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1998 Fiscal Year Final Research Report Summary

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
KeywordsBryophytes / Liverworts / Mosses / GC-MS / Monoterpenes / Sesquiterpenes / Fragrance / Chemosystematics
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

  • Research Products

    (58 results)

All Other

All Publications (58 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-12-08  

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