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Bioorganic Studies on the Fragrance Formation during Flower Opening.

花开放期间香气形成的生物有机研究。

基本信息

批准号：
07660133
负责人：
WATANABE Naoharu
金额：
$ 1.41万
依托单位：
Shizuoka University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1996
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07660133/
关键词：
flower fragrance formation aroma precursor enzyme glycosides

项目摘要

In the course of the studies on the fragrance formation during flower opening, we have purified alcoholic aroma precursors of Gardenia jasminoides and Jasminum sambac. The isolation of these glycosides was guided by the crude enzyme assay. All the alcoholic aroma precursors isolated from these flower buds were beta-vicianoside, beta-primeveroside, beta-rutinoside, and 6'-O-malonyl-beta-D-glucopyranoside. Besides these alcoholic aromas, several geranyl and citronellyl disaccharide glycosides have been isolated-from rose flowers. This is for the first time that the disaccharide glycosides of monoterpene alcohols have been isolated from rose flowers.In order to clarify the mechanism of alcoholic aroma formation, we tried to prepare and purify the enzymes catalyzing the hydrolysis of the alcoholic aroma glycosides from the flowers of G.jasminoides flowers picked at the opening stage. The enzyme activity was determined by monitoring the hydrolysis activity toward rho-nitrophenyl beta-D-gluc … More opyranoside (rhoNP-Glc) and rhoNP-primeveroside (rhoNP-Pri). The acetone powder obtained from the flowers at the opening stage was solubilized in citrate buffer (pH 6.0). The supernatant was subjected to the precipitation with cold acetone and then by ammonium sulfate. The protein thus obtained was chromatographed on a CM-Toyopearl 650M column to give Glucosidases I and II,and Primeverosidase I.The Primeverosidase I was further subjected to FPLC on CM-Toyopearl column to give a primeverosidase as a single peak. rhoNP-Pri was hydrolyzed by the primeverosidase and the resultant hydrolysate was analyzed by TLC.Neither xylose nor glucose was detected. Only primeverose was detected as the sole saccharide in the hydrolysate. This result strongly suggested that the primeverosidase hydrolyzed disaccharide glycoside of slcoholic aromas like an endo-beta-glucosidase in a single step to liberate alcoholic aroma and disaccharide. To detect the low level of glycosidase activities on the gel after electro-phoreisis, the substrates with fluorecsence, 4-methylumberifellyl disaccharide glycosides, were synthesized for the first time.The use of aroma sensor and microwave oven-extraction has made it possible to monitor the aroma release and the change in the contents of alcoholic aroma precusors during flower opening.The results obtained so far have given important information and prompt further studies on the subject. Less

在研究栀子和茉莉花开放过程中香气形成的过程中，我们对栀子和茉莉花的醇类香气前体物质进行了分离纯化。这些糖苷的分离由粗酶测定指导。从这些花蕾中分离出的所有醇类香气前体均为β-vicianoside、β-樱草苷、β-芸香糖苷和6 ′-O-丙二酰-β-D-吡喃葡萄糖苷。除了这些醇的香气，几个香叶基和香茅基二糖糖苷已被分离，从玫瑰花。本研究首次从玫瑰花中分离到单萜醇类的二糖苷，为阐明醇类香气的形成机理，我们尝试从开放期采摘的茉莉花中制备并纯化醇类香气糖苷水解催化酶。通过监测对对硝基苯基β-D-葡萄糖的水解活性来确定酶活性 ...更多信息吡喃糖苷（rhoNP-Glc）和rhoNP-樱草苷（rhoNP-Pri）。将从开放阶段的花获得的丙酮粉末溶解在柠檬酸盐缓冲液（pH 6.0）中。上清液用冷丙酮沉淀，然后用硫酸铵沉淀。将由此获得的蛋白质在CM-Toyoprophin 650M柱上层析，得到葡糖苷酶I和II，以及樱草糖苷酶I。樱草糖苷酶I进一步在CM-Toyoprophin柱上进行FPLC，得到呈单峰的樱草糖苷酶。用樱草糖苷酶水解rhNP-Pri，用薄层层析法对水解产物进行分析，未检测到木糖和葡萄糖。在水解产物中仅检测到樱草素作为唯一的糖。这一结果强烈地表明樱草糖苷酶像内切-β-葡糖苷酶一样在单一步骤中水解醇类香气的二糖糖苷以释放醇类香气和二糖。为了检测电泳后凝胶上低水平的糖苷酶活性，使用了具有荧光的底物，4-甲基琥珀酰二糖糖苷，首次合成了一种新型的芳香化合物-提取的醇类香气物质，使人们有可能监测花开放过程中香气的释放和醇类香气前体物质含量的变化，这些结果为进一步研究和开发醇类香气前体物质提供了重要的信息和提示进一步研究这个问题。少