天然产物研究与开发 ›› 2025, Vol. 37 ›› Issue (12): 2258-2266.doi: 10.16333/j.1001-6880.2025.12.009 cstr: 32307.14.1001-6880.2025.12.009

• 研究简报 • 上一篇    下一篇

薰鲁香中两个新的齐墩果烷型三萜类化合物

孙禹薇1,安学瑞1,余泽南1,杨佳乐1,刘  伟1*,袁  涛1,2*   

  1. 1伊犁师范大学化学化工学院 新疆维吾尔自治区教育厅天然产物化学与应用重点实验室,伊宁 835000;2江西师范大学健康学院 天然与仿生药物研究江西省重点实验室,南昌 330022
  • 出版日期:2025-12-30 发布日期:2025-12-29
  • 基金资助:
    国家自然科学基金(82060774);天然与仿生药物研究江西省重点实验室开放课题(2024SSY07051)

Two new oleanane-type triterpenoids from mastic

SUN Yu-wei1,AN Xue-rui1,YU Ze-nan1,YANG Jia-le1,LIU Wei1*,YUAN Tao1,2*   

  1. 1Key Lab of Natural Product Chemistry and Application at Universities of Education Department of Xinjiang Uygur Autonomous Region,School of Chemistry and Chemical Engineering,Yili Normal University,Yining 835000,China;2 Jiangxi Provincial Key Laboratory of Natural and Biomimetic Drugs Research,School of Health,Jiangxi Normal University,Nanchang 330022,China
  • Online:2025-12-30 Published:2025-12-29

摘要:

研究薰鲁香中的化学成分及其抗炎活性。综合运用多种柱色谱和半制备色谱技术,对薰鲁香甲醇-乙酸乙酯提取物进行分离纯化,通过质谱、核磁共振、圆二色谱等波谱技术并结合文献对比鉴定化合物结构。最终分离鉴定了7个齐墩果烷型三萜类化合物,分别为(5R,8R,9R,10S,14S,17S,18S)-17β-formyloxy-28-norolean-12-ene-3,11-dione(1)、(3S,5R,8S,10S,14R,17S,18S)-3β-hydroxy-9(11),12-oleanadien-28-hydroxymethyl(2)、juglangenin A(3)、3-oxo-11α-methoxyl-12-oleane-28-oic acid(4)、3-oxo-11α,12α-epoxyoleanan-28,13β-olide(5)、13β,28-epoxy-3β-hydroxy-olean-11-ene(6)、11,13(18)-oleanadien-28-hydroxymethyl-3-one(7)。其中,化合物12为新化合物,所得化合物均为从薰鲁香中首次发现。采用脂多糖(lipopolysaccharide,LPS)刺激小鼠单核巨噬细胞(RAW 264.7)建立的模型评价化合物抗炎活性。结果表明,化合物1可显著抑制LPS诱导的RAW 264.7细胞中NO的产生,IC50为7.44 ± 0.49 μmol/L,强于阳性对照地塞米松(IC50为9.93±1.17 μmol/L);化合物3表现出和地塞米松相当的抗炎效果,IC50为9.63±2.47 μmol/L;其余化合物的抗炎效果均弱于地塞米松,IC50值介于12.62~19.74 μmol/L。

关键词: 薰鲁香, 化学成分, 齐墩果烷型三萜, 抗炎活性

Abstract:

This study aims to investigate the chemical constituents of mastic and screen their anti-inflammatory activities. Compounds were isolated and purified from the methanol-ethyl acetate extract by various chromatographic techniques, along with semi-preparative HPLC. Their structures were elucidated by MS, NMR, ECD and comparisons with the data reported in the literature. Seven oleanane-type triterpenoids were identified as (5R,8R,9R,10S,14S,17S,18S)-17β-formyloxy-28-norolean-12-ene-3,11-dione (1), (3S,5R,8S,10S,14R,17S,18S)-3β-hydroxy-9(11),12-oleanadien-28-hydroxymethyl (2), juglangenin A (3), 3-oxo-11α-methoxyl-12-oleane-28-oic acid (4), 3-oxo-11α,12α-epoxyoleanan-28,13β-olide (5), 13β,28-epoxy-3β-hydroxy-olean-11-ene (6), and 11,13(18)-oleanadien-28-hydroxymethyl-3-one (7). Among them, compounds 1 and 2 are new compounds, and all the compounds were isolated for the first time from mastic. The anti-inflammatory activity was evaluated using the lipopolysaccharide (LPS)-induced mouse macrophage (RAW 264.7) model. The results indicated that compound 1 significantly inhibited the production of NO in RAW 264.7 cells induced by LPS, with an IC50 value of 7.44±0.49 μmol/L, which is stronger than that of the positive control, dexamethasone, with an IC50 of 9.93±1.17 μmol/L. Compound 3 showed comparable anti-inflammatory effects to dexamethasone, with an IC50 of 9.63±2.47 μmol/L. The remaining compounds showed weaker anti-inflammatory effects than dexamethasone, with IC50 values ranging between 12.62 and 19.74 μmol/L.

Key words: mastic, chemical composition, oleanane-type triterpenes, anti-inflammatory activity

中图分类号:  R284.2