2. Academic Validation
  3. Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

  • J Nat Prod. 2019 Oct 25;82(10):2852-2858. doi: 10.1021/acs.jnatprod.9b00596.
Katsunori Miyake 1,  Chihiro Morita 2,  Airi Suzuki 2,  Natsuko Matsushita 2,  Yohei Saito 2,  Masuo Goto 3,  David J Newman 4,  Barry R O'Keefe 5 6,  Kuo-Hsiung Lee 3 7,  Kyoko Nakagawa-Goto 2 3
Affiliations

Affiliations

  • 1 Tokyo University of Pharmacy and Life Sciences , Hachioji , Tokyo 192-0392 , Japan.
  • 2 School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences , Kanazawa University , Kanazawa , 920-1192 , Japan.
  • 3 Natural Products Research Laboratories, UNC Eshelman School of Pharmacy , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-7568 , United States.
  • 4 NIH Special Volunteer , Wayne , Pennsylvania 19087 , United States.
  • 5 Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis , National Cancer Institute, NCI at Frederick , Frederick , Maryland 21702-1201 , United States.
  • 6 Molecular Targets Program, Center for Cancer Research , National Cancer Institute, NCI at Frederick , Frederick , Maryland 21702-1201 , United States.
  • 7 Chinese Medicine Research and Development Center , China Medical University and Hospital , Taichung , 40447 , Taiwan.
PMID: 31550158 DOI: 10.1021/acs.jnatprod.9b00596
Abstract

The isolation of 12 secondary metabolites, including seven new acetophenone monomers, from the 50% CH3OH/CH2Cl2 extract (N089419-L/6) of Acronychia trifoliolata was reported previously. In the present work, three new prenylated acetophenone dimers (1-3) and five known dimers (4-8) were isolated, and their structures were elucidated by using various NMR spectroscopic techniques and HRMS. Among the new dimers, an unprecedented 4-isobutyl-3-isopropyltetrahydro-2H-pyran ring was observed in the structure of 1. This study is the first to report the formation of a 2H-pyran ring between two prenylated acetophloroglucinols. Only four related dimers have been reported before, and they were formylated phloroglucinol dimers from the family Eucalypteae. Compounds 2 and 3 are acrovestone-like dimers, and the structure of 3 was confirmed by total synthesis. The evaluation of the antiproliferative activity of isolated and synthesized acrovestone-like dimers indicated that a double bond in the prenyl-like moiety as found in the more active compounds might be important for mediating activity, while the pendant isobutyl group seems to be less important.

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