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Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new pentacyclic ring system from the leaf-associated fungus Delitschia sp. FL1581.

ABSTRACT: Delitschiapyrone A (1), an ?-pyrone-naphthalenone adduct with an unprecedented pentacyclic ring system, was isolated from a solid culture of the leaf-associated fungus Delitschia sp. FL1581. The structure of 1 was elucidated by spectroscopic analysis and X-ray crystallography, and its absolute configuration was defined by experimental and calculated ECD. Biosynthetically, the unique 6/6/5/7/6 pentacyclic core of 1 may be formed by an intermolecular Diels-Alder-type addition of the precursors derived from (1'R)-2',3'-dihydropyrenocine C (2) and 6-ethyl-2,7-dimethoxyjuglone (3) found to co-occur with 1 in this fungus.

SUBMITTER: Luo JG

PROVIDER: S-EPMC4251527 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new pentacyclic ring system from the leaf-associated fungus Delitschia sp. FL1581.

Luo Jian-Guang JG Wang Xiao-Bing XB Xu Ya-Ming YM U'Ren Jana M JM Arnold A Elizabeth AE Kong Ling-Yi LY Gunatilaka A A Leslie AA

Organic letters 20141103 22

Delitschiapyrone A (1), an α-pyrone-naphthalenone adduct with an unprecedented pentacyclic ring system, was isolated from a solid culture of the leaf-associated fungus Delitschia sp. FL1581. The structure of 1 was elucidated by spectroscopic analysis and X-ray crystallography, and its absolute configuration was defined by experimental and calculated ECD. Biosynthetically, the unique 6/6/5/7/6 pentacyclic core of 1 may be formed by an intermolecular Diels-Alder-type addition of the precursors der ...[more]

PMID: 25365379

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