and C (3) and four known pyranonaphthoquinones (4-7), was isolated from the sea hare associated fungus Torula herbarum. The structures of the new compounds were elucidated by detailed spectroscopic analysis, and the absolute configurations were determined by solution TDDFT/ECD calculations. Absolute configurations of the known compounds were studied by ECD measurements and calculations. The isolation of heptaketide 1 suggests that an intramolecular aldol reaction takes place to form the tricyclic scaffold.
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, People's Republic of China.
authors.forename: Wan-Li
authors.initials: WL
authors.lastname: Geng
authors.forename: Xian-You
authors.initials: XY
authors.lastname: Wang
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.forename: Hua
authors.initials: H
authors.lastname: Tang
authors.forename: Barbara
authors.initials: B
authors.lastname: Schulz
authors.forename: Peng
authors.initials: P
authors.lastname: Sun
authors.forename: Wen
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001048:Aplysia / Q000382:microbiology*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002681:China; D003454:Cryptococcus / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D001643:Bridged Bicyclo Compounds; D009285:Naphthoquinones; C577719:ent-astropaquinone B; C577720:ent-astropaquinone C; C577718:herbarone