{"title":"苹果叶片中的3,4-二羟基-7,8-二氢-β- ionone - 3- O -β- d - glucopyranoside及其他糖苷类成分","authors":"C. Stingl, H. Knapp, P. Winterhalter","doi":"10.1080/10575630290019976","DOIUrl":null,"url":null,"abstract":"3,4-Dihydroxy-7,8-dihydro- -ionone 3- O - - d -glucopyranoside 1 has been isolated from a methanolic extract of apple ( Malus domestica ) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2 , which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3 , 3-oxo- -ionol - d -glucopyranoside 4 , benzoic acid - d -glucose ester 5 , kaempferol 3- O -rhamnoside 6 , (+)-syringaresinol - d -glucopyranoside 7 and 4-hydroxy-5-(3\"-methyl-2\"-butenyl)-benzoic acid methylester 3- - d -glucopyranoside 8 . The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract.","PeriodicalId":18873,"journal":{"name":"Natural Product Letters","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"7","resultStr":"{\"title\":\"3,4-Dihydroxy-7,8-Dihydro-β-Ionone 3- O -β- d -Glucopyranoside and Other Glycosidic Constituents from Apple Leaves\",\"authors\":\"C. Stingl, H. Knapp, P. Winterhalter\",\"doi\":\"10.1080/10575630290019976\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"3,4-Dihydroxy-7,8-dihydro- -ionone 3- O - - d -glucopyranoside 1 has been isolated from a methanolic extract of apple ( Malus domestica ) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2 , which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3 , 3-oxo- -ionol - d -glucopyranoside 4 , benzoic acid - d -glucose ester 5 , kaempferol 3- O -rhamnoside 6 , (+)-syringaresinol - d -glucopyranoside 7 and 4-hydroxy-5-(3\\\"-methyl-2\\\"-butenyl)-benzoic acid methylester 3- - d -glucopyranoside 8 . The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract.\",\"PeriodicalId\":18873,\"journal\":{\"name\":\"Natural Product Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2002-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"7\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural Product Letters\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1080/10575630290019976\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Product Letters","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1080/10575630290019976","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 7
摘要
采用XAD-2吸附层析、高速逆流色谱(HSCCC)和高效液相色谱(HPLC)纯化从苹果(Malus domestica)叶片甲醇提取物中分离得到3,4-二羟基-7,8-二氢- -ionone 3- O - -d -glucopyranoside 1。在酸性条件下,这种糖苷会产生许多挥发性化合物,包括1,1,6-三甲基-1,2-二氢萘(TDN) 2,这是葡萄酒中众所周知的异味化合物。在研究过程中,从苹果叶中分离到另外6种糖缀合物,分别是玫瑰苷3,3 -氧-离子醇- d -葡萄糖苷4,苯甲酸- d -葡萄糖酯5,山奈酚3- O -鼠李糖苷6,(+)-丁香醇- d -葡萄糖苷7和4-羟基-5-(3′-甲基-2′-丁烯基)-苯甲酸甲基lester 3- d -葡萄糖苷8。后一种化合物是首次从自然界分离出来的。为了避免TDN引起的“煤油脱味”,对甲醇提取物进行了酵母发酵。这种处理减少了TDN的形成量,并改善了甲醇提取物的风味印象。
3,4-Dihydroxy-7,8-Dihydro-β-Ionone 3- O -β- d -Glucopyranoside and Other Glycosidic Constituents from Apple Leaves
3,4-Dihydroxy-7,8-dihydro- -ionone 3- O - - d -glucopyranoside 1 has been isolated from a methanolic extract of apple ( Malus domestica ) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2 , which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3 , 3-oxo- -ionol - d -glucopyranoside 4 , benzoic acid - d -glucose ester 5 , kaempferol 3- O -rhamnoside 6 , (+)-syringaresinol - d -glucopyranoside 7 and 4-hydroxy-5-(3"-methyl-2"-butenyl)-benzoic acid methylester 3- - d -glucopyranoside 8 . The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract.