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研究生:黃文程
研究生(外文):Huang, Wen-Cheng
論文名稱:生物活性導向分離鑑定山苦瓜緩解痤瘡丙酸桿菌誘導發炎反應之活性成分
論文名稱(外文):Bioassay-guided isolation and identification of anti-inflammatory compounds from wild bitter melon leaf against Propionibacterium acnes
指導教授:蔡帛蓉
指導教授(外文):Tsai, Po-Jung
學位類別:博士
校院名稱:國立臺灣師範大學
系所名稱:人類發展與家庭學系
學門:教育學門
學類:普通科目教育學類
論文種類:學術論文
論文出版年:2016
畢業學年度:104
語文別:中文
論文頁數:178
中文關鍵詞:發炎性痤瘡山苦瓜葫蘆烷型三萜類化合物酚類化合物抗發炎
外文關鍵詞:inflammatory acnewild bitter meloncucurbitane type triterpenoidsphenolicsanti-inflammatory
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尋常性痤瘡(acne vulgaris)俗稱青春痘,其致病因子複雜。痤瘡丙酸桿菌(Propionibacterium acnes)在痤瘡病灶中增殖並活化角質與皮脂腺細胞等釋出過量的促發炎介質(例如interleukin (IL)-8、tumor necrosis factor (TNF)-α或IL-1β),是發炎性痤瘡(inflammatory acne)的主要致病因子之一。山苦瓜(Momordica charantia Linn. var. abbreviata Ser.)為台灣坊間常見的一種具醫藥用途的蔬菜。
本研究以P. acnes刺激人類單核球THP-1細胞作為生物活性導向方法,探討山苦瓜中具抑制P. acnes誘導發炎之活性物質,並釐清該活性成分的作用機轉。另外也分析存在於山苦瓜葉甲醇萃取物己烷層的活性物質和存在於苦瓜種子之癸酸(capric acid)對於P. acnes誘導發炎反應的影響。
實驗結果發現山苦瓜葉乙醇/乙酸乙酯萃取物有效抑制P. acnes誘導發炎反應,此萃取物含有多酚類與三萜類化合物。利用液相層析或管柱層析等方法分離並鑑定其組成分,包括酚類化合物(gallic, chlorogenic, caffeic, ferulic, and cinnamic acids, myricetin, quercetin, luteolin, apigenin, and thymol)與葫蘆烷型三萜類化合物(5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol 和3β,7β,25-trihydroxycucurbita-5,23-dien-19-al)。利用GC/MS分析比對發現於山苦瓜葉甲醇萃取物己烷層的活性成分為β-ionone。
山苦瓜葉萃取物之酚類化合物、三萜類化合物、β-ionone與capric acid皆能有效降低促發炎細胞激素生成。這些化合物(如山苦瓜葉萃取物、三萜類化合物與capric acid)可經由抑制mitogen-activated protein kinases (MAPKs)或nuclear factor-kappa B (NF-κB)的活化作用、抑制促發炎細胞激素mRNA表現,因而抑制P. acnes誘導的發炎介質釋出。而葫蘆烷型三萜類化合物和β-ionone另可透過抑制MyD88、caspase-1等訊息傳遞途徑達到降低P. acnes引起之發炎反應。
以P. acnes注射小鼠耳朵誘發腫脹模式的結果顯示,山苦瓜葉乙醇/乙酸乙酯萃取物、葫蘆烷型三萜類化合物、β-ionone與capric acid均能有效降低免疫細胞浸潤現象、緩解耳朵發炎腫脹。除此之外,山苦瓜葉乙醇/乙酸乙酯萃取物、葫蘆烷型三萜類化合物和β-ionone可顯著減少小鼠耳朵發炎病灶IL-1β的生成,而capric acid亦可降低小鼠耳朵P. acnes活菌生長。
綜合上述結果,本研究推論山苦瓜葉萃取物和其活性組成分具有緩解發炎性痤瘡發炎之應用潛力。
Acne vulgaris, the medical term for common acne, is the most common skin disease with multiple pathogenic factors. Propionibacterium acnes is a key pathogen involved in acne inflammation by activating inflammatory cells, keratinocytes and sebocytes to secrete pro-inflammatory cytokines such as interleukin (IL)-8, IL-1β, and tumor necrosis factor (TNF)-α.
Wild bitter melon (WBM, Momordica charantia L. var. abbreviate Seringe), is consumed as both a vegetable and as folk medicine in Taiwan. Activity-directed fractionation and purification processes were employed to identify the anti-inflammatory active compounds using P. acnes-stimulated human monocytic THP-1 cells in vitro. The inhibitory activity and action mechanism of ethanol/ethyl acetate extract of WBM leaf on P. acnes-induced inflammatory responses were examined. Secondly, the effects of the bioactive components in the hexane layer of methanolic extract from WBM leaf and capric acid (present in seeds of bitter melon) on P. acnes-induced inflammatory responses were also investigated.
Our results showed that ethanol/ethyl acetate extract significantly suppressed P. acnes-induced cytokine releases. The bioactive compounds of ethanol/ethyl acetate extract were identified as phenolics (gallic, chlorogenic, caffeic, ferulic, and cinnamic acids, myricetin, quercetin, luteolin, apigenin, and thymol) and cucurbitane type triterpenoids (5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol and 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al) by using a column chromatography method. In addition, β-ionone was found in hexane layer of methanolic extract, and measured by GC/MS.

These ten phenolics, two cucurbitane type triterpenoids, β-ionone, and capric acid effectively inhibited P. acnes-induced pro-inflammatory cytokine production or mRNA level, such as IL-8, TNF-α or IL-1β. Some of the above compounds (including extract of WBM leaf, cucurbitane type triterpenoid and capric acid) inhibited the activations of mitogen-activated protein kinases (MAPKs) or nuclear factor-kappa B (NF-κB) in vitro, these actions may partially account for their inhibitory effect on cytokine production. In addition, both cucurbitane type triterpenoids and β-ionone also suppressed MyD88 and caspase-1 signaling.
Ethanol/ethyl acetate extract, two cucurbitane type triterpenoids, β-ionone, and capric acid significantly attenuated P. acnes-induced ear swelling in mice along with microabscess. Treatments of ethanol/ethyl acetate extract, two cucurbitane type triterpenoids and β-ionone significantly decreased the migration of neutrophils and IL-1β+ populations in vivo. Capric acid exhibited anti-microbial activity against P. acnes in vitro and in vivo.
Our results suggested that WBM leaf extract and its bioactive components can be potential therapeutic agents against P. acnes-induced skin inflammation.
中文摘要 I
英文摘要 III
縮寫對照表 V
總目錄 VI
圖目錄 XI
表目錄 XV
第一章 緒論 1
第一節 前言 1
第二節 文獻回顧 2
壹、痤瘡的成因 2
貳、痤瘡丙酸桿菌誘導發炎反應 6
(一) TLRs (toll-like receptors; TLRs)簡介 6
(二) TLRs的信息傳遞途徑 8
(三) 痤瘡丙酸桿菌之發炎機轉 9
叁、痤瘡的藥物治療 12
肆、實驗材料簡介 14
(一) 苦瓜 14
(二) 多酚類化合物 20
(三) 中鏈脂肪酸 25
第三節 研究目的與實驗假說 27
壹、研究目的 27
貳、實驗假說 27
叁、實驗設計 27

(一) 山苦瓜葉萃取物對痤瘡丙酸桿菌誘導發炎之影響 27
(二) 山苦瓜葉中活性成分之純化分離與結構鑑定 27
(三) 活性成分對痤瘡丙酸桿菌誘導發炎之影響 28
(四) 癸酸對痤痤瘡丙酸桿菌誘導發炎之影響 28
第二章 材料與方法 29
第一節 研究材料 29
壹、實驗樣品與實驗耗材 29
(一) 山苦瓜葉 29
(二) 萃取溶劑與耗材 29
(三) 總多酚萃取物樣品製備 30
(四) 山苦瓜葉中三萜類化合物之分離鑑定 32
貳、實驗細胞株與實驗菌株 42
叁、實驗藥品與試劑配方 43
(一) 培養基與相關耗材 43
(二) 實驗藥品 44
(三) 實驗試劑配方 45
(四) 試劑套組 50
(五) 一級抗體 50
(六) 二級抗體 51
(七) Primer 序列 51
(八) Flow cytometry 抗體 52
肆、儀器用具 52
第二節 研究方法 53
(一) 細胞培養 53
(二) 細菌培養 55
(三) 抑菌實驗 56
(四) 細胞存活率檢測 57
(五) 抗發炎指標評估 57
(六) 西方墨點法(Western blotting) 61
(七) 轉錄因子NF-κB活性分析 64
(八) 動物實驗 66
(九) 統計分析 70
第三章 山苦瓜葉萃取物之抗發炎作用 71
第一節 前言 71
壹、實驗架構 72
第二節 材料與方法 73
壹、實驗材料 73
貳、實驗方法 73
第三節 結果與討論 73
壹、總多酚萃取物成分分析 73
(一) 總多酚萃取萃取物回收率 73
(二) 酚酸化合物分析 73
(三) 總三萜類化合物含量 73
貳、總多酚萃取物之抗發炎活性評估 75
(一) In vitro模式:P. acnes-induced THP-1 cells 75
(二) In vivo模式:P. acnes-stimulated mice ear edema 91
叁、討論 96
第四章 山苦瓜葉中三萜類化合物之抗發炎功效 100
第一節 前言 100
第二節 材料與方法 101
壹、實驗材料 101
貳、實驗方法 101
叁、實驗架構 101
第三節 結果與討論 102
壹、山苦瓜葉中三萜類化合物之抗發炎活性評估 102
(一) In vitro模式:P. acnes-induced THP-1 cells 102
(二) In vivo模式:P. acnes-stimulated mice ear edema 113
貳、討論 118
第五章 探討山苦瓜葉甲醇萃取物已烷層之活性成分 121
第一節 前言 121
第二節 材料與方法 122
壹、實驗材料 122
貳、實驗方法 122
叁、實驗架構 122
第三節 結果與討論 123
壹、β-ionone和dihydroactinidiolide之活性評估 123
(一) In vitro模式:P. acnes-induced THP-1 cell 123
(二) In vivo模式:P. acnes-stimulated mice ear edema 123
貳、β-ionone對IL-1β生成之影響 126
(一) In vivo模式:P. acnes-stimulated mice ear edema 126
(二) In vitro模式:P. acnes-induced THP-1 cell 126
叁、討論 129
第六章 癸酸與月桂酸(苦瓜種子油脂組成分)之活性評估 130
第一節 前言 130
第二節 材料與方法 131
壹、實驗材料 131
貳、實驗方法 131
叁、實驗架構 131
第三節 結果與討論 132
壹、Capric acid和lauric acid對痤瘡丙酸桿菌生長之影響 132
貳、Capric acid和lauric acid之抗發炎活性評估 132
(一) In vitro模式:P. acnes-induced SZ-95/THP-1 cells 132
(二) In vivo模式:P. acnes-stimulated mice ear edema 144
叁、討論 146
第七章 綜合討論 149
第八章 參考文獻 153
附錄 171
一、山苦瓜葉中三萜類化合物之光譜圖 171
二、山苦瓜葉甲醇萃取物已烷層之成分分析 177

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