Development of new molecules based on the structure-activity relationship of naturally occurring flower-inducing compound

• Project/Area Number: 26292059
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Bioorganic chemistry
• Research Institution: Shizuoka University
• Principal Investigator: Watanabe Naoharu 静岡大学, 創造科学技術大学院, 特任教授 (90230979)
• Co-Investigator(Renkei-kenkyūsha): MASE Nobuyuki 静岡大学, 工学部, 教授 (40313936) ; OHNISHI Toshiyuki 静岡大学, 農学部, 准教授 (60542165) ; NARUMI Tetsuo 静岡大学, 工学部, 准教授 (50547867)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥16,250,000 (Direct Cost: ¥12,500,000、Indirect Cost: ¥3,750,000); Fiscal Year 2016: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000); Fiscal Year 2015: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000); Fiscal Year 2014: ¥7,670,000 (Direct Cost: ¥5,900,000、Indirect Cost: ¥1,770,000)
• Keywords: 花芽誘導 / オキシリピン / レムナ / 構造活性相関 / 構造要求性 / 代謝経路 / アオウキクサ / 全合成 / 花芽誘導物質 / 有機合成 / 代謝抵抗性 / 合成 / 遺伝子発現

Outline of Final Research Achievements

We have isolated a flower-inducing compound, LDS1, from a free-floating aquatic plant, Lemna paucicostata. To afford the sufficient amounts of LDS1, we successfully synthesized LDS1. We also synthesized LDS1 analogs by modifying carbon-chain length, number of hydroxyl groups, kept-reduction, position of double bounds to investigate structure-activity relationships. By using the LDS1 chemically synthesized, we have analyzed metabolic pathways for LDS1 in Lemna plants. One of the metabolites was tentatively identified as a reduction product of LDS1 in its double bound. Substantial amounts of LDS1 was produced in Lemna plants grown in the high-density stress conditions.

Research Products

• [Journal Article] Optimization of the production of 1-phenylethanol using enzymes from flowers of tea (Camellia sinensis) plants. (2017)
  • Author(s): Dong, F., Zhou, Y., Zeng, L., Watanabe, N., Su, X., Yang, Z
  • Journal Title: Molecules Volume: 22 Pages: 131-131
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Analytical method for metabolites involed in biosynthesis of plant volatile compounds (2017)
  • Author(s): Fu, X., Zhou, Y., Zeng, L., Dong, F., Mei, X., Liao,,Y.,Watanabe, N., Yang. Z.
  • Journal Title: RSC Advances Volume: 31 Pages: 19363-19372
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Regulation of biosynthesis and emission of volatile phenylpropanoids/benzenoids in petunia x hybrida fowers by multi-factors of circadian clock, light, and temperature (2016)
  • Author(s): Cheng S, Fu X, Mei X, Zhou Y, Du B, Watanabe N, Yang Z
  • Journal Title: Plant Physiol Biochem Volume: 107 Pages: 1-8
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Formation of characteristic aroma compound indole during the oolong tea manufacturing process (2016)
  • Author(s): Zeng, L, Zhou, Y, Gui, J, Fu, X, Mei, X, Zhen, Y, Ye, T, Du, B, Dong, F, Watanabe, N, Yang. Z.
  • Journal Title: J. Agric Food Chem Volume: 64 Pages: 5011-5019
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Elucidation of differential accumulation of 1-phenylethanol in flowers and leaves of tea (Camellia sinensis) plants (2016)
  • Author(s): Dong, F., Shou, Y., Peng, Q., Chen, Y., Zhang, L., Su, X., Watanabe, N., Yang, Z.
  • Journal Title: Molecules Volume: 21 Issue: 9 Pages: 1106-1106
  • DOI: 10.3390/molecules21091106
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Recent advances in the emission and functions of plant vegetative volatiles (2016)
  • Author(s): Dong, F., Fu, X., Watanabe, N., Su, X., Yang
  • Journal Title: Molecules Volume: 21 Issue: 2 Pages: 124-124
  • DOI: 10.3390/molecules21020124
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Seasonal induction of alternative principal pathway for rose flower scent (2016)
  • Author(s): Hirata, H., Ohnishi, T., Tomida, K., Ishida, H., Kanda, M., Sakai, M., Yoshimura, J., Suzuki, H., Ishikawa, T., Dohra, H., Watanabe, N
  • Journal Title: Sci. Rep. Volume: 6
  • NAID: 120005771327
  • Peer Reviewed / Open Access
• [Journal Article] Characteristic fluctuations in glycosidically bound volatiles during tea processing and identification of their unstable derivatives (2016)
  • Author(s): Cui, J., Katsuno, T., Totsuka, K., Ohnishi,T., Takemoto, H., Mase,N., Toda, M.,Narumi, T.,Sato, K., Matsuo, T., Mizutani, K., Yang, Z., Watanabe, N., Tong, H.
  • Journal Title: J. Agric. Food Chem. Volume: 64 Issue: 5 Pages: 1151-1157
  • DOI: 10.1021/acs.jafc.5b05072
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions. (2016)
  • Author(s): Soti, P.Z., Yamashita,H., Sato,K., Narumi, T., Toda, M., Watanabe, N., Marosi,G., Mase, N.
  • Journal Title: Tetrahedron Volume: 72 Issue: 16 Pages: 1984-1990
  • DOI: 10.1016/j.tet.2016.02.065
  • NAID: 120006411284
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Does enzymatic hydrolysis of glycosidically bound volatile compounds really contribute to the formation of volatile compounds during the oolong tea manufacturing process? (2015)
  • Author(s): Gui, J.; Fu, X.; Zhou, Y.; Katsuno, T.; Mei, X.; Deng, R.; Xu, X.; Zhang, L.; Dong, F.; Watanabe, N.; Yang, Z
  • Journal Title: J. Agric. Food Chem. Volume: 63 Issue: 31 Pages: 6905-6914
  • DOI: 10.1021/acs.jafc.5b02741
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Position-Specific Isotope Analysis of Xanthines: A 13C Nuclear Magnetic Resonance Method to Determine the 13C Intramolecular Composition at Natural Abundance. (2015)
  • Author(s): D. G. Diomande, E. Martineau, A. Gilbert, P. Nun, A. Murata, K. Yamada, N. Watanabe, I. Tea, R. J. Robins, N. Yoshida, G. S. Remaud
  • Journal Title: Analytical Chemistry Volume: 87 Issue: 13 Pages: 6600-6606
  • DOI: 10.1021/acs.analchem.5b00559
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Volatile glycosylation in tea plants: Sequential glycosilations for the biosynthesis of aroma b-primeverosides are catalyzed by two Camellia sinensis glycosyltransferases. (2015)
  • Author(s): Ohgami, S., Ono, E., Horikawa, M., Murata, M., Totsuka, K., Toyonaga, H., Ohba, Y., Dohra, H., Asai, T., Matsui, K., Mizutani, M., Watanabe, N., Ohnishi, T.
  • Journal Title: Plant Physiol. Volume: 168 Issue: 2 Pages: 464-477
  • DOI: 10.1104/pp.15.00403
  • Peer Reviewed / Open Access
• [Journal Article] Developmental patterns of emission of scent compounds and related gene expression in roses of cultivar Rosa x hybrida cv. ‘Yves Piaget’’ (2015)
  • Author(s): Xiaomin Chen, Susanne Baldermann, Shuyan Cao, Yao Lu, Cixia Liu, Hiroshi Hirata, Naoharu Watanabe.
  • Journal Title: Plant Physiol. Biochem Volume: 87 Pages: 109-114
  • DOI: 10.1016/j.plaphy.2014.12.016
  • Peer Reviewed / Open Access
• [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] Occurrences of glycosidically-conjugated 1-phenylethanol and their hydrolase β-primeverosidase in tea (Camellia sinensis) flowers (2014)
  • Author(s): Zhou, Ying; Dong, Fang; Kunimasa, Aiko; Zhang, Yuqian; Cheng, Sihua; Lu, Jiamin; Zhang, Ling; Murata, Ariaki; Frank, Mayer; Fleischmann, Peter; Watanabe, Naoharu; Yang, Ziyin
  • Journal Title: J. Agric Food Chem Volume: 62 Issue: 32 Pages: 8042-8050
  • DOI: 10.1021/jf5022658
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis and Characterization of Quantum Dot Nanoparticles Bound to the Plant Volatile Precursor of Hydroxy-apo-10 '-carotenal (2014)
  • Author(s): Tu, V. A.; Kaga, A.; Gericke, K. H.; Watanabe, N.; Narumi, T.; Toda, M.; Brueckner, B.; Baldermann, S.; Mase, N.
  • Journal Title: Journal of Organic Chemistry Volume: 79 (15) Issue: 15 Pages: 6808-6815
  • DOI: 10.1021/jo500605c
  • Peer Reviewed / Open Access
• [Journal Article] Discrimination of green, oolong, and black teas by GC-MS analysis of characteristic volatile flavor compounds. (2014)
  • Author(s): Susanne Baldermann, Ziyin Yang, Tsuyoshi Katsuno, Vo Anh Tu, Nobuyuki Mase, Yoriyuki Nakamura, Naoharu Watanabe
  • Journal Title: American J. Analytical Chemistry Volume: 5 Pages: 620-632
  • Peer Reviewed / Open Access
• [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
• [Presentation] アオウキクサ起源花芽誘導分子LDS1の合成と代謝物の探索 (2017)
  • Author(s): 山田優作,土屋諒,廣住操俊,竹本裕之,佐藤浩平,鳴海哲夫,戸田三津夫,大西利幸,間瀬暢之,渡辺修治
  • Organizer: 日本農芸化学会2017年度大会
  • Place of Presentation: 京都女子大学・京都府・京都市
  • Year and Date: 2017-03-19
• [Presentation] Synthesis of LDS1 and Its Structurally Related Compounds with Flower Inducing Activity toward Lemna Plant (2016)
  • Author(s): Yusaku Yamada,Kohei Sato,Tetsuo Narumi,Mitsuo Toda,Toshiyuki Ohnishi,Nobuyuki Mase,Naoharu Watanabe
  • Organizer: 6th Shizuoka University International Symposium 2016
  • Place of Presentation: Shizuoka University, Hamamatsu, Shizuoka,Japan
  • Year and Date: 2016-12-01
  • Int'l Joint Research
• [Presentation] 花芽誘導物質LDS1 構造要求性の解明 (2016)
  • Author(s): 山田 優作、土屋 諒、廣住 操俊、佐藤 浩平、鳴海 哲夫、戸田 三津夫、大西 利幸、間瀬 暢之、渡辺 修治
  • Organizer: 日本農芸化学会2016年度大会
  • Place of Presentation: 札幌コンベンションセンター(札幌市)
  • Year and Date: 2016-03-28
• [Presentation] クロロアルケン型ジペプチドイソスターにおける塩素原子の水素結合能の評価 (2016)
  • Author(s): 千葉 拓矢, 今井 智之, 佐藤 浩平, 戸田 三津夫, 間瀬 暢之, 渡辺 修治, 鳴海 哲夫
  • Organizer: 日本薬学会第１３６回年会
  • Place of Presentation: パシフィコ横浜（神奈川県横浜市）
  • Year and Date: 2016-03-28
• [Presentation] ハロアルケン型ジペプチドイソスターの代謝安定性の向上を目的とした構造活性相関研究 (2016)
  • Author(s): 今井 智之, 千葉 拓矢, 佐藤 浩平, 間瀬 暢之, 渡辺 修治, 鳴海 哲夫
  • Organizer: 日本薬学会第１３６回年会
  • Place of Presentation: パシフィコ横浜（神奈川県横浜市）
  • Year and Date: 2016-03-28
• [Presentation] 化学選択的誘導体化によるイオン強度増大を指向したイメージング質量分析におけるラベル化剤の開発 (2016)
  • Author(s): 岡村 拓磨・瀬藤 光利・佐藤 浩平・鳴海 哲夫・渡辺 修治・間瀬 暢之
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学（京都市）
  • Year and Date: 2016-03-25
• [Presentation] PETイメージングにおける比放射能向上を指向したトリフルオロメチル化反応の開発 (2015)
  • Author(s): 岡村拓磨, 小川美香子, 間賀田泰寛, 佐藤浩平, 鳴海哲夫, 渡辺修治, 間瀬暢之
  • Organizer: 第5回CSJ化学フェスタ2015
  • Place of Presentation: タワーホール船越（東京都江戸川区）
  • Year and Date: 2015-10-24
• [Presentation] 化学結合検出用蛍光プローブの開発：エナミン／イミニウム有機分子触媒系の迅速評価 (2015)
  • Author(s): 増田嗣也・佐藤浩平・鳴海哲夫・渡辺修治・間瀬暢之
  • Organizer: 第5回CSJ化学フェスタ2015
  • Place of Presentation: タワーホール船越（東京都江戸川区）
  • Year and Date: 2015-10-24
• [Presentation] チャ香気に関与するテルペン生合成酵素の機能解明 (2015)
  • Author(s): 大西利幸, 井上智宏, 渡辺修治, 鈴木秀幸
  • Organizer: 植物化学調節学会第50回大会
  • Place of Presentation: 東京大学農学部（東京都文京区）
  • Year and Date: 2015-10-01
• [Presentation] 花芽誘導物質LDS1および構造改変体の合成 (2015)
  • Author(s): 山田優作、土屋諒、廣住操俊､佐藤浩平、鳴海哲夫、戸田三津夫、大西利幸、間瀬暢之、渡辺修治
  • Organizer: 2015年度日本農芸化学会中部・関西支部合同大会
  • Place of Presentation: 富山県立大学（富山県射水市）
  • Year and Date: 2015-09-29
• [Presentation] 比放射能向上を指向したトリフルオロメチル化反応による高感度PETプローブ合成手法の開発 (2015)
  • Author(s): 岡村拓磨、小川美香子、間賀田泰寛、佐藤浩平、鳴海哲夫、渡辺修治、間瀬暢之
  • Organizer: 第47回若手ペプチド夏の勉強会
  • Place of Presentation: アスティかたおか（長野県塩尻市）
  • Year and Date: 2015-08-10
• [Presentation] アオウキクサ花芽誘導物質LDS1およびその誘導体の合成 (2015)
  • Author(s): 土屋諒、山田優作、河橋辰哉、間瀬暢之、鳴海哲夫、戸田三津夫、轟泰司、渡辺修治
  • Organizer: 日本農芸化学会2015年度大会
  • Place of Presentation: 岡山市岡山大学津島キャンパス（岡山県，岡山市）
  • Year and Date: 2015-03-28
• [Presentation] バラ香気成分2-Phenynlethanolの高温期特異的な生成に関する転写解析 (2015)
  • Author(s): 平田拓、大西利幸、鈴木秀幸、渡辺修治
  • Organizer: 日本農芸化学会2015年度大会
  • Place of Presentation: 岡山大学津島キャンパス（岡山県，岡山市）
  • Year and Date: 2015-03-27
• [Presentation] 花の香りの秘密～香りをつくり発散する仕組み、香りの科学と夢への挑戦～ (2015)
  • Author(s): 渡辺修治
  • Organizer: 園芸大学・花と緑の学舎
  • Place of Presentation: 伊丹市柿衛文庫（兵庫県，伊丹市）
  • Year and Date: 2015-03-14
  • Invited
• [Presentation] 花も進化するー花は分子によって環境に適応しているー (2014)
  • Author(s): 渡辺修治
  • Organizer: 第3回浜松発!未来の社会、静岡大学・中日新聞連携講座2014
  • Place of Presentation: 静岡大学浜松キャンパス（静岡県，浜松市）
  • Year and Date: 2014-12-13
  • Invited
• [Presentation] 乾燥ストレスによって生成するアオウキクサ花芽誘導性オキシリピン (2014)
  • Author(s): 渡辺修治
  • Organizer: 第27回植物脂質シンポジウム、日本植物脂質科学研究会
  • Place of Presentation: 静岡市産学交流センター（静岡県，静岡市）
  • Year and Date: 2014-11-28
  • Invited
• [Presentation] Metabolic analyses of volatile compounds and their precursors during the withering process of tea leaves. (2014)
  • Author(s): Naoharu Watanabe, Jilai Cui, Kojiro Totsuka, Toshiyuki Ohnishi, Nobuyuki Mase, Tsuyoshi Katsuno
  • Organizer: International Tea Symposium 2014 -Innovation and Development-
  • Place of Presentation: Hangzhou, China.
  • Year and Date: 2014-11-10 – 2014-11-13
  • Invited
• [Presentation] 性転換植物テンナンショウの性分化制御物質の探索 (2014)
  • Author(s): 井上智宏、渡辺修治、大西利幸
  • Organizer: 植物化学調節学会第4９回大会
  • Place of Presentation: 京都大学農学部キャンパス（京都府，京都市）
  • Year and Date: 2014-10-17 – 2014-10-19
• [Presentation] チャにおける加害応答性モノテルペンアルコール生合成酵素の同定 (2014)
  • Author(s): 井上智宏、阪井直哉、戸塚紘二郎、水谷正治、渡辺修治、大西利幸
  • Organizer: 植物化学調節学会第4９回大会
  • Place of Presentation: 京都大学農学部キャンパス（京都府，京都市）
  • Year and Date: 2014-10-17 – 2014-10-19
• [Presentation] ブラシノステロイド不活性に関わるシトクロムP450酵素CYP2C1の酵素機能解明 (2014)
  • Author(s): 佐原瑞穂、渡辺文太、横田孝雄、渡辺修治、水谷正治、大西利幸
  • Organizer: 植物化学調節学会第4９回大会
  • Place of Presentation: 京都大学農学部キャンパス（京都府，京都市）
  • Year and Date: 2014-10-17 – 2014-10-19
• [Presentation] 花における香気成分の生成・発散メカニズム (2014)
  • Author(s): 渡辺修治
  • Organizer: 第58回香料・テルペンおよび精油化学に関する討論会TEAC 2014
  • Place of Presentation: 和歌山大学システム工学部（和歌山県，和歌山市）
  • Year and Date: 2014-09-20 – 2014-09-22
  • Invited
• [Presentation] 超臨界二酸化炭素中における有機分子触媒的高分子合成：金属・有機溶媒・残存モノマーフリーポリ乳酸 (2014)
  • Author(s): 山本翔司、鳴海哲夫、渡辺修治、間瀬暢之
  • Organizer: プロセス科学会2014サマーシンポジウム
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2014-07-31 – 2014-08-01
• [Presentation] マイクロバブル・ナノバブル手法を用いた酸化反応プロセスの開発 (2014)
  • Author(s): 坪井拓也、稲澤克幸、鳴海哲夫、渡辺修治、間瀬暢之
  • Organizer: プロセス科学会2014サマーシンポジウム
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2014-07-31 – 2014-08-01
• [Presentation] 環境ストレス応答性花芽誘導分子・香気成分生合成の分子機構 (2014)
  • Author(s): 渡辺修治
  • Organizer: 第7回超領域研究会
  • Place of Presentation: 静岡大学浜松キャンパス（静岡県，浜松市）
  • Year and Date: 2014-06-20
  • Invited
• [Presentation] 低温萎凋緑茶の香気成分と生成・代謝経路の解析 (2014)
  • Author(s): 渡辺修治
  • Organizer: サーモフィッシャー機器分析ユーザーズフォーラムFood & Agriculture
  • Place of Presentation: フクラシア東京ステーション（東京都，千代田区）
  • Year and Date: 2014-05-14
  • Invited
• [Book] ナノバイオ・テクノロジー (2016)
  • Author(s): 原正和,渡辺修治,間瀬暢之,河岸洋和,森田達也,丑丸敬史,朴龍洙,猪川洋,岩田太,川田善正,三重野哲,加藤竜也,徳元俊伸,山崎昌一,小林健二,山中正道(著)
  • Total Pages: 645
  • Publisher: 静岡大学創造科学技術大学院・グリーン科学技術研究所・ナノバイオプロジェクト
• [Book] 原正和, 渡辺修治, 間瀬暢之, 河岸洋和, 森田達也, 丑丸敬史, 朴龍洙, 猪川洋, 岩田太, 川田善正, 三重野哲, 加藤竜也, 徳元俊伸, 山崎昌一, 小林健二, 山中正道 (2016)
  • Author(s): ナノバイオ・テクノロジー
  • Total Pages: 268
  • Publisher: 静岡学術出版
• [Remarks] Laboratory of Bioorganic Chemistry
  • URL: http://www.ipc.shizuoka.ac.jp/~tnmase/watanabe_lab/
• [Remarks] 静岡大学教員データベース-教員個別情報：渡辺修治 WATANABE, Naoharu
  • URL: https://tdb.shizuoka.ac.jp/RDB/public/Default2.aspx?id=10746&l=0