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Review
. 2022 Oct 28;85(10):2399-2405.
doi: 10.1021/acs.jnatprod.2c00618. Epub 2022 Sep 28.

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

Yoshihisa Asada  1 , Kouharu Otsuki  1 , Miki Morooka  1 , Li Huang  2 , Chin-Ho Chen  2 , Kazuo Koike  1 , Wei Li  1
Affiliations
Review

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

Yoshihisa Asada et al. J Nat Prod. .

Abstract

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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Figures

Figure 1.
Figure 1.
Skeleton of macrocyclic daphnane orthoesters.
Figure 2.
Figure 2.
Key 1H–1H COSY and HMBC correlations of compounds 1–3.
Figure 3.
Figure 3.
Key NOESY correlations of compounds 1–3.
Figure 4.
Figure 4.
Key 1H–1H COSY and HMBC correlations of compounds 4 and 5.
Figure 5.
Figure 5.
Key NOESY correlations of compounds 4 and 5.
See this image and copyright information in PMC

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