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Enzymatic acylation of vitamin C with medium-chain fatty acids and estimation of intestinal absorbability of the products

Research Project

Project/Area Number 09650874
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 生物・生体工学
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

ADACHI Shuji  Graduate School of Agriculture, KYOTO UNIVERSITY Associate Professor, 農学研究科, 助教授 (90115783)

Co-Investigator(Kenkyū-buntansha) KIMURA Yukitaka  Graduate School of Agriculture, KYOTO UNIVERSITY Instructor, 農学研究科, 助手 (70211878)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1998: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1997: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsVitamin C / ascorbic acid / lipase / acylation / condensation / enzyme reaction in microaqueous system / Intestinal absorption / Caco-2
Research Abstract

The absorbability of vitamin C (ascorbic acid) in the intestine is low because of its hydrophilicity. It has been known that medium-chain fatty acids enhance the intestinal absorption of hydrophilic substances. In this context, this projects intended to improve the absorbability of vitamin C by its enzymatic acylation with medium-chain fatty acid. The products are also expected to be oil-soluble reducing agent and surfactant with reducing ability. It was found that immobilized lipase from Candida antarctic could catalyze the condensation of ascorbic acid and lauric acid in acetonitrile, and that the equilibrium yield of the condensation became higher at the lower water content of the solvent. The chain length of acyl residue of fatty acids scarcely affected the equilibrium yield of the products. Because acetonitrile would not be adequate for application to food, some water-miscible organic solvents were tested for the reaction medium of the condensation to find more adequate solvent. Acetone, which could be easily removed in the purification step of the products due to its high volatility, was also a good solvent for the condensation, and the equilibrium yield was higher at the lower water content in the solvent. The mechanism on the absorption of hydrophilic substances at the intestine was examined by using the cultured Caco-2 cell. Surfactant property of medium-chain fatty acids was concerned in the adsorption enhancement. Ascorbic acid acylated with medium-chain fatty acid was fairly strongly surface active. Thus, the method for enzymatic acylation of ascorbic acid has been established, and the basic knowledge on the improvement of absorption of ascorbic acid in the intestine has been obtained.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Y.Watanabe: "Condensation of L-Ascorbic Acid and Medium-chain Fatty Acids by Immobilized Lipase in Acetonitrile with Low Water Content." Food Sci.Technol.Res.5(2) 印刷中. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Shima: "The Relationship between Transport-enhancement Effects and Cell Viability by Capric Acid Sodium Salt, Monocaprin, and Dicaproin." Biosci.Biotech.Biochem.62(1). 83-86 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Shima: "Effects of Medium-chain Fatty Acids and Their Acylglycerols on Transport of Penicillin V across Caco-2 Cell Monolayers." Biosci.Biotech.Biochem.61(7). 1150-1155 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Watanabe, S.Adachi, K.Nakanishi, and R.Matsuno: "Condensation of L-Ascorbic Acid and Medium-chain Fatty Acids by Immobilized Lipase in Acetonitrile with Low Water Content." Food Sci.Technol.Res.5(2)(in press.). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Shima, Y.Kimura, S.Adachi, and R.Matsuno: "The Relationship between Transport-enhancement Effects and Cell Viability by Capric Acid Sodium Salt, Monocaprin, and Dicaproin." Biosci.Biotech.Biochem.62(1). 83-86 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Shima, K.Yohdoh, M.Yamaguchi, Y.Kimura, S.Adachi, and R.Matsuno: "Effects of Medium-chain Fatty Acids and Their Acylglycerols on Transport of Penicillin V across Caco-2 Cell Monolayers." Biosci.Biotech.Biochem.61(7). 1150-1155 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Watanabe: "Condensation of L-Ascorbic Acid and Medium-chain Fatty Acids by Immobilized Lipase in Acetonitrile with Low Water Content." Food Sci.Technol.Res.5(2)(印刷中). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Shima: "Effects of Medium-chain Fatty Acids and Their Acylglycerols on Transport of Penicillin V across Caco-2 Cell Monolayers." Biosci.Biotech.Biochem.61(7). 1150-1155 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Shima: "The Relationship between Transport-enhancement Effects and Cell Viability by Capric Acid Sodium Salt,Monocaprin,and Dicaproin." Biosci.Biotech.Biochem.62(1). 83-86 (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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