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

世界上有两万种苔藓植物(地钱、苔藓和地钱)。重点对苔藓植物的特征香气成分进行了GE-MS分析鉴定和结构确定，并对其化学体系进行了研究。共采集苔藓植物标本300余份，计100种。用乙醚提取，用毛细管柱气相色谱-质谱法对其粗提物进行分析。还采用了Tenax和固相微萃取方法来鉴定每种香料的挥发性成分。所有的苔类植物主要含有单萜、倍半萜和二萜。双环香叶烯、β-巴巴烯和1-辛烯-3-乙酸乙酯的含量分别占总苔类的52%、43%和25%。这些化合物可能在每种香气的发生中起着重要的作用。通过手性柱对分离出的化合物进行分析，证实了分离出的化合物具有良好的对映体过量。The Volatil…纤毛下巴拉维辛的主要成分以双环马齿烯为主。它还含有5个新的二萜类化合物。Leptlejeunea Eliptica，Frullania Tamarsici亚种。化学成分分析鉴定了新的倍半萜、二萜类化合物、乙苯类化合物和脂肪族内酯。圆锥花的化学型有三种：β-莎草烯型、乙酸龙脑型和肉桂酸甲酯型。后一类型被归为新的属或亚种。固相微萃取法比Tenax法更能灵敏地检测出更多的挥发性成分。苔藓已被证明不能生物合成倍半萜类化合物。然而，其中一种日本苔藓-尖叶斜杉含有对位雪松和多拉贝烷型二萜类化合物。这一事实表明，一些苔藓植物与苔藓植物具有进化亲缘关系，尽管存在苔类植物与苔藓植物进化过程不同的假说。一些苔类植物的特征苔藓可以在不久的将来应用于香料和调味品。较少

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