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Development of an anti-HIV agent from plant meroterpenoids

Research Project

Project/Area Number 17K08337
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Natural medicines
Research InstitutionThe University of Tokushima

Principal Investigator

TANAKA Naonobu  徳島大学, 大学院医歯薬学研究部(薬学域), 准教授 (40455598)

Co-Investigator(Kenkyū-buntansha) 柏田 良樹  徳島大学, 大学院医歯薬学研究部(薬学域), 教授 (30169429)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2017: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords抗HIV薬 / 天然物 / メロテルペン / 植物 / 海洋生物 / 抗HIV活性物質 / 薬学
Outline of Final Research Achievements

A library of meroterpenes possessing unique chemical structures was prepared by phytochemical investigations on plants collected at Yunnan province and Guangxi Zhuang Autonomous Region, China, Mongolia, Uzbekistan, Hokkaido and Tokushima prefectures, Japan, and on plants cultivated at Tokushima. Marine sponges collected at Okinawa and Tokushima prefectures were also investigated. In an evaluation of anti-HIV activity, hyperdioxane A, a novel heptacyclic meroterpene isolated from the roots of Hypericum ascryon (Hypericaceae), demonstrated an inhibitory effect on HIV replication.

Academic Significance and Societal Importance of the Research Achievements

抗HIV活性を見い出したhyperdioxane Aは、特異な七環性構造をもつ新規メロテルペンである。同時に単離した生合成前駆体と考えられる天然物には、抗HIV活性がみられなかったことから、hyperdioxane Aの特異な化学構造が抗HIV活性に関与することが示唆された。今回、hyperdioxane Aに加えて、数多くの新規メロテルペンを単離することができた。様々な新興感染症が社会問題となる中、新規な化学構造を有する天然物は感染症治療薬リードとして重要である。今回得た新規メロテルペンについても今後各種スクリーニングを行う予定である。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (49 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (5 results) Journal Article (12 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 12 results,  Open Access: 5 results) Presentation (32 results) (of which Int'l Joint Research: 1 results)

  • [Int'l Joint Research] 中国広西壮族自治区中国科学院広西植物研究所(中国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] モンゴル国立医科大学(モンゴル)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ウズベキスタン科学アカデミー(ウズベキスタン)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ノースカロライナ大学薬学部(米国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Guangxi Institute of Botany/Guangxi Zhuang Autonomous Region/and Chinese Academy of Sciences(中国)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Linaburiosides A-D, acylated iridoid glucosides from Linaria buriatica.2020

    • Author(s)
      Niwa K, Yi R, Tanaka N, Kitaguchi S, Tsuji D, Kim SY, Tsogtbaatar A, Bunddulam P, Kawazoe K, Kojoma M, Damdinjav D, Itoh K, Kashiwada Y
    • Journal Title

      Phytochemistry

      Volume: 171 Pages: 112247-112247

    • DOI

      10.1016/j.phytochem.2019.112247

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Prenylated benzophenone derivatives from Hypericum patulum2020

    • Author(s)
      Tanaka, N.; Niwa, K.; Yano, Y.; Kashiwada, Y.
    • Journal Title

      Journal of Natural Medicines

      Volume: 74 Issue: 1 Pages: 264-268

    • DOI

      10.1007/s11418-019-01350-3

    • NAID

      40022130343

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sarcaglabrin A, a conjugate of C15 and C10 terpenes from the aerial parts of Sarcandra glabra.2020

    • Author(s)
      Yang XR, Tanaka N, Tsuji D, Lu FL, Yan XJ, Itoh K, Li DP, Kashiwada Y
    • Journal Title

      Tetrahedron Letters

      Volume: in press Issue: 25 Pages: 151916-151916

    • DOI

      10.1016/j.tetlet.2020.151916

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Limonoids from the aerial parts of Munronia pinnata.2019

    • Author(s)
      Yang X, Tanaka N, Tsuji D, Lu FL, Yan X, Itoh K, Li DP, Kashiwada Y
    • Journal Title

      Tetrahedron Letters

      Volume: 75 Issue: 52 Pages: 130779-130779

    • DOI

      10.1016/j.tet.2019.130779

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Hypascyrins A-E, Prenylated Acylphloroglucinols from Hypericum ascyron.2019

    • Author(s)
      Niwa K, Tanaka N, Tatano Y, Yagi H, Kashiwada Y.
    • Journal Title

      J Nat Prod

      Volume: 82 Issue: 10 Pages: 2754-2760

    • DOI

      10.1021/acs.jnatprod.9b00354

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Lanostane-type triterpenes from the sclerotium of Inonotus obliquus (Chaga mushrooms) as proproliferative agents on human follicle dermal papilla cells2019

    • Author(s)
      Sagayama, K.; Tanaka, N.; Fukumoto, T.; Kashiwada, Y.
    • Journal Title

      Journal of Natural Medicines

      Volume: 73 Issue: 3 Pages: 597-601

    • DOI

      10.1007/s11418-019-01280-0

    • NAID

      40021912721

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hyperdioxane A, a Conjugate of Dibenzo-1,4-dioxane and Sesquiterpene from Hypericum ascyron2018

    • Author(s)
      Niwa Kanji、Tanaka Naonobu、Kim Sang-Yong、Kojoma Mareshige、Kashiwada Yoshiki
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 18 Pages: 5977-5980

    • DOI

      10.1021/acs.orglett.8b02739

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Phloroglucinol derivatives and a chromone glucoside from the leaves of Myrtus communis2018

    • Author(s)
      Tanaka Naonobu、Jia Yuyu、Niwa Kanji、Imabayashi Kiyoshi、Tatano Yutaka、Yagi Hideki、Kashiwada Yoshiki
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 1 Pages: 117-123

    • DOI

      10.1016/j.tet.2017.11.044

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rigenolides D-H, norsecoiridoid and secoiridoids from Gentiana rigescens Franch2018

    • Author(s)
      Suyama Yoshihiro、Tanaka Naonobu、Kawazoe Kazuyoshi、Murakami Kotaro、Li Shun-Lin、Sun Han-Dong、Kashiwada Yoshiki
    • Journal Title

      Journal of Natural Medicines

      Volume: 72 Issue: 2 Pages: 576-581

    • DOI

      10.1007/s11418-018-1181-2

    • NAID

      40021511490

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stereochemical assignments of rubiaquinones A?C, naphthoquinone derivatives from Rubia yunnanensis2017

    • Author(s)
      Suyama Yoshihiro、Higashino Yusuke、Tanaka Naonobu、Tatano Yutaka、Yagi Hideki、Kawazoe Kazuyoshi、Murakami Kotaro、Li Shun-Lin、Sun Han-Dong、Kashiwada Yoshiki
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 48 Pages: 4568-4571

    • DOI

      10.1016/j.tetlet.2017.10.051

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Guianolactones A and B, Two Rearranged Pentacyclic Limonoids from the Seeds of Carapa guianensis2017

    • Author(s)
      Higuchi K., Tani Y., Kikuchi T., In Y., Yamada T., Muraoka O., Tanaka N., Tanaka R.
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 12 Issue: 23 Pages: 3000-3004

    • DOI

      10.1002/asia.201701298

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Agelamasines A and B, diterpene alkaloids from an Okinawan marine sponge Agelas sp.2017

    • Author(s)
      Lee Sanghoon、Tanaka Naonobu、Kobayashi Jun’ichi、Kashiwada Yoshiki
    • Journal Title

      Journal of Natural Medicines

      Volume: 72 Issue: 1 Pages: 364-368

    • DOI

      10.1007/s11418-017-1157-7

    • NAID

      40021456246

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 桂皮成分に関する研究-桂皮ジテルペンの化学的再検討-2020

    • Author(s)
      丹羽莞慈、田中直伸、柏田良樹
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Studies on unutilized parts of medicinal plants: Secocycloartane triterpenes from the roots of Schisandra chinensis2020

    • Author(s)
      Amuti Saidanxia、Naonobu Tanaka、Yoshiki Kashiwada
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ウズベキスタン産薬用植物に関する研究(38)-シソ科植物Perovskia scrophulariifolia由来の新規ノルアビエタン型ジテルペンの構造-2020

    • Author(s)
      田中直伸、梶原聖太、丹羽莞慈、Mamadalieva Nilufar、柏田良樹
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] セリ科Ferula communis根の成分研究(4)2019

    • Author(s)
      吉野悠希、田中直伸、柏田良樹
    • Organizer
      日本生薬学会第66回年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Studies on traditional herbal medicines in Guangxi (2): New limonoids from the aerial parts of Munronia pinnata (Meliaceae)(2)2019

    • Author(s)
      Xue-Rong Yang, Naonobu Tanaka, Feng-Lai Lu, Xia-Jie Yan, Dian-Peng Li, Yoshiki Kashiwada
    • Organizer
      日本生薬学会第66回年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究(51)-Hypericum ascyron由来のメロテルペンの構造と生物活性-2019

    • Author(s)
      丹羽莞慈、田中直伸、多田納豊、八木秀樹、Chin-Ho Chen、Kuo-Hsing Lee、柏田良樹
    • Organizer
      第63回香料・テルペンおよび精油化学に関する討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ウズベキスタン産薬用植物に関する研究(37)-Perovskia scrophulariifoliaの成分研究-2019

    • Author(s)
      梶原聖太、田中直伸、Mamadalieva Nilufar、柏田良樹
    • Organizer
      第58回日本薬学会中国四国支部学術大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] セリ科Ferula communis根の成分研究 (3)2019

    • Author(s)
      吉野悠希,田中直伸,柏田良樹
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Studies on traditional herbal medicines in Guangxi (1): new limonoids from the aerial parts of Munronia pinnata (Meliaceae)2019

    • Author(s)
      Xue-Rong Yang, Naonobu Tanaka, Feng-Lai Lu, Dian-Peng Li, Yoshiki Kashiwada
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] モンゴル民族伝統薬物に関する研究 (12)-オオバコ科植物Linaria buriatica地上部の成分研究(2)-2019

    • Author(s)
      任翌,田中直伸,川添和義,村上光太郎,Ariuntuya Tsogtabaatar,Perleidulam Bunddaulam,Damdinjav Davaadagva,柏田良樹
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究 (48)-トモエソウ根由来のphloroglucinol誘導体の構造-2018

    • Author(s)
      丹羽莞慈,田中直伸,柏田良樹
    • Organizer
      日本生薬学会第65回年会
    • Related Report
      2018 Research-status Report
  • [Presentation] モンゴル民族伝統薬物に関する研究(11)ゴマノハグサ科植物Linaria buriatica地上部の成分研究-2018

    • Author(s)
      任翌,田中直伸,川添和義,村上光太郎,Ariuntuya Tsogtabaatar,Perleidulam Bunddaulam,Damdinjav Davaadagva,柏田良樹
    • Organizer
      日本生薬学会第65回年会
    • Related Report
      2018 Research-status Report
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究(47)-トモエソウ由来の新規ジベンゾジオキサン誘導体hyperdioxane A-Cの構造-2018

    • Author(s)
      丹羽莞慈,田中直伸,柏田良樹
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究(49)-H. ascyron(トモエソウ)根の成分研究-2018

    • Author(s)
      丹羽莞慈,田中直伸,柏田良樹
    • Organizer
      第22回天然薬物の開発と応用シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] Bromopyrrole alkaloids from an Okinawan marine sponge Agelas sp.2018

    • Author(s)
      Lee Sanghoon,Naonobu Tanaka,Jun’ichi Kobayashi,Yoshiki Kashiwada
    • Organizer
      第57回日本薬学会中国四国支部学術大会
    • Related Report
      2018 Research-status Report
  • [Presentation] セリ科Ferula communis根の成分研究 (2)2018

    • Author(s)
      吉野悠希,田中直伸,柏田良樹
    • Organizer
      第57回日本薬学会中国四国支部学術大会
    • Related Report
      2018 Research-status Report
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究(50)-トモエソウ根から単離したフロログルシノール誘導体の構造-2018

    • Author(s)
      丹羽莞慈,田中直伸,柏田良樹
    • Organizer
      第57回日本薬学会中国四国支部学術大会
    • Related Report
      2018 Research-status Report
  • [Presentation] New diterpene alkaloids and bromopyrrole alkaloids from Okinawan marine sponges Agelas spp.2018

    • Author(s)
      Lee Sanghoon, Naonobu Tanaka, Jun’ichi Kobayashi, Yoshiki Kashiwada
    • Organizer
      The 10th KSP-JSP-CSP Joint Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] オトギリソウ科Hypericum属植物に関する研究(46)―キンシバイより単離した新規ベンゾフェノン誘導体hypatulin Cの構造―2018

    • Author(s)
      矢野優希、田中直伸、柏田良樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] モンゴル民族伝統薬物に関する研究(9)―「チャーガ」子実体由来の発毛・育毛活性成分の探索研究―2018

    • Author(s)
      嵯峨山和美、丹羽莞慈、田中直伸、福元隆俊、柏田良樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] モンゴル民族伝統薬物に関する研究(10)―「シソ科植物Lophanthus chinensisの成分研究(2)2018

    • Author(s)
      山田健太、田中直伸、川添和義、村上光太郎、Damdinjav Davaadagva、Dorjval Enkhiargal、柏田良樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] セリ科植物Ferula communis根の成分研究2018

    • Author(s)
      吉野悠希、田中直伸、柏田良樹
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] New diterpene alkaloids from an Okinawan marine sponge Agelas sp.2017

    • Author(s)
      Sanghoon Lee, Naonobu Tanaka, Jun'ichi Kobayashi, Yoshiki Kashiwada
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] センリョウ科Chloranthus属植物の成分研究(14)-ヒトリシズカ地上部より単離した新規C25テルペノイドHitorin G及びHの構造-2017

    • Author(s)
      森岡諒、金尚永、長嶋紘紗子、田中直伸、柏田良樹、小林淳一、高上馬希重
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] フトモモ科植物ギンバイカ由来の新規フロログルシノール誘導体の構造(2)2017

    • Author(s)
      丹羽莞慈、賈玉鈺、田中直伸、柏田良樹
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 雲南省産伝統薬物に関する研究(28)-アカネ科植物Rubia yunnanensis根の成分研究-2017

    • Author(s)
      東野勇佑、洲山佳寛、田中直伸、川添和義、村上光太郎、李順林、孫漢董、柏田良樹
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 発酵霊芝の高脂肪食摂取マウスに及ぼす影響2017

    • Author(s)
      位上健太郎、下条洋輔、野渕翠、小坂邦男、宮崎寿次、伊藤久富、田中直伸、柏田良樹
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] ヒトリシズカ(Chloranthus japonicus)地上部より単離した新規C25テルペノイドHitorin E-H2017

    • Author(s)
      金尚永、森岡諒、長嶋紘紗子、田中直伸、柏田良樹、小林淳一、高上馬希重
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] アカネ科植物Rubia yunnanensis根由来の新規ナフトキノン誘導体の構造2017

    • Author(s)
      洲山佳寛、東野勇佑、田中直伸、川添和義、村上光太郎、李順林、孫漢董、柏田良樹
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] モンゴル民族伝統薬物に関する研究(8)-シソ科植物Lophanthus chinensis地上部の成分研究-2017

    • Author(s)
      山田健太、田中直伸、川添和義、村上光太郎、Damdinjav Davaadagva、Dorjval Enkhiargal、柏田良樹
    • Organizer
      第56回日本薬学会中国四国支部学術大会
    • Related Report
      2017 Research-status Report
  • [Presentation] New diterpene alkaloids and bromopyrrole alkaloids from marine sponges Agelas sp.2017

    • Author(s)
      Lee Sanghoon、Naonobu Tanaka、Jun’ichi Kobayashi、Yoshiki Kashiwada
    • Organizer
      第56回日本薬学会中国四国支部学術大会
    • Related Report
      2017 Research-status Report
  • [Presentation] ギンバイカ由来の新規フロログルシノール誘導体myrtcommunin A-Hの構造2017

    • Author(s)
      丹羽莞慈、賈玉鈺、田中直伸、柏田良樹
    • Organizer
      第7回食品薬学シンポジウム
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2021-02-19  

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