蜜炙枇杷叶中1个新酚苷类化合物
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摘要
综合利用硅胶,Sephadex LH-20,RP-18和制备型HPLC等色谱技术,从蜜炙枇杷叶水提物乙酸乙酯萃取部位分离得到12个化合物,并通过MS和NMR等多种波谱技术鉴定其结构分别为japonicanoside A(1)、nerolidol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside(2)、nerolidol-3-O-α-L-rhamnopyranosyl-(l→4)-α-L-rhamnopyranosyl-(1→2)-[α-L-(4-trans-feruloyl)-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside(3)、儿茶素[(+)-catechin,4]、表儿茶素[(-)-epicatechin,5]、山柰酚-3-O-α-L-鼠李糖苷(kaempferol-3-O-α-L-rhamnopyranoside,6)、槲皮素-3-O-α-L-鼠李糖苷(quercitrin,7)、槲皮素-3-O-β-D-半乳糖苷(quercetin-3-O-β-D-galactopyranoside,8)、槲皮素-3-O-β-D-葡萄糖苷(quercetin-3-O-β-glucopyranoside,9)、香草醛(vanillin,10)、原儿茶醛(protocatechuic aldehyde,11)、麦芽酚(maltol,12)。其中,化合物1为1个新的酚苷类化合物。
A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-β-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-β-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-β-D-galactopyranoside( 8),quercetin-3-O-β-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.
A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-β-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-β-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-β-D-galactopyranoside( 8),quercetin-3-O-β-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.
引文
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[3] Cha D S,Eun J S,Jeon H. Anti-inflammatory and antinociceptive properties of the leaves of Eriobotrya japonica[J]. J Ethnopharmacol,2011,134(2):305.
[4]林玉霖,林文津.枇杷叶的研究现状与开发前景[J].中药材,2016,29(10):1111.
[5] Liu Y L,Zhang W N,Xu C J,et al. Biological activities of extracts from Loquat(Eriobotrya japonica Lindl.):a review[J]. Int J Mol Sci,2016,17(12):1983.
[6] Wu J B,Kuo Y H,Lin C H,et al. Tormentic acid,a major component of suspension cells of Eriobotrya japonica,suppresses high-fat diet-induced diabetes and hyperlipidemia by glucose transporter 4 and AMP-activated proteinkinase phosphorylation[J]. J Agric Food Chem,2014,62(44):10717.
[7]叶广亿,李书渊,陈艳芬,等.枇杷叶不同提取物的止咳化痰平喘作用比较研究[J].中药药理与临床,2013,29(2):100.
[8]王辛秋,张洪春,陈燕.晁恩祥辨治“风咳”经验介绍[J].北京中医药,2010,29(9):667.
[9]晃恩祥.咳嗽变异型哮喘证治[J].世界中医药,2006,1(1):37.
[10]李舒丰,刘芹燕,刘文东,等.苏黄止咳胶囊及其挥发油中间体中挥发性成分的分析[J].中成药,2017,39(11):2329.
[11]刘芹燕,巫兴东,陈东,等.苏黄止咳胶囊中非挥发性成分的LC-MS分析[J].中成药,2019,41(6):1434.
[12] Katagiri S,Watanabe Y,Yaoita Y,et al. Two new phenolic glycosides from Viburnum plicatum var. plicatum f. plicatum[J].Nat Prod Commun,2011,6(12):1901.
[13] Kasai R,Okihara M,Asakawa J,et al.13C NMR study ofα-andβ-anomeric pairs of D-mannopyranosides and L-rhamnopyranosides[J]. Tetrahedron,1979,35(11):1427.
[14] Schmid C,Dawid C,Peters V,et al. Saponins from european licorice roots(Glycyrrhiza glabra)[J]. J Nat Prod,2018,81(8):1734.
[15] Tommasi N D,Simone F D,Aquino R,et al. Plant metabolites.New sesquiterpene glycosides from Eriobotrya japonica[J]. J Nat Prod,1990,53(4):810.
[16] Tommasi N D,Aquino R,Simone F D,et al. Plant metabolites.New sesquiterpene and ionone glycosides from Eriobotrya japonica[J]. J Nat Prod,1992,55(8):1025.
[17]胡红军,杨郁,于能江,等.牡丹皮化学成分研究[J].中国中药杂志,2006,31(21):1793.
[18]纳智,许又凯.版纳藤黄化学成分的研究[J].中国中药杂志,2009,34(18):2338.
[19] Strack D,Heilemann J,Momken M,et al. Cell wall-conjugated phenolics from coniferae leaves[J]. Phytochemistry,1988,27(11):3517.
[20] Duan C H,Lee J N,Lee C M,et al. Phytochemical constituents from Metasequoia glyptostroboids leaves[J]. Nat Prod Sci,2009,15(1):12.
[21] Park C J,Hwang Y H,Choi D R,et al. A triterpenoid glucoside and phenolic compounds from Rosa davurica[J]. Nat Prod Sci,2003,9(1):31.
[22] Merfort I,Wendisch D. Flavonoid glycosides from Arnica montana and Arnica chamissonis[J]. Planta Med,1987,53(5):434.
[23]段洁,李巍,胡旭佳,等.九子参化学成分研究[J].中草药,2008,40(4):528.
[24] Li H B,Zhou C X,Pan Y X,et al. Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus[J]. Planta Med,2005,71(12):1128.
[25] Sun P Y,Ye W,Zhao J F,et al. Studies on the constituents of Epimedium koreanum[J]. Chem Pharm Bull,1995,43(4):703.