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Exploration of a factor in diversifying plant secondary metabolism based on intra-specific diversity and plant cell culture

Research Project

Project/Area Number 26860066
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Natural medicines
Research InstitutionNagasaki University

Principal Investigator

SAITO Yoshinori  長崎大学, 医歯薬学総合研究科(薬学系), 准教授 (30441588)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2014: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywords種内多様性 / 細胞培養 / 高等植物 / テルペノイド / 薬用資源 / 系統分類
Outline of Final Research Achievements

Higher plants belonging to different geographical populations within a single species were collected, and their chemical ingredients were analyzed using LC-MS and then exhaustively separated. The presence of intra-specific diversity in chemicals was revealed in some species. Of these, Eupatorium heterophyllum was classified into three groups based on their major components, which corresponded to the result of clustering of neutral DNA sequences. Calluses were successfully induced from intra-specifically diverse plants for studying a relationship between culture conditions and secondary metabolite profiles.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (39 results)

All 2016 2015 2014

All Journal Article (22 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 22 results,  Acknowledgement Compliant: 7 results,  Open Access: 2 results) Presentation (17 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Eudesmane sesquiterpenoids from the wood of Platycarya strobilacea2016

    • Author(s)
      Hitomi Morikawa, Yoshinori Saito, Yosuke Matsuo, Hajime Maeda, and Takashi Tanaka
    • Journal Title

      Natural Product Communications

      Volume: 印刷中

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Three New Eremophilanes from Ligularia Collected in China2016

    • Author(s)
      Yoshinori Saito, Yuriko Takashima, Yasuko Okamoto, Xun Gong, Ryo Hanai, Chiaki Kuroda, Motoo Tori
    • Journal Title

      Natural Product Communications

      Volume: 印刷中

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Two new diterpenoids from Salvia przewalskii2016

    • Author(s)
      Haruka Tsukada, Hiroshi Kawabe, Aya Ohtaka, Yoshinori Saito, Yasuko Okamoto, Motoo Tori, Hiroyuki Kagechika, Hiroshi Hirota, Xun Gong, Chiaki Kuroda, Ayumi Ohsaki
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 159-161

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chemical lineages of Ligularia fischeri2016

    • Author(s)
      Chiaki Kuroda, Chiemi Shibayama, Kyosuke Inoue, Yasuko Okamoto, Motoo Tori, Yoshinori Saito, Ryo Hanai, Xun Gong
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 139-143

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Three new oxidation products produced from epigallocatechin-3-O-gallate and epicatechin-3-O-gallate2016

    • Author(s)
      Yan Li, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 189-192

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Triterpene galloyl esters from edible acorn of Castanopsis cuspidata2016

    • Author(s)
      Misaki Ogata, Yoshinori Saito, Yosuke Matsuo, Hajime Maeda, Takashi Tanaka
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 179-181

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereochemistry of the Black Tea Pigments, Theacitrins A and C.2016

    • Author(s)
      Matsuo, Y., Okuda, K., Morikawa, H., Oowatashi, R., Saito, Y., Tanaka, T.
    • Journal Title

      Journal of Natural Products

      Volume: 79 Issue: 1 Pages: 189-195

    • DOI

      10.1021/acs.jnatprod.5b00832

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chalcane-stilbene conjugates and oligomeric flavonoids from Chinese Dragon’s Blood produced from Dracaena cochinchinensis2015

    • Author(s)
      Qian Hao, Yoshinori Saito, Yosuke Matsuo, Hai-Zhou Li, Takashi Tanaka
    • Journal Title

      Phytochemistry

      Volume: 119 Pages: 76-82

    • DOI

      10.1016/j.phytochem.2015.09.009

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Terpenoids from Ligularia virgaurea collected in China: the first example of two bakkane derivatives with an anhydride-type ring C and nineteen new chemical constituents2015

    • Author(s)
      Yoshinori Saito, Saori Iga, Katsuyuki Nakashima, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 44 Pages: 8428-8435

    • DOI

      10.1016/j.tet.2015.09.011

    • NAID

      120006986881

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Oxidation mechanism of black tea pigment theaflavin by peroxidase2015

    • Author(s)
      Kusano, R., Matsuo, Y., Saito, Y., Tanaka, T.
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 36 Pages: 5099-5102

    • DOI

      10.1016/j.tetlet.2015.07.037

    • NAID

      120006986985

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diastereomeric Ellagitannin Isomers from Penthorum chinense.2015

    • Author(s)
      Era, M., Matsuo, Y., Shii, T., Saito, Y., Tanaka, T., Jiang, Z.-H.
    • Journal Title

      Journal of Natural Products

      Volume: 78 Issue: 8 Pages: 2104-2109

    • DOI

      10.1021/acs.jnatprod.5b00439

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Three new flavans in dragon’s blood from Daemonorops draco2015

    • Author(s)
      Qian Hao, Yoshinori Saito, Yosuke Matsuo, Hai-Zhou Li, Takashi Tanaka
    • Journal Title

      Natural Product Research

      Volume: 29 Issue: 15 Pages: 1419-1425

    • DOI

      10.1080/14786419.2014.1003137

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Four new sesquiterpenoids from Ligularia subspicata collected in China; isolation of a bakkane-type lactone, an eremophilane-type lactone, and two ortho esters2015

    • Author(s)
      Yoshinori Saito, Takanori Otsubo, Yuko Iwamoto, Katsuyuki Nakashima, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori
    • Journal Title

      Natural Product Communications

      Volume: 10 Pages: 831-833

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Hypolipidemic Property of a New Fermented Tea Made with Third Crop Green Tea (<i>Camellia sinensis</i>) Leaves and Unripe Satsuma Mandarin (<i>Citrus unshiu</i>) Fruits2015

    • Author(s)
      Hisayuki Nakayama, Naho Yuito, Yuji Miyata, Kei Tamaya, Takashi Tanaka, Yoshinori Saito, Toshiro Matsui, Sadayuki Aramaki, Yasuo Nagata, Shizuka Tamaru, Kazunari Tanaka
    • Journal Title

      Food Science and Technology Research

      Volume: 21 Issue: 1 Pages: 77-86

    • DOI

      10.3136/fstr.21.77

    • NAID

      130005061937

    • ISSN
      1344-6606, 1881-3984
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective oxidation of pyrogallol-type catechins with unripe fruit homogenate of Citrus unshiu and structural revision of oolongtheanins2015

    • Author(s)
      Matsuo, Y.; Tadakuma, F.; Shii, T.; Saito, Y.; Tanaka, T.
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 17 Pages: 2540-2548

    • DOI

      10.1016/j.tet.2015.03.016

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea2014

    • Author(s)
      Takuya Shii, Chiori Asada, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Journal of Natural Medicines

      Volume: 68 Issue: 2 Pages: 459-464

    • DOI

      10.1007/s11418-014-0816-1

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Twelve new compounds from Ligularia melanothyrsa; isolation of melanothyrsins A-E, normelanothyrsin A, and other eremophilane sesquiterpenoids2014

    • Author(s)
      Y. Saito, M. Ichihara, Y. Okamoto, X. Gong, C. Kuroda, M. Tori
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 16 Pages: 2621-2628

    • DOI

      10.1016/j.tet.2014.02.080

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 中国横断山脈地域に生育するキク科Ligularia属植物の生産するフラノエレモフィラン化合物の多様性2014

    • Author(s)
      黒田智明,花井 亮,通 元夫,岡本育子,齋藤義紀,永野 肇,大崎愛弓,廣田 洋,河原孝行,Xun Gong
    • Journal Title

      有機合成化学協会誌

      Volume: 72 Pages: 717-725

    • NAID

      130004548619

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structure and cytotoxic evaluation of 12-oxygenated eremophilanes from Ligularia lingiana2014

    • Author(s)
      Saito, Y.; Sasaki, Y.; Komiyama, T.; Ohsaki, A.; Okamoto, Y.; Gong, X.; Kuroda, C.; Tori, M.
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 35 Pages: 5878-5883

    • DOI

      10.1016/j.tet.2014.06.030

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Germacranolides and their diversity of Eupatorium heterophyllum collected in P. R. China.2014

    • Author(s)
      Yoshinori Saito, Tomomi Mukai, Yuko Iwamoto, Makiko Baba, Koji Takiguchi, Yasuko Okamoto, Xun Gong, Takayuki Kawahara, Chiaki Kuroda, Motoo Tori
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 62 Pages: 1092-1099

    • NAID

      130004687227

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isolation and structure of three bislactones, eremopetasitenin B4, eremofarfugins F, and G, from Ligularia przewalskii and revision of the structure of an epoxy-lactone isolated from Ligularia intermedia2014

    • Author(s)
      Y. Saito, A. Kamada, Y. Okamoto, X. Gong, C. Kuroda, M. Tori
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 11 Pages: 1740-1742

    • DOI

      10.1246/cl.140745

    • NAID

      130004677612

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structures of six new compounds from Ligularia brassicoides.2014

    • Author(s)
      Yoshinori Saito, Yoko Sasaki, Ayumi Ohsaki, Yasuko Okamoto, Xun Gong, Chiaki Kuroda, Motoo Tori
    • Journal Title

      Tetrahedron

      Volume: 70 Pages: 9726-9730

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] キク科ツワブキ (Farfugium japonicum) の新規エレモフィラン型セスキテルペン2016

    • Author(s)
      汐崎優子、齋藤義紀、松尾洋介、田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 中国雲南省産Euphorbia griffithiiの新規ジテルペノイド2016

    • Author(s)
      緒方美咲、齋藤義紀、松尾洋介、Xun GONG、田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Intra-specific diversity in cytotoxic sesquiterpene lactone constituents of Eupatorium heterophyllum collected in P. R. China2015

    • Author(s)
      Ogata, Misaki; Saito, Yoshinori; Nakashima, Katsuyuki; Okamoto, Yasuko; Tori, Motoo; Kawahara, Takayuki; Hanai, Ryo; Matsuo, Yosuke; Tanaka, Takashi; Gong, Xun; Kuroda, Chiaki
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Chemical and genetic diversity of Ligularia virgaurea2015

    • Author(s)
      Yoshinori Saito, Yuriko Takashima, Aya Kamada, Saori Iga, Mizuho Taniguchi, Kie Hoshiyama, Chika Hayami, Katsuyuki Nakashima, Yasuko Okamoto, Motoo Tori, Ryo Hanai, Xun Gong, and Chiaki Kuroda
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 中国四川省産Ligularia pleurocaulis の化学的種内多様性2015

    • Author(s)
      齋藤 義紀、高橋 宏明、岡本 育子、中島 勝幸、通 元夫、黒田 智明、 花井 亮、Xun Gong
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール(神奈川県横浜市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] 中国産Ligularia virgaureaの新規化学成分と多様性(4)2015

    • Author(s)
      通 元夫,星山紀恵,速水智加,中島勝幸,齋藤義紀,岡本育子,Xun Gong,花井 亮,黒田智明
    • Organizer
      第59回 香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      近畿大学(大阪府東大阪市)
    • Year and Date
      2015-09-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] 中国雲南省産Ligularia lankongensisの高度に酸化されたビサボラン型化合物2015

    • Author(s)
      齋藤義紀,岡本育子,花井 亮,平井美咲,松尾洋介,田中 隆,Xun Gong,廣田 洋,黒田智明
    • Organizer
      第59回 香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      近畿大学(大阪府東大阪市)
    • Year and Date
      2015-09-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] Chemical and Genetic Diversity of Eupatorium heterophyllum Collected in China2015

    • Author(s)
      Y. Saito, M. Ogata, K. Nakashima, Y. Okamoto, R. Hanai, T. Kawahara, Y. Matsuo, T. Tanaka, M. Tori, X. Gong, C. Kuroda
    • Organizer
      Inaugural Sympodium of the Phytochemical Society of Asia
    • Place of Presentation
      徳島文理大学(徳島県徳島市)
    • Year and Date
      2015-08-30
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 重慶市産キク科Eupatorium heterophyllumの化学的種内多様性2015

    • Author(s)
      緒方美咲,齋藤義紀,中島勝幸,通 元夫,河原孝行,松尾洋介,田中 隆,Xun Gong,黒田智明
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸サンボーホール(兵庫県神戸市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国四川省北西部におけるLigularia lamarumの化学成分と種内多様性2015

    • Author(s)
      日高基貴,齋藤義紀,中島勝幸,岡本育子,通 元夫,松尾洋介,田中 隆,Xun Gong,黒田智明
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸サンボーホール(兵庫県神戸市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 中性条件下における紅茶色素テアフラビン類の酸化機構2014

    • Author(s)
      大渡遼介,松尾洋介,齋藤義紀,田中 隆
    • Organizer
      第31回日本薬学会九州支部大会
    • Place of Presentation
      第一薬科大学(福岡県福岡市)
    • Year and Date
      2014-12-06
    • Related Report
      2014 Research-status Report
  • [Presentation] 数種の中国横断山脈産 Ligularia 雑種の化学成分2014

    • Author(s)
      黒田智明,花井 亮,清水杏菜,鈴木結里香,渡辺 静,山田ひろか,永野 肇,通 元夫,岡本育子,齋藤義紀,河原孝行,Jiao-Jun Yu,Xun Gong
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      三翠園(高知県高知市)
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国横断山脈産 Ligularia vellerea および L. melanothyrsa のケモタイプ2014

    • Author(s)
      清水杏菜,井上恭輔,市原麻由,花井 亮,齋藤義紀,岡本育子,通 元夫,Xun Gong,黒田智明
    • Organizer
      第58回香料・テルペンおよび精油科学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山県和歌山市)
    • Year and Date
      2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国雲南省および重慶市産キク科 Eupatorium heterophyllum の新規セスキテルペノイド2014

    • Author(s)
      緒方美咲,齋藤義紀,中島勝幸,通 元夫,河原孝行,松尾洋介,田中 隆,Xun Gong,黒田智明
    • Organizer
      第58回香料・テルペンおよび精油科学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山県和歌山市)
    • Year and Date
      2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国四川省産 Aquilegia 未同定種の新規アビエタン型ジテルペン2014

    • Author(s)
      齋藤義紀,日高基貴,中島勝幸,岡本育子,通 元夫,河原孝行,松尾洋介,田中 隆,Xun Gong,黒田智明
    • Organizer
      第58回香料・テルペンおよび精油科学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山県和歌山市)
    • Year and Date
      2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国産キク科 Ligularia sagitta の新規化学成分2014

    • Author(s)
      通 元夫,谷口瑞穂,大坪孝徳,岩本夢子,中島勝幸,岡本育子,齋藤義紀,Xun Gong,黒田智明
    • Organizer
      第58回香料・テルペンおよび精油科学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山県和歌山市)
    • Year and Date
      2014-09-20
    • Related Report
      2014 Research-status Report
  • [Presentation] 中国産キク科 Ligularia pleurocaulis の新規化学成分と多様性2014

    • Author(s)
      通 元夫,高橋宏明,齋藤義紀,中島勝幸,岡本育子,Xun Gong,黒田智明,花井 亮
    • Organizer
      第58回香料・テルペンおよび精油科学に関する討論会
    • Place of Presentation
      和歌山大学(和歌山県和歌山市)
    • Year and Date
      2014-09-20
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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