Enantiomeric pairs of macrocyclic acylphloroglucinols from Syzygium szemaoense.

Bioorg Chem

School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China; School of Pharmacy, Fudan University, Shanghai 201203, People's Republic of China. Electronic address:

Published: March 2023

Two enantiomeric pairs of macrocyclic acylphloroglucinols (1a/1b and 2a/2b) with an unprecedented carbon skeleton featuring a bicyclo[12.3.1]octadecane core, together with an undescribed biogenetically related long-chain acylphloroglucinol (3), were isolated from Syzygium szemaoense. Their structures were fully established by spectroscopic method, X-ray crystallographic analysis, and ECD calculation. Compounds 1b and 2a/2b exhibited inhibition against death-associated protein kinase-related apoptosis inducing protein kinase 2 (DRAK2) and ATP citrate lyase (ACLY), respectively.

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http://dx.doi.org/10.1016/j.bioorg.2023.106381DOI Listing

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