Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

Xing Wei Yang, Robert B. Grossman, Gang Xu

Research output: Contribution to journalReview articlepeer-review

185 Scopus citations

Abstract

Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structure and bioactivity diversity. This review discusses the progress of research into the chemistry and biological activity of 421 natural PPAPs in the past 11 years as well as in-depth studies of biological activities and total synthesis of some PPAPs isolated before 2006. We created an online database of all PPAPs known to date at http://www.chem.uky.edu/research/grossman/PPAPs. Two subclasses of biosynthetically related metabolites, spirocyclic PPAPs with octahydrospiro[cyclohexan-1,5′-indene]-2,4,6-trione core and complicated PPAPs produced by intramolecular [4 + 2] cycloadditions of MPAPs, are brought into the PPAP family. Some PPAPs' relative or absolute configurations are reassigned or critically discussed, and the confusing trivial names in PPAPs investigations are clarified. Pharmacologic studies have revealed a new molecular mechanism whereby hyperforin and its derivatives regulate neurotransmitter levels by activating TRPC6 as well as the antitumor mechanism of garcinol and its analogues. The antineoplastic potential of some type B PPAPs such as oblongifolin C and guttiferone K has increased significantly. As a result of the recent appearances of innovative synthetic methods and strategies, the total syntheses of 22 natural PPAPs including hyperforin, garcinol, and plukenetione A have been accomplished.

Original languageEnglish
Pages (from-to)3508-3558
Number of pages51
JournalChemical Reviews
Volume118
Issue number7
DOIs
StatePublished - Apr 11 2018

Bibliographical note

Funding Information:
The work was financially supported by the Natural Sciences Foundation of Yunnan Province (No. 2015FA032, 2016FB017), foundation from the Youth Innovation Promotion Association CAS to X.W.Y. (No. 2016350), and foundation from Kunming Institute of Botany (KIB2017001). The authors thank Prof. Hong-Xi Xu, Drs. Juan Huang and Liang-Qun Li, and Mr. Yao-Tao Duan for their valuable suggestions during the preparation of this review. Thanks also to Dr. Helen Jacobs for her contributions to this project.

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

  • Chemistry (all)

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