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

世界上有2万种苔藓植物（苔类、苔藓类和蕨类）。利用Ge-MS分析和化学系统学方法对苔藓植物的芳香成分进行了鉴定和结构分析。我们采集了苔藓植物标本300余份，包括100种。采用乙醚提取，粗提物采用毛细管柱气相色谱-质谱分析。采用固相微萃取法和Tenax法对各品种的挥发性成分进行了鉴定。所有苔类植物主要含有单萜类、倍萜类和二萜类。双环革烯、β -巴巴丁烯和1-辛烯-3-乙酸酯分别在总数的52%、43%和25%中检出。这些化合物可能在各物种特有香味的产生中起重要作用。用手性柱对分离化合物进行分析，证实了分离化合物具有良好的对映过量。金缕柏挥发物的挥发性成分以双环丙烯为主要成分。它还含有5种新的二萜类化合物。椭圆瘦带绦虫，绢果绦虫亚种。通过化学分析，分别鉴定出了新的半萜类、二萜类、乙苯衍生物和脂肪内酯类化合物。圆锥圆锥有三种化学型；-杉木烯型，醋酸龙脑酯型和甲基肉桂酸型。后一种分类为新种或亚种。固相微萃取法对挥发性成分的检测灵敏度高于Tenax法。苔藓已被证明不能生物合成倍半萜。然而，其中一种日本苔藓，斜藓，含有松烯和美元莲型二萜。这一事实表明，尽管存在苔类与藓类的进化过程不同的假说，但某些藓类与苔类存在进化关系。在不久的将来，一些苔属植物所特有的苔藓气味可用于香水和香精。少

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