New antimicrobial terpenoids and phloroglucinol glucosides from Syzygium szemaoense

Wen Xu; Junfeng Tan; Yu Mu; Dan Zheng; Xueshi Huang; Liya Li

doi:10.1016/j.bioorg.2020.104242

New antimicrobial terpenoids and phloroglucinol glucosides from Syzygium szemaoense

Bioorg Chem. 2020 Oct:103:104242. doi: 10.1016/j.bioorg.2020.104242. Epub 2020 Aug 28.

Authors

Wen Xu¹, Junfeng Tan¹, Yu Mu¹, Dan Zheng¹, Xueshi Huang², Liya Li³

Affiliations

¹ Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China.
² Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: huangxs@mail.neu.edu.cn.
³ Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, PR China. Electronic address: lyli@mail.neu.edu.cn.

PMID: 32916541
DOI: 10.1016/j.bioorg.2020.104242

Abstract

Six new terpenoids (1-6) and two new phloroglucinol glucosides (7 and 8) were isolated from the extract of Syzygium szemaoense leaves. Among the isolates, compounds 1 and 2 (named syzygiumursanolides A and B) were unusual 28-norursane type triterpenoids with 19(18→17)-abeo spirocyclic skeleton. And syzygiumone B (8) was rare ascorbyl-modified phloroglucinol glucoside. Their structures were elucidated on the basis of comprehensive 1D and 2D NMR, HRESIMS spectroscopic data analysis, as well as experimental and calculated ECD spectra and acid hydrolysis. Antimicrobial bioassay revealed that syzygiumursanolide D (4) displayed the most potent antifungal activities with MIC values ranging from 6.25 to 25 μg/mL against a panel of fungi.

Keywords: Antimicrobial activity; Phloroglucinol; Syzygium szemaoense; Terpenoid.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Antifungal Agents / chemistry
Antifungal Agents / isolation & purification
Antifungal Agents / pharmacology*
Aspergillus / drug effects
Bacillus subtilis / drug effects
Candida / drug effects
Cryptococcus neoformans / drug effects
Escherichia coli / drug effects
Glucosides / chemistry
Glucosides / isolation & purification
Glucosides / pharmacology
Microbial Sensitivity Tests
Phloroglucinol / analogs & derivatives*
Phloroglucinol / isolation & purification
Phloroglucinol / pharmacology*
Plant Leaves / chemistry
Staphylococcus aureus / drug effects
Syzygium / chemistry*
Terpenes / chemistry
Terpenes / isolation & purification
Terpenes / pharmacology*

Substances

Anti-Bacterial Agents
Antifungal Agents
Glucosides
Terpenes
Phloroglucinol