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研究生: 林鈺庭
Lin, Yu-Ting
論文名稱: 大葉桃花心木果殼化學成分及生物活性之研究
Studies on the chemical constituents and biological activities of the pericarps of Swietenia macrophylla King
指導教授: 張誌益
Chang, Chi-I
學位類別: 碩士
Master
系所名稱: 農學院 - 生物科技系
Department of Biological Science and Technology
論文出版年: 2022
畢業學年度: 110
語文別: 中文
論文頁數: 101
中文關鍵詞: 大葉桃花心木血管收縮素轉化酶脂肪酶
外文關鍵詞: Swietenia macrophylla King, Angiotensin-converting enzyme, Lipase
DOI URL: http://doi.org/10.6346/NPUST202200205
相關次數: 點閱:22下載:4
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  • 大葉桃花心木 (Swietenia macrophylla King) 的果實,俗稱向天果,具有治療糖尿病、高血壓、高固醇、內分泌失調等民俗療效,相關藥理研究表明大葉桃花心木具抗氧化、降血糖、降血脂等功效。將乾燥之大葉桃花心木果殼以甲醇浸泡萃取得到粗萃物,再利用分配萃取得到乙酸乙酯層、正丁醇層及水層萃取物。將乙酸乙酯層萃取物進行分離純化,利用管柱層析分為五十八個分液,續以重複管柱層析、高效液相層析以及再結晶法得到純化合物,經由核磁共振光譜和質譜分析並利用文獻詳細比對確定化合物結構。目前共鑑定出九個已知化合物,四個固醇類:β-sitosterol (S1)、(3β, 7α)-7-methoxystigmast-5-en-3-ol (S2)、β-sitostenone (S3)、ergosterol peroxide (S4);一個芳香類:ethyl 4-hydroxybenzoate (A1);四個檸檬苦素類:swietenine (L1)、3-O-tigloylswietenolide (L2)、swietenine acetate (L3)、7-deacetoxy-7-oxogedunin (L4)。乙酸乙酯層萃取物在濃度為250 μg/mL對脂肪酶具有抑制作用,抑制率為44.44%,而標準品熊果酸的抑制率為16.40% (25 μg/mL)。乙酸乙酯層萃取物顯示出對血管收縮素轉化酶(ACE)具有抑制作用,其IC50為95.0 μg/mL,而標準品captopril的IC50值為0.02 pg/mL。總酚含量最高為正丁醇層萃取物(3.28±0.55 mg GAE/g DW),而三種抗氧化活性試驗結果皆為正丁醇層萃取物有良好的效果,透過皮爾森相關分析,得多酚含量影響抗氧化能力有密切相關。

    Swietenia macrophylla King, known as sky fruit or big leaf mahogany, is used in traditional folk medicine to treat diabetes, hypertension, hypercholesterolemia, and endocrine disorders. Pharmacological studies have shown that the extracts of plant has antioxidant, hypoglycemic and hypolipidemic effects. The methanol extract of the pericarps was suspended in water and partitioned into ethyl acetate, n-butanol, and water-soluble fractions with ethyl acetate and n-butanol. The ethyl acetate layer was further purified by column chromatography and high performance liquid chromatography to give nine compounds. Their structures were identified by detailed comparison of their NMR and MS spectral data with literature values. The inhibitory activities of the plant on angiotensin-converting enzyme (ACE), α-glucosidase and lipase were investigated by in vitro methods. Nine known compounds were identified from the plant, including four sterols: β-sitosterol (S1), (3β, 7α)-7-methoxystigmast-5-en-3-ol (S2), β-sitostenone (S3), ergosterol peroxide (S4); one aromatic: ethyl 4-hydroxybenzoate (A1); four limonoids: swietenine (L1), 3-O-tigloylswietenolide (L2), swietenine acetate (L3), 7-deacetoxy-7-oxogedunin (L4). The ethyl acetate fraction showed inhibitory effects against lipase inhibitory percentage of 44.44% at concentration of 250 μg/mL while the standard ursolic acid had an inhibitory effect of 16.40% (25 μg/mL). The ethyl acetate fraction also exhibited inhibitory effect against ACE with an IC50 value of 95.0 μg/mL lower than the standard captopril with an IC50 value of 0.02 pg/mL. The highest total phenolic content was observed in the n-BuOH layer (3.28±0.55 mg GAE/g DW), and the n-BuOH layer also had the best antioxidant activity. The results showed that the phenolic content and the antioxidants activity have a correlation by Pearson’s correlation.

    摘要 I
    Abstract II
    致謝 III
    目錄 IV
    圖目錄 VIII
    表目錄 X
    1. 前言 1
    1.1 研究背景 1
    1.2 研究動機與目的 2
    2. 文獻回顧 4
    2.1 藥理活性 4
    2.1.1 抗病毒 4
    2.1.2 抗發炎 4
    2.1.3 抗蟲害 4
    2.1.4 抗腫瘤 5
    2.1.5 抑制細胞內脂肪的生成 5
    2.2 植物化學成分 6
    3. 材料與方法 26
    3.1植物簡介 26
    3.2大葉桃花心木果殼化學成分之分離與純化 27
    3.2.1 實驗材料與儀器 27
    3.2.2實驗方法 28
    3.3脂肪酶抑制活性試驗 31
    3.3.1 實驗原理 31
    3.3.2 實驗材料與設備 31
    3.3.3 實驗方法 32
    3.4血管收縮素轉化酶抑制活性試驗 33
    3.4.1 實驗原理 33
    3.4.2 實驗材料與設備 33
    3.4.3 實驗方法 34
    3.5 DPPH自由基清除活性 35
    3.5.1 實驗原理 35
    3.5.2 實驗材料與設備 35
    3.5.3 實驗方法 36
    3.6還原力測定 37
    3.6.1實驗材料與設備 37
    3.6.2實驗方法 38
    3.7清除超氧陰離子之能力測定 39
    3.7.1 實驗原理 39
    3.7.2 實驗材料與設備 39
    3.7.3 實驗方法 40
    3.8 總酚含量測定 41
    3.8.1 實驗原理 41
    3.8.2 實驗材料與設備 41
    3.8.3 實驗方法 42
    3.9 總類黃酮含量測定 43
    3.9.1 實驗原理 43
    3.9.2 實驗材料與設備 43
    3.9.3 實驗方法 44
    3.10 統計方法 44
    4. 結果與討論 45
    4.1大葉桃花心木果殼之活性試驗篩選 45
    4.1.1 脂酶抑制活性試驗 45
    4.1.2 血管收縮素轉化酶抑制活性試驗 46
    4.1.3 總酚與總類黃酮之含量測定 48
    4.1.4 抗氧化活性試驗結果 49
    4.1.5 總酚與總類黃酮含量與三種抗氧化活性試驗之相關性 54
    4.2大葉桃花心木殼化學成分之分離與純化 55
    4.3化合物結構摘要 57
    4.4化合物重量 58
    4.5化合物結構解析 59
    4.5.1 固醇類化合物 (Steroids) 59
    4.5.2 芳香族類化合物 (Aromatics) 70
    4.5.3 檸檬苦素類化合物 (Limonoids) 73
    5. 結論 92
    6. 化合物數據 94
    參考文獻 97

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