Isolation and Biomimetic Oxidation of Prenylbruceol A, an Anticipated Meroterpenoid Natural Product from Philotheca myoporoides

Reinvestigation of the coumarin meroterpenoids of Philotheca myoporoides using pressurized hot water extraction (PHWE) procedures led to the isolation of prenylbruceol A, a proposed biosynthetic precursor of seven previously reported bruceol derivatives, prenylbruceols B–H. Protobruceol-I, ostruthin...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-07, Vol.83 (7), p.2305-2309
Main Authors: Day, Aaron J, George, Jonathan H
Format: Article
Language:English
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Summary:Reinvestigation of the coumarin meroterpenoids of Philotheca myoporoides using pressurized hot water extraction (PHWE) procedures led to the isolation of prenylbruceol A, a proposed biosynthetic precursor of seven previously reported bruceol derivatives, prenylbruceols B–H. Protobruceol-I, ostruthin, dipetalactone, and a new dihydrocoumarin natural product were isolated alongside prenylbruceol A. A biomimetic singlet oxygen ene reaction of prenylbruceol A allowed the semisynthesis of prenylbruceols B, C, and D.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.0c00348