4.7 Article

Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 85, Issue 10, Pages 2399-2405

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00618

Keywords

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Funding

  1. Japan Society for the Promotion of Science KAKENHI [21K06619]
  2. Japan Science Society [2021-3002]
  3. United States National Institute of Allergy and Infectious Diseases (NIAID) [R01 AI165473]

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Edgeworthianins A-E, a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring structure formed from a C14 aliphatic chain, were isolated from Edgeworthia chrysantha. Compounds 2, 4, and 5 showed potent anti-HIV activity against HIV-1 infection of MT4 cells, with EC50 values of 29.3, 8.4, and 2.9 nM, respectively.
Edgeworthianins A-E (1-5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. These compounds broaden the findings of the structure-activity relationship of macrocyclic daphnane orthoesters for further anti-HIV drug development.

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