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

• Project/Area Number: 08651016
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: YAMAGATA UNIVERSITY
• Principal Investigator: SATO Shingo Faculty of Engineering, Associate Professor, 工学部, 助教授 (30215793)
• Co-Investigator(Kenkyū-buntansha): ONODERA Jun-ichi Faculty of Engineering, Professor, 工学部, 教授 (30007017)
• Project Period (FY): 1996 – 1998
• Project Status: Completed (Fiscal Year 1998)
• Budget Amount: ¥2,100,000 (Direct Cost: ¥2,100,000); Fiscal Year 1998: ¥300,000 (Direct Cost: ¥300,000); Fiscal Year 1997: ¥300,000 (Direct Cost: ¥300,000); Fiscal Year 1996: ¥1,500,000 (Direct Cost: ¥1,500,000)
• Keywords: 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 / キノカルコン / ベニバナ色素 / 山葵墨入り病菌 / ワサビジエノンA / アシル基の転位反応 / サフラワーイエロ-B / モデル化合物 / 分解反応条件 / ベニバナ / カルタミン

Research Abstract

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.

Research Products

• [Publications] 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)
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] 佐藤 慎吾: "Synthesis of Wasabidienone A via a Novel Acyl Rearrangement Reaction from Carbon to Oxygen." Synthesis. 889-893 (1998)
  • Description: 「研究成果報告書概要(和文)」より
• [Publications] 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)
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] 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." Synthesis. 889. (1998)
  • Description: 「研究成果報告書概要(欧文)」より
• [Publications] 佐藤慎吾 他: "Synthesis of Wasabidienone. A via a Novel Acyl Reassangement Reaction from Ceabon to Oxyger." Synthesis.
• [Publications] 佐藤慎吾: "Synthesis of (+),(-)-Model Compounds and Absolate Configuration of Corthamin ; A Red Pigment in the Flower Petals of Safflower" Chemistry Letters. 10. 833-834 (1996)