Elucidation of phenylpropene biosynthetic pathway leading to aromatic compounds in plants and its application to metabolic engineering

• Project/Area Number: 15K18690
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Bioorganic chemistry
• Research Institution: Yamaguchi University
• Principal Investigator: Koeduka Takao 山口大学, 大学院創成科学研究科, 助教 (30565106)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 香気成分 / 二次代謝産物 / 二次代謝 / 二次代謝物

Outline of Final Research Achievements

In this study, we performed a screening of plants producing high levels of aromatic volatile compounds, phenylpropenes, and isolation of methylene-dioxy bridge forming enzymes and prenyltransferase, which are responsible for the diversification of phenylpropene structures. As the results, we found that dill, chervil, parsley, basil, illicium, and wild ginger produce high amounts of phenylpropenes including myristicine, dillapiole, and dimethylally eugenol. In addition, we successfully isolated putative genes encoding methylene-dioxy bridge forming enzymes and prenyltransferase from dill and illicium.

Research Products

• [Journal Article] Functional evolution of biosynthetic enzymes that produce plant volatiles. (2018)
  • Author(s): Koeduka, T.
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 82 Issue: 2 Pages: 192-199
  • DOI: 10.1080/09168451.2017.1422968
  • Peer Reviewed
• [Journal Article] Aromatic amino acid decarboxylase is involved in volatile phenylacetaldehyde production in loquat (<i>Eriobotrya japonica</i>) flowers (2017)
  • Author(s): Koeduka, T., Fujita, Y., Furuta, T., Suzuki, H., Tsuge, T. and Matsui, K.
  • Journal Title: Plant Biotechnology Volume: 34 Issue: 4 Pages: 193-198
  • DOI: 10.5511/plantbiotechnology.17.0926a
  • NAID: 130006321254
  • ISSN: 1342-4580, 1347-6114
  • Peer Reviewed
• [Journal Article] An improved synthesis of the potent and selective γ-glutamyl transpeptidase inhibitor GGsTop together with an inhibitory activity evaluation of its potential hydrolysis products. (2017)
  • Author(s): Watanabe, B., Morikita, T., Tabuchi, Y., Kobayashi, R., Koeduka, T. and Hiratake, J.
  • Journal Title: Tetrahedron Letters Volume: 58 Issue: 38 Pages: 3700-3703
  • DOI: 10.1016/j.tetlet.2017.08.019
  • Peer Reviewed
• [Journal Article] An adenylyl cyclase with a phosphodiesterase domain in basal plants with a motile sperm system (2017)
  • Author(s): Kasahara, M., Suetsugu, N., Urano, Y., Yamamoto, C., Ohmori, M., Takada, Y., Okuda, S., Nishiyama, T., Sakayama, H., Kohchi, T., and Takahashi, F.
  • Journal Title: Sci. Rep. Volume: 6 Issue: 6 Pages: 39232-39232
  • DOI: 10.1080/09168451.2017.1285688
  • Peer Reviewed / Open Access
• [Journal Article] Biosynthesis of volatile terpenes that accumulate in the secretory cavities of young leaves of Japanese pepper (<i>Zanthoxylum piperitum</i>): Isolation and functional characterization of monoterpene and sesquiterpene synthase genes (2017)
  • Author(s): Fujita, Y., Koeduka, T., Aida, M., Suzuki, H., Iijima, Y., & Matsui, K.
  • Journal Title: Plant Biotechnology Volume: 34 Issue: 1 Pages: 17-28
  • DOI: 10.5511/plantbiotechnology.16.1231a
  • NAID: 130005519607
  • ISSN: 1342-4580, 1347-6114
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Acrolein-detoxifying isozymes of glutathione transferase in plants. (2017)
  • Author(s): Mano, J., Ishibashi, A., Muneuchi, H., Morita, C., Sakai, H., Biswas, Md. S., Koeduka, T. and Kitajima, S.
  • Journal Title: Planta Volume: 245 Issue: 2 Pages: 255-264
  • DOI: 10.1007/s00425-016-2604-5
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Characterization of an O-methyltransferase specific to guaiacol-type benzenoids from the flowers of loquat (Eriobotrya japonica) (2016)
  • Author(s): Koeduka, T., Kajiyama, M., Furuta, T., Suzuki, H., Tsuge, T. and Matsui, K.
  • Journal Title: Journal of Bioscience and Bioengineering Volume: 122 Issue: 6 Pages: 679-684
  • DOI: 10.1016/j.jbiosc.2016.06.012
  • NAID: 40021044912
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Direct evidence of specific localization of sesquiterpenes and marchantin A in oil body cells of Marchantia polymorpha L.. (2016)
  • Author(s): Tanaka, M., Esaki, T., Kenmoku, H., Koeduka, K., Kiyoyama, Y., Masujima, T., Asakawa, Y. and Matsui, K.
  • Journal Title: Phytochemistry Volume: 130 Pages: 77-84
  • DOI: 10.1016/j.phytochem.2016.06.008
  • Peer Reviewed
• [Journal Article] Benzenoid biosynthesis in the flowers of Eriobotrya japonica: molecular cloning and functional characterization of p-methoxybenzoic acid carboxyl methyltransferase. (2016)
  • Author(s): Koeduka, T., Kajiyama, M., Suzuki, H., Furuta, T., Tsuge, T. and Matsui, K.
  • Journal Title: Planta Volume: 244 Issue: 3 Pages: 725-736
  • DOI: 10.1007/s00425-016-2542-2
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Arabidopsis lipoxygenase 2 is essential for formation of green leaf volatiles and five-carbon volatiles (2016)
  • Author(s): S. Mochizuki, K. Sugimoto, T. Koeduka, K. Matsui
  • Journal Title: FEBS Letters Volume: 590 Issue: 7 Pages: 1017-1027
  • DOI: 10.1002/1873-3468.12133
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Biochemical characterization of allene oxide syntheses from the liverwort Marchantia polymorphs and green micro algae klebsormidium flaccid provides insight into the evolutionary divergence of the plant CYP74 family (2015)
  • Author(s): Koeduka T, Ishizaki K, Mwenda CM, Hori K, Sasaki-Sekimoto Y, Ohta H, Kohchi T, Matsui K
  • Journal Title: Planta Volume: 242 Issue: 5 Pages: 427-443
  • DOI: 10.1007/s00425-015-2355-8
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] Biosynthesis of volatile terpenes that accumulate in the secretory cavities of young Japanese pepper (Zanthoxylum piperitum) leaves. (2018)
  • Author(s): Koeduka T, Fujita Y, Takaishi M, Aida M, Iijima Y, Matsui K
  • Organizer: Gordon Research Conferences-Plant Volatiles
  • Int'l Joint Research
• [Presentation] サンショウ油胞特異的に蓄積する揮発性テルペンの生成に関する研究 (2017)
  • Author(s): 肥塚崇男、藤田芳勧、飯島陽子、相田光宏、鈴木秀幸、松井健二
  • Organizer: 日本農芸化学会2017年度大会
  • Place of Presentation: 京都府京都市 京都女子大学
  • Year and Date: 2017-03-17
• [Presentation] ショウブ由来レスベラトロールO-メチル基転移酵素の機能解析 (2017)
  • Author(s): 肥塚崇男, 畑田珠希, 鈴木秀幸, 鈴木史朗, 松井健二
  • Organizer: 第35回日本植物細胞分子生物学会大会
• [Presentation] 植物の進化とみどりの香り生成能の獲得 (2017)
  • Author(s): 肥塚崇男, 松井健二
  • Organizer: イメージング研究会 第九回光塾
• [Presentation] フェニルプロペン香気成分の生合成に関わるモノリグノールアセチル化酵素遺伝子の単離と機能解析 (2016)
  • Author(s): 肥塚崇男、鈴木史朗、飛松裕基、宮本託志、梅澤俊明、松井健二
  • Organizer: 第61回 リグニン討論会
  • Place of Presentation: 京都府宇治市 京都大学
  • Year and Date: 2016-10-27
• [Presentation] ビワの揮発性ベンゼノイド生合成に関与するカルボン酸メチル化酵素の機能解析 (2016)
  • Author(s): 肥塚崇男、梶山眞未、望月智史、古田巧、鈴木秀幸、柘植知彦、松井健二
  • Organizer: 第34回日本植物細胞分子生物学会
  • Place of Presentation: 長野県上田市 信州大学
  • Year and Date: 2016-09-01
• [Presentation] 植物香気成分の多様性と生合成酵素の機能進化 (2016)
  • Author(s): 肥塚崇男
  • Organizer: 日本農芸化学会中四国支部 第23回若手シンポジウム（第8回農芸化学の未来開拓セミナー）
  • Place of Presentation: 岡山県岡山市 岡山大学
  • Invited
• [Presentation] The origin and evolution of plant CYP74 superfamily involved in oxylipin biosynthesis (2015)
  • Author(s): Koeduka T, Ishizaki K, Mwenda CM, Hori K, Nishihama R, Sasaki-Sekimoto Y, Ohta H, Kohchi T, Matsui K
  • Organizer: 6th Asian Symposium on Plant Lipids
  • Place of Presentation: シンガポール、シンガポール共和国
  • Year and Date: 2015-12-02
  • Int'l Joint Research
• [Presentation] 脂肪酸ヒドロペルオキシドを基質とするCYP74ファミリーの分子進化 (2015)
  • Author(s): 肥塚崇男、石崎公庸、Cynthia Mugo Mwenda、堀孝一、佐々木(関本)結子、太田啓之、河内孝之、松井健二
  • Organizer: 第33回 植物分子細胞生物学会
  • Place of Presentation: 東京都文京区 東京大学弥生キャンパス
  • Year and Date: 2015-08-09