Molecular mechanism on the seasonal change in biosynthetic pathways of rose scent compound in response to the environment

• Project/Area Number: 23380063
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Shizuoka University
• Principal Investigator: WATANABE Naoharu 静岡大学, 創造科学技術大学院, 教授 (90230979)
• Co-Investigator(Renkei-kenkyūsha): HARA Masakazu 静岡大学, 農学研究科, 教授 (10293614) ; OHNISHI Toshiyuki 静岡大学, 農学研究科, 准教授 (60542165)
• Project Period (FY): 2011-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000); Fiscal Year 2013: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000); Fiscal Year 2012: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000); Fiscal Year 2011: ¥9,880,000 (Direct Cost: ¥7,600,000、Indirect Cost: ¥2,280,000)
• Keywords: 生合成 / バラ香気成分 / 環境要因 / 芳香族アミノ酸脱アミノ酵素 / ケト酸脱炭酸酵素 / プロトプラスト / GCMS / LCMS / バラ / 2-フェニルエタノール / 季節変化 / AAAT / PDC / ２－フェニルエタノール / 芳香族アミノ酸アミノ基転移酵素 / ピルビン酸脱炭酸酵素

Research Abstract

The objective of the research is to clarify the molecular mechanism on the seasonal change in biosynthetic pathways of rose scent 2-phenylethanol (2PE) in response to environment. Based on the feeding experiments of L-[2H8]phenylalanin ([2H8]LPhe) to rose flowers and the GCMS, and LCMS analyses, we have clarified that two new enzymes, AAAT and PPDC are involved in the new biosynthetic pathway from LPhe to 2PE (LPhe, PPA, PAld, 2PE). We have also confirmed that the pathway is actively operating under the environmental conditions at high temperature.

Research Products

• [Journal Article] Molecular cloning and characterization of a short chain dehydrogenase showing activity with volatile compounds isolated from Camellia sinensis (2014)
  • Author(s): Ying Zhou, Ling Zhang, Jiadong Gui, Fang Dong, Sihua Cheng, Xin Mei, Linyun Zhang, Yongqing Li, Xinguo Su, Susanne Baldermann, Naoharu Watanabe, Ziyin Yang
  • Journal Title: Plant Molecular Biology Reporter Volume: 33 Issue: 2 Pages: 253-263
  • DOI: 10.1007/s11105-014-0751-z
  • Peer Reviewed / Open Access
• [Journal Article] Characterization of odorant compounds and their biochemical formation in green tea with a low temperature storage process (2014)
  • Author(s): Tsuyoshi Katsuno, Hisae Kasuga, Yumi Kusano, Yoshihiro Yaguchi, Miho Tomomura, Jilai Cui, Ziyin Yang, Susanne Baldermann, Yoriyuki Nakamura, Toshiyuki Ohnishi, Nobuyuki Mase, Naoharu Watanabe
  • Journal Title: Food Chem Volume: 148 Pages: 388-395
  • DOI: 10.1016/j.foodchem.2013.10.069
  • Peer Reviewed / Open Access
• [Journal Article] Determination of volatile compounds in four commercial samples of Japanese green algae using solid phase microextraction gas chromatography mass spectrometry. (2014)
  • Author(s): Yamamoto,M., Baldermann,S., Yoshikawa,K.,, Fujita,A., Mase,N., Watanabe,N.
  • Journal Title: The Scientific World Journal Volume: Article ID 289780 Pages: 8-8
  • Peer Reviewed
• [Journal Article] Characterization of flower-inducing compound in Lemna paucicostata exposed to drought stress. (2014)
  • Author(s): Murata, A. Akaike,R., Kawahashi, T., Tsuchiya, R., Takemoto,H., Ohnishi, T., Todoroki, Y., Mase, N., Yokoyama, M., Takagi, K., Winterhalter, P., Watanabe..N.
  • Journal Title: Tetrahedron Volume: 印刷中 Issue: 33 Pages: 4969-4976
  • DOI: 10.1016/j.tet.2014.03.099
  • NAID: 110009757825
  • Peer Reviewed / Open Access
• [Journal Article] (2013)
  • Author(s): Ariaki Murata, Ulrich H. Engelhardt, Peter Fleischmann, Keita Yamada, Naohiro Yoshida, Dieter Juchelka, Andreas Hilkert, Toshiyuki Ohnishi, Naoharu Watanabe, Peter Winterhalter
  • Journal Title: J. Agric. Food Chem Volume: 61 Issue: 47 Pages: 11321-11325
  • DOI: 10.1021/jf403605a
  • Peer Reviewed
• [Journal Article] Recent studies of the volatile compounds in tea. (2013)
  • Author(s): Yang, Z., Baldermann, S., Watanabe, N
  • Journal Title: Food Res. International, Volume: 53 Issue: 2 Pages: 585-599
  • DOI: 10.1016/j.foodres.2013.02.011
  • Peer Reviewed
• [Journal Article] Influence of exogenously applied abscisic acid on carotenoid content and water uptake in flowers of the tea plant (Camellia sinensis). (2013)
  • Author(s): Baldermann,S., Yang,Z., Sakai, M., Fleischmann, P., Morita,A., Todoroki,Y. Watanabe, N.
  • Journal Title: J Sci Food Agric. Volume: 93 Issue: 7 Pages: 1660-1664
  • DOI: 10.1002/jsfa.5944
  • Peer Reviewed
• [Journal Article] nsight into the chemistry of cycloaddition between α-ketol oxylipin and epinephrine: isolation and structure elucidation of a new reaction product. (2013)
  • Author(s): Kai,K., Oba,Y., Akaike,R., Murata,A., Nishikawa, T., Watanabe,N.
  • Journal Title: Tetrahedron Lett., Volume: 54 Issue: 18 Pages: 2247-2250
  • DOI: 10.1016/j.tetlet.2013.02.062
  • Peer Reviewed
• [Journal Article] Characterization of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark (2012)
  • Author(s): Ziyin Yang, Eiji Kobayashi, Tsuyoshi Katsuno, Toshimichi Asanuma, Tamaki Fujimori, Takamasa Ishikawa, Miho Tomomura, Kazuo Mochizuki, Takaya Watase, Yoriyuki Nakamura, Naoharu Watanabe
  • Journal Title: Food Chem Volume: 135 Issue: 4 Pages: 2268-2276
  • DOI: 10.1016/j.foodchem.2012.07.066
  • Peer Reviewed
• [Journal Article] Roses Shift Biosynthetic Pathways of Floral Scent in Response to Seasonal Change (2012)
  • Author(s): 平田拓, 大西利幸, 渡辺修治
  • Journal Title: KAGAKU TO SEIBUTSU Volume: 50 Issue: 8 Pages: 570-576
  • DOI: 10.1271/kagakutoseibutsu.50.570
  • NAID: 10030982495
  • ISSN: 0453-073X, 1883-6852
  • Peer Reviewed
• [Journal Article] Functional characterization of aromatic amino acid aminotransferase involved in 2-phenylethanol biosynthesis in isolated rose petal protoplasts (2012)
  • Author(s): Hiroshi Hirata, Toshiyuki Ohnishi, Haruka Ishida, Kensuke Tomida, Miwa Sakai, Masakazu Hara, Naoharu Watanabe
  • Journal Title: J. Plant Physiol Volume: 169 Issue: 5 Pages: 445-451
  • DOI: 10.1016/j.jplph.2011.12.005
  • NAID: 120004247736
  • Peer Reviewed
• [Journal Article] Biosynthesis of α-and β-ionones, prominent scent compounds, in flowers of Osmanthus fragrans (2012)
  • Author(s): Susanne Baldermann, Masaya Kato, Peter Fleischmann, Naoharu Watanabe
  • Journal Title: Acta Biochim. Pol Volume: 59 Pages: 79-81
  • Peer Reviewed
• [Journal Article] Characterization of L-phenylalanine metabolism to acetophenone and 1-phenylethanol in the flowers of Camellia sinensis using stable isotope labeling (2012)
  • Author(s): Fang Dong, Ziyin Yang, Susanne Baldermann, Yutaka Kajitani, Shogo Ota, Hisae Kasuga, Yumi Imazeki, Toshiyuki Ohnishi, Naoharu Watanabe
  • Journal Title: J.Plant Physiol. Volume: 169 Issue: 3 Pages: 217-225
  • DOI: 10.1016/j.jplph.2011.12.003
  • Peer Reviewed
• [Journal Article] Herbivore-induced volatiles from tea (Camellia sinensis) plants and their involvement in intraplant communication and changes in endogeno us nonvolatile metabolites (2012)
  • Author(s): Fang Dong, Ziyin Yang, Susanne Baldermann, Yasushi Sato, Tatsuo Asai, Naoharu Watanabe
  • Journal Title: J.Sci.Food Agric Volume: 59 Issue: 24 Pages: 13131-13135
  • DOI: 10.1021/jf203396a
  • Peer Reviewed
• [Journal Article] Characterization of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark (2012)
  • Author(s): Yang, Z.
  • Journal Title: Food Chemistry Volume: 135 Pages: 2269-2276
  • Peer Reviewed
• [Journal Article] Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet. (2012)
  • Author(s): Murata, A.
  • Journal Title: Tetrahedron Volume: 68 Pages: 5583-5589
  • Peer Reviewed
• [Journal Article] Biosynthesis of α- and β-ionone, prominent scent compounds, in flowers of Osmanthus fragrans (2012)
  • Author(s): Susanne Baldermann, Masaya Kato, Peter Fleischmann, Naoharu Watanabe
  • Journal Title: Acta Biochim.Pol Volume: 59(Free Article) Pages: 79-81
  • Peer Reviewed
• [Journal Article] 花香気成分生合成・発散制御の分子機構に関する生物有機化学的研究 (2011)
  • Author(s): 渡辺修治
  • Journal Title: 植物の生長調節 Volume: 46 Pages: 11-18
  • Peer Reviewed
• [Journal Article] Application of centrifugal precipitation chromatography and counter-current chromatography equipped with a spiral tubing support rotor for the isolation and partial characterization of carotenoid cleavage-like enzymes in Enteromorpha compressa (L.) Nee (2011)
  • Author(s): Susanne Baldermann, Andriati Ningrum Mulyadi, Ziyin Yang, Ariaki Murata, Peter Fleischmann, Peter Winterhalter, Martha Knigh, Thomas M.Finn, Naoharu Watanabe
  • Journal Title: J.Sep.Sci. Volume: 34 Issue: 19 Pages: 2759-2764
  • DOI: 10.1002/jssc.201100508
  • Peer Reviewed
• [Presentation] バラ香気成分2-phenylethanoln の生合成経路はどうして季節変動するのか? (2013)
  • Author(s): 神田桃代, 平田拓, 渡辺修治, 大西利幸
  • Organizer: 植物化学調節学会2013年度大会
  • Place of Presentation: 新潟市
  • Year and Date: 2013-10-31
• [Presentation] Rose scent 2-phenylethanol wasproduced via two biosynthetic pathways in response to seasonal change in environment (2013)
  • Author(s): Momoyo Kanda, Hiroshi Hirata, Toshiyuki Ohnishi, Naoharu Watanabe
  • Organizer: VI International Symposium on Rose Research and Cultivation
  • Place of Presentation: Hannover, Germany
  • Year and Date: 2013-08-27
• [Presentation] 植物香気成分の整合性経路，生育環境要因の解析 (2013)
  • Author(s): 渡辺修治
  • Organizer: GC-MSユーザーズセミナー２０１３
  • Place of Presentation: 東京・丸の内トラストタワー
  • Invited
• [Presentation] Rose scent 2-phenylethanol was produced via two biosynthetic pathways in response to seasonal change in environment (2013)
  • Author(s): Kanda, M., Hirata, H., Ohnishi, T., Watanabe, N.
  • Organizer: Sixth International Symposium on Rose Research and Cultivation
  • Place of Presentation: Hannnover, Germany
• [Presentation] バラ香気成分2-phenlethanol生合成経路はどのようにして季節変動するのか？ (2013)
  • Author(s): Kanda, M., Hirata, H., Watanabe, N., Ohnishi, T.
  • Organizer: 植物化学調節学会2013年度
  • Place of Presentation: 新潟大学（新潟市）
• [Presentation] バラ香気成分２－フェニルエタノール生合成経路の変化に関与する環境要因の解析 (2013)
  • Author(s): 神田桃代
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 東北大学，仙台市
• [Presentation] バラ香気成分2-phenylethanol の新規生合成経路の解明 (2012)
  • Author(s): 平田拓, 石田晴香, 神田桃代, 渡辺修治, 大西利幸
  • Organizer: 植物化学調節学会2011年度大会
  • Place of Presentation: 宇都宮市
  • Year and Date: 2012-11-02
• [Presentation] Occurrence formation, and importance of volatile apocarotenoids in flowers of Osmanthus fragrans and Rosa chinensis mutabilis (2012)
  • Author(s): Baldermann, S., Kato, M., Fujita, A., Fleischmann, P., Winterhalter, P., Watanabe, N.
  • Organizer: ACS symposium 2012
  • Place of Presentation: San Diego, U.S.A.(招待講演)
  • Year and Date: 2012-03-26
• [Presentation] バラ香気成分2-phenylethanol生合成経路を変化させる要因と中間体解析 (2012)
  • Author(s): 神田桃代、平田拓、石田晴香、大西利幸、渡辺修治
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 2012-03-25
• [Presentation] バラ開花時における香気前駆配糖体2PEGと2PEG生合成酵素の変動解析 (2012)
  • Author(s): 大場幸江、平田拓、大西利幸、渡辺修治
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 2012-03-25
• [Presentation] バラ香気成分2-phenylethanol 生合成経路を変化させる要因と中間体解析 (2012)
  • Author(s): 神田桃代, 平田拓, 石田晴香, 大西利幸, 渡辺修治
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都市
  • Year and Date: 2012-03-24
• [Presentation] Roses Produce the Floral Scent Compound 2-Phenylethanol via a New Biosynthetic Pathway in Response to Seasonal Change in Environment. (2012)
  • Author(s): Hirata, H.
  • Organizer: Inter Academia 2012
  • Place of Presentation: ラマダホテル, Budapest, Hungary
• [Presentation] 花の香りの仕組み (2012)
  • Author(s): 渡辺修治
  • Organizer: アロマサイエンスフォーラム第１６回香りのセミナー
  • Place of Presentation: 北沢産業ビル，大阪市
  • Invited
• [Presentation] バラ香気成分2-phenylethanol 生合成経路の季節に伴う変化 (2011)
  • Author(s): 平田拓, 冨田健介, 石田晴香, 坂井美和, 大西利幸, 渡辺修治
  • Organizer: 日本農芸化学会中部支部,第163回例会
  • Place of Presentation: 静岡市
  • Year and Date: 2011-12-03
• [Presentation] 花香・花芽誘導関連分子の生合成・代謝経路 (2011)
  • Author(s): 渡辺修治
  • Organizer: ガスクロマトグラフィー研究懇談会第316回特別講演会,(社)日本分析化学会ガスクロマトグラフィー研究懇談会共催
  • Place of Presentation: 東京(招待講演)
  • Year and Date: 2011-12-02
• [Presentation] バラ香気成分2-phenylethanolの新規生合成経路 (2011)
  • Author(s): 平田拓、大西利幸、石田晴香、神田桃代、渡辺修治
  • Organizer: 日本植物細胞分子生物学会
  • Place of Presentation: 福岡
  • Year and Date: 2011-09-07
• [Presentation] 環境変化に適応した花香気成分生合成 (2011)
  • Author(s): 渡辺修治
  • Organizer: 第6回化学生態学研究会
  • Place of Presentation: 函館(招待講演)
  • Year and Date: 2011-06-18
• [Book] Formation of damascenone and its related compounds from carotenoids in tea. Chapter 31, In: Tea in Health and Disease Prevention (2013)
  • Author(s): Ziyin Yang, Susanne Baldermann, Naoharu Watanabe
  • Publisher: Elsevier Inc
• [Remarks]
  • URL: http://www.ipc.shizuoka.ac.jp/%7Etnmase/watanabe_lab/
• [Remarks] 一押し研究者
  • URL: http://gsst.shizuoka.ac.jp/kyoiku/ichioshi.html
• [Remarks]
  • URL: http://www.agr.shizuoka.ac.jp/abc/npchem/index_en.html
• [Remarks]
  • URL: http://www.agr.shizuoka.ac.jp/abc/npchem/index.html
• [Remarks]
  • URL: http://www.agr.shizuoka.ac.jp/c/npchem/index.html