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DEVELOPMENT OF MEDICINAL DRUGS FROM SOUTHERN HEMISPHERIC TASTY BRYOPHYTES AND FERNS AND THEIR CHEMOSYSTEMATICS

Research Project

Project/Area Number 14403014
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section海外学術
Research Field Chemical pharmacy
Research InstitutionFACULTY OF PHARMACEUTICAL SCIENCES, TOKUSHIMA BUNRI UNIVERSITY

Principal Investigator

ASAKAWA Yoshinori  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (50033874)

Co-Investigator(Kenkyū-buntansha) TORI Motoo  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (90163956)
HASHIMOTO Toshihiro  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Associated Professor, 薬学部, 助教授 (10075955)
TOYOTA Masao  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Lecturer, 薬学部, 講師 (50122586)
NAGASHIMA Fumihiro  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Research Assistant, 薬学部, 助手 (60228012)
Project Period (FY) 2002 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥8,400,000 (Direct Cost: ¥8,400,000)
Fiscal Year 2005: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2004: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2003: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2002: ¥4,500,000 (Direct Cost: ¥4,500,000)
KeywordsPharmaceutical Sciences / Biological activity / Bryonhytes / Pteridophytes / Apontosis / Anticholesteremia / NO production inhibitory / Chemosystematics / 蘚苔類化学成分 / シダ類化学成分 / テルペノイド / フェノール化合物 / 細胞毒性 / ビスビベンジル / ent-カウレン型ジテルペン / ネクローシス / マダガスカル / ニュージーランド / 苔類 / 苔類の辛味成分 / テルペン / GC-MS / LC-MS / 進化 / 蘇苔類 / ビスビベンジル類 / セスキテルペン類
Research Abstract

In the southern hemisphere, there are a great number of endemic bryophyte (liverworts, mosses and hornworts) and pteridophyte (ferns) species many of which contain pungent, bitter or sweet taste. Since the crude extracts of these tasty species showed potent antimicrobial and antifungal, insect and killing, antitumor, and muscle relaxing activity, we collected the New Zealand, Argentinean, Malgasy and Malaysian bryophytes and ferns and extracted with ether. 1.New Zealand liverworts : From Jungermannia species 12 new and 4 known ent-kaurane-type diterpenoids of which ent-11α-hydroxy-16-kauren-15-one and jugermannenone D showed strong cytotoxicity and apoptosis against HL-60. Lepidozia spinosissima contained a new gorgonae-type sesquiterpene the similar compound to which was isolated from some marine gorgonanian species. Balantiopsis rosea produced quite interesting 1-cyclohexy1-2-phenyl ethane derivatives which were suggested to be the biosynthetic precursors of the typical bibenzyls and … More bisbibinzyls which were peculiar secondary metabolites of liverworts. 2.Argentinean liverworts and fern : Frullania brasiliensis contained eremophilanolides which caused potent allergy. Porella swartziana elaborated africane-type and its related sesquiterpenoids which resembled those of Japanese species. The strong pungency of the fern, Thelypteris hispidula was responsible for polygodial which was also found in the liverwort Porella vernicosa complex as well as the New Zeland fern, Brechnum species. Such a chemical identity is very important to understand that some ferns might originate from the some genera of liverworts. 3.Malgasy liverworts : Several Bazzania, Plagiochila and Marchantia species produced many sesquiterpenes and bisbibenzyls, however, the new compounds were not isolated. 4.Malaysian liverworts : Two Marchantia species contained a large amount of marchanin A which showed NO production inhibitory activity. Riccardin C, which is a macrocyclic bisbibenzyl found in some New Zealand and Japanese liverwort, such as Reboulia hemisphaerica functioned as a liver X captor (LXR)α agonist and an LXRβ antagonist, thus this compound is now recognized as one of the most important potential antichorestemic drug. The present results were reported in the international and domestic symposia for1 and 35 times, respectively and 40 papers (7 are in press), four reviews and one book were published. The representative of this research project obtained the 35^<th> International Award of ISEO (International symposium on Essential Oils) and Tucman University award (Argentina) during this research project. Less

Report

(5 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (97 results)

All 2006 2005 2004 2003 2002 Other

All Journal Article (87 results) Publications (10 results)

  • [Journal Article] Diterpenids and aromatic compounds from three New Zealand liverworts, Jungermannia kirkii, Balantiopsis rosea and Radula species.2006

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem. Pharm. Bull. 54(7) (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Malagasy liverworts, Part V : Prenyl bibenzyls and clerodane diterpenoids with nitric oxide inhibitory activity from Radula appressa and Thysananthus spathulistipus.2006

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem. Pharm. Bull. 54(In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Isolation and structure of new cyclpmyltaylane and ent-chamigrane-type sesquiterpenoids from the liverwort, Reboulia hemisphaerica and their biotransformation by the fungus Aspergillus niger.2006

    • Author(s)
      Furusawa, M.
    • Journal Title

      Chem. Pharm. Bull. 54(7) (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cinnafragrins A-C, novel dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans. Structure revision of capsicodendrin.2006

    • Author(s)
      Harinatenaina, L.
    • Journal Title

      J. Nat. Prd. (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Biotransformation of aristolane-and 2,3-secoarimadendrane-type sesquiterpenoids having a 1,1-dimethylcyclopropane rind by Chlorella fusca var. vaculolata, Mucor species and Aspergillus niger.2006

    • Author(s)
      Furusawa, M.
    • Journal Title

      Chem. Pharm. Bull. 54(7) (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Screening of novel nuclear receptor agonists by a convenient reporter gene assay system using green fluorescent protein derivatives.2006

    • Author(s)
      Suzuki, T.
    • Journal Title

      Phytomedicine (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Frullania chvalieri (Jubulaceae) in New Zealand, with a reassessment of Shusterella.2006

    • Author(s)
      von Konrat, M.
    • Journal Title

      The Bryologist (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Diterpenids and aromatic compounds from three New Zealand liverworts, Jungermannia kirkii, Balantiopsisrosea and Radula species.2006

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem.Pharm.Bull. 54(7)(in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Isolation and structure of new cyclpmyltaylane and ent-chamigrane-type sesquiterpenoids from the liverwort, Reboulia hemisphaerica and their biotransformation by the fungus Aspergillus niger.2006

    • Author(s)
      Furusawa, M.
    • Journal Title

      Chem.Pharm.Bull. 54(7)(in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Biotransformation of aristolane- and 2,3-secoarimadendrane-type sesquiterpenoids having a 1,1-dimethylcyclopropane rind by Chlorella fusca var. vaculolata, Mucor species and Aspergillus niger.2006

    • Author(s)
      Furusawa, M.
    • Journal Title

      Chem.Pharm.Bull. 54(7)(in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Screening of novel nuclear receptor agonists by a convenient reporter gene assay system using green fluorescent protein derivatives.2006

    • Author(s)
      T.Suzuki, T.-N.Mogami, H.Kawai, T.Kobayashi, T.Hashimoto, Y.Asakawa, K.Inoue,.Y.Ohno, T.Hayakawa, T.Kawanishi
    • Journal Title

      Phytomedicine (In press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Frullania chevaliers (Jubulaceae) in New Zealand, with a reassessment of Shusterella.2006

    • Author(s)
      M.von Konrat, J.E.Braggins, Y.Asakawa, M.Toyota
    • Journal Title

      The Bryologist (In press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Diterpenoids and aromatic compounds from three New Zealand liverworts Jamesoniella kirkii, Balantiopsis rosea and Radula species.2006

    • Author(s)
      F.Nagashissma, Y.Kuba, Y.Asakawa
    • Journal Title

      Chemical Pharmaceutical Bulletin (In press)

    • NAID

      110004836402

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Africane-type sesquiterpenoids from the Argentine liverwort Porella swartziana and their antibacterial activity.2005

    • Author(s)
      Mitre, G.V.
    • Journal Title

      J. Nat. Prod. 67

      Pages: 31-36

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Novel cytotoxic karuane-type diterpenoids from the New Zealand liverwort Jungermannia species.2005

    • Author(s)
      Nagashima, F.
    • Journal Title

      Tetrahedron 61

      Pages: 4531-4544

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Activation of p38 mitogen-activate protein kinase during ent-11□-hydroxy-16-kauren-15-one-induced apoptosis in guman leukemia HL-60 cells.2005

    • Author(s)
      Kondoh, M.
    • Journal Title

      Planta Medica 71(3)

      Pages: 275-277

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Composition of essential oil of the liverwort Radula perrottetii of Japanese origin.2005

    • Author(s)
      Tesso, H.
    • Journal Title

      Phytochemistry 66

      Pages: 941-949

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Ent-verticillane-type diterpenoids from the Japanese liverwort Jackilella javanica.2005

    • Author(s)
      Nagashima, F.
    • Journal Title

      Phytochemistry, 66

      Pages: 1662-1670

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New sesquiterpenoid from the New Zealand liverwort Lepidozia spinosissma.2005

    • Author(s)
      Nagashima, F.
    • Journal Title

      Nat. Prod. Res 19(7)

      Pages: 679-683

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Riccardin C : a natural product that functions as a liver X receptor (LXR)α agonist and (LXR)β□ antagonist.2005

    • Author(s)
      Tamehiro, N.
    • Journal Title

      FEBS,Federation of European Biochemical Societies 579.

      Pages: 5299-5304

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Bis(bibenzyls)from liverworts inhibit lipopolysacchariade-inducible NOS in RAW 264.7 cells : a study of structure-activity relationships and molecular mechanism.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      J. Nat. Prod 68(12),1

      Pages: 779-1781

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Penicillium sclerotiorum catalyzes the conversion of herbertenediol into its dimmers : Mastigophorenes A and B.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem. Pharm. Bull. 53(2)

      Pages: 256-257

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Malagasy liverworts, Part III : Sesquiterpenoids from Bazzania decrescens and Bazzania madagasa.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem. Pharm. Bull. 53(5)

      Pages: 515-518

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Screening of novel nuclear receptor agonists by a convenient reporter gene assay system using green fluorescent protein derivatives.2005

    • Author(s)
      Suzuki, T.
    • Journal Title

      Phytomedicine (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Frullania chvalieri (Jubulaceae) in New Zealand, with a reassessment of Shusterella.2005

    • Author(s)
      Von Konrat, M.
    • Journal Title

      The Bryologist (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Activation of p38 mitogen-activate protein kinase during ent-11□- hydroxy-16-kauren-15-one-induced apoptosis in human leukemia HL-60 cells.2005

    • Author(s)
      Kondoh, M.
    • Journal Title

      Planta Medica 71(3)

      Pages: 275-277

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Ent-verticillane-type diterpenoids from the Japanese liverwort Jackilella javanica.2005

    • Author(s)
      Nagashima, F.
    • Journal Title

      Phytochemistry 66

      Pages: 1662-1670

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New sesquiterpenoid from the New Zealand liverwort Lepidozia spinosissma.2005

    • Author(s)
      Nagashima, F.
    • Journal Title

      Natural Products Research 19(7)

      Pages: 679-683

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Riccardin C : a natural product that functions as a liver X receptor (LXR)α agonist and (LXR)β□ antagonist.2005

    • Author(s)
      Tamehiro, N.
    • Journal Title

      FEBS(Federation of European Biochemical Societies) 579

      Pages: 5299-5304

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Bis(bibenzyls)from liverworts inhibit lipopolysacchariade-inducible NOS in RAW 264.7 cells : a study of structure-activity relationships and molecular mechanism.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      J.Nat.Prod. 68(12)

      Pages: 1779-1781

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Penicillium sclerotiorum catalyzes the conversion of herbertenediol into its dimmers : Mastigophorenes A and B.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem.Pharm.Bull. 53(2)

      Pages: 256-257

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Malagasy liverworts, Part III : Sesquiterpenoids from Bazzania decrescens and Bazzania madagasa.2005

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem.Pharm.Bull. 53(5)

      Pages: 515-518

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Novel cytotoxic kaurane-type diterpenoids from the New Zealand liverwort Jungermannia species.2005

    • Author(s)
      F.Nagashima, M.Kondoh, M.Fujii, S.Takaoka, Y.Watanabe, Y.Asakawa
    • Journal Title

      Tetrahedron 61

      Pages: 4531-4544

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Activation of p38 mitogen-activated protein kinase during ent-11α-hydroxy-16-kauren-15-one-induced apoptosis in human leukemia HL-60 cells.2005

    • Author(s)
      M.Kondoh, I.Suzuki, I.M.Harada, F.Nagashima, M.Fujii, Y.Asakawa, Y.Watanabe
    • Journal Title

      Planta Medica 71・3

      Pages: 275-277

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Composition of essential oil of the liverwort Radula perrottetii of Japanese origin.2005

    • Author(s)
      H.Tesso, W.A.Konig, Y.Asakawa
    • Journal Title

      Phytochemistry 66

      Pages: 941-949

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Ent-verticillane-type diterpenoids from the Japanese liverwort Jackilella javanica.2005

    • Author(s)
      F.Nagashima, K.Kishi, Y.Hamada, S.Takaoka, Y.Asakawa
    • Journal Title

      Phytochemistry 66

      Pages: 1662-1670

    • Related Report
      2005 Annual Research Report
  • [Journal Article] New sesquiterpenoid from the New Zealand liverwort Lepidozia spinosissma.2005

    • Author(s)
      F.Nagashima, T.Sekiguchi, Y.Asakawa
    • Journal Title

      Natural Products Research 19・7

      Pages: 679-683

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Riccardin C: a natural product that functions as a liver X receptor (LXR)α agonist and (LXR)β antagonist.2005

    • Author(s)
      N.Tamehiro, Y.Sato, T.Suzuki, T.Hashimoto, Y.Asakawa, S.Yokoyama, T.Kawanishi, Y.Ohno, K.Inoue, T.Nagao, T.-N.Mogami
    • Journal Title

      FEBS Letters, Federation of European. Biochemical Societies 579

      Pages: 5299-5304

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Biotransformatoin of (-)-Maalioxide by Aspergillus niger and Aspergillus cellulosae.2004

    • Author(s)
      Hashimoto, T.
    • Journal Title

      Heterocycles 66

      Pages: 655-666

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Isotachis auberrtii(isotachidaceae)collected Madagascar.2004

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Biochem. System. Ecol. 32

      Pages: 1073-1078

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New humulane-type sesquiterpenes from the liverworts Tylimanthus tenellus and Marchantia emarginata subsp.tosana.2004

    • Author(s)
      Toyota, M.
    • Journal Title

      Chem.Pharm.Bull 52

      Pages: 481-484

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Terpenods and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila,and Heteroscyphus species.2004

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem. Pharm. Bull. 52(5)

      Pages: 556-560

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A comparison of apoptosis and necrosis inducedby ent-kaurene-type diterpenoinds in HL-60 cells.2004

    • Author(s)
      Suzuki, I.
    • Journal Title

      Planta Medica 70

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New sesquiterpenoids from the New Zealand liverwort Chiloscyphus subporosus.2004

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem. Pharm. Bull. 52(8)

      Pages: 949-952

    • NAID

      110003615692

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Efficient synthesis of isoplagiochin macrocyclic bis(bibenzyls), by utilizing an intramolecular Suzuki-Miyaura reaction.2004

    • Author(s)
      Esumi, T.
    • Journal Title

      Tetrahedron Lett., 45(37)

      Pages: 6941-6945

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical Constituents of Malagasy Liverworts, Part II : Mastigophoric acid methyl ester of biogenetic interest from Mastigophora diclados (Lepicoleaceae subf. Mastigophoroideae).2004

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem. Pharm. Bull. 52(11)

      Pages: 1382-1384

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Kaurene diterpene induces apoptosisin guman leukemia cells partly through a caspase-8-dependent pathway.2004

    • Author(s)
      Kondh, M.
    • Journal Title

      J. Pharmacol. Exp. Ther. 311(1)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An ent-kaurene diterpene enhances apoptosis induced by tumornecrosis factor in guman leukemia cells.2004

    • Author(s)
      Suzuki, I.
    • Journal Title

      Planta Medica 70(8)

      Pages: 723-727

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Biotransformation of (-)-Maalioxide by Aspergillus niger and Aspergillus cellulosae.2004

    • Author(s)
      Hashimoto, T.
    • Journal Title

      Heterocycles 62

      Pages: 655-666

    • NAID

      80016354302

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Isotachis auberrtii (Isotachidaceae) collected Madagascar.2004

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Biochem.System.Ecol. 32

      Pages: 1073-1078

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New humulane-type sesquiterpenes from the liverworts Tylimanthus tenellus and Marchantia emarginata subsp. tosana.2004

    • Author(s)
      Toyota, M.
    • Journal Title

      Chem.Pharm.Bull. 52

      Pages: 481-484

    • NAID

      110003615597

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Terpenoids and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila, and Heteroscyphus species.2004

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem.Pharm.Bull. 52(5)

      Pages: 556-560

    • NAID

      110003615613

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New sesquiterpenoids from the New Zealand liverwort Chiloscyph us subporosus.2004

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem.Pharm.Bull. 52(8)

      Pages: 949-952

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Efficient synthesis of isoplagiochin macrocyclic bis(bibenzyls), by utilizing an intramolecular Suzuki-Miyaura reaction.2004

    • Author(s)
      Esumi, T.
    • Journal Title

      Tetrahedron Lett. 45(37)

      Pages: 6941-6945

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical Constituents of Malagasy Liverworts, Part II : Mastigophoric acid methyl ester of biogenetic interest from Mastigophora diclados (Lepicoleaceae subf. Mastigophoroideae).2004

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem.Pharm.Bull. 52(11)

      Pages: 1382-1384

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Kaurene diterpene induces apoptosis in human leukemia cells partly through a caspase-8-dependent pathway.2004

    • Author(s)
      Kondoh, M.
    • Journal Title

      J.Pharmacol.Exp.Ther. 311(1)

      Pages: 115-122

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An ent-kaurene diterpene enhances apoptosis induced by tumor necrosis factor in human leukemia cells.2004

    • Author(s)
      Suzuki, I.
    • Journal Title

      Planta Medica 70(8)

      Pages: 723-727

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Africane-type sesquiterpenoids from the Argentine liverwort Porella swartziana and their antibacterial activity.2004

    • Author(s)
      Mitre, G.V.
    • Journal Title

      J.Nat.Prod. 67

      Pages: 31-36

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Constituents of Isotachis aubveritii (Isotachidaceae) collected in Madagascar2004

    • Author(s)
      L.Harinantenaina, Y.Asakawa
    • Journal Title

      Biochem.System.Ecol. 32

      Pages: 1073-1078

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Chemical constituents of Margasy liverworts, part II : Masgiophoric acid methyl ester of Biogenetic interest from Mastigophora diclados (Lecoleaceae subf. ) Mastigophoroideae)2004

    • Author(s)
      L.Harinantenaina, Y.Asakawa
    • Journal Title

      Chem.Pharm.Bull. 52,11

      Pages: 1383-1384

    • Related Report
      2004 Annual Research Report
  • [Journal Article] New Humulane-type sesquiterpenes form the liverworts Tylimanthus tenellus and Marchatia emarginata subs. tosana2004

    • Author(s)
      M.Toyota, I.Omatsu, J.Braggins, Y.Asakawa
    • Journal Title

      Chem.Pharm.Bull. 52,4

      Pages: 481-484

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Terpenoids and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila, and Heteroscyphus species2004

    • Author(s)
      F.Nagashima, T.Sekiguchi, S.Takaoka, Y.Asakawa
    • Journal Title

      Chem.Pharm.Bull. 52,5

      Pages: 556-560

    • NAID

      110003615613

    • Related Report
      2004 Annual Research Report
  • [Journal Article] New sesquiterpenoids from the New Zealand liverworts Chiloscyphus subporsus2004

    • Author(s)
      F.Nagashima, M.Murakami, S.Takaoka, Y.Asakawa
    • Journal Title

      Chem.Pharm.Bull. 52,8

      Pages: 949-952

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A comparison of apoptosis and necrosis induced by ent-kaurene-type diterpenoids in HL-60 cells2004

    • Author(s)
      I.Suzuki, M.Kondo, F.Nagashima, M.Fujii, Y.Asakawa, Y.Watanabe
    • Journal Title

      Planta Medica 70

      Pages: 401-406

    • Related Report
      2004 Annual Research Report
  • [Journal Article] First synthesis of 1,9-dideoxyforskolin from ptychantin A.2003

    • Author(s)
      Hagihara, H.
    • Journal Title

      Tetrahedron Letters 44

      Pages: 2305-2306

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Volatile components of selected species of the liverwort genera Frullania and Schusterella(Frullaninaeceae)from New Zealand, Australia and South America : A chemosystematic approach.2003

    • Author(s)
      Asakawa, Y.
    • Journal Title

      Phytochemistry 62

      Pages: 439-452

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Structures of two new highly oxygenated labdane-type diterpenoids and a new cadinane-type sesquiterpenoid possessing a cyclic ether linkage from the liverwort ptychantyus stiriatus.2003

    • Author(s)
      Hashimoto, T
    • Journal Title

      Heterocycles 59

      Pages: 645-659

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Apoptosis-inducing properties of ent-kaurene-type diterpenoids from the liverwort Jungermannia truncata.2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      Planta Medica 69

      Pages: 377-379

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sesquiterpene constituents from the liverwort Bazzaina japonica.2003

    • Author(s)
      Lu, R
    • Journal Title

      Phytochemistry 63

      Pages: 581-587

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of the liverworts Bryopteris filicina, Plagiochila asplenioides and Porella canariensis2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      J.Hattori Bot. Lab 94

      Pages: 197-204

    • NAID

      40005891208

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New ent-kaurene-type diterpenoids possessing cytotoxicity from the New Zealand Liverwort Jungermannia species.2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem. Pharm. Bull. 51(10)

      Pages: 1189-1192

    • NAID

      110003615182

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima.2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      Phytochemistry 64

      Pages: 1319-1325

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Bioactive new bitter-tasting p-hydroxystyrene glycoside and other constituents from the fern Elaphoglossum spathulatum.2003

    • Author(s)
      Socolsky, C.
    • Journal Title

      Arkivoc 10

      Pages: 347-355

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Volatile components of selected species of the liverwort genera, Frullania and Schusterella (Frullaninaeceae) from New Zealand, Australia and South America : A chemosystematic approach.2003

    • Author(s)
      Asakawa, Y.
    • Journal Title

      Phytochemistry 62

      Pages: 439-452

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Structures of two new highly oxygenated labdane-type diterpenoids and a new cadinane-type sesquiterpenoid possessing a cyclic ether linkage from the liverwort Ptychantyus stiriatus.2003

    • Author(s)
      Hashimoto, T.
    • Journal Title

      Heterocycles 59

      Pages: 645-659

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sesquiterpene constituents from the liverwort Bazzania japonica.2003

    • Author(s)
      Lu, R.
    • Journal Title

      Phytochemistry 63

      Pages: 581-587

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of the liverworts Bryopteris filicina, Plagiochila asplenioides and Porella canariensis2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      J.Hattori Bot.Lab. 94

      Pages: 197-204

    • NAID

      40005891208

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New ent-kaurene-type diterpenoids possessing cytotoxicity from the New Zealand Liverwort Jungermannia species.2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem.Pharm.Bull. 51(10)

      Pages: 1189-1192

    • NAID

      110003615182

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] ent-Isopimarane-type diterpenoids from the New Zealand liverwort, Trichocolea mollissima.2003

    • Author(s)
      Nagashima, F.
    • Journal Title

      Phytochemistry 64

      Pages: 1319-1325

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Eremophilanolides and other constituents from the Argenine liverwort Frullania brasiliensis.2002

    • Author(s)
      Bardon, A.
    • Journal Title

      Phytochemistry 59

      Pages: 205-213

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata Nees.2002

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem. Pharm. Bull. 50

      Pages: 808-813

    • NAID

      110003616247

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New bibenzyl cannabinoid from the New Zealand Liverwort Radula marginata.2002

    • Author(s)
      Toyota, M.
    • Journal Title

      Chem.Pharm.Bull. 50

      Pages: 1390-1392

    • NAID

      110003615085

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Total synthesis of (-)-(7S,10R)-calamenene and (-)-7S,10R)-2-hydroxylcalamenene by use of a ring-closing metathesis reaction. A comparison of the cis- and trans-isomers.2002

    • Author(s)
      Nakashima, K.
    • Journal Title

      Molecules 7

      Pages: 517-527

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata Nees.2002

    • Author(s)
      Nagashima, F.
    • Journal Title

      Chem.Pharm.Bull. 50

      Pages: 808-813

    • NAID

      110003616247

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata.2002

    • Author(s)
      Toyota, M.
    • Journal Title

      Chem.Pharm.Bull. 50

      Pages: 1390-1392

    • NAID

      110003615085

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Chemical constituents of Malagasy liverworts, Part V : Prenyl bibenzyls and clerodane diterpenoids with nitric oxide inhibitory activity from Radula appressa and Thysananthus spathulistipus.

    • Author(s)
      Harinantenaina, L.
    • Journal Title

      Chem.Pharm.Bull. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cinnafragrins A-C, novel dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans. Structure revision of capsicodendrin.

    • Author(s)
      Harinatenaina, L.
    • Journal Title

      J.Nat.Prod. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Publications] Asakawa, Y.: "Chemosystematics of the Hepaticae."Phytochemistry. 65. 623-669 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Nagashima, F.: "ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima."Phytochemistry. 64. 1319-1325 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Nagashima, F.: "New ent-kaurene-type diterpenoids possessing cytotoxicity from the New Zealand liverwort Jungermannia species."Chem.Pharm.Bull.. 51(10). 1189-1192 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Lu, R., Paul: "Sesquiterpene constituents from the liverwort Bazzania japonica."Phytochemistry. 63. 581-587 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Nagashima, F.: "Apoptosis-induced properties of ent-kaurene-type diterpenoids form the liverwort Jungermannia truncata."Planta Medica. 69. 377-379 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Asakawa, Y.: "Volatile components of selected species of the liverwort genera Frullania and Schusterella (Frullaniaceae) from New Zealand, Australia and South America"Phytochemistry. 62. 439-452 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Asakawa, Y.: "Volatile components of Selected Species of the Liverworts genera Frullania and Schusterella (Frullaniaceae) from New Zealand, Australia and South America: A Chemosystematic Approach"Phytochemistry. 62(3). 439-452 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Toyota, M.: "New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata"Chem.Pharm.Bull.. 50(10). 1390-1392 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Nagashima, F.: "Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata Nees"Chem.Pharin.Bull.. 50(6). 808-813 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Toyota, M.: "New glycosides from the Japanese fern Hymenophyllum barbatum"Chem.Pharm.Bull.. 50(4). 508-514 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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