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Biosyntheis of volatile C-13 norisoprenoid

Research Project

Project/Area Number 13460047
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionShizuoka University

Principal Investigator

WATANABE Naoharu  Shizuoka University, Department of Applied Biological Chemistry, Faculty of Agriculture, Professor, 農学部, 教授 (90230979)

Co-Investigator(Kenkyū-buntansha) YAMANO Yumiko  Kobe College of Pharmacy, Faculty of Pharmacy, Instructor, 薬学部, 講師 (50208831)
HARA Masakazu  , 助教授 (10293614)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥16,000,000 (Direct Cost: ¥16,000,000)
Fiscal Year 2003: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2002: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥9,500,000 (Direct Cost: ¥9,500,000)
KeywordsC-13 norisoprenoid / aroma precursors / damascenone / Rosa damascena Mill. / star fruit / quince fruit / green tea leaves / carotenoid cleavage enzymes / C13ノルソプレノイド / Rosa damascena Mill / C13-ノルイソプレノイド / バラ / 茶葉 / star fruit
Research Abstract

1.Damascenone progenitors in the flowers of Rosa damascena Mill.
Two damascenone progenitors have been isolated from the flowers of R. damascena Mill. Their chemical structures were determined to be megastigma-6,7-dien-3,5,9-triol 9-Ο-β-D-glucolyranosides. The stereo chemistry for each compound was also determined by the direct comparison of their NMR spectra as well as chromatographic profiles on HIPLC.
2.Damascenone progenitors in green te extracts
During the course of sterilization of green tea extract for production of canned or bottled green tea drinks, damascenone was generated as off-flavor compound. The progenitors were isolated and identified to be acetylenic diol and allenic triol glucosides. Their stereo chemistries were also determined by comparison with synthetic specimens. We have also proposed the conversion routes for these compounds to damascenone.
3.Carotenoid cleavage enzymes being involved in the formation of C13-norisoprenoids
C-13 Norisoprenoid volatile compounds are speculated to be generated from carotenoids such as β-caroten, neoxantin by the action of carotenoid cleavage enzymes in plant tissues, such as some fruits and flowers. We have, for the first time, characterized an enzyme from star fruit (Averrhoa carambola) and green tea leaves. Similar enzymes were characterized from animals and quince fruits by the group of Prof. Winterhlater. We have characterized not only the biochemical profiles, but also the products on the enzymatic reaction from b-carotene.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Seung-Jin Ma et al.(4名, 2番): "The (3R,9R)-3-hydroxy-7,8-dihydro-β-ionol disaccharide glycoside is an aroma Precursor in tea leaves"Phytochemistry. 56. 819-825 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki et al.(12名, 12番): "Identification of (3S,9R)- and (3S,9S)-megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill."Biosci.Biotech.Biochem.. 66. 2692-2697 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yumiko Yamano et al.(4名, 3番): "Stereocontrolled synthesis of glucosidic damascenone precursors."J.Chem.Soc.Perkin I. 2002. 2833-2844 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Peter Fleischmann et al.(3名, 2番): "Characterization of a carotenoid cleavage enzyme from star fruit (Averrhoa carambola)"Phytochemistry. 63. 131-137 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki et al.(7名, 7番): "Identification of β-damscenone progenitors and their biogenesis in rose flowers (Rosa damascena Mill.). p.89-101 in "Carotenoid-Derived Aroma Compounds, ACS Symposium Series 802"American Chemical Society, Washington, DC. 323 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Peter Fleischmann et al.(4名, 4番): "Carotenoid cleavage enzymes in animals and plants. P.76-88 in "Carotenoid-Derived Aroma Compounds, ACS Symposium Series 802"American Chemical Society, Washington, DC. 323 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 渡辺修治, 坂田完三: "植物の香り、農芸化学の事典(鈴木昭憲,荒井綜一編集)"朝倉書店. 869 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Seung-Jin Ma, Naoharu Watanabe, Akihito Yagi, Kanzo Sakata: "The (3R,9R)-3-hydroxy-7,8-dihydro-β-ionol disaccharide glycoside is an aroma precursor in tea leaves"Phytochemistry. 56. 819-825 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki, Shigetaka Matsumoto, Hans-Peter Fleischmann, Hiroshi Shimada, Yumiko Yamano, Masayoshi Ito, Naoharu Watanabe: "Identification of β-damscenone progenitors and their biogenesis in rose flowers (Rosa damascena Mill.)."Carotenoid-Derived Aroma Compounds, Chapter 7 of ACS Symposium Series 802, American Chemical Society, Washington, DC, 2001. 0-8412-3729-8. 89-101 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Peter Fleischmann, Andrea.Lutz.Roeder, Peter Winterhalter, Naoharu Watanabe: "Carotenoid cleavage enzymes in animals and plants."Carotenoid-Derived Aroma Compounds, Chapter 7 of ACS Symposium Series 802, American Chemical Society, Washington, DC, 2001. 0-8412-3729-8. 76-88 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Ssuzuki, Shigetaka Matsumoto, Masaya Mizuguchi, Satoshi Hirata, Kazuteru Takagi, Ikue Hashimoto, Yumiko Yamano, Masayoshi Ito, Peter Fleischmann, Peter Winterhalter, Tetuichiro Morita, Naoharu Watanabe: "Identification of (3S,9R)-and (3S,9S)-megastigma-6,7-dien-3,5,9-triol 9-Ο-β-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill."Biosci.Biotech.Biochem. 66. 2692-2697 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yumiko Yamano, Yasuko Watanabe, Naoharu Watanabe, Masayoshi Ito: "Stereocontrolled synthesis of glucosidic damascenone precursors."J.Chem.Soc.Perkin I. 2833-2844 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Peter Fleischmann, Naoharu Watanabe, Peter Winterhalter: Phytochemistry. 63. 131-137 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naoharu Watanabe, Kanzo Sakata, Plant Volatiles: "Dictionary of Agricultural and Biological Chemistry"Asakura Shoten(Akinori Suzuki Edt.). 869 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Peter Fleischmann et al. (3名, 2番): "Characterization of a carotenoid cleavage enzyme from star fruit (Averrhoa carambola)"Phytochemistry. 63. 131-137 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 渡辺修治, 坂田完三: "植物の香り、農芸化学の事典"鈴木昭憲, 荒井綜一編集 朝倉書店. 869 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yumiko Yamano: "Stereocontrolled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7,8-didehydro-β-ionol"Chem.Pharm.Bull.. 48. 2017-2018 (2000)

    • Related Report
      2002 Annual Research Report
  • [Publications] Seung-Jin Ma: "The(3R,9R)-3-hydroxy-7,8-dihydro-b-ionol disaccharide glycoside is an aroma Precursor in tea leaves"Phytochemistry. 56. 819-825 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Peter Fleischmann: "Carotenoid cleavage enzymes in animals and plants"ACS Symposium series : Carotenoid-Derived Aroma. 802. 76-88 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Masayuki Suzuki: "Identification of β-damascenone progenitors and their biogenesis in rose flowers(Rosa damascena Mill)"ACS Symposium series : Carotenoid-Derived Aroma. 802. 89-101 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Masayuki Suzuki: "Identification of(3S,9R)-and (3S,9S)-megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides as damascenonoe progenitors in the flowers of Rosa damascena Mill."Biosci.Biotech.Biochem.. 66. 2692-2697 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Yumiko Yamano: "Stereocontrolled synthesis of glucosidic damascenone precursors"J.Chem.Soc.Perkin I. 2002. 2833-2844 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Peter Fleischmann: "Characterization of a carotenoid cleavage enzyme from star fruit(Averrhoa carambola)"Phytochemistry. (In press).

    • Related Report
      2002 Annual Research Report
  • [Publications] Yumiko Yamano: "Stereocontrolled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7,8-didehydro-β-ionol"Chem.Pharm.Bull.. 48. 2017-2018 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] Seung-Jin Ma: "The (3R,9R)-3-hydroxy-7,8-dihydro-b-ionol disaccharide glycoside is an aroma Precursor in tea leaves"Phytochemistry. 56. 819-825 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Peter Fleischmann: "Carotenoid cleavage enzymes in animals and plants"ACS Symposium series: Carotenoid-Derived Aroma. 802. 76-88 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Masayuki Suzuki: "Identification of β-damascenone progenitors and their biogenesis in rose flowers (Rosa damascena Mill.)"ACS Symposium series: Carotenoid-Derived Aroma. 802. 89-101 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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