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Structures and absolute configurations of penicillactones A-C from an endophytic microorganism, Penicillium dangeardii Pitt.

Penicillactones A-C (1-3) are structurally related natural products with a spirocyclic anhydride structure and were isolated from the endophytic fungus Penicillium dangeardii Pitt. Penicillactones B and C showed inhibition of the release of β-glucuronidase from polymorphonuclear leukocytes with ED50 values of 2.58 and 1.57 μM. A 2D INADEQUATE experiment of 1 was performed at natural abundance to confirm the arrangement of its carbon skeleton. The configurations of 1-3 were established through extensive NMR spectroscopic analysis, selective structural modifications, and CD analysis.