Enantiomeric pairs of macrocyclic acylphloroglucinols from Syzygium szemaoense

Jin-Chang Huang; Hong-Hong Xu; Qing Shi; Chun Lei; Jing-Ya Li; Ai-Jun Hou

doi:10.1016/j.bioorg.2023.106381

Enantiomeric pairs of macrocyclic acylphloroglucinols from Syzygium szemaoense

Bioorg Chem. 2023 Mar:132:106381. doi: 10.1016/j.bioorg.2023.106381. Epub 2023 Jan 20.

Authors

Jin-Chang Huang¹, Hong-Hong Xu², Qing Shi¹, Chun Lei³, Jing-Ya Li⁴, Ai-Jun Hou⁵

Affiliations

¹ 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.
² Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
³ School of Pharmacy, Fudan University, Shanghai 201203, People's Republic of China.
⁴ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China. Electronic address: jyli@simm.ac.cn.
⁵ 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: ajhou@sjtu.edu.cn.

PMID: 36706532
DOI: 10.1016/j.bioorg.2023.106381

Abstract

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.

Keywords: ATP citrate lyase; Acylphloroglucinol enantiomers; Death-associated protein kinase-related apoptosis inducing protein kinase 2; Syzygium szemaoense.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Molecular Structure
Spectrum Analysis
Syzygium*