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

IF 3.4 2区 生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2025-07-01 Epub 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[7.5.1.04,9.01,11]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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兰开斯特金丝桃中含有双环聚戊烯基酰基间苯三酚支架的巯基萜类化合物及其抗炎活性
从兰开斯特金丝桃(Hypericum lancasteri,金丝桃科)中分离得到12个具有双环聚戊酰化酰基间苯三酚(BPAP)支架的未描述的双萜类化合物,(±)-lancasternoids A-D和lancasternoids E-H,以及14个已知的类似物,并进行了结构表征。(±)-Lancasternoids A-D是第一个以对映体形式存在的双环[3.2.1]辛烷型BPAP萜类化合物,而(±)-Lancasternoids A-C则是前所未有的5-草四环[7.5.1.04,9.01,11]五烷体系。Lancasternoids E-H是两对具有[3.3.1]型BPAP支架的外端。部分菌株在缺氧诱导因子-1α (HIF-1α)反应元件(HRE)荧光素酶检测中表现出抑制作用,uraloidin A进一步降低了脂多糖(LPS)诱导的促炎因子IL-1β在RAW 264.7细胞中的表达水平。
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来源期刊
Phytochemistry
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.
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