杜仲叶化学成分及其神经保护活性研究

doi:10.3969/j.issn.0253-2417.2023.03.002

摘要/Abstract

摘要：

以杜仲叶为原料，对其乙醇提取物进行分离纯化，从中分离得到了13个化合物, 包括1个新化合物和12个已知化合物，通过波谱数据分析鉴定化合物结构分别为：(R, 9Z, 12E, 15Z)-11-羟基-9，12，15-十八烷三烯酸(1)，7-羟基香豆素(2)，紫云英苷(3)，槲皮素(4)，槲皮素-3-O-葡萄糖苷(5), 2-(3, 4-二羟基苯氧基)-5, 7-二羟基-3-[(3-O-α-D-吡喃木糖基-α-D-半乳吡喃糖基)氧]-4H-1-苯并吡喃-4-酮(6), (2R, 3S)-3-(4-羟基-3-甲氧基苯)-3-甲氧基丙烷-1, 2-二醇(7)，(2S, 3R)-3-(4-羟基-3-甲氧基苯)-3-甲氧基丙烷-1, 2-二醇(8)，氯原酸(9)，栀二醇(10)，4-羟基苯甲酸(11)，香草酸(12)和肉豆蔻酸(13)，其中化合物1是新的脂肪酸类化合物。对分离得到的13个化合物的抗神经炎活性和神经保护活性进行研究，结果表明：化合物4、5和10通过抑制脂多糖(LPS)诱导的小鼠小胶质细胞(BV-2细胞)中NO的释放，表现出显著的抗神经炎活性，半数抑制浓度(IC₅₀)值分别为(10.8±0.9)、(9.7±1.1)和(10.7±0.3) μmol/L；化合物5在氧化应激下表现出较强的神经保护活性，20 μmol/L预处理H₂O₂诱导的大鼠肾上腺嗜铬细胞瘤(PC-12细胞)后，其细胞存活率为(86.5±0.5)%，高于阳性对照橙皮苷。

关键词: 杜仲叶, 化学成分, 抗神经炎, 神经保护

Abstract:

The ethanolic extracts of Eucommia ulmoides Oliv. leaves were isolated and purified, where thirteen compounds were obtained, including one new compound and twelve known compounds. The structures of the compounds were identified by spectral data as follows: (R, 9Z, 12E, 15Z)-11-hydroxyoctadeca-9, 12, 15-trienoic acid(1), 7-hydroxycoumarin(2), astragaline(3), quercetine(4), quercetin-3-O-glucoside(5), 2-(3, 4-dihydroxyphenyl)-5, 7-dihydroxy-3-[(3-O-α-D-xylopyranosyl-α-D-galactopy-ranosyl)oxy]-4H-1-benzopyran-4-one(6), (2R, 3S)-3-(4-hydroxy-3-methoxyphenyl)-3-methoxypropane-1, 2-diol(7), (2S, 3R)-3-(4-hydroxy-3-methoxyphenyl)-3-methoxypropane-1, 2-diol(8), chlorogenic acid(9), gardendiol(10), 4-benzyloxy benzoic acid(11), vanillic acid(12) and myristic acid(13). Among them, compound 1 was a new fatty acid compound. The anti-neuroinflammatory and neuroprotective activities of 13 compounds were studied. The results showed that compounds 4, 5 and 10 exhibited significant anti-neuroinflammatory activity by inhibiting the release of nitric oxide(NO) production in lipopolysaccharide(LPS)-induced in mouse microglia(BV-2 cells), with half inhibitory concentration(IC₅₀) values of (10.8±0.9), (9.7±1.1) and (10.7±0.3) μmol/L, respectively. Compound 5 exhibited significant neuroprotective activity under oxidative stress. After pretreatment with 20 μmol/L H₂O₂-induced rat adrenal pheochromocytoma cells(PC-12 cells), the cell survival rate was (86.5±0.5)%, which was higher than that of the positive control hesperidin.

Key words: Eucommia ulmoides leaves, chemical constituents, anti-neuroinflammatory, neuroprotection

中图分类号:

TQ35

胡凤成, 韩锐, 郭聪, 汤江江, 高锦明. 杜仲叶化学成分及其神经保护活性研究[J]. 林产化学与工业, 2023, 43(3): 9-15.

Fengcheng HU, Rui HAN, Cong GUO, Jiangjiang TANG, Jinming GAO. Chemical Constituents of the Leaves of Eucommia ulmoides and Its Neuroprotective Activity[J]. Chemistry and Industry of Forest Products, 2023, 43(3): 9-15.

图/表 4

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图2

表1

表2

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序号No.	δ_C	δ_H
1	174.9(COOH)
2	34.2(CH₂)	2.19(m)
3	25.1(CH₂)	1.47(m)
3	25.1(CH₂)	1.22(m)
4	29.0(CH₂)	1.25-1.31(m)
5	29.1(CH₂)	1.25-1.31(m)
6	28.9(CH₂)	1.25-1.31(m)
7	29.6(CH₂)	1.25-1.31(m)
8	27.6(CH₂)	2.11(m); 1.96(m)
9	131.5(CH)	5.33(d, J=5.54)
10	128.8(CH)	5.96(t, J=10.73)
11	71.0(CH)	4.01(m)
12	137.8(CH)	5.64(dd, J=5.52, 14.96)
13	124.5(CH)	6.42(t, J=14.05)
14	35.8(CH₂)	2.17(m)
15	125.8(CH)	5.38(d, J=6.57)
16	132.9(CH)	5.40(d, J=7.84)
17	20.7(CH₂)	1.97(m)
18	14.5(CH₃)	0.90(t, J=7.18)
11-OH		11.96(s)

化合物compound	NO		PC-12细胞存活率/%cell viability of PC-12
化合物compound	IC₅₀/(μmol·L^-1)	抑制率(20 μmol·L^-1)/%inhibitory rate	PC-12细胞存活率/%cell viability of PC-12
1	13.7±0.7	71.7±1.4	79.0±3.0
2	18.4±0.1	67.1±0.6	85.0±9.0
3	15.2±0.5	78.5±0.06	80.5±11.5
4	10.8±0.9	73.0±2.5	52.2±1.2
5	9.7±1.1	78.3±1.7	86.5±0.5
6	18.9±0.4	62.5±1.0	60.6±0.8
7	＞20	7.1±0.65	43.2±1.2
8	＞20	47.1±0.9	54.0±5.7
9	17.4±0.4	66.7±0.9	79.0±0.2
10	10.7±0.3	81.5±0.8	77.0±0.1
11	16.1±0.8	71.1±0.5	83.5±2.5
12	19.5±0.8	57.7±0.5	69.0±1.1
13	17.8±0.6	61.1±1.0	69.0±1.0
橙皮苷hesperidin			77.0±1.2

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