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GC-MS Analysis of Fragrant Odor of Japanese Bryophytes, Their Chemical Structures and Chemosystematics

Research Project

Project/Area Number 08459026
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 広領域
Research InstitutionFaculty of Pharmaceutical Sciences, Tokushima Bunri University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) NAGASHIMA Fumuhiro  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Assistant Dr., 薬学部, 助手 (60228012)
TOYOTA Masao  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Assistant Dr., 薬学部, 助手 (50122586)
HASHIMOTO Toshihiro  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Associate Profes, 薬学部, 助教授 (10075955)
TORI Motoo  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Professor, Dr., 薬学部, 教授 (90163956)
Project Period (FY) 1996 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥8,300,000 (Direct Cost: ¥8,300,000)
Fiscal Year 1998: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥7,200,000 (Direct Cost: ¥7,200,000)
KeywordsBryophytes / Liverworts / Mosses / GC-MS / Monoterpenes / Sesquiterpenes / Fragrance / Chemosystematics / ケモシステマティスク
Research Abstract

There are 20,000 species of the bryophytes (liverwort, moss and horuwort) in the world. We focused on the identification and structural determination of characteristic fragrant components of the bryophytes by Ge-MS analysis and their chemosystematics. We collected more than 300 specimens of the bryophytes including 100 species. All species were extracted with ether and their crude exracts were analyzed by Gc-MS using capillary column. Tenax and solid phase micro extraction methods were also carried out to identify the volatile components of each sepcies.
1. All liverworts contained mainly mono-, sesqui- and diterpenoids. Bicyclogermacrene, beta-barbatene and 1-octen-3-yl acetate has been detected in 52%, 43% and 25% of the total liverworts, respectively. These compounds might play an important role in occurrence of charcteristic fragrance of each species. The good enantio excess of the isolated compounds are confirmed by the analysis of isolated compounds by chiral column.
2. The volatil … More e component of Pallavicinia subciliata contained bicyclogermacrene as the main component. It also contained 5 novel diterpenoids. Leptolejeunea eliptica, Frullania tamarsici subsp. obscura, Plagiochila ovalifolia, Reboulia hemisphaerica, Chiloscyphus polyanthos, Porella perrott etiana and Cheilolejeunea imblicata etc. were also analyzed chemically to identify a nmuber of new sesqui-and diterpenoids, ethyl benzene derivative and aliphatic lactones, respectively.
3. There are three chemo-type of Conocephalun conicum ; beta-sabinene-type, bornyl acetate-type and methyl cinnamate-type. The latter type is classified to the new sepceis or subspecies.
4. The method of solid phase micro extraction was more sensitive than that of Tenax to detect more volatile components.
5. Mosses have been shown not to biosynthesize sesquiterpenoids. However, one of the Japanese mosses, Plagiomnium acutum contained ent-cedrenes and dolabellane-type diterpenoids. This fact suggested that some mosses are evolutionary related to liverworts although the presence of the hypothesis that the evolution process of liverworts is different from that of the mosses.
6. The characteristic mossy sent of a number of the liverwort species could be applied to perfume and flavor near future. Less

Report

(4 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • Research Products

    (76 results)

All Other

All Publications (76 results)

  • [Publications] M.Toyota: "A phenethyl glycoside from the liverwort Conocephalum conicum." Phytochemistry. 43・5. 1087-1088 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.-J.Liu: "Nudenoic acid : A novel tricyclic sesquiterpenoid from the Taiwanese liverwort Mylia nuda." Tetrahedron Letters. 37・52. 9307-9308 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Dumortenols, Novel skeletal sesquiterpenoids from the Argentinian liverwort Dumortiera hirsuta." Chem.Pharm.Bull.45・12. 2119-2121 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Asakawa: "Heterocyclic Compounds found in bryophytes." Heterocycles. 46. 795-848 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Asakawa: "Chemical Constituents of liverwort Preissia quadrata (Scop.) Nees." J.Hattori Bot.Lab.81. 243-247 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Asakawa: "Distribution of terpenoids and aromatic compounds in the liverwort Isotachis species." J.Hattori Bot.Lab.83. 257-263 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Sesquiterpene and other constituents of the liverwort Dumortiera hirsuta" Phytochemistry. 44・2. 293-298 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Nagashima: "ent-Kaurane-type diterpenoids from the liverwort Jungermannia rotundata." Phytochemistry. 44・4. 653-657 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Volatile components of the liverworts Archilejeunea olivacea, Cheilolejeunea imbricata and Leptolejeunea elliptica." Phytochemistry. 44・7. 1261-1264 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "A Comparative study on three chemo-types of the liverwort Conocephalum conicum using volatile constituents." Phytochemistry. 44・7. 1265-1270 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Nagashima: "Eudesmane-type sesquiterpene lactones from the Japanese liverwort Frullania densiloba." Phytochemistry. 45・3. 555-558 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Sesquiterpenoids from the three Japanese liverworts Lejeunea aquatica, L. flava and L. japonica." Phytochemistry. 46・1. 145-150 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Butenolides from the liverwort Marchanita paleacea subsp. diptera." Phytochemistry. 46・2. 293-296 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Nagashima: "Terpenoids from the Japanese liverworts Jackiella javanica and Jungermannia infusca." Phytochemistry. 46・7. 1203-1208 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Yoshida: "Scapaundulins A and B, Two novel Dimeric Labdane diterpenoids, and related compounds from the Japanese liverwort Scapania undulata (L. ) Dum." Tetrahedron Letters. 38. 1975-1978 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Novel Skeletal Diterpenoids from the Japanese Liverwort Pallavicinia subciliata." Chem.Pharm.Bull.46・1. 178-180 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Eudesmane-type Sesquiterpenoids from Japanese Liverwort Frullania tamarisci subsp.obscura." Chem.Pharm.Bull.46・3. 542-544 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Occurrence of ent-Sesquiterpene in the Japanese Moss-Plagiomnium acutum : First Isolation and Identification of the ent-Sesqui-and Dolabellane-type Diterpenoidfs from the Musci." Chem.Pharm.Bull.46・9. 1488-1489 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hashimoto: "Chemical conversion of Labdane-type Diterpenoid Isolate from the Liverwort Porella perrottetiana into (-)-Ambrox." Heterocyles. 49. 315-325 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hashimoto: "Chemical constituents of the Japanese Liverworts Odontoschisma denudatum, Porella japonica, P. acutifolia subsp. tosana and Frullania hamatiloba." J.Hattori Bot.Lab.84. 309-314 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Cytotoxic 2,3-Secoaromadendrane-type Sesquiterpenoids from the Liverwort Plagiochila ovalifolia." Planta Medica. 64. 462-464 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Triterpenoid Constituents of the Moss Floribundaria aurea subsp. nipponica." Phytochemistry. 48・2. 297-299 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hashimoto: "Novel ent-Vibsane- and Dolabellane-type Diterpenoids from the Livwerwort Odontoschisam denudatum." Tetrahedron Letters. 39. 579-582 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hashimoto: "Two Novel Diles-Alder Reaction-Type Dimeric Pinguisane Sesquiterpenoides and Related Compounds from the Liverwort Porella acutifolia subsp. tosana." Tetrahedron Letters. 39. 2977-2980 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hashimoto: "Two Novel Skeletal Diterpenoids, Neodenudatenones A and B, from the liverwort Odontoschisma denudatum." Tetrahedron Letters. 39. 3791-3794 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "Terpenoid constituents of the liverwort Reboulia hemisphaerica." Phytochemistry. in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Nagashima: "Sesqui- and diterpenoids from Ptilidium ciliare and Barbilophozia specides (Liverwrots)." Phytochemistry. in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Toyota: "The absolute configuration of endesmane-type sesquiterpenoids found in the Japanese liverwort Chiloscyphus polyanthos." Phytochemistry. in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Bardon: "A-7 nordumortane and other dumortane derivatives from the Argentine livwerwort Dumortiera hirsuta." Phytochemistry. in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Saito, T.and Asakawa, Y.: "A phenethyl glycoside from Conocephalum conicum." Phytochemistry. 43(5). 1087-1088 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Liu, H.-J., Wu, C.-L., Hashimoto, T.and Asakawa, Y.: "Nudenoic acid : a novel tricyclic sesquiterpenoid from the Taiwanese liverwort Mylia nuda." Tetrahedron Letters. 37(57). 93-7-9308 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Yoshida, T., Matsunami, J.and Asakawa, Y.: "Sesquiterpene and other constituents of the liverwort Dumortiera hirsuta." Phytochemistry. 44(2). 293-298 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Nagashima, F., Tanaka, H.and Asakawa, Y.: "Ent-kaurene-type diterpenoids from the liverwort Jungermannia rotundata." Phytochemistry. 44(4). 653-657 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Koyama, H.and Asakawa, Y.: "Volatile components of the liverworts Archilejeunea olivacea, Chilolejeinea imbricata and Leptolejeunea elliptica." Phytochemistry. 44(7). 1261-1264 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Saito, T., Matsunami, J.and Asakawa, Y.: "A comparative study on three chemo-types of the liverwortConcephalum conicum using volatile constituents." Phytochemistry. 44(7). 1265-1270 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Nagashima, F., Tanaka, H., Takaoka, S.and Asakawa, Y.: "Eudesmane-type sesquiterpene lactones from the Japanese liverwort Frullania densiloba." Phytochemistry. 45(3). 555-558 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Koyama, H.and Asakawa, Y.: "Sesquiterpenoids from the three Japanese liverworts Leujeunea aquatica, L.flava and L.japonica." Phytochemistry. 46(1). 145-150 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Konoshima, M., Nagashima, F., Hirata, S.and Asakawa, Y.: "Butenolides from Marchantia paleacea subsp.diptera." Phytochemistry. 46(2). 293-296 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Nagashima, F., Tamada, A., Fujii, N.and Asakawa, Y.: "Terpenoids from the Japanese liverworts Jackiella javanica and Jungermannia infusca." Phytochemistry. 46(7). 1203-1208 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Asakawa, Y., Hashimoto, T., Akazawa, K.and Huneck, S.: "Chemical constituents of the liverwort Preissia quadrata (Scop.) Nees." J.Hattori Bot.Lab.81. 243-247 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshida, T., Toyota, M.and Asakawa, Y.: "Scapaundulins A and B,two novel dimeric labdane diterpenoids, and related compounds from the Japanese liverwort Scapania undulata (L.) Dum." Tetrahedron Letters. 38. 1975-1978 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Asakawa.Y., Toyota, M., Nakaishi, E.and Tada, Y.: "Distribution of terpenoids and aromatic compounds in the liverwort Isotachis species." J.Hattori Bot.Lab.83. 257-263 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Bardon, A., Kamiya, M., Takaoka, S.and Asakawa, Y.: "Dumortenols, novel sesquiterpenoids from the Argentinian liverwort Dumortiera hirsuta." Chem.Pharm.Bull.45(2). 2119-2121 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Asakawa, Y.: "Heterocyclic compounds found in bryophytes." Heterocycles. 46. 795-848 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Masuda, K.and Asakawa, Y.: "Triterpenoid constituents of the moss Florobundaria aurea subsp.nipponica." Phytochemistry. 48(2). 297-299 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Saito, T.and Asakawa, Y.: "Novel skeletal diterpenoids from the Japanese liverwort Pallavicinia subcilitata." Chem.Pharm.Bull.46(1). 178-180 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hashimoto, T., Toyota, M., Koyama, H., Kikkawa, A., Yoshida, M., Tanaka, M., Takaoka, S.and Asakawa, Y.: "Novel ent-vibsane- and dolabellane-type diterpenoids from the liverwort Odontoschisma denudatum." Tetrahedron Letters. 39. 579-582 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Nishimoto, C.and Asakawa, Y.: "Eudesmane-type sesquiterpenoids from Japanese liverwort Frullania tamarsici subsp.obscura." Chem.Pharm.Bull.46(3). 542-544 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hashimoto, T., Irita, H., Tanaka, M., Takaoka, S.and Asakawa, Y.: "Two novel Diels-Alder reaction type dimeric pinguisane sesquiterpenoids and related compounds from the liverwort Porella acutifolia subsp.tosana." Tetrahedron Letters. 39. 2977-2980 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hashimoto, T., Kikkawa, A., Yoshida, M., Tanaka, M.and Asakawa, Y.: "Two novel skeletal diterpenoids, neodenudatenones A and B,from the liverwort Odontoschisma denudatum." Tetrahedron Letters. 39. 3791-3794 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Tanimura, K.and Asakawa, Y.: "Cytotoxic 2,3-secoaromadendrane-type sesquiterpenoids from the liverwwort Plagiochila ovalifolia." Planta Medica. 64. 462-464 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hashimoto, T., Irita, H., Yoshida, M., Kikkawa, A., Toyota, M., Koyama, H., Motoike, Y.and Asakawa, Y.: "Chemical constituents of the Japanese liverworts Odontoschisma denudatum, Porella japonica, P.acutifolia subsp.tosana and Frullania hamatiloba." J.Hattori Bot.Lab.84. 309-314 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Kimura, K.and Asakawa, Y.: "Occurrence of ent-sesquiterpene in the Japanese Moss-Plagiomnium acutum : First isolation and identification of the ent-sesqui- and dolabellane-tyupe diterpenoids from the Musci." Chem.Pharm.Bull.46(9). 1488-1489 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hashimoto, T., Shiki, K., Tanaka, M., Takaoka, S.and Asakawa, Y.: "Chemical conversion of labdane-type diterpenoid isolated from the liverwort Porella perrottetiana into (-)-ambrox." Heterocycles. 49. 315-325 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Konoshima, M.and Asakawa, Y.: "Terpenoid constituents of the liverwort Reboulia hemisphaerica." Phytochemistry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Bardon, A., Kimiya, N., Toyota, M.and Asakawa, Y.: "A 7-nordumortenone and other dumortane derivatives from the Argentine liverwort Dumortiera hirsuta." Phytochemsitry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Nagashima, F., Takaoka, S., Huneck, S.and Asakawa, Y.: "Sesqui-and diterpenoids from Ptilidium ciliare and Barbilophozia species (Liverworts)." Phytochemistry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Toyota, M., Saito, T.and Asakawa, Y.: "The absolute configuration of eudesmane-type sesquiterpenoids found in the Japanese liverwort Chiloscyphus polyanthos." Phytochemistry. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Nagashima: "New Sesqui-and Diterpenoids from the Japanese Liverwort Jungermannia infusca(Mitt.)Steph." Chem.Pharm.Bull.46・7. 1184-1185 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Toyota: "Occurrence of ent-sesquiterpene in the Japanese moss-Plagiomnium acutum:First isolation and identification of the ent-sesqui-and dolabellane-type diterpenoids from the musci." Chem.Pharm.Bull.46・9. 1488-1489 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hashimoto: "Chemical conversion of Labdane-Type Diterpenoid Isolated from the Liverwort Porella perrottetiana into(-)-Ambrox." Heterocycles. 49. 315-325 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Nagashima: "Diterpenoids from the Japanese Liverwort Jungermannia tnfusca." Phytochemistry. 49・2. 601-608 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hashimoto: "Novel ent-Vibsane-and dolabellane-type diterpenoids from the liverwort Odontoschisma denudatum." Tetrahedron Letters. 39. 579-582 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Toyota: "Terpenoid constituents of the liverwort Reboulia hemisphaerica." Phytochemistry. (印刷中). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Asakawa: "Distribution of terpenoids and aromatic compounds in the liverworts Isotachis species" J.Hattori Bot.Lab.83. 257-263 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyota: "Dumortenols,novel skeletal sesquiterpenoids from the Argentinian liverwort Dumortiera hirsuta" Chem.Pharm.Bull.45・12. 2119-2121 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyota: "Novel skeletal diterpenoids from the Japanese liverwort Pallavicinia subciliata" Chem.Pharm.Bull.46・1. 178-180 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyato: "Eudesmane-type sesquiterpenoids from Japanese liverwort Frullania tamarisci subsp.obscura" Chem.Pharm.Bull.(印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyato: "Triterpenoid constituents of the moss Floribundaria aure subsp.nipponica" Phytochemistry. (印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyato: "Cytotoxic 2,3-secoaromadendrane-type sesquiterpenoids from the liverwort Plagiochila ovalifolia Mitt." Planta Medica. (印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Toyota: "A phenethyl glycoside from Conocephalum conicum" Phytochemistry. 43・5. 1087-1088 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Toyota: "Constituents of the liverwort Dumortiera hirsuta" Phytochemistry. 44・2. 293-298 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Toyota: "Volatile components of the liverworts Archilejeunea olivacea, Cheilejeunea imbricata and Leptolejeunea elliptica" Phytochemistry. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Toyota: "A comparative study on three chemo-types of the liverwort Concephalum conicum using volatile constituents" Phytochemistry. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Toyota: "Sesquiterpenoids form the three Japanese liverworts Lejeunea aquatica, L. flava and L. japonica" Phytochemistry. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Toyota: "Butenolides of the liverwort Marchantia paleacea subsp. diptera (Nees et Mont.)" Phytochemistry. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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