Meroterpenoids with bicyclic polyprenylated acylphloroglucinol scaffold and anti-inflammatory activity from Hypericum lancasteri

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2025-03-17 DOI:10.1016/j.phytochem.2025.114484

Jin-Qiu You , Yun-Qi Jin , Yu-Meng Miao , Xin-Yu Sun , Jia-Yu Yang , Jin-Chang Huang , Jing-Ya Li , Ai-Jun Hou

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Abstract

Twelve undescribed meroterpenoids possessing bicyclic polyprenylated acylphloroglucinol (BPAP) scaffold, (±)-lancasternoids A–D and lancasternoids E–H, together with fourteen known analogues, were isolated from Hypericum lancasteri (Hypericaceae) and structurally characterized. (±)-Lancasternoids A–D are the first examples of bicyclo[3.2.1]octane-type BPAP meroterpenoids present as enantiomeric pairs, while (±)-lancasternoids A–C incorporate an unprecedented 5-oxatetracyclo[7.5.1.0^4,9.0^1,11]pentadecane system. Lancasternoids E–H are two pairs of epimers with [3.3.1]-type BPAP scaffold. Some of the isolates showed inhibition in hypoxia-inducible factor-1α (HIF-1α) responsive element (HRE) luciferase assay, and uraloidin A further decreased the lipopolysaccharide (LPS)-induced pro-inflammatory factor IL-1β expression level in RAW 264.7 cells.

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.