Development of medicinal plant resources of liverworts growing in southern hemisphere and research for the clucidation of the evolution and differentiation process based on the precision chemical analysis.

我们重点研究了南半球的苔类和蕨类植物的化学成分，因为新西兰和阿根廷有许多特有物种。通过微量化学分析，分离得到的成分对地菜的化学系统和进化研究具有重要意义。同时，采用LC-MS和GC-MS分析方法比较了苔类植物和蕨类植物的化学成分。分析了阿根廷毛茸和凤尾草的醚提取物。前一种含有两种新的倍半萜，命名为dumortane和nordumortane-type skeleton。后一种产生藿烷型三萜，这是对半球绿足和红足的化学系统分类的重要化学指标。对厄瓜多尔jackiphs进行了化学分析，鉴定出一些新的倍半萜类、马来烷类和德国烷类。其中挥发性乙烯苯类化合物为厄瓜多尔苔类植物的芳香物质，在新西兰共收集到Marchesinia brachiata.2.250份，估计种类约为100种。对新西兰蓖麻属植物进行化学分析，发现其主要成分为新型倍半萜类化合物。对12种拉杜拉属植物进行了化学分析，并根据化学成分将其划分为4个化学类群。通过进一步研究，分离出了与大麻素结构相关的化合物，该化合物有望显示出有趣的生物活性。已知的辛辣味化合物分布在苔类植物（porrella和Plagiochila等）中。新西兰苔类植物黄膜藓中含有1-（2,4,6 -三甲氧基苯基）-丁-2-烯-1- 1的刺激性成分。这是本研究中讨论苔类和蕨类植物进化路线的最重要的结果，因为蕨类植物Arachinoides standishii也含有相同的刺激性化合物。Perrottetin H属联苯类化合物，广泛存在于苔类植物中，但尚未在高等植物成分中发现。日本产的Hymenophyllum barbatum中含有双联苯（bisbibenzyl）、Perrottetin H.这两种化合物均为化学化石，存在于苔类植物和蕨类植物中。少

We focused on the chemical constituents of the liverworts and ferns in southern hemisphere, as many endemic species are growing in New Zealand and Argentine. The constituents isolated from the liverworts based on the micro chemical analysis, are important for the chemosystematic and evolutionary study of the liverworts. We also compared between the chemical constituents of the liverworts and those of ferns by LC-MS and GC-MS analysis.1.The ether extract of Argentine Dumortiera hirsuta and Plagiochasma rupestre were analysed. Former species contained two novel sesquiterpenes, named as dumortane and nordumortane-type skeletons. Latter species produced hopane-type triterpenoid, which is important chemical indicator for the chemosystematics of Reboulia hemisphaerica and P. rupestre. Ecuadorian Leptoscyphus jackii was analysed chemically to identify a number of new sesquiterpenes, maaliane and germacrane types. The volatile vinylbenzenoids were found as fragrance of the Ecuadorian liverwort … More s Marchesinia brachiata.2.250 materials were collected in New Zealand, and the number of species was estimated as about 100.New Zealand Riccardia species were analysed chemically to give new sesquiterpenoid as a major constituent. 12 Radula species were analysed chemically and they were divided into four chemo-taxa with their constituents. Further investigation of the ether extract of Radula marginata resulted in the isolation of cannabinoid structure-related compound which was expected to show an interesting biological activity.3.Pungent tasting compounds distributed in liverworts (Porella and Plagiochila etc) are known. New Zealand liverwort Hymenophyton flabellatum contained 1-(2, 4, 6-trimethoxy-phenyl)-but-2-en-1-one as the pungent tasting constituent. This is the most important result for the discussion of the evolutionary line of liverworts and ferns in the present investigation, since the same pungent compounds were also contained in the fern, Arachinoides standishii. Perrottetin H classified into bibenzyl compound, which is widely distributed in the liverworts, but not found in constituents of higher plants, yet. The Japanese ferm Hymenophyllum barbatum contained bisbibenzyl, Perrottetin H. These two compounds are chemical fossils, contained both in the liverworts and ferns. Less