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論文名稱: | 大豆屬一條根抑制脂質氧化成分
| Separation and Identification of An BioactiveAnti-Lipid Oxidation Compound in I-Tiao Gung (Glycine tomentella Hayata)
研究生: | 游家芷 Chia Chih Yu
指導教授: | 孫寶年 Bonnie Sun Pan
| 廖若川 York Liao
學位類別: | 碩士
學校名稱: | 國立臺灣海洋大學
系所名稱: | 食品科學系
學號: | M93320003
畢業學年度: | 93
語文別: | 中文
關鍵字: | 一條根, Glycine tomentella Hayata I-Tiao Gung, Glycine tomentella Hayata
全文點閱次數: | 11

全文影像連結:

論文全文(pdf)

論文頁數: | 76
摘要: | 大豆屬一條根 (Glycine tomentella Hayata) 具有降低血液黏度、抑制不飽和脂肪酸氧化、清除自由基、及螯合鐵離子之抗氧化能力，已確定含有daidzein、malonyldaidzein、daidzin及glycitin，但尚有較異黃酮有效之成分未被鑑定。本研究為分離一條根95%乙醇萃取物 (GTE)，並以抑制血紅素催化亞麻油酸氧化之能力為篩選試驗，找出抗氧化力最高之成分，及其抑制LDL氧化之功效。
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| GTE經乙酸乙酯極性劃分、silica gel管柱層析可得6個區分，以第三區分 (GTE-EA-Ⅲ) 抑制血紅素催化亞麻油酸氧化之能力最高，於濃度12.5 μg/mL之抗氧化力約為同濃度daidzein之3.4倍，略高於濃度2.5 μg/mL之trolox。GTE-EA-Ⅲ經silica gel管柱層析得GTE-EA-Ⅲ-D，其抗氧化力於濃度12.5 μg/mL約為同濃度daidzein之4.5倍，RP-HPLC主要波峰之滯留時間約為41分鐘，為較daidzein (30分鐘) 非極性之化合物。GTE-EA-Ⅲ-D經silica gel管柱層析得GTE-EA-Ⅲ-D-4，再經製備式TLC得GTE-EA-Ⅲ-D-4-b，其抑制血紅素催化亞麻油酸氧化之IC50為5.71 μg/mL，與daidzein、trolox抗氧化力相同時 (20%)，濃度約為daidzein之1/9，trolox之3倍。根據FeCl3/K3Fe(CN)6及硫酸顯色反應及吸收波峰初步推測GTE-EA-Ⅲ-D-4-b為黃酮之衍生物。
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| 在in vitro實驗中，分別添加濃度為0.8 μg/mL之GTE及其各區分物抑制Cu2+ 誘導人之LDL氧化，由GTE、GTE-EA、GTE-EA-Ⅲ、GTE-EA-Ⅲ-D、及GTE-EA-Ⅲ-D-4，其LDL遲滯期分別為126、241、367、486、500分鐘，均比未添加者高 (73.4 分鐘)；氧化速率 (△A232 nm/min) 分別為4.4、3.6、3.0、3.1、2.5，均較未添加者低 (5.7)，顯示隨GTE之非極性成分純度愈高，抑制脂質氧化能力隨之增加，此成分之分子量為366，含有分子量為254之片斷，很可能為prenylated polyhydroxy (methoxy) 之flavone。
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| I-Tiao-Gung, root of Glycine tomentella Hayata, consisted of isoflavones and possessed antioxidant activity enabling the reduction of blood viscosity, inhibition of the oxidation of unsaturated fatty acids, scavenging free radical, and chelation of iron ion. Compounds more effective than isoflavones were present but were not identified. The objective of this study was to separate compounds present in the 95% ethanol extract (GTE) of I-Tiao-Gung using the inhibitiory effect on hemoglobin-induced linoleic acid oxidation as a screening test, thus to identify the unknown antioxidant in GTE and its effect on LDL oxidation.
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| The GTE was separated by ethyl acetate partition and silica gel chromatography into 6 fractions. Fraction Ⅲ (GTE-EA-Ⅲ) showed the highest inhibition of hemoglobin-induced linoleic acid oxidation, equal concentration of the antioxidant activity at 12.5 μg/mL was about 3.4 times of daidzein, slightly higher than trolox at 2.5 μg/mL. GTE-EA-Ⅲ was further purified by silica gel chromatography and obtained GTE-EA-Ⅲ-D. The antioxidant activity of which at 12.5 μg/mL was about 4.5 times of daidzein at the same concentration. The retention time (RT) of the main peak of GTE-EA-Ⅲ-D in RP-HPLC was about 41 min, the RT of daidzein was 30 min, indicated that GTE-EA-Ⅲ-D was more hydrophobic than daidzein. Furether separation by silica gel chromatography from GTE-EA-Ⅲ-D resulted in GTE-EA-Ⅲ-D-4, which was further seperated by TLC to get GTE-EA-Ⅲ-D-4-b, of which the IC50 value was 5.71 μg/mL on inhibition of hemoglobin-induced linoleic acid oxidation. To achieve equal 20％ inhibition, the concentration of GTE-EA-Ⅲ-D-4-b was about 1/9 of daidzein, 3 times of trolox. Preliminary identification of GTE-EA-Ⅲ-D-4-b using TLC followed by spraying with FeCl3/K3Fe(CN)6  or sulphuric acid showed it was possibly a flavone derivative.
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| In vitro experiment showed that GTE, GTE-EA, GTE-EA-Ⅲ, GTE-EA-Ⅲ-D and GTE-EA-Ⅲ-D-4 at 0.8 μg/mL, all prolonged the lag phase of Cu2+-induced human LDL oxidation to 126, 241, 367, 486 and 500 min, respectively, longer than that of the control (73.4 min), while the oxidative rate (△A232 nm/min) was reduced to 4.4, 3.6, 3.0, 3.1 and 2.5, respectively. The rate of the contol was 5.7, indicative of that purification of GTE increased the anti-lipid oxidation ability as the hydrophobic component(s) turned to be the main compound, of which the molecular weight was 366 consisting a 245 fragment. This compound was highly possible to be a prenylated polyhydroxy (methoxy) flavone.
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論文目次: | 目錄
| 目錄    i
| 圖目錄    iv
| 表目錄    v
| 摘要    vii
| 英文摘要    ix
| 壹、前言    1
| 貳、文獻整理    4
| 一、黃酮類與異黃酮類之基本構造及分類    4
| 二、黃酮類之生理功能    7
| 1. 預防紅血球溶血    8
| 2. 預防心血管疾病    10
| 三、異黃酮類之生理功能    11
| 1. 減緩更年期症候群    12
| 2. 預防癌症    13
| 3. 預防心血管疾病    14
| 四、黃酮類之抗氧化機制    15
| 1. 清除活性氧與自由基    15
| 2. 螯合金屬離子    15
| 五、低密度脂蛋白與動脈硬化之關係    16
| 六、造成低密度脂蛋白氧化之原因    18
| 1. 金屬離子    18
| 2. 脂氧合酶 (lipoxygenase, LOX)    18
| 3. myeloperoxidase (MPO)    19
| 七、黃酮類抑制脂氧合酶的作用    20
| 參、材料與方法    21
| 一、材料    21
| 二、方法    22
| 1. 一條根萃取物之製備    22
| 2. 一條根萃取物之分離    22
| 2.1 極性劃分 (partition)    22
| 2.2 silica gel管柱層析    23
| 2.4 呈色反應    24
| 2.5 製備型TLC分析    25
| 2.6 分離物之HPLC分析    25
| 2.7 製備型HPLC分析    26
| 3. 抗氧化性之分析測定    27
| 3.1 抑制血色素催化亞麻油酸氧化之作用    27
| 3.2 抑制LDL氧化    28
| 3.2.1 脂蛋白之分離    28
| 3.2.2 LDL透析    29
| 3.2.3 膽固醇定量    30
| 3.2.4 Cu2+誘導LDL之氧化反應    30
| 4. 核磁共振光譜    31
| 5. 統計分析    31
| 肆、結果與討論    32
| 一、一條根95%乙醇萃取物抗氧化成分之分離    32
| 1. 一條根95%乙醇萃取物 (GTE) 之產率    32
| 2. 乙酸乙酯極性分層之產率與抗氧化性    33
| 3. Silica gel管柱層析之產率與抗氧化性    35
| 3.1 GTE-EA之管柱層析    35
| 3.2 GTE-EA-Ⅲ之管柱層析    39
| 3.3 GTE-EA-Ⅲ-D之管柱層析    42
| 4. GTE-EA-Ⅲ-D-4製備式TLC之產率與抗氧化性    48
| 二、一條根有效區分物抑制LDL氧化之能力    54
| 三、有效成分之初步鑑定    63
| 伍、結論    68
| 陸、參考文獻    70
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| 圖目錄
| 附圖一、黃酮類之基本結構    4
| 附圖二、黃酮類之結構分類 (Peterson and Dwyer, 1998)    6
| 附圖三、常見的異黃酮配醣體之結構    7
| 附圖四、flavone A, diosmin, hesperidin, rutin, quercetin之化學結構    10
| 附圖五、女性荷爾蒙 (estrogen, 17β-estradiol) 與異黃酮 (isoflavones)          之化學結構    12
| 附圖六、黃酮類掃除自由基 (R˙) 之機制    15
| 附圖七、螯合金屬離子之可能位置    16
| 附圖八、闊葉大豆Glycine tomentella Hayata一條根    21
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| 圖一、一條根GTE-EA-Ⅲ及GTE-EA-Ⅲ-B、D、E區分之RP-HPLC圖譜    41
| 圖二、一條根GTE-EA-Ⅲ-D-4、5、6、10之RP-HPLC圖譜    46
| 圖三、一條根GTE-EA-Ⅲ-D-4及其a~e分層之TLC圖譜    49
| 圖四、黃酮類與酚酸標準品之TLC圖譜    50
| 圖五、一條根GTE-EA-Ⅲ-D-4-b濃度與抗氧化性之關係    53
| 圖六、一條根GTE、GTE-EA、GTE-EA-Ⅲ對人LDL氧化之影響    58
| 圖七、一條根GTE-EA-Ⅲ-D、GTE-EA-Ⅲ-D-4對人LDL氧化之影響    59
| 圖八、人LDL氧化遲滯期與一條根分離物劑量之依存性    61
| 圖九、人LDL氧化速率與一條根分離物劑量之依存性    62
| 圖十、一條根GTE-EA-Ⅲ-D-4-b之吸光圖譜    64
| 圖十一、一條根GTE-EA-Ⅲ-D-4-b之RP-HPLC圖譜 (A345 nm)    65
| 圖十二、一條根GTE-EA-Ⅲ-D-4-b-3、4之波長掃瞄圖譜    65
| 圖十三、一條根GTE-EA-Ⅲ-D-4-b之liquid chromatography-mass
| Spectrometry□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□□ 67
|
|
| 表目錄
| 表一、一條根粒度對95%乙醇萃取物 (GTE) 產率之影響    33
| 表二、一條根GTE、GTE-EA之產率及抗氧化性    34
| 表三、一條根GTE-EA經silica gel管柱層析之各區分乾重及回收率    36
| 表四、一條根GTE-EA及GTE-EA-Ⅰ~Ⅵ之組成與Rf值    37
| 表五、一條根GTE-EA經silica gel管柱層析各分層之抗氧化性    38
| 表六、一條根GTE-EA-Ⅲ經silica gel管柱層析各分層之抗氧化性    40
| 表七、一條根GTE-EA-Ⅲ-D經silica gel管柱層析各分層之產率    44
| 表八、一條根GTE-EA-Ⅲ-D經silica gel管柱層析各分層之抗氧化性    45
| 表九、一條根GTE-EA-Ⅲ-D-4、5、6、10之RP-HPLC於A262 nm及A203 nm之吸收波峰    47
| 表十、一條根GTE-EA-Ⅲ-D-4及其a~e分層之組成與Rf值    51
| 表十一、一條根GTE-EA-Ⅲ-D-4經製備式TLC各分層之抗氧化性    52
| 表十二、一條根乙醇萃取物及其各區分對人LDL氧化遲滯期、氧化速率    60
| 表十三、一條根GTE-EA-Ⅲ-D-4-b 之TLC呈色反應    64
| 表十四、黃酮類化合物的紫外光吸光範圍    66
|
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2009 年 11 月 22 日 23:32