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

doi:10.6023/cjoc202404024

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3526-3530.DOI: 10.6023/cjoc202404024 Previous Articles Next Articles

NOTE

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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Abstract

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

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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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Fig. & Tab. 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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