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

日本苔藓植物香气、化学结构和化学系统学的 GC-MS 分析

• 批准号: 08459026
• 负责人: ASAKAWA Yoshinori
• 金额: $ 5.31万
• 依托单位: Faculty of Pharmaceutical Sciences, Tokushima Bunri University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 1996
• 资助国家: 日本
• 起止时间: 1996 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-08459026/
• 关键词: Bryophytes; Liverworts; Mosses; GC-MS; Monoterpenes; Sesquiterpenes; Fragrance; Chemosystematics; ケモシステマティスク

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

世界上有20，000种苔藓植物（苔类，苔藓和horuwort）。本论文主要研究了紫丁香属植物特征香气成分的Ge-MS分析和结构鉴定，并对其进行了化学系统学研究。共采集标本300余件，计100余种。用乙醚提取，粗提物用毛细管柱气相色谱-质谱联用分析。采用Tenax和固相微萃取法对各样品的挥发性成分进行了鉴定.所有地钱含有主要的单，倍半和二萜类化合物。双环大根香叶烯、β-胡萝卜素和1-辛烯-3-乙酸酯的含量分别占总苔量的52%、43%和25%。这些化合物可能对各物种特征香气的产生起重要作用。通过手性柱分析，证实了分离的化合物具有良好的对映体过量.挥发物 ...更多信息 Pallavicinia subciliata的主要成分为双环大根香叶烯。它还含有5种新型二萜类化合物。椭圆薄鳞藓（Leptolejeunea eliptica）、塔玛果藓（Frullania tamarsici subsp.）对其中的倍半萜、二萜、乙苯衍生物和脂肪族内酯等化合物进行了化学分析. Conocephalun conicum有三种化学类型：β-桧烯型、乙酸正丁酯型和肉桂酸甲酯型。后一类型被划分为新的sepceis或亚种。固相微萃取法比Tenax法更灵敏，能检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，日本的藓类植物，斜灯藓acutum含有ent-cedrenes和dolabellane型二萜。这一事实表明，尽管存在苔类植物与苔藓植物的进化过程不同的假说，但某些苔藓植物与苔类植物在进化上是相关的.许多苔类植物特有的苔状物质在不久的将来可用于香料和香精。少

项目成果

M.Toyota: "A phenethyl glycoside from the liverwort Conocephalum conicum." Phytochemistry. 43・5. 1087-1088 (1996)

M.Toyota：“来自地钱 Conocephalum conicum 的苯乙基糖苷。” 43・5（1996）。

M.Toyota: "A Comparative study on three chemo-types of the liverwort Conocephalum conicum using volatile constituents." Phytochemistry. 44・7. 1265-1270 (1997)

M.Toyota：“使用挥发性成分对地钱的三种化学类型进行比较研究”，44·7（1997）。

M.Toyota: "Triterpenoid Constituents of the Moss Floribundaria aurea subsp. nipponica." Phytochemistry. 48・2. 297-299 (1998)

M. Toyota：“Moss Floribundaria aurea subsp. nipponica 的三萜成分” 48・2（1998）。

T.Hashimoto: "Novel ent-Vibsane- and Dolabellane-type Diterpenoids from the Livwerwort Odontoschisam denudatum." Tetrahedron Letters. 39. 579-582 (1998)

T.Hashimoto：“来自 Livwerwort Odontoschisam denudatum 的新型 ent-Vibsane 型和 Dolabellane 型二萜类化合物。”

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)

Nagashima, F.、Tanaka, H.、Takaoka, S. 和 Asakawa, Y.：“来自日本苔类 Frullania densilloba 的Eudesmane 型倍半萜内酯。”