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研究生:楊雅婷
研究生(外文):Ya-Ting Yang
論文名稱:水溶性N-亞甲基亞磷酸幾丁聚醣衍生物之製備及其結合檸檬精油對髮癬菌與鬚毛癬菌之抗菌活性
論文名稱(外文):Preparation of water soluble N-methylene phosphonic chitosan derivative and effects of its combination with lemon essential oil on antifungal activity for Trichophyton rubrum and Trichophyton mentagrophytes
指導教授:洪良邦洪良邦引用關係
指導教授(外文):Lang-Bang Hung
學位類別:碩士
校院名稱:國立臺灣海洋大學
系所名稱:食品科學系
學門:農業科學學門
學類:食品科學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:69
中文關鍵詞:水溶性幾丁聚醣衍生物髮癬菌鬚毛癬菌檸檬精油
外文關鍵詞:water-solublechitosanderivativeTrichophyton rubrumTrichophyton mentagrophyteslemon essential oil
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以N-乙醯化程度為16%之幾丁聚醣為原料,添加亞磷酸及甲醛後,分別以不同反應條件:溫度70℃迴流6小時、90℃迴流3小時及6小時,凍結乾燥得到N-亞甲基亞磷酸幾丁聚醣衍生物。以高效能液相層析法測定其N-乙醯化程度,約11%到12%,以質子核磁共振光譜法求得之取代程度約為9到12%,以膠體滴定法測定其取代程度,約為13%到17%,兩種方法取代程度相關性為r2=0.9929。
N-亞甲基亞磷酸幾丁聚醣衍生物溶解範圍可達pH 11,採用濾紙過濾法進行濾過度測試,並推算溶解度,取代程度越高者具有較高溶解度,反應條件90℃迴流6小時反應之N-亞甲基亞磷酸幾丁聚醣衍生物,在濃度20%時仍有高達92%的濾過度,溶解度為18.5 g/dL。
以氣相層析儀分析檸檬精油中組成成分,主要成分為檸檬烯,含量為790.18 mg/g,其次為月桂烯21.24 mg/g。
單獨使用N-亞甲基亞磷酸幾丁聚醣衍生物樣品及檸檬精油乳化物對髮癬菌之最小抑制濃度分別為0.500%及2%,結合檸檬精油乳化物0.125%對髮癬菌之最小抑制濃度分別為樣品A 0.125%,樣品B 0.0625%及樣品C 0.125%,微量抑制濃度指數小於0.5,顯示兩者間對於髮癬菌之抑菌效果具有協同作用;單獨使用N-亞甲基亞磷酸幾丁聚醣衍生物及檸檬精油乳化物對鬚毛癬菌之最小抑制濃度分別為0.0625%及0.5%,合併使用最小抑制濃度為N-亞甲基亞磷酸幾丁聚醣衍生物0.03125%及檸檬精油0.0625%,微量抑制濃度指數介於0.5和1之間,表示兩者間對於鬚毛癬菌之抑菌效果是為相加作用。
N-methylene phosphonic chitosan derivatives was synthesized by adding phosphonic acid and formaldehyde with original material chitosan, which had degree of N-acetylation of 16%. There were three different reaction conditions, bathed at 70℃ for 6 hours, 90℃ for 3 hours, and 90℃for 6 hours. Degrees of N-acetylation of N-methylene phosphonic chitosan derivatives was determined by HPLC method were about 11% to 12%. Degrees of substitution obtained by 1H NMR spectroscopy were 9% to 12%. Degrees of substitution obtained by colloidal titration method were 13% to 17%. The coefficient of correlation value (r2) was 0.9929.
N-methylene phosphonic chitosan derivatives dissolved in wide pH range. The water solubility was improved by introducing methylene phosphonic group to chitosan. With higher degree of substitution gained higher solubility. N-methylene phosphonic chitosan derivative prepared with 90℃and 6 hour had good solubility, and it could reach up to 18.5 g/dL.
The constituents of lemon essential oil were analyzed by GC. The major component was limonene 790.18 mg/g, and the second most is myrcene 21.24 mg/g.
N-methylene phosphonic chitosan derivatives and emulsified lemon essential oil were used to do the antifungal test for Trichophyton rubrum and T. mentagrophytes. In the antifungal test against T. rubrum, the minimum inhibitory concentration (MIC) of N-methylene phosphonic chitosan derivatives or emulsified lemon essential oil alone was 0.500% and 2%. Combination with emulsified lemon essential oil 0.125% reduced the MIC of N-methylene phosphonic chitosan derivatives to 0.0625%-0.125%. The fractional inhibitory concentration index (FICI) was lower than 0.5, which indicated the synergism between N-methylene phosphonic chitosan derivatives and lemon essential oil. In an experiment with T. mentagrophytes, the MIC of N-methylene phosphonic chitosan derivatives or emulsified lemon essential oil alone was 0.0625% and 0.5%. Adding 0.0625% of emulsified lemon essential oil to N-methylene phosphonic chitosan derivatives decreased the MIC to 0.03125%. The FICI was between 0.5 and 1, which represent additive effect between N-methylene phosphonic chitosan derivatives and lemon essential oil.
摘要
目錄
表目錄
圖目錄
壹、前言
貳、文獻整理
一、幾丁質╱幾丁聚醣來源與結構
(一)幾丁質╱幾丁聚醣來源
(二)幾丁質╱幾丁聚醣結構
(三)幾丁質之種類
二、幾丁聚醣及其衍生物之應用
(一)廢水處理方面
(二)食品方面
(三)生物醫藥方面
三、幾丁質╱幾丁聚醣溶解性
(一)幾丁質之溶解性
(二)幾丁聚醣之溶解性
四、影響幾丁質╱幾丁聚醣溶解度之因子
(一)微細結晶區
(二)N-乙醯化程度及乙醯基分布
(三)分子量
五、水溶性幾丁聚醣之製備
(一)降低分子質量
(二)改變乙醯基分布
(三)化學修飾法
(四)N-亞甲基亞磷酸幾丁聚醣衍生物之簡介
六、幾丁聚醣抗菌機制及效果
(一)幾丁聚醣之抗菌機制
(二)幾丁聚醣對黴菌之抗菌效果
七、精油
(一)精油之簡介
(二)精油之應用
(三)檸檬精油組成成分
(四)柑橘類精油之抗菌效果
(五)精油之抗菌機制
(六)幾丁聚醣結合精油之抗菌效果
八、足癬及皮癬菌
(一)足癬之簡介
(二)髮癬菌及鬚毛癬菌之簡介
(三)幾丁聚醣對皮癬菌群之抗菌效果
(四)精油對皮癬菌群之抗菌效果
?、材料與方法
一、材料
(一)樣品
(二)標準品
(三)藥品
(四)菌株
(五)培養基
(六)層析管柱
(七)透析膜
(八)儀器
二、實驗方法
(一)製備N-亞甲基亞磷酸幾丁聚醣衍生物
(二)溶解度測定
(三)N-乙醯化程度測定
(四)取代程度測定
(五)檸檬精油成分分析
(六)抗菌活性試驗
肆、結果與討論
一、N-亞甲基亞磷酸幾丁聚醣衍生物
二、溶解性測定
三、N-亞甲基亞磷酸幾丁聚醣衍生物之抗菌活性
四、檸檬精油之組成
五、N-亞甲基亞磷酸幾丁聚醣衍生物合併檸檬精油之抗菌活性
伍、結論
陸、參考文獻
表目錄
表一、N-亞甲基亞磷酸幾丁聚醣衍生物之合成反應條件
表二、幾丁聚醣及N-亞甲基亞磷酸幾丁聚醣衍生物之N-乙醯化程度
表三、N-亞甲基亞磷酸幾丁聚醣衍生物之取代程度
表四、N-亞甲基亞磷酸幾丁聚醣衍生物在pH 7至13之溶解度
表五、1% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表六、2% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表七、5% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表八、10% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表九、15% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表十、20% N-亞甲基亞磷酸幾丁聚醣衍生物之濾過度及溶解度
表十一、N-亞甲基亞磷酸幾丁聚醣衍生物對髮癬菌及鬚毛癬菌之最小抑制濃度表十二、檸檬精油主要成分含量
表十三、N-亞甲基亞磷酸幾丁聚醣衍生物與檸檬精油乳化物對髮癬菌及鬚毛癬菌之最小抑菌濃度、微量抑制濃度及微量抑制濃度指數
圖目錄
圖一、原料幾丁聚醣之高效能液相層析圖譜
圖二、樣品A之高效能液相層析圖譜
圖三、樣品B之高效能液相層析圖譜
圖四、樣品C之高效能液相層析圖譜
圖五、樣品A之1H核磁共振光譜圖
圖六、樣品B之1H核磁共振光譜圖
圖七、樣品C之1H核磁共振光譜圖
圖八、質子核磁共振光譜法與膠體滴定法所得取代程度之比較
附圖一、N-亞甲基亞磷酸幾丁聚醣衍生物製備圖
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