Hypoglycemic cucurbitane-type triterpenoids from fruits of Citrullus colocynthis

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2025-06-23 DOI:10.1016/j.phytochem.2025.114600

Hua-Wei Lv , Yu Wan , Wen-Lin Fan , Meng-Di Zhu , Qiao-Liang Wang , Zhong-Bo Zhou , Chang-Chun Chen , Hong Wang , Xing-Nuo Li

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Abstract

Three previously undescribed cucurbitacins J-L (1–3) and two undescribed cucurbitane-type triterpenoid glycosides (4–5) were isolated, along with seven known analogues, from the 95 % ethanol extract of the fruits of Citrullus colocynthis under the guidance of bioassay and molecular networking. The structures of these previously undescribed compounds were elucidated using HRESIMS, 1D and 2D nuclear magnetic resonance data analysis. Absolute configurations were determined through quantum chemical electronic circular dichroism calculations and acid hydrolysis analysis. Compounds 1, 3–4, and 6–11 elicited stimulatory effects on glucagon-like peptide-1 (GLP-1) secretion in Caco-2 cells. Compound 6 has a better effect in promoting GLP-1 secretion at low concentration, with a 1.5-fold changes in GLP-1 secretion compared to the basal group at 5 μM. Compound 8 promoted GLP-1 secretion in a dose-dependent manner, with a 1.54-fold changes in GLP-1 secretion in Caco-2 cells at 20 μM compared to the basal level. These compounds showed the potential to reduce blood glucose levels.

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从西瓜果实中提取的降糖葫芦烷型三萜

在生物测定和分子网络的指导下，从瓜泥95%乙醇提取物中分离得到3个未被描述的葫芦素J-L（1-3）和2个未被描述的葫芦烷型三萜苷（4-5），以及7个已知的类似物。这些先前描述的化合物的结构通过HRESIMS、1D和2D核磁共振数据分析得到了阐明。通过量子化学电子圆二色性计算和酸水解分析确定了绝对构型。化合物1、3-4和6-11对Caco-2细胞的胰高血糖素样肽-1 （GLP-1）分泌有刺激作用。化合物6在低浓度下促进GLP-1分泌的效果较好，在5 μM时，与基础组相比，GLP-1分泌变化了1.5倍。化合物8以剂量依赖的方式促进GLP-1的分泌，与基础水平相比，20 μM时Caco-2细胞中GLP-1的分泌变化为1.54倍。这些化合物显示出降低血糖水平的潜力。

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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.