1H NMR guided isolation of flavans from Broussonetia papyrifera and their α-glucosidase inhibitory activity

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2026-02-01 Epub Date: 2025-10-21 DOI:10.1016/j.phytochem.2025.114714

Tingting Guo , Kepu Huang , Qingfang Wang , Chen Peng , Xingping Zhang , Congxi Gao , Kou Wang , Hongping He , Mingming Li

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Abstract

Six undescribed flavans (1–6) and four known analogues (7–10) were isolated from the leaves of Broussonetia papyrifera with the guidance of ¹H NMR. Among them, 1 and 2 were characterized as prenylflavan derivatives with hydroxymethyl and ethoxy moiety, respectively. Their structures were established through comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR. The absolute configurations were determined by theoretical calculations of electronic circular dichroism. Notably, compounds 5 and 6 exhibited superior α-glucosidase inhibitory activities with IC₅₀ values of 5.87 and 6.26 μM, respectively. Additionally, molecular docking and molecular dynamics simulations were performed using 5 and 6 with IMA1, an α-glucosidase derived from Saccharomyces cerevisiae, to analyze their potential binding sites.

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1H NMR引导下纸浆菌黄酮类化合物的分离及α-葡萄糖苷酶抑制活性研究。

利用1H NMR从纸莎草（Broussonetia papyrifera）叶中分离得到6个未描述的黄烷（1-6）和4个已知的类似物（7-10）。其中，1和2分别被表征为具有羟甲基和乙氧基片段的丙烯基黄烷衍生物。通过综合分析光谱数据，包括hremsims、1D和2D NMR，确定了它们的结构。通过电子圆二色性的理论计算确定了绝对构型。其中化合物5和6具有较好的α-葡萄糖苷酶抑制活性，IC50值分别为5.87和6.26 μM。此外，利用5和6与酿酒酵母α-葡萄糖苷酶IMA1进行分子对接和分子动力学模拟，分析其潜在结合位点。

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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.