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2002•Journal of Medicinal ChemistryRequires access

Biosynthesis of Hyperforin in Hypericum perforatum

Petra Adam, D. Arigoni, Adelbert Bacher, Wolfgang Eisenreich

Open publisher page 143 citations

Abstract

Cut sprouts of Hypericum perforatum were proffered solutions containing [1-(13)C]glucose or [U-(13)C(6)]glucose. Hyperforin was isolated and analyzed by quantitative NMR spectroscopy. The labeling patterns show that the biosynthesis of hyperforin involves five isoprenoid moieties, which are derived entirely or predominantly (>98%) via the deoxyxylulose phosphate pathway. The phloroglucinol moiety is generated via a polyketide type mechanism.

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What this paper is about

Cut sprouts of Hypericum perforatum were proffered solutions containing [1-(13)C]glucose or [U-(13)C(6)]glucose. Hyperforin was isolated and analyzed by quantitative NMR spectroscopy. The labeling patterns show that the biosynthesis of hyperforin involves five isoprenoid moieties, which are derived entirely or predominantly (>98%) via the deoxyxylulose phosphate pathway. The phloroglucinol moiety is generated via a polyketide type mechanism.

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Available abstract

Cut sprouts of Hypericum perforatum were proffered solutions containing [1-(13)C]glucose or [U-(13)C(6)]glucose. Hyperforin was isolated and analyzed by quantitative NMR spectroscopy. The labeling patterns show that the biosynthesis of hyperforin involves five isoprenoid moieties, which are derived entirely or predominantly (>98%) via the deoxyxylulose phosphate pathway. The phloroglucinol moiety is generated via a polyketide type mechanism.

Key concepts: Hyperforin, Phloroglucinol, Chemistry, Hypericum perforatum, Hypericin, Hypericum, Stereochemistry, Moiety

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