番石榴根中酚酸类化学成分分离鉴定
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摘要
目的:桃金娘科Myrrhinaceae番石榴Psidium guajava不同部位具有不同药用功效,其叶和果实化学成分研究深入,但有关根的化学物质基础报道甚少,为明确番石榴根的化学成分,对番石榴根进行了系统地化学成分分离与鉴定。方法:采用硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱,大孔树脂柱色谱,反相硅胶柱色谱(ODS)及半制备高效液相色谱(HPLC)等多种色谱方法对番石榴根醇提浸膏分离纯化,应用核磁共振(NMR)和质谱,结合理化性质,鉴定化合物的结构。结果:从番石榴根中分离出16个酚酸类化合物,分别为3,3',4'-三甲基鞣花酸(1),3,3',4-三甲基鞣花酸-4'-O-β-D-葡萄糖苷(2),3-甲基鞣花酸-4'-O-α-L-鼠李糖苷(3),3'-O-methyl-3,4-O,O-metheneellagic acid-4'-O-β-D-glucopyranoside(4),没食子酸(5),没食子酸甲酯(6),没食子酸乙酯(7),3,4,5-trimethoxypheny-1-β-D-glucopyranoside(8),3,5-二甲氧基-4-羟基-苯甲酸-7-O-β-D-葡萄糖苷(9),1-hydroxy-3,4,5-trimethoxyphenyl-1-O-[6'-O-(4″-carboxy-1″,3″,5″-trihydroxy) phenyl]-β-Dglucopyranoside(10),香草酸(11),原儿茶酸(12),开环异落叶松脂素9-O-β-D-葡萄糖苷(13),根皮素4'-O-β-D-葡萄糖苷(14),cinchonain Ib(15),表儿茶素(16)。结论:化合物3,4,6,8～10,13～15为首次从该植物中分离得到。
Objective: The different parts of Psidium guajava( Myrrhinaceae) have different bioactivities. There are intensive studies for chemical constituents of its leaves and fruits at present. However,there are a few studies for the roots. Therefore,we systematically investigated the chemical constituents of phenolic acids in roots of P. guajava. Method: The chemical constituents were isolated and purified by various column chromatography methods and semi-preparative HPLC. The isolated compounds were identified by physicochemical properties and spectral analysis. Result: Sixteen phenolic components were isolated from the ethanol extract and identified as 3, 3', 4'-tri-O-methylellagic acid( 1), 3, 3', 4-tri-O-methylellagic acid-4'-O-β-Dglucopyranoside( 2), 3-O-methylellagic acid-4'-O-α-L-rhamnopyranoside( 3), 3'-O-methyl-3, 4-O, Ometheneellagic acid-4'-O-β-D-glucopyranoside( 4),gallic acid( 5),methyl gallate( 6),ethyl gallate( 7),3,4,5-trimethoxypheny-1-β-D-glucopyranoside( 8),3,5-dimethoxy-4-hydroxy-benzoic acid-7-O-β-D-glucoside( 9),1-hydroxy-3,4,5-trimethoxyphenyl-1-O-[6'-O-( 4″-carboxy-1″, 3″, 5″-trihydroxy) phenyl]-β-Dglucopyranoside( 10), vanillic acid( 11), protocatechuic acid( 12), secoisolariciresinol 9-O-β-Dglucopyranoside( 13),phloretin 4'-O-β-D-glucopyranoside( 14),cinchonain Ib( 15) and epicatechin( 16).Conclusion: Compounds 3,4,6,8-10,13-15 were isolated from this plant for the first time.
Objective: The different parts of Psidium guajava( Myrrhinaceae) have different bioactivities. There are intensive studies for chemical constituents of its leaves and fruits at present. However,there are a few studies for the roots. Therefore,we systematically investigated the chemical constituents of phenolic acids in roots of P. guajava. Method: The chemical constituents were isolated and purified by various column chromatography methods and semi-preparative HPLC. The isolated compounds were identified by physicochemical properties and spectral analysis. Result: Sixteen phenolic components were isolated from the ethanol extract and identified as 3, 3', 4'-tri-O-methylellagic acid( 1), 3, 3', 4-tri-O-methylellagic acid-4'-O-β-Dglucopyranoside( 2), 3-O-methylellagic acid-4'-O-α-L-rhamnopyranoside( 3), 3'-O-methyl-3, 4-O, Ometheneellagic acid-4'-O-β-D-glucopyranoside( 4),gallic acid( 5),methyl gallate( 6),ethyl gallate( 7),3,4,5-trimethoxypheny-1-β-D-glucopyranoside( 8),3,5-dimethoxy-4-hydroxy-benzoic acid-7-O-β-D-glucoside( 9),1-hydroxy-3,4,5-trimethoxyphenyl-1-O-[6'-O-( 4″-carboxy-1″, 3″, 5″-trihydroxy) phenyl]-β-Dglucopyranoside( 10), vanillic acid( 11), protocatechuic acid( 12), secoisolariciresinol 9-O-β-Dglucopyranoside( 13),phloretin 4'-O-β-D-glucopyranoside( 14),cinchonain Ib( 15) and epicatechin( 16).Conclusion: Compounds 3,4,6,8-10,13-15 were isolated from this plant for the first time.
引文
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[22] Kubo I,Matsumoto A. Isolation of an insect-antifeedant,phloretin 4'-O-β-D-glucopyranoside,by rotation locuar counter-current chromatography and determination of its preferred conformation in solution by nuclear magnetic resonance analysis[J]. Chem Pharm Bull,1985,33(9):3817-3820.
[23]梁东,刘彦飞,郝志友,等.珍珠菜中黄酮及Megastigmane类化学成分研究[J].天然产物研究与开发,2015,27(7):1171-1175.
[24]胡江苗,陈纪军,赵友兴,等.山竺果壳的化学成分[J].云南植物研究,2006,28(3):319-322.
[2]邵萌,王英,翦雨青,等.番石榴叶乙醇提取物的化学成分研究[J].中国中药杂志,2014,39(6):1024-1029.
[3]徐智慧,路华,张宗禹,等.番石榴根抗生育有效成分的初步研究[J].南京药学院学报,1979(2):24-32.
[4]陈继培.番石榴——营养药用两相宜[N].中国医药报,2003-06-16.
[5]吴艳,曲玮,梁敬钰.番石榴叶的研究进展[J].海峡药学,2013,25(12):14-19.
[6]刘纯,每乐,李鑫,等.番石榴果实药学研究概况[J].安徽农业科学,2013,41(17):7460-7462.
[7]彭财英,黄应正,刘建群,等.番石榴根中一个新的三萜类成分[J].药学学报,2017,52(11):1731-1736.
[8] YE G,PENG H,FAN M,et al. Ellagic acid derivatives from the stem bark of Dipentodon sinicus[J]. Chem Nat Compd,2007,43(2):125-127.
[9]朱华旭,闵知大.假奓包叶化学成分研究[J].中草药,2004,35(11):1220-1222.
[10] GUO Q M,YANG X W. A new ellagic acid derivative from the fruits of Eucalyptus globulus Labill[J]. Die Pharmazie,2005,60(9):708-710.
[11]王莉,喻明明,迟宇前,等.蒿状大戟化学成分研究[J].中国中药杂志,2014,39(20):3969-3973.
[12] LI X,Elsohly H N,Hufford C D,et al. NMR assignments of ellagic acid derivatives[J]. Magn Reson Chem,1999,37(11):856-859.
[13]徐辰琛.小花八角的化学成分研究[J].中国实验方剂学杂志,2012,18(15):124-126.
[14]李斌,高洁莹,刘清茹,等.盐肤木果粕化学成分研究(Ⅱ)[J].中药材,2016,39(4):786-788.
[15]王泽宇,王丽娜,邱玲,等.地榆中酚酸类化学成分的分离与鉴定[J].中国实验方剂学杂志,2017,23(8):82-85.
[16]宣伟东,陈海生,卞俊.胆木茎中一个新的吲哚生物碱苷[J].药学学报,2006,41(11):1064-1067.
[17]董礼,李磊,廖志华,等.柴胡红景天化学成分的研究[J].西北植物学报,2007,27(12):2564-2567.
[18] Wibowo A,Ahmat N,Hamzah A S,et al. Identification and biological activity of secondary metabolites from Dryobalanops beccarii[J]. Phytochem Lett,2014,9(1):117-122.
[19]王健伟,梁敬钰,李丽.小叶买麻藤的化学成分[J].中国天然药物,2006,4(6):432-434.
[20]王暐,杨崇仁,张颖君.草果果实中的酚性成分[J].云南植物研究,2009,31(3):284-288.
[21]魏伟,范春林,王贵阳,等.广王不留行的化学成分研究[J].中草药,2014,45(5):615-621.
[22] Kubo I,Matsumoto A. Isolation of an insect-antifeedant,phloretin 4'-O-β-D-glucopyranoside,by rotation locuar counter-current chromatography and determination of its preferred conformation in solution by nuclear magnetic resonance analysis[J]. Chem Pharm Bull,1985,33(9):3817-3820.
[23]梁东,刘彦飞,郝志友,等.珍珠菜中黄酮及Megastigmane类化学成分研究[J].天然产物研究与开发,2015,27(7):1171-1175.
[24]胡江苗,陈纪军,赵友兴,等.山竺果壳的化学成分[J].云南植物研究,2006,28(3):319-322.