2003 Fiscal Year Final Research Report Summary
Biosyntheis of volatile C-13 norisoprenoid
| Project/Area Number |
13460047
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Shizuoka University |
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Principal Investigator |
WATANABE Naoharu Shizuoka University, Department of Applied Biological Chemistry, Faculty of Agriculture, Professor, 農学部, 教授 (90230979)
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| 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)
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| Project Period (FY) |
2001 – 2003
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| Keywords | C-13 norisoprenoid / aroma precursors / damascenone / Rosa damascena Mill. / star fruit / quince fruit / green tea leaves / carotenoid cleavage enzymes |
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| 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.
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[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
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[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
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