中国中药杂志

2022, v.47(18) 4959-4965

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海南黄花梨中1个新的异黄酮类化合物及其酪氨酸酶抑制活性
A new isoflavone from Dalbergia odorifera and inhibitory activity of its tyrosinase

张雪;方万;李晓青;王瑞;严诗楷;金慧子;
CHEUNG Suet;FANG Wan;LI Xiao-qing;WANG Rui;YAN Shi-kai;JIN Hui-zi;School of Pharmacy, Shanghai Jiao Tong University;Peking-Tsinghua Center for Life Sciences, Peking University;

摘要(Abstract):

采用加热回流提取、溶剂萃取、重结晶及正相硅胶、Sephadex LH-20、MCI、HPLC等多种色谱技术,对海南黄花梨干燥枝叶化学成分进行研究,分离得到12个黄酮类化合物。结合NMR、MS等波谱方法对分离得到的化合物进行结构鉴定,分别为6,7,8-三甲氧基-5,4′-二羟基异黄酮(1)、美迪紫檀素(2)、7,2′-二羟基-4′-甲氧基-异黄烷醇(3)、鹰嘴豆芽素A(4)、樱黄素(5)、染料木素(6)、红车轴草素(7)、3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one(8)、鸢尾黄素(9)、尼泊尔鸢尾异黄酮(10)、维斯体素(11)和芒柄花黄素(12)。其中化合物1为新的异黄酮类化合物,化合物8为首次从海南黄花梨中分离得到。对分离得到的化合物进行体外酪氨酸酶抑制活性测试显示化合物1~3对酪氨酸酶有抑制作用,在1.0 mmol·L(-1)的浓度下,抑制率分别为35.58%、38.63%、51.34%。
Twelve flavonoids were isolated and purified from the ethyl acetate fraction of 95% ethanol extract of Dalbergia odorifera by heat reflux extraction, solvent extraction, recrystallization, normal phase silica gel, Sephadex LH-20, MCI gel and HPLC methods. The structures were identified with multiple spectroscopic methods, including 1 D-NMR, 2 D-NMR and MS. The compounds were identified as 6,7,8-trimethoxy-5,4′-dihydroxy isoflavone(1), medicarpin(2), 7,2′-dihydroxy-4′-methoxy-isoflavanol(3), biochanin A(4), prunetin(5), genistein(6), pratensein(7), 3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one(8), tectorigenin(9), irisolidone(10), vestitol(11), and formononetin(12). Compound 1 was a new isoflavone, and compound 8 was isolated from D. odorifera for the first time. The results showed that compounds 1-3 had inhibitory effects on tyrosinase, with inhibition rates of 35.58%, 38.63% and 51.34% at the concentration of 1.0 mmol·L(-1)的浓度下,抑制率分别为35.58%、38.63%、51.34%。
Twelve flavonoids were isolated and purified from the ethyl acetate fraction of 95% ethanol extract of Dalbergia odorifera by heat reflux extraction, solvent extraction, recrystallization, normal phase silica gel, Sephadex LH-20, MCI gel and HPLC methods. The structures were identified with multiple spectroscopic methods, including 1 D-NMR, 2 D-NMR and MS. The compounds were identified as 6,7,8-trimethoxy-5,4′-dihydroxy isoflavone(1), medicarpin(2), 7,2′-dihydroxy-4′-methoxy-isoflavanol(3), biochanin A(4), prunetin(5), genistein(6), pratensein(7), 3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one(8), tectorigenin(9), irisolidone(10), vestitol(11), and formononetin(12). Compound 1 was a new isoflavone, and compound 8 was isolated from D. odorifera for the first time. The results showed that compounds 1-3 had inhibitory effects on tyrosinase, with inhibition rates of 35.58%, 38.63% and 51.34% at the concentration of 1.0 mmol·L(-1), respectively.

关键词(KeyWords): 海南黄花梨;黄酮类化合物;酪氨酸酶抑制作用
Dalbergia odorifera;flavonoids;tyrosinase inhibition

Abstract:

Keywords:

基金项目(Foundation): 国家自然科学基金面上项目(81973191)

作者(Authors): 张雪;方万;李晓青;王瑞;严诗楷;金慧子;
CHEUNG Suet;FANG Wan;LI Xiao-qing;WANG Rui;YAN Shi-kai;JIN Hui-zi;School of Pharmacy, Shanghai Jiao Tong University;Peking-Tsinghua Center for Life Sciences, Peking University;

DOI: 10.19540/j.cnki.cjcmm.20220422.202

参考文献(References):

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