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Herbarone, a Rearranged Heptaketide Derivative from the Sea Hare Associated Fungus Torula herbarum
journal contribution
posted on 2012-10-26, 00:00 authored by Wan-Li Geng, Xian-You Wang, Tibor Kurtán, Attila Mándi, Hua Tang, Barbara Schulz, Peng Sun, Wen ZhangHerbarone (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.
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calculationheptaketide 1tricyclic scaffoldskeletonTDDFTAbsolute configurationspyranonaphthoquinonesea haretetrahydrocompoundRearranged HeptaketideFunguintramolecular aldol reactionfungus Torula herbarumHerbaroneAssociatedspectroscopic analysisisolationHaresolutionherbarumHerbaroneECD measurementsnovel heptaketide