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Research Progress of Polycyclic Polyprenylated Acylphloroglucinols
Xing-Wei Yang1, Robert B Grossman2, Gang Xu1
1State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry , Kunming 650201 , People's Republic of China.
Chemical Reviews
|February 21, 2018
Summary
This review summarizes 421 polycyclic polyprenylated acylphloroglucinols (PPAPs), detailing their chemistry, bioactivity, and synthesis. New insights reveal PPAP mechanisms in neurotransmitter regulation and antitumor activity, expanding their therapeutic potential.
Area of Science:
- Natural Product Chemistry
- Medicinal Chemistry
- Organic Synthesis
Background:
- Polycyclic polyprenylated acylphloroglucinols (PPAPs) are diverse hybrid natural products derived from mevalonate/methylerythritol phosphate and polyketide pathways.
- Research has identified 421 natural PPAPs with varied structures and bioactivities, necessitating a comprehensive review.
- Previous studies focused on PPAPs isolated before 2006, with limited exploration of newer compounds.
Purpose of the Study:
- To review advancements in the chemistry and biological activity of 421 natural PPAPs over the last 11 years.
- To consolidate information on biological activities and total synthesis of previously isolated PPAPs.
- To establish a comprehensive online database for all known PPAPs.
Main Methods:
- Literature review of research on PPAPs published within the last 11 years.
- In-depth analysis of biological activities and total synthesis studies of PPAPs isolated before 2006.
- Creation of an online database (http://www.chem.uky.edu/research/grossman/PPAPs) for cataloging known PPAPs.
Main Results:
- The PPAP family now includes spirocyclic PPAPs and complex PPAPs formed via intramolecular [4 + 2] cycloadditions.
- Reassignment and critical discussion of relative/absolute configurations and clarification of trivial names for several PPAPs.
- Pharmacological studies identified hyperforin's TRPC6 activation mechanism for neurotransmitter regulation and garcinol's antitumor mechanism.
- Significant increase in the antineoplastic potential of type B PPAPs, such as oblongifolin C and guttiferone K.
- Successful total synthesis of 22 natural PPAPs, including hyperforin, garcinol, and plukenetione A, driven by innovative synthetic strategies.
Conclusions:
- This review provides a comprehensive overview of PPAP research, encompassing chemistry, bioactivity, and synthesis.
- New PPAP subclasses and clarified nomenclature enhance understanding of this natural product class.
- Identified molecular mechanisms and demonstrated antineoplastic potential highlight PPAPs as promising therapeutic agents.
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