红树植物白骨壤果实化学成分及抗炎活性研究

Study on chemical constituents and anti-inflammatory activities of the fruits of the mangrove plant Avicennia marina

摘要:

目的 对湛江红树林自然保护区中红树植物白骨壤果实进行化学成分及其抗炎活性研究。方法 综合 运用开放硅胶柱层析、TLC、HPLC等色谱学方法，对红树植物白骨壤果实的粗提取物进行分离和纯化；结合NMR、 MS 等现代波谱法以及与相关文献数据比较，对获得的单体化合物进行结构鉴定。采用 LPS 诱导小鼠巨噬细胞 RAW264.7 炎症模型评价化合物的抗炎活性。结果 从红树植物白骨壤果实中共分离、鉴定了22个单体化合物，分 别是：marinoid D（1），10-O-E-p-coumaroylgeniposidic acid（2），木犀草素（3），反式咖啡酸甲酯（4），反式对香豆酸 （5），绿原酸甲酯（6），（E）-2，3-dihydroxycyclopentyl-3-（3′，4′-dihydroxyphenyl）acrylate（ 7），medioresino（l 8），5-羟甲 基糠醛（9），对羟基苯乙醇（10），原儿茶醛（11），香草酸（12），丁香酸（ 13），对羟基苯甲酸（ 14），α-d-甲基半乳糖苷 （15），（2E，6R）-8-hydroxy-2，6-dimethyl-2-octenoic acid（16），亚麻酸甲酯（17），α-亚麻酸（18），（5Z，9Z）-17-甲基-非 十七烯酸-5，9-二酯（19），亚油酸（20），reversetro（l 21），棕榈酸甲酯（22）。其中化合物5~13和15~21为首次从该属 （Avicennia）中分离得到。考察了化合物1~8和11的抗炎活性，结果显示：化合物1~4、6和11在25 μmol/L浓度下可 抑制LPS诱导RAW264.7细胞产生NO，其中化合物1更优于阳性对照地塞米松。结论 化合物5~13和15~21为首 次从该属植物中分离得到，进一步丰富了白骨壤化学成分的结构多样性。药理活性研究表明化合物1具有显著的 抗炎活性。

Abstract:

Abstract: Objective A study on the chemical constituents and anti-inflammatory activities of the fruits of Avicennia marina, a mangrove plant from the Zhanjiang Mangrove National Nature Reserve. Methods Chromatographic methods, including open silica gel column chromatography, thin-layer chromatography (TLC), and high-performance liquid chromatography (HPLC), were comprehensively used to isolate and purify the crude extract from the fruits of A. marina. The structures of the isolated compounds were identified using modern spectroscopic methods, including nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS), as well as by comparison with the relevant literature data. The anti-inflammatory activities of the compounds were evaluated by using an inflammation model of mouse macrophages RAW264.7 induced by lipopolysaccharide (LPS). Results A total of 22 compounds were isolated from the fruits of A. marina, and their structures were identified as follows: marinoid D (1), 10- O-E-p-coumaroylgeniposidic acid (2), luteolin (3), trans-methyl caffeate (4), trans-p-coumaric acid (5), chlorogenic acid methyl ester (6), (E)-2,3-dihydroxycyclopentyl-3-(3′, 4′-dihydroxyphenyl)acrylate (7), medioresinol (8), 5-hydroxymethylfurfural (9), 4-hydroxyphenethyl alcohol (10), 3, 4-dihydroxybenzaldehyde (11), vanillic acid (12), syringic acid (13), p-hydroxybenzoic acid (14), α-d-methylgalactoside (15), (2E,6R)-8-hydroxy-2,6-dimethyl-2-octenoic acid (16), methyl linolenate (17), α -linolenic acid (18), (5Z, 9Z) -17-methyl-nonadecadienoic acid 5, 9-diester (19), linoleic acid (20), reversetrol (21), and methyl palmitate (22). Among them, compounds 5-13 and 15-21 were found for the first time in the genus Avicennia. The anti-inflammatory activities of compounds 1-8 and 11 were investigated. The results showed that compounds 1-4, 6, and 11 could inhibit the production of nitric oxide in RAW264.7 cells induced by LPS at a concentration of 25 μmol/L. Notably, compound 1 was even more effective than the positive control, dexamethasone. Conclusion Compounds 5-13 and 15-21 were identified for the first time in the genus Avicennia, further enriching the structural diversity of the chemical constituents of A. marina. Pharmacological activity studies indicated that compound 1 exhibited significant anti-inflammatory activity.