Five new triterpenoids isolated from mastic: Structural identification and their anti-inflammatory activity

IF 2.6 3区医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2025-03-01 Epub Date: 2025-01-20 DOI:10.1016/j.fitote.2025.106395

Wentian Xiang , Yangkai Luo , Xuerui An , Ting He , Ping Cai , Minawar Kurban , Wei Liu , Tao Yuan

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Abstract

Five new oleanane-type triterpenoids were isolated from mastic. Their structures including absolute configurations were determined by extensive spectroscopic methods and single-crystal X-ray crystallographic experiments. Compound 1 is distinguished by its rare furan ring. Compounds 3–5 are formed by the oxidative ring-opening reaction of the A ring in oleanane-type triterpenes, while compounds 3 and 4 are nor-triterpenes with a carbon atom missing at the C-28 position. The anti-inflammatory potential of the compounds was anticipated through network pharmacology, followed by a detailed molecular docking analysis. Finally, the anti-inflammatory effects were verified through the establishment of an in vitro model. Notably, compounds 3 and 4 exhibited significant inhibitory effects on NO production in RAW264.7 cells induced by lipopolysaccharide, with IC₅₀ values of 8.68 ± 2.58 and 5.00 ± 3.06 μM, respectively. These values are lower than that of the positive control drug, dexamethasone, which has an IC₅₀ of 9.93 ± 1.17 μM. The significant anti-inflammatory activity of these compounds suggests their potential as treatment candidates for inflammatory diseases.

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乳胶油中新分离的五种三萜：结构鉴定及其抗炎活性。

从乳胶油中分离到5个新的齐墩烷型三萜。通过广泛的光谱方法和单晶x射线晶体学实验确定了它们的结构，包括绝对构型。化合物1以其稀有的呋喃环而闻名。化合物3-5是齐墩烷型三萜的A环氧化开环反应形成的，而化合物3和4是C-28位缺失1个碳原子的非三萜。通过网络药理学预测化合物的抗炎潜力，然后进行详细的分子对接分析。最后，通过建立体外模型验证其抗炎作用。值得注意的是，化合物3和4对脂多糖诱导的RAW264.7细胞NO生成有明显的抑制作用，其IC50值分别为8.68 ± 2.58和5.00 ± 3.06 μM。阳性对照药物地塞米松的IC50值为9.93 ± 1.17 μM。这些化合物具有显著的抗炎活性，表明它们有可能成为炎症性疾病的候选治疗药物。

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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.