Total Synthesis and Determination of Absolute Configuration of Carthamin ; A Red Pigment in the Petals of Safflower

红花素的全合成及绝对构型测定；

• 批准号: 08651016
• 负责人: SATO Shingo
• 金额: $ 1.34万
• 依托单位: YAMAGATA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1996
• 资助国家: 日本
• 起止时间: 1996 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-08651016/
• 关键词: Coloring components of Safflower Petals; X-ray crystallographic analysis; CD Spectra; Biosynthetic Pathway; Absolute Configuration; C-glucosylquinochalcone; Wasabidienone A; Phoma wasabidiae; X線構造解析; カルタミンプレカーサー; サフラワーイエローB; サフロミンA; サフロミンC; キ

Absolute configuration of Carthamin which is the red coloring component of safflower petals, was determined to be S, S.Furthermore, absolute configurations of the other yellow coloring components in which carthamin precursor, safflower yellow B, safflomin A, Safflomin C, and isosafflomin C bear C-glucosylquinochalcone as a common structural unit, were also determined to be S, S in the same way. Model compound of safflower yellow B which includes a chain-type glucose was first synthesized and its hydrolysis produced a small amount of carthamin-model compounds, as well as carthamin's biosynthetic pathway.Next, we first synthesized Wasabidienone A which is one of the metabolites of phoma wasabidiae, highly oxidized structure, and a mixture of keto-enol tautomers like carthamin.

红花花瓣的红色着色成分红花素的绝对构型被确定为S，S。此外，红花素前体、红花黄色素B、红花红色素A、红花红色素C和异红花红色素C以C-葡萄糖基喹查尔酮为共同结构单元的其他黄色着色成分的绝对构型也以相同的方式被确定为S，S。首先合成了含有链状葡萄糖的红花黄色素模型化合物B，并对其水解产生少量红花素模型化合物，以及红花素的生物合成途径进行了研究;其次，我们首次合成了山葵茎点霉的代谢产物之一，具有高度氧化结构，与红花素一样是酮-烯醇互变异构体的混合物。

项目成果

Shingo SATO,Heitaro OBARA,Katsuhiro YUSA,Kazuhiro SUDO,Masaharu SADO,Hiroyuki KAGAYA,Hiroki IJICHI,Shigeru MATSUBA,Toshihiro KUMAZAWA,and Jun-ichi ONODERA: "Synthesis of Wasabidienone A via a Novel Acyl Rearrangement Reaction from Carbon to Oxygen." Synth

Shingo SATO、Heitaro OBARA、Katsuhiro YUSA、Kazuhiro SUDO、Masaharu SADO、Hiroyuki KAGAYA、Hiroki IJICHI、Shigeru MATSUBA、Toshihiro KUMAZAWA 和 Jun-ichi ONODERA：“通过从碳到氧的新型酰基重排反应合成芥末二烯酮 A。”

佐藤慎吾 他: "Synthesis of Wasabidienone. A via a Novel Acyl Reassangement Reaction from Ceabon to Oxyger." Synthesis.

Shingo Sato 等人：“芥二烯酮的合成。通过从 Ceabon 到 Oxyger 合成的新型酰基重排反应。”

佐藤 慎吾: "Synthesis of (+),(-)-Model Compounds and Absolute Configuration of Carthamin ; A Red Pigment in the Flower Petals of Safflower" Chemistry Letters. 833-834 (1996)

Shingo Sato：“(+),(-)-模型化合物的合成和红花素的绝对构型；红花花瓣中的红色颜料”化学快报 833-834 (1996)。

Shingo SATO,Heitaro OBARA,Toshihiro KUMAZAWA,Jun-ichi ONODERA,and Kimio FURUHATA: "Synthesis of (+), (-) -Model Compounds and Absolute Configuration of Carthamin ; A Red pigment in the Flower Petals of Safflower." Chem.Lett.833. (1996)

Shingo SATO、Heitaro OBARA、Toshihiro KUMAZAWA、Jun-ichi Onodera 和 Kimio FURUHATA：“( )、(-) -模型化合物的合成和红花素的绝对构型；红花花瓣中的红色素。”

佐藤 慎吾: "Synthesis of Wasabidienone A via a Novel Acyl Rearrangement Reaction from Carbon to Oxygen." Synthesis. 889-893 (1998)

Shingo Sato：“通过新型酰基重排反应从碳到氧的合成芥二烯酮 A”（889-893）。