红树植物海漆中二萜类化合物及其抗神经炎症活性

doi:10.6023/cjoc202404024

有机化学 ›› 2024, Vol. 44 ›› Issue (11): 3526-3530.DOI: 10.6023/cjoc202404024 上一篇下一篇

研究简报

红树植物海漆中二萜类化合物及其抗神经炎症活性

李俊义^†,a, 杨璐^†,b, 陈明宾^a, 饶勇^a, 江仲平^a^,^*(), 黄玲^a^,^*()

a 海南大学药学院海南大学热带生物资源教育部重点实验室海口 570228
b 海南大学食品科学与工程学院海口 570228

收稿日期:2024-04-17 修回日期:2024-05-27 发布日期:2024-07-10
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(82204275); 国家自然科学基金(82160653); 海南省自然科学基金(323MS014)

Diterpenoids from Mangrove Plant Excoecaria agallocha L. and Their Anti-neuroinflammatory Activities

Junyi Li^†,a, Lu Yang^†,b, Mingbin Chen^a, Yong Rao^a, Zhongping Jiang^a,*(), Ling Huang^a,*()

a Key Laboratory of Tropical Biological Resources of Ministry of Education, School of Pharmaceutical Sciences, Hainan University, Haikou 570228
b School of Food Science and Engineering, Hainan University, Haikou 570228

Received:2024-04-17 Revised:2024-05-27 Published:2024-07-10
Contact: *E-mail:zpjiang@hainanu.edu.cn;Linghuang@hainanu.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(82204275); National Natural Science Foundation of China(82160653); Hainan Provincial Natural Science Foundation(323MS014)

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摘要/Abstract

采用正相、反相硅胶柱层析和半制备高效液相色谱等分离方法对海南红树植物海漆(Excoecaria agallocha L.)茎和枝条的化学成分进行研究, 从中分离得到一个新的3,4位开环对映-贝壳杉烷型二萜agallochanin acid A (1)和一个新的降4个碳的对映-半日花烷型二萜agallochanin acid B (2), 以及4个已知的二萜化合物. 通过高分辨质谱、一维、二维核磁共振波谱以及电子圆二色谱(ECD)计算的方法确定了这些二萜类化合物的结构. 测试了所有化合物对脂多糖(LPS)诱导BV-2小胶质细胞中NO释放的抑制作用, ent-3,4-seco-17-oxo-kaur-4(19),15(16)-dien-3-oic acid (3)和ent-15- hydroxy-labda-8(17),13E-dien-3-one (5)具有显著的抑制NO释放作用, 其IC₅₀值分别为(14.32±1.99)和(4.24±0.37) μmol/L.

关键词: 海漆, 红树植物, 贝壳衫烷二萜, 半日花烷二萜, 抗神经炎症

Normal-phase and reversed-phase silica gel column chromatography and semi-preparative high performance liquid chromatography were applied to study the chemical constituents of the stems and twigs of the Hainan mangrove plant, Excoecaria agallocha L. A new 3,4-seco-ent-kaurane diterpenoid, named agallochanin acid A (1), and a rare ent-tetranorlabdane diterpenoid, named agallochanin acid B (2), along with four known diterpenoids were isolated. Their structures including absolute configurations were characterized via HR-ESI-MS, extensive 1D and 2D NMR investigations and calculated and experimental electronic circular dichroism (ECD) data. All isolates were tested for their inhibitory effects on NO production in lipopolysaccharide (LPS)-activated BV-2 cells. ent-3,4-Seco-17-oxo-kaur-4(19),15(16)-dien-3-oic acid (3) and ent-15-hydroxy- labda-8(17),13E-dien-3-one (5) exhibited considerable anti-neuroinflammatory activities with IC₅₀ values of (14.32±1.99) and (4.24±0.37) μmol/L.

Key words: Excoecaria agallocha L., mangrove plant, kaurane diterpenoid, labdane diterpenoid, anti-neuroimflamation

引用此文

李俊义, 杨璐, 陈明宾, 饶勇, 江仲平, 黄玲. 红树植物海漆中二萜类化合物及其抗神经炎症活性[J]. 有机化学, 2024, 44(11): 3526-3530.

Junyi Li, Lu Yang, Mingbin Chen, Yong Rao, Zhongping Jiang, Ling Huang. Diterpenoids from Mangrove Plant Excoecaria agallocha L. and Their Anti-neuroinflammatory Activities[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3526-3530.

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图/表 5

Figure 1. Structures of diterpenoid compounds 1~6

Figure 2. Key 1H-1H COSY and HMBC correlations of 1 and 2

Figure 3. Key NOESY correlations of 1 and 2

Figure 4. Calculated ECD spectra and the experimental ECD spectra of compounds 1 and 2

Figure 5. (A) Evaluation of the anti-neuroinflammation ability of compounds 1~6 (20 μmol/L) and Dexamethasone (20 μmol/L) in LPS-treated BV2 microglia, and (B) IC50 values of compounds 3 and 5

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红树植物海漆中二萜类化合物及其抗神经炎症活性

Diterpenoids from Mangrove Plant Excoecaria agallocha L. and Their Anti-neuroinflammatory Activities

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