肉桂酸類衍生物抑制真菌之活性

Antifungal Activity of Cinnamic Acid Derivatives

周珊沂(Shan-Yi Chou)

指導教授 ： 張惠婷

國立臺灣大學/生物資源暨農學院/森林環境暨資源學研究所/碩士(2015年)

https://doi.org/10.6342/NTU.2015.10916

摘要

肉桂屬 (Cinnamomum) 植物中含有許多芳香族化合物，其中，肉桂醛已被證實具有許多生物活性。肉桂醛在生合成路徑屬於肉桂酸類衍生物，本研究在探討化學結構與肉桂醛及肉桂酸相似的肉桂酸衍生物，抑制黴菌、木材腐朽菌及植物病原菌生長的能力，期望找出更多具抗真菌效果的化合物，可用於減少真菌造成的危害。
將肉桂酸衍生物分為肉桂酸類化合物、肉桂醛類化合物、烷基肉桂醛化合物三大類，評估對真菌的抗菌能力。trans-cinnamaldehyde對於植物病原菌Fusarium oxysporum、木材腐朽菌Trametes versicolor及黴菌Aspergillus terreus均有良好的抗菌活性。肉桂醛類化合物中的p-methoxycinnamaldehyde、2-methoxy cinnamaldehyde及烷基肉桂醛化合物α-methylcinnamaldehyde、α-amyl cinnamaldehyde、α-hexylcinnamaldehyde均具有顯著抑制植物病原菌中Rhizoctonia solani、Colletotrichum gloeosporioides及黴菌Chaetomium globosm的能力，五種化合物的抗菌活性較trans-cinnamaldehyde更優異。又對於植物病原菌Ganoderma australe及黴菌A. niger而言，抗真菌活性最佳皆為2-methoxycinnamaldehyde，其次為trans-cinnamaldehyde與p-methoxycinnamaldehyde。除此之外，烷基肉桂醛化合物α-methylcinnamaldehyde最能有效抑制植物病原菌F. solani的生長。
化合物2-methoxycinnamaldehyde與trans-cinnamic acid均能有效抑制木材腐朽菌Lenzites betulina的生長；另外，肉桂醛類化合物中2-methoxycinnamaldehyde、p-methoxycinnamaldehyde和4-hydroxy-3-methoxycinnamaldehyde也對木材腐朽菌Laetiporus sulphureus具有比肉桂醛更佳的抗真菌能力。對於木材腐朽菌Gloeophyllum trabeum來說，肉桂醛類化合物α-amylcinnamaldehyde、烷基肉桂醛化合物2-methylcinnamaldehyde均較肉桂醛具有更好的抗真菌效果。

關鍵字

抗真菌活性 ； 黴菌 ； 植物病原菌 ； 肉桂酸衍生物 ； 肉桂醛 ； 木材腐朽菌

並列摘要

Cinnamon contains many aromatic compounds, among these compounds, trans-cinnamaldehyde has been proven to possess many bioactivities, and which belongs to trans-cinnamic acid derivatives in the biosynthesis pathway. The objective of this research is to find more cinnamic acid dervitaves to against plant pathogenic fungi, wood rotting fungi and mildew, expecting to reduce the damage from fungi diseases.
In order to evaluate antifungal activities of cinnamaldehyde congeners, we classified them into three groups, cinnamic acid congeners, cinnamaldehyde congeners and alkyl cinnamaldehyde congeners. Results demonstrated that trans-cinnamaldehyde had the best antifungal effects against Fusarium oxysporum, Trametes versicolor and Aspergillus terreus. Five compounds, p-methoxycinnamaldehyde, 2-methoxy cinnamaldehyde, α-methylcinnamaldehyde, α-amylcinnamaldehyde and α-hexyl cinnamaldehyde showed superior antifungal activities against Rhizoctonia solani, Colletotrichum gloeosporioides and Chaetomium globosm, which were better than that of trans-cinnamaldehyde. Besides, 2-methoxycinnamaldehyde, trans-cinnamaldehyde and p-methoxycinnamaldehyde were the top three compounds of inhibiting the mycelial growth of Ganoderma australe and Aspergillus niger. Furthermore, α-methylcinnamaldehyde showed the best antifungal ability against F. solani.
With regard to wood rotting fungi, both 2-methoxycinnamaldehyde and trans-cinnamic acid could efficiently inhibited the mycelial growth of Lenzites betulina. And, 2-methoxycinnamaldehyde, p-methoxycinnamaldehyde and 4-hydroxy-3-methoxy cinnamaldehyde presented high antifungal activities against Laetiporus sulphureus. Finally, both α-amylcinnamaldehyde and 2-methoxycinnamaldehyde had better abilities to against Gloeophyllum trabeum than that of trans-cinnamaldehyde.

並列關鍵字

antifungal activity ； mildew ； plant pathogenic fungi ； cinnamic acid derivatives ； trans-cinnamaldehyde ； wood rotting fungi

參考文獻

何振隆、蘇裕昌 (2008) 精油之抗菌活性。林業研究專訊15(3): 31-37。

李鴻麟、夏滄琪、許富蘭、林勝傑 (2005) 新型水溶性木材防腐劑對木材保存性與燃燒性之影響。臺灣林業科學 20(2): 139-156。

夏滄琪、張東柱、傅春旭 (2001) 微波處理應用於紙張滅菌之初探。臺灣林業科學 16(4): 327-332。

Aoki, T., K. O’Donnell, and D. M. Geiser (2014) Systematics of key phytopathogenic Fusarium species: currentstatus and future challenges. Journal of General Plant Pathology 80: 189-201.

Bang, K. H., D. W. Lee, H. M. Park, and Y. H. Rhee (2000) Inhibition of fungal cell wall synthesizing enzymes by trans-cinnamaldehyde. Bioscience, Biotechnology, and Biochemistry 64: 1061-1063.