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

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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