Anti-diabetic sesquiterpenoids from the heartwood of Entandrophragma cylindricum

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-03-29 DOI:10.1016/j.fitote.2025.106515

Hong-Yan Mu , Kai-Wen Kang , Yan Zhang , Ju-Cai Xu , Dong-Li Li , Jing-Wei Jin , Jia-Le Gan , Hong-Guang Li , Li-She Gan

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Abstract

()-(7S,8S)-10,11-dihydro-curcumene-3,8-diol (1) and one new cadinane-type sesquiterpenoid, ()-(1R,4S,6S,7S,10R)-cadinan-1,4-diol (2), together with six known ones (3–8), were isolated from 95 % ethanol extract of the heartwood of Entandrophragma cylindricum. Structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis and quantum chemical calculations, including GIAO calculation of NMR chemical shifts and TDDFT calculation of ECD spectrum, which verified the relative and absolute configurations on the flexible side chain of 1, respectively. All sesquiterpenoids were evaluated for their potential to enhance glucose uptake in C2C12 myotubes. Compound 2 (20 μM) significantly increased glucose uptake to the same level as that of metformin (2 mM). Western blot analysis on AMPKα, GLUT4, and ACC1 revealed that compound 2 activated the AMPK-GLUT4 signaling pathway in C2C12 myotubes.

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白芍心材中抗糖尿病倍半萜类化合物的研究

从白茅心材95%乙醇提取物中分离得到（）-(7S,8S)-10,11-二氢姜黄烯-3,8-二醇(1)和1个新的苯胺型倍半萜类化合物（）-(1R,4S,6S,7S,10R)- cadine -1,4-二醇(2)，以及6个已知化合物（3-8）。在详细的光谱分析和量子化学计算的基础上，对新化合物的结构进行了阐述，包括核磁共振化学位移的GIAO计算和ECD谱的TDDFT计算，分别验证了1柔性侧链上的相对构型和绝对构型。评估了所有倍半萜类化合物在C2C12肌管中增强葡萄糖摄取的潜力。化合物2 （20 μM）显著增加葡萄糖摄取，与二甲双胍（2 mM）相同。Western blot分析AMPKα、GLUT4和ACC1发现，化合物2激活了C2C12肌管中AMPK-GLUT4信号通路。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.