臺灣博碩士論文加值系統

臺灣杉 (Taiwania cryptomerioides Hay.) 為柏科 (Cupressaceae) 臺灣杉屬 (Taiwania) 下的單種屬植物 (monotypic species)，木材抗腐朽性質良好，同時也是臺灣重要造林樹種之一。臺灣杉的萜類化合物是木材高耐久性 (durability) 的原因，特別是具有良好抗真菌與抗白蟻活性的倍半萜類化合物 cadinol，以及與雙萜類化合物ferruginol，被視為臺灣杉重要的防禦物質。萜類合成酶 (terpene synthases, TPSs) 是萜類生合成當中決定化學主要架構的關鍵酵素，且隨著演化推進，植物漸漸形成物種特有的萜類合成酶群，以應付環境中不同的逆境，然而許多柏科特有的萜類生合成途徑仍然未知。要探討柏科特有的萜類化合物的生合成途徑，以及萜類合成酶在裸子植物的功能演化歷程，必須結合轉錄體、蛋白質體與代謝體的研究，而臺灣杉具有特殊演化地位及豐富萜類化合物，能為柏科植物萜類生合成相關研究建立一個指標性的參考模板。本研究從臺灣杉的轉錄體中分離出萜類，從序列親緣性與生化功能都顯示了臺灣杉在演化上的獨特性。其中十二個酵素功能是尚未在裸子植物 (gymnosperms) 發現過的，包括兩個單功能的class II 雙萜合成酶 (labda-13-en-8-ol diphosphate 合成酶 (TcCPS2) 與(+)-copalyl diphosphate 合成酶 (TcCPS4))、六個class I雙萜合成酶 (manoyl oxide合成酶 (TcKSL1、TcKSL3～TcKSL7)，biformene 合成酶 (TcKSL1)，levopimaradiene合成酶 (TcKSL3) 與phyllocladanol 合成酶 (TcKSL5)) 以及四個倍半萜合成酶 (zingiberene合成酶 (TcTPS1)、germacrene-4-ol 合成酶 (TcTPS4與TcTPS12)與cedrol合成酶 (TcTPS6)。當中TcCPS4與TcKSL3藉由levopimaradiene這個中間產物參與abietatriene的生合成，並且相當可能參與臺灣杉防禦用雙萜化合物ferruginol生合成途徑。特別的是，裸子植物特有雙萜類化合物生合成，倚賴雙功能性的class I/II 雙萜類合成酶上兩個催化位置來完成兩步驟的催化作用，而臺灣杉則是由單功能的class II 與 class I 雙萜類合成酶，以接力的方式分開完成反應。加上臺灣杉特有的倍半萜合成酶基因分群的內隱子遺失現象 (intron loss)，顯示基因與蛋白質結構改變使得這些酵素擁有尚未在裸子植物發現的特質，並且造就臺灣杉獨特的萜類化合物組成。本研究為裸子植物萜類化合物代謝的分子演化與蛋白質功能性構象帶來更深刻的見解，更有助於了解萜類化合物在針葉樹化學防禦上所扮演的角色。 

Taiwania cryptomerioides is a monotypic gymnosperm species, valued for the high decay resistance of its wood. This durability has been attributed to the abundance of terpenoids, especially the sesquiterpenoid cadinene and diterpenoid ferruginol with antifungal and antitermite activity. The important committed step in terpenoid biosynthesis is the backbone formation catalyzed by terpene synthases (TPSs), and to adapt to the environment, plants have evolved their own group of TPSs along with the species evolution. However, the biosynthesis pathways of many Cupressaceae-specific terpenoids remained unknown. To expand our knowleage of terpene biosyntehesis and evolution of TPSs in Cupressaceae, a research included transcriptome, proteome and metabolome is recquired, and T. cryptomerioides can provide a good model for terpenoid research in Cupressaceae species because of its unique evolutionary opposition and high numbers of terepnoids. In this study, we identified unrecognized groups of TPSs in T. cryptomerioides, including monofunctional diTPSs, which suggests a distinct evolutionary divergence of the TPS family in this species. Specifically, twelve TPS functions not previously observed in gymnosperms were characterized, including two monofunctional class II diTPSs ((labda-13-en-8-ol diphosphate synthase (TcCPS2) and (+)-copalyl diphosphate synthase (TcCPS4)), six class I diTPSs (manoyl oxide synthase (TcKSL1, TcKSL3~TcKSL7)，biformene synthase (TcKSL1)，levopimaradiene synthase (TcKSL3) and phyllocladanol synthase (TcKSL5)), and four sesquiterpene synthases (zingiberene synthase (TcTPS1)、germacrene-4-ol synthase (TcTPS4 and TcTPS12) and cedrol synthase (TcTPS6)). Furthermore, TcCPS4 and TcKSL3 likely contribute to abietatriene biosynthesis via levopimaradiene as an intermediate in ferruginol biosynthesis in Taiwania. Notably, diterpene biosynthesis in Pinaceae speciese denpends on bifunctional diterpene synthases to catalylyze two-step reaction on two catalytic sites of an enzyme, but Taiwania employs dominantly pairs of monofunctional diterpene synthases to complete the two-step reaction successively. In addition, the uncharacterized genome structures with intron loss were also observed in a phylogenetically distant group of Taiwania sesquiterpene synthases, suggesting the terpenoid biosynthesis of Taiwania is unique and diverse due to the genome and protein strucuture modification. This study provides deeper insight into the functional landscape and molecular evolution of specialized terpenoid metabolism in gymnosperms as a basis to better understand the role of these metabolites in tree chemical defenses.

口試委員會審訂書 I
致謝 II
目錄 III
圖目錄 VI
表目錄 VIII
附錄表目錄 IX
摘要 X
Abstract XI
第一章 緒論 1
第二章 文獻探討 4
2.1 植物萜類化合物的功能 4
2.2 植物累積萜類的誘發機制 6
2.3 萜類化合物的類型 8
2.4 臺灣杉的萜類化合物 14
2.5 萜類化合物的生合成 15
2.6 萜類合成酶的演化 19
2.7 兼具物種普遍性與特有性的萜類化合物 21
2.8 臺灣杉的萜類合成酶 23
第三章 研究方法 25
3.1 植物材料 25
3.2 RNA萃取與轉錄體分析 25
3.3 萜類基因選殖 26
3.4 親源關係分析 26
3.5 以大腸桿菌共表現酵素 26
3.6 小圓葉菸草的暫時性酵素共表現 27
3.7 純化重組蛋白與酵素反應 29
3.8 代謝物分析 30
3.8.1 雙萜類化合物萃取與氣相層析 30
3.8.2 倍半萜化合物萃取與氣相分析 30
3.8.3 核磁共振波譜分析 30
3.9 倍半萜合成酶蛋白質結構模擬 31
3.10 萜類合成酶於臺灣杉不同部位基因與產物累積量分析 31
3.11 甲基茉莉酸誘導基因實驗 32
3.12.1 甲基茉莉酸誘導試驗 32
3.12.2 微陣列及基因表現分析 32
3.12 基因庫與基因登錄編號 33
第四章 結果 34
4.1. 臺灣杉雙萜類化合物生合成途徑的建立 35
4.1.1. 臺灣杉雙萜合成酶的選殖與功能預測 35
4.1.2. 臺灣杉雙萜類合成酶的親源分析 39
4.1.3. 臺灣杉雙萜類合成酶功能鑑定為單功能class II 與class I酵素 43
4.1.4. 植物內雙萜類化合物與相關基因的表現分析 57
4.1.5. 甲基茉莉酸誘導雙萜類合成酶基因表現 59
4.2. 臺灣杉倍半萜化合物生合成途徑的建立 63
4.2.1. 臺灣杉倍半萜合成酶的選殖與親源分析 63
4.2.2. 臺灣杉倍半萜合成酶群可合成多元化學結構 67
4.2.3. TcTPS仍存留關鍵催化殘基的保守性 74
4.2.4. TcTPS與臺灣杉主要倍半萜化合物-cadinene型化合物的累積有關 77
第五章 研究討論 80
5.1. 柏科與松科萜類合成酶在親緣關係有明顯的分歧 83
5.2. 臺灣杉有個功能多樣的單功能雙萜類合成酶家族 86
5.3. 臺灣杉單功能雙萜類合成酶演化自雙功能的先祖基因 88
5.4. TcTPS的內含子遺失事件造就臺灣杉與眾不同的倍半萜化合物組成 90
5.5. 臺灣杉萜類合成酶在植物防禦機制中扮演重要角色 92
第六章 結論 93
參考文獻 94
附錄 120

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