Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity
Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity
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DOI：
10.1021/jf010396d
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发表时间：
2001-06-01
影响因子：
6.1
通讯作者：
Winterhalter, P
中科院分区：
文献类型：
--
作者：
Baderschneider, B;Winterhalter, P
用逆流色谱法对德国雷司令葡萄酒进行了分离。经高效液相色谱纯化后，通过质谱和核磁共振谱确定了101个化合物的结构。73个分离的化合物表现出酚或苄基结构。其中54种化合物为首次报道的雷司令葡萄酒成分。这项工作中发现的新化合物包括十二种苯甲酸和肉桂酸衍生物。除了两种异构体（E）-咖啡酰乙基酒石酸酯外，还首次在雷司令葡萄酒中鉴定出（E）-肉桂酸、（E）-对香豆酸和（E）-阿魏酸的葡萄糖酯，以及（E）-和（Z）-阿魏酸的4-O-葡萄糖苷。另外两个苯丙素类化合物的结构被鉴定为3-羟基-1-（4-羟基-3-甲氧基苯基）-丙-1-酮和2，3-二羟基-1-（4-羟基-3-甲氧基苯基）-丙-1-酮。此外，两种乙酯，即，原儿茶酸乙酯和没食子酸乙酯以及香草酸葡萄糖酯是雷司令葡萄酒中新发现的。类黄酮组中的新代表是二氢山奈酚、二氢槲皮素和四种二氢黄酮醇糖缀合物，即，二氢山奈酚和二氢槲皮素的3-O-葡糖苷，以及二氢槲皮素的3-O-木糖苷和3 ′-O-葡糖苷。此外，六种新的木脂素，即，分离出落叶松树脂酚4-O-葡糖苷、三种异落叶松树脂酚衍生物、两种开环异落叶松树脂酚以及三种新木脂素。新分离的葡萄酒成分的结构解析报告一起测定其抗氧化活性。
A German Riesling wine has been fractionated with the aid of countercurrent chromatography. After purification by HPLC, the structures of 101 compounds were established by mass spectrometry and NMR spectroscopy. Seventy-three of the isolated compounds exhibited a phenolic or benzylic structure. Fifty-four compounds were reported for the first time as Riesling wine constituents. New compounds identified in this work included twelve benzoic and cinnamic acid derivatives. In addition to two isomeric (E)-caffeoyl ethyl tartrates, the glucose esters of(E)-cinnamic, (E)-p-coumaric, and (E)-ferulic acid, as well as the 4-O-glucosides of (E)- and (Z)-ferulic acid, have been identified for the first time in Riesling wine. The structures of two additional phenylpropanoids were elucidated as 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one and 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one. Moreover, two ethyl esters, i.e., ethyl protocatechuate and ethyl gallate, as well as the glucose ester of vanillic acid, were newly detected in Riesling wine. Novel representatives in the flavonoid group were dihydrokaempferol, dihydroquercetin, and four dihydroflavonol glycoconjugates, i.e., the 3-O-glucosides of dihydrokaempferol and dihydroquercetin, as well as the 3-O-xyloside and the 3 ' -O-glucoside of dihydroquercetin. Additionally, six novel lignans, i.e., lariciresinol 4-O-glucoside, three isolariciresinol derivatives, and two secoisolariciresinols, as well as three neolignans were isolated. Structural elucidation of the newly isolated wine constituents is reported together with the determination of their antioxidant activity.