Highly oxygenated sesquiterpenoids with neurotrophic and neuroprotective activities from the fruits of Illicium henryi Diels

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-05-03 DOI:10.1016/j.fitote.2025.106588

Zhen-Xiang Liu , Xue-Yu Zhao , Jin-Da Li , Liu-Dong Song , Lin-Fen Ding , Xing-De Wu

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Abstract

Illihenrolides A (1) and B (2), and illihenrin A (3), three highly oxygenated sesquiterpenoids were isolated from the fruits of Illicium henryi Diels, together with eight known analogs. The structures of 1–3 were elucidated using HRESIMS data and extensive ¹H, ¹³C, and 2D NMR (¹H¹H COSY, HSQC, HMBC and ROESY) analyses. In addition, the absolute configurations of 1 and 2 were determined by single crystal X-ray diffraction experiment and electronic circular dichroism calculations. Structurally, compounds 1 and 2 were determined as seco-prezizaane-type sesquiterpenoids, while 3 was identified to be allo-cedrane-type sesquiterpenoid. Furthermore, neurotrophic and neuroprotective activities of 1–11 were evaluated. As a result, compounds 5, 10, and 11 had significant promoting effect on NGF-induced neurite outgrowth in PC12 cell at the concentration of 10 μM with the differentiation rate of 13.64, 10.53, and 11.67 %, respectively. Compound 9 showed moderate neuroprotective activity against MPP⁺-induced PC12 cell damage with PC12 cell viability of 72.36 ± 1.70 % at the concentration of 20 μM, compared to the model group with 66.80 ± 0.65 %.

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具有神经营养和神经保护活性的高氧倍半萜类化合物

从百合果实中分离出三种高氧倍半萜类化合物Illihenrolides A(1)、B(2)和illihenryin A(3)，以及八种已知的类似物。利用hresms数据和广泛的1H， 13C和2D NMR （1H1H COSY， HSQC， HMBC和ROESY）分析阐明了1-3的结构。另外，通过单晶x射线衍射实验和电子圆二色性计算，确定了1和2的绝对构型。在结构上，化合物1和2被鉴定为邻苯二甲酸酯型倍半萜，而化合物3被鉴定为异氰酸酯型倍半萜。进一步评价了1-11的神经营养和神经保护活性。结果表明，化合物5、10和11在10 μM浓度下对ngf诱导的PC12细胞神经突生长有显著促进作用，分化率分别为13.64%、10.53%和11.67%。化合物9对MPP+诱导的PC12细胞损伤具有中等的神经保护作用，浓度为20 μM时PC12细胞存活率为72.36±1.70%，而模型组为66.80±0.65%。

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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.