八角茴香果实化学成分及其抗氧化活性研究

Chemical constituents from fruits of Illicium verum and their antioxidant activities

关键词:  八角茴香, 新天然产物, 苯丙素, 化学成分, 结构鉴定, DPPH

Key words:   Illicium verum, new natural product, phenylpropanoid, chemical constituents, structure identification, DPPH

摘要:

为探究八角茴香(Illicium verum)果实的化学成分及其抗氧化活性,该研究采用硅胶、Sephadex LH-20和HPLC等色谱技术对八角茴香果实的化学成分进行分离提纯,利用理化特性和波谱数据及结合 参考文献确定所得天然产物的分子结构,并采用DPPH法评价化合物抗氧化活性。结果表明:(1)从八角茴香果实中分离得到23个化合物,分别鉴定为1-hydroxy-1-(4'-methoxyphenyl)-2-one(1)、ethyl 5-(acetyloxy)-3, 4-dihydroxy-1-cyclohexene-1-carboxylate(2)、isoshonanin(3)、yunnanensin A(4)、isolariciresinol-9-acetate(5)、isolariciresinol-9'-acetate(6)、kinsenone(7)、对羟基肉桂酸(8)、杜荆素(9)、芹菜素-7-O-芸香糖苷(10)、槲皮素(11)、(2E, 4Z)-脱落酸(12)、paratrimerins H(13)、1-(4-乙基苯基)-1, 2-乙二醇(14)、麦芽酚(15)、丁香酸(16)、莽草酸(17)、莽草酸乙酯(18)、莽草酸正丁酯(19)、原儿茶酸(20)、原儿茶酸甲酯(21)、原儿茶酸乙酯(22)和原儿茶酸丁酯(23)。其中,化合物1、2为新天然产物,化合物1-10、13-15、19、21-23为首次从八角属植物中分离得到,化合物12、18为首次从八角茴香果实中分离得到。(2)化合物11、16、21-23比阳性对照VC表现出更强的DPPH自由基清除活性,其IC₅₀值分别为(60.15±1.72)、(35.51±0.50)、(52.25±0.73)、(33.34±0.94)、(30.29±0.67)μmol·L^-1。该研究结果揭示了八角茴香的化学成分,为深入开展八角茴香抗氧化活性研究提供了科学依据。

Abstract:

To study chemical constituents and antioxidant activities of fruits of Illicium verum, various chromatography techniques, like silica gel, Sephadex LH-20, and HPLC, etc., were used to isolate and purify chemical constituents of I. verum fruits. The structures of the isolates were identified using physicochemical constants, spectral data, and references. DPPH method was used to evaluate antioxidant activities of compounds. The results were as follows:(1)A total of 23 compounds were isolated and identified as 1-hydroxy-1-(4'-methoxyphenyl)-2-one(1), ethyl 5-(acetyloxy)-3,4-dihydroxy-1-cyclohexene-1-carboxylate(2), isoshonanin(3), yunnanensin A(4), isolariciresinol-9-acetate(5), isolariciresinol-9'-acetate(6), kinsenone(7), p-hydroxycinnamic acid(8), vitexin(9), apigenin-7-O-rutinoside(10), quercetin(11),(2E, 4Z)-abscisic acid(12), paratrimerins H(13), 1-(4-ethylphenyl)-1,2-ethanediol(14), maltol(15), syringic acid(16), shikimic acid(17), shikimic acid ethyl ester(18), shikimic acid n-butyl ester(19), protocatechuic acid(20), protocatechuic acid methyl ester(21), protocatechuic acid ethyl ester(22)and protocatechuic acid butyl ester(23). Among with, compounds 1 and 2 were new natural products, compounds 1-10, 13-15, 19, and 21-23 were isolated from Illicium for the first time, while compounds 12 and 18 were isolated from I. verum for the first time.(2)Compounds 11, 16, and 21-23 exhibited stronger DPPH radical scavenging activity than the positive control(VC), IC₅₀ values of five compounds were(60.15±1.72),(35.51±0.50),(52.25±0.73),(33.34±0.94),(30.29±0.67)μmol·L^-1, respectively. This study reveals the chemical constituents of I. verum, and provides a reference for indepth research on the antioxidant activity of I. verum.