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Bio-organic Chemical Studies on the Floral Scent Formation and Flower Induction

Research Project

Project/Area Number 12045230
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionShizuoka University

Principal Investigator

WATANABE Naoharu  Faculty of Agriculture of Shizuoka University, Professor, 農学部, 教授 (90230979)

Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥14,600,000 (Direct Cost: ¥14,600,000)
Fiscal Year 2002: ¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2001: ¥4,800,000 (Direct Cost: ¥4,800,000)
Fiscal Year 2000: ¥6,400,000 (Direct Cost: ¥6,400,000)
Keywordsflower opening / floral scent formation / rose flowers / 2-phenylethanol / biogenesis / flower induction / Pharbitis nil / KODA / 2-phehylethanol / β-glucosidase / methyltransferase / 2-phenylethanol / FIF / 香気発散 / ローフェニルエタノール / C_<13>-ノルイソプレノイド
Research Abstract

1.Diurnal Floral Scent Emission form flowrs of Rosa damascena, R.'Hoh-Jun' Rhythmic cycles in the emission of 2-phenyletanol (1) are observed in Rosa damascena quatra saison and R.'Hoh-Jun', although R.damascena Mill.transiently emits 1.
2.Role of glucosidase inhibitor in 2-phenylethanol emission During the day-time after the feeding of β-glucosidase-inhibitor commenced, the level of 2-phenylethyl β-D-glucopyranoside (2) remained fairly constant in the fed group, but decreased in feeding commenced in the control group, but the concentration was almost constant during the unfurling process in the fed group One β-glucosidase clone was obtained from the petals of Rose damascena Mill.although its function is not clarified yet.
3.Biogenesis of 1 and 2 [^2H_8]-1 and [^2H_8]-2 must be biosynthesized from [^2H_8] L-phenylalanine with a retention of the deuterium atom at α-position of [^2H_8] L-phenylalanine.We fed deuterium-labeled intermediates into R.'Hoh-Jun' flowers.A high incorporation of phenylacetaldoxime was confirmed.We have proposed a plausible biosynthetic pathway for 1 and 2.
4.Cloning of O-methyltransferases involved in the biosynthesis of floral scent compounds. New OMT, POMT, was purified from flower petals, and characterized the partial sequences by MALDI-TOFMS.We also confirmed the presence of carotenoid cleavage enzymes in rose flowers.
5.KODA, a compound involved in flower-induction of Pharbitis nil.Violet (collaborative reseearch with Dr.Yokoyama, Shiseido Co. Ltd) α-Ketol linolenic acid (KODA) was identified for the first time in seedlings of Pharbitis grown under a flower-inductive condition (16-h dark exposure), by means of LC-SIM and LC-MS/MS analyses.One of the metabolites of KODA has been characterized by LC-MS-MS and NMR.

Report

(4 results)
  • 2003 Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (45 results)

All Other

All Publications (45 results)

  • [Publications] Joanne M.Picone, et al.(5名, 3番): "Rhythmic emission of floral volatiles from Rosa damascena semperf lorens cv. 'Quatra Saisons'."Planta. (In press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuiqin Wu, et al. (7名, 3番): "The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1,3,5-trimethoxybenzene"Plant Physiol.. (In press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shunsuke Hayashi, et al.(12名, 12番): "Emission of 2-phenylethanol from its β-D-glucopyranoside and their biogenesis from [^2H_8] L-phenylalanine in rose flowers"Tetrahedron. (In press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuiqin Wu, et al., (6名, 2番): "Two O-methyltransferases isolated from flower petals of Rosa chinens var.spontanea involved in scent biosynthesis"J.Biosci.Bioeng. 96. 119-128 (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. (6名, 6番): "Changes in catecholamine levels in short day-induced cotyledons of Pharbitis nil"Z.Naturforschung. 58. 220-224 (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. (10名, 9番): "Endogenous α-ketol linolenic acid (KODA) levels in short day-induced cotyledons are closely related to flower induction in Pharbitis nil."Plant Cell Pysiol.. 44. 35-43 (2003)

    • 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. 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] 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] Shuzo Watanabe, et al., (8名, 8番): "Biogenesis of 2-phenylethanol in rose flowers ; Incorporation of [^2H_8] L-phenylalanine into 2-phenylethanol and its β-D-glucopyranoside during the flower opening of Rosa 'Hoh-Jun' and Rosa damascene Mill"Biosci.Biotech.Biochem.. 66. 713-717 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuzo Watanabe, et al., (10名, 10番): "Isolation and identification of 2-phenylethyl disaccharide glycosides and its mono glycosides from rose flowers, and their potential role in scent formation."Biosci.Biotech.Biochem.. 65. 442-445 (2001)

    • 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): "Stereo-controlled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7,8-didehvdro-β-ionol."Chem.Pharm Bull.. 48. 2017-2018 (2000)

    • 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. (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. (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. (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuiqin Wu: "The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1, 3, 5-trimethoxybenzene."Plant Physiol.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Jonne M. Picone: "Rhythmic emission of floral volatiles from Rosa damascena semperflorens cv.'Quatra Saisons'."Planta. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shunsuke Hayashi: "Emission of 2-phenylethanol from its β-D-glucopyranoside and their biogenesis from [^2H_8] L-phenylalanine in rose flowers"Tetrahedron. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuiqin Wu: "Two O-methyltransferases isolated from flower petals of Rosa chinensis var.spontanea involved in scent biosynthesis"J. Biosci. Bioeng. 96. 119-128 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki: "Changes in catecholamine levels in short day-induced cotyledons of Pharbitis nil"Z.Naturforschung. 58. 220-224 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki: "Endogenous α-ketol linolenic acid (KODA) levels in short day-induced cotyledons are closely related to flower induction in Pharbitis nil."Plant Cell Physiol.. 44. 35-43 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yumiko Yamano: "Stereocontrolled synthesis of glucosidic damascenone precurosors."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] Masayuki Ssuzuki: "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(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuzo Watanabe: "Biogenesis of 2-phenylethanol in rose flowers : Incorporation of [^2H_8] L-phenylalanine into 2-phenylethanol and its β-D-glucopyranoside during the flower opening of Rosa 'Hoh-Jun' and Rosa damascena Mill"Biosci. Biotech. Biochem.. 66. 713-717 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Shuzo Watanabe: "Isolation and identification of 2-phenylethyl disaccharide glycosides and its mono glycosides from rose flowers, and their potential role in scent formation."Biosci. Biotech. Biochem. 65. 442-445 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yumiko Yamano: "Stereo-controlled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7, 8-didehydro-β-ionol."Chem. Pharm Bull.. 48. 2017-2018 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masayuki Suzuki: "Identification of β-damscenone progenitors and their biogenesis in rose flowers (Rosa damascena Mill.)."Carotenoid-Derived Aroma Compounds, ACS Symposium Series 802, American Chemical Society, Washington, DC. 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: "Carotenoid cleavage enzymes in animals and plants."Carotenoid-Derived Aroma Compounds, ACS Symposium Series 802, American Chemical Society, Washington, DC. 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] 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] Kentaro Hayashi: "A rhythmic floral scent emission and the circadian rhysms"Aroma Research. 2. 2-9 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuzo Watanabe: "Biogenesis of 2-Phenylethanol in Rose Flowers : Incorporation of [^2H_8] L-Phenylalanine into 2-Phenylethanol and Its β-D-Glucopyranoside during the Flower Opening of Rosa 'Hoh-Jun' and Rosa damascena Mill"Biosci. Biotech. Biochem. (In press).

    • Related Report
      2002 Annual Research Report
  • [Publications] Masayuki Suzuki: "Endogeneous α-ketol linolenic acid (KODA) levels in short day-induced cotyledons are closely related to flower induction in Pharbitis nil"Plant Cell Physiol.. 44. 35-43 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Masayuki Suzuki: "Changes in Catecholamine Levels in Short Day-Induced Cotyledons of Pharbitis nil"Z. Naturforschung c. (In press).

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuiqin Wu: "Two O-methyltransferases isolated from flower petals of Rosa chinensis var.spontanea involved in scent biosynthesis"J. Biosci. Bioeng.. (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
  • [Publications] Kentaro Hayashi: "A rhythmic floral scent emission and the circadian rhysms"Aroma Research. 2. 2-9 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shuzo Watanabe: "Biogenesis of 2-Phenylethanol in Rose Flowers : Incorporation of [^2H_8] L-Phenylalanine into 2-Phenylethanol and Its β-D-Glucopyranoside during the Flower Opening of Rosa 'Hoh-Jun' and Rose damascena Mill"Biosci. Biotech. Biochem. (in press).

    • Related Report
      2001 Annual Research Report
  • [Publications] Watanabe,S., et al.,: "Isolation and identification of 2-phenylethyl disaccharide glycosides and mono glycosides from rose flowers, and their potential role in scent formation"Biosci.Biotech.Biochem.,. 65・2. 442-445 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yamano,Y. et al.,: "Stereo-controlled synthesis of optically active β-P-glucopyranosides of 3-hydroxy-7.8-didehgdro β-ionol"Chem.Pharm.Ball.,. 48・12. 2017-2018 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Watanabe,N. et al.,: "Identification of βdomascenore progenitors and their biogenesis in rose flowers (Rose damascena Moli)"Ioi "Caroteroid-derived aroma compounds", ACS Symposium Sories. (印刷中).

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2018-03-28  

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