臺灣博碩士論文加值系統

臺灣杉（Taiwania cryptomerioides Hayata）是臺灣特有種植物，因其木質特性與含有精油成分中的萜類化合物，為臺灣相當重要的針葉樹種。過去已有相當多的研究是針對臺灣杉生成產物的辨認及應用，對生合成的途徑的研究相對較少；本研究的目標是從臺灣杉選殖出重要功能的基因，瞭解各基因的生合成功能，且針對各基因做演化與生產相關的探討，透過氣相層析質譜儀分析，依各基因之主產物進行命名，依序為：Tc-βFar/Lin、Tc-Lin、Tc-Zin/βOci、Tc-βFar/Ger、Tc-αFar/Ger、Tc-Lin為單一產物的單萜合成酶，其餘四者皆屬於倍半萜合成酶，除Tc-Zin/βOci能夠生產出單環的zingiberene外，Tc-βFar/Lin、Tc-βFar/Ger、Tc-αFar/Ger所生成的單萜產物與倍半萜產物皆為線型萜類；在臺灣杉各部位的反轉錄聚合酶連鎖反應（RT-PCR）結果中，五個基因皆會在幼葉與雌毬果中表現，唯一亦會在木材中表現的基因為Tc-βFar/Ger。從親緣樹關係圖的分析結果中，發現Tc-βFar/Lin與臺灣杉中目前已知且親緣較近的倍半萜合成酶基因都有運輸胜肽遺失的現象，表示這群基因在演化的過程中可能先經歷了γ-domain遺失，最後才造成運輸生肽的遺失。透過大腸桿菌代謝工程生產系統，Tc-Zin/βOci能夠大量產生出zingiberene，Tc-βFar/Ger能夠產生出大量的β-farnesene，顯示未來可利用微生物系統來大量生產有效成分。

Taiwania cryptomerioides Hayata is an endemic species in Taiwan. It is an important coniferous species in Taiwan, because of its timber properties and its terpenoids in the essential oil. Most previous researches about the products and applications of T. cryptomerioides Hayata have been discussed, however, the biosynthesis pathway of T. cryptomerioides Hayata has rarely been discussed in the past. This study focuses on cloning the genes and their characteristic. Through using gas chromatography mass spectrometry (GC/MS) analysis, we identified the product of the five terpene synthases. According to the main product that synthase synthesize, they are called Tc-βFar/Lin, Tc-Lin, Tc-Zin/βOci, Tc-βFar/Ger, and Tc-αFar/Ger. Tc-Lin is a monoterpene synthase, the others are sesquiterpene synthases. Except Tc-Zin/βOci synthesizes the single ring zingiberene, all of Tc-βFar/Lin, Tc-βFar/Ger, and Tc-αFar/Ger synthesize the linear monoterpenes or sesquiterpenes; the results of reverse transcription polymerase chain reaction (RT-PCR) demonstrate that these five genes can express in the young leaf and female cone, and only Tc-βFar/Ger can also express in the wood. From the analysis of the phylogenetic tree, we can find that Tc-βFar/Lin and other closer genes of sesquiterpene synthases which are known in Taiwania are all lost the trainsit peptides. This result represents that these genes may have the process which has lost γ-domain at first and lost trainsit peptides finally. Using heterologous expression of diverse synthases in the E. coli, Tc-Zin/βOci can produce large amounts of zingiberene, and Tc-βFar/Ger can produce large amounts of β-farnesene. Thus, large amounts of these sesquiterpenes production system by using microorganism were established in this study.

誌謝 I
摘要 II
Abstract III
目錄 IV
圖目錄 VII
表目錄 XII
第一章、前言 1
第二章、文獻回顧 3
2-1 萜類化合物 3
2-2揮發性萜類化合物之生合成途徑（volatile terpenoid biosynthesis pathway） 4
2-3 揮發性萜類合成酶之分類群（volatile terpene synthase subfamily） 8
2-4 揮發性萜類合成酶之多受質（substrate）特性 10
2-5 揮發性萜類合成酶之保守性功能區域與演化過程 10
2-6 利用大腸桿菌系統提高揮發性萜類化合物之產量 13
2-7 萜類合成酶之基因組分布狀況及演化（terpene synthase genome and evolution） 15
第三章、材料與方法 17
3-1 實驗材料 17
3-2 臺灣杉RNA之萃取 17
3-3 臺灣杉萜類合成酶之基因選殖 17
3-4 各萜類合成酶基因全長之比對及親緣關係樹狀圖之分析 19
3-5 蛋白質分子量（MW）、等電點（pI）與ChloroP 1.1 Server運輸胜肽（transit peptide）之預測 20
3-6 蛋白質表現質體之建構（construction） 20
3-7 西方墨點法（western blotting） 21
3-8 誘導目標蛋白質大量表現（induction） 23
3-9 目標蛋白質之純化（purification） 23
3-10 目標蛋白質之活性反應 24
3-11 氣相層析質譜儀之分析（GC/MS） 25
3-12 臺灣杉五基因於各部位之表現量 26
3-13 大腸桿菌異源基因生產系統之建立 27
3-14 核磁共振（nuclear magnetic resonance, NMR）之分析 28
3-15 Genomic DNA之選殖 28
第四章、結果 29
4-1 臺灣杉揮發性萜類合成酶之選殖 29
4-2 臺灣杉揮發性萜類合成酶基因序列之比對及保守性功能區域之預測 30
4-3 五基因與其他萜類合成酶基因親緣樹關係之分析 32
4-4 臺灣杉萜類合成酶之質體建構 33
4-5 臺灣杉萜類合成酶重組蛋白質之表現 34
4-6 臺灣杉萜類合成酶重組蛋白質之純化 40
4-7 五萜類合成酶之產物以GC/MS分析之結果 44
4-8 Tc-Zin/βOci、Tc-βFar/Ger、Tc-βFar/Lin透過NMR之功能鑑定 58
4-9 五基因小量生產與大量生產之狀況 64
4-10 五基因於臺灣杉各部位基因表現狀況 66
4-11 五基因之genomic DNA分布狀況 67
第五章、討論 69
5-1 五基因序列與臺灣杉已知序列親緣樹關係圖分析 69
5-2 Tc-βFar/Lin、Tc-Zin/βOci、Tc-βFar/Ger功能鑑定之探討 72
5-3 線型單萜的生合成過程 74
5-4 genomic DNA分布狀況之探討 75
5-5 萜類合成酶各產物之生物活性探討與應用 76
第六章、結論 80
附錄 91
附錄表.1 各基因片段增幅引子序列 91
附錄表.2 各基因3’RACE引子序列 92
附錄表.3 各基因5’RACE引子序列 93
附錄表.4 各基因全長引子序列 94
附錄表.5 蛋白質質體建構引子序列 95
附錄表.6 各基因之RT-PCR引子序列 96
附錄圖1 pET-21a（+）載體示意圖 97
附錄圖2 pET-28a（+）載體示意圖 98
附錄圖3 pCOLADurt-1載體示意圖（Zverev and Khmel, 1985） 99

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