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A roselle (Hibiscus sabdariffa Linn.) tea extract was found to have high inhibitory activity against porcine pancreatic alpha-amylase. Hibiscus acid and its 6-methyl ester were respectively isolated as active principles from the 50% methanol and acetone extracts of roselle tea. The activity of each isolate was compared to that of structurally related citric acid, a previously known inhibitor of fungal alpha-amylase.

[Structure: see text]. Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of 1 with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).

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