臺灣博碩士論文加值系統

毛柿 (Diospyros discolor Willd.) 屬於柿樹科 (Ebenaceae)，為常綠喬木，原產於菲律賓、臺灣。柿科植物富含萘醌類 (naphthoquinones) 和三萜類 (triterpenoids) 化合物，這些成分被發現具抗菌及抗癌活性，毛柿小枝甲醇萃取物在初期藥理試驗中，顯示抗癌與抗氧化活性，引起我們分析其活性成分之興趣。毛柿小枝經由切片乾燥後，以甲醇浸泡萃取，萃取液經濃縮後進行分配萃取，分成乙酸乙酯層、正丁醇層及水層。依生物活性試驗引導活性化合物純化，共得 23 個化合物，概分為十六個三萜類、一個環烷類、兩個萘醌類、三個固醇類及一個黃烷類。其中3β-methoxy-24-methylenelanost-9(11)-en-25-ol (T1)、3β-methoxy-24-methyllanosta-9(11),25-dien-24-ol (T2)、3β-methoxy-25-methyl-24-methylenelanost-9(11)-en-21-ol (T3)、24-ethyl-3β-methoxylanost-9(11)-en-25-ol (T4) 為新化合物。此外，betulinic acid 與 ursolic acid 對於人類肝癌細胞 (SK-Hep 1) 具毒殺效果，其 IC50 分別為 9.2、14.5 μM。


蘭嶼肉豆蔻 (Myristica ceylanica A. DC. var. cagayanensis) 為肉荳蔻科 (Myristicaceae) 植物，屬常綠喬木，原產於蘭嶼、臺灣。肉荳蔻植物富含木酚素類 (lignans) 化合物，此成分具抗菌活性。蘭嶼肉豆蔻甲醇萃取物在初期藥理試驗中，顯示抗癌與抗氧化活性，引起我們分析其活性成分之興趣。蘭嶼肉豆蔻小枝經由切片乾燥後，以甲醇浸泡萃取，萃取液經濃縮後進行分配萃取，分成乙酸乙酯層、正丁醇層及水層。依生物活性試驗引導活性化合物純化，共得 22 個化合物，概分為兩個黃烷類、兩個查酮類、四個黃酮類、四個芳香族化合物、四個木酚素類、一個異香豆素類、三個固醇類、一個多烯酮類及一個 diarylnonanoid 類。其中 (2S)-3’-hydroxy-4’,7-dimethoxyflavan (Fl2) 為新化合物，(+)-oxo-
parabenzlactone (L3) 為天然物首次發現之化合物。此外， biochanin A (F3) 與 1-(2,6-dihydroxyphenyl)-9-(3,4-methylenedioxyphenyl)nonan-1-
one (D1) 對於人類肝癌細胞 (SK-Hep 1) 具毒殺效果，其 IC50 分別為 60.6、20.3 μM。

Diospyros discolor Willd. (Ebenaceae), a medium-sized to large evergreen tree, is indigenous to Philippines and Taiwan. Plants of the Diospyros genus (Ebenacea) are well documented as a rich sources of naphthoquinones and triterpenes, which have been found to exhibit antimicrobial and antitumor activities. The MeOH extract of the twigs of D. discolor exhibited cytotoxic and antioxidant activities, which led us to investigate the bioactive principles from this plant. The dried twigs of D. discolor were cut into sections and extracted with MeOH. The extract was evaporated in vacuo to yield a black residue, which was suspended in H2O, and then partitioned with EtOAc. The aqueous layer was partitioned again with n-BuOH. Bioassay-guided fractionation of those extracts led to the isolation of twenty-three compounds including sixteen triterpenoids, one napthene, two naphthoquinones, three steroids and one flavans. Among those, 3β-methoxy-24-methylenelanost-9(11)-en-25-ol (T1), 3β-methoxy-24-methyllanosta-9(11),25-dien-24-ol (T2), 3β-methoxy-25-methyl-24-methylenelanost-9(11)-en-21-ol (T3), 24-ethyl-3β-methoxylanost-9(11)-en-25-ol (T4) are new compounds. In addition, betulinic acid and ursolic acid showed strong cytotoxic activity against SK-Hep 1 cell lines with IC50 values of 9.2, 14.5 μM, respectively.

Myristica ceylanica A. DC. var. cagayanensis (Myristicaceae), a medium-sized to large evergreen tree, is indigenous to Lanyu and Taiwan. Plants of the Myristica genus (Myristicaceae) are well documented as a rich sources of lignans, which have been found to exhibit antimicrobial activity. The MeOH extract of the twigs of M. cagayanensis exhibited cytotoxic and antioxidant activities, which led us to investigate the bioactive principles from this plant. The dried twigs of M. cagayanensis were cut into sections and extracted with MeOH. The extract was suspended in H2O, and then partitioned with EtOAc. The aqueous layer was partitioned again with n-BuOH. Bioassay-guided fractionation of those extracts led to the isolation of twenty-two compounds including two flavans, two chalcones, four flavonoids, four aromatics, four lignans, one isocoumarins, three steroids, one polyketides and one diarylnonanoid. Among those, (2S)-3’-hydroxy-4’,7-dimethoxyflavan (Fl2) are new compounds, (+)-oxo-parabenzlactone (L3) were found from the natural products for the first time. In addition, biochanin A (F3) and 1-(2,6-dihydroxyphenyl)-9-
(3,4-methylenedioxyphenyl)nonan-1-one (D1) showed strong cytotoxic activity against SK-Hep 1 cell lines with IC50 values of 60.6, 20.3 μM, respectively.

目錄
摘要…………………………………………………………………………Ⅰ
Abstract……………………………………………………………………Ⅲ
誌謝…………………………………………………………………………Ⅴ
目錄……………………………………………………………………….... Ⅵ
圖表目錄 …………………………………………………………………...Ⅷ
1、緒論.……………………………………………………………………1
1.1植物簡介……………………………………………………………2
1.2臺灣柿樹屬及肉豆蔻屬植物成分研究之回顧…..…………………4
1.3抗氧化與癌症之簡介 …………………………………………… 19
1.4研究目的.……………..…………………………………………….19
2、結果與討論…………………………………………………….………20
2.1化合物結構解析……………………………………………………32
2.1.1化合物T1之結構鑑定 ……………………………………32
2.1.2化合物T2之結構鑑定 ……………………………………39
2.1.3化合物T3之結構鑑定 ……………………………………46
2.1.4化合物T4之結構鑑定 ……………………………………53
2.1.5化合物Fl2之結構鑑定…………………………..…………60
2.1.6化合物Fl3之結構鑑定…………………………………… 67
2.1.7化合物C1之結構鑑定………………………………………74
2.1.8化合物C2之結構鑑定………………………………………81
2.2藥理活性試驗結果……………………………………………… 88
2.2.1清除DPPH自由基試驗……………………………………88
2.2.2細胞毒殺試驗 ………………………………………………91
3、實驗部份…………………………………………………….…………97
3.1試劑與儀器設備………………………………………………… 97
3.2萃取與分離……………………………………………………… 99
3.3藥理活性試驗 ………………………………………………… 104
3.3.1 DPPH自由基清除效應測定……………………………… 104
3.3.2 抗癌試驗 ………………………………………………… 104
4、結論………………………………………………………………… 105
參考文獻……………………………………………………..…………….106
附錄……………………………………………………..………………….115
作者簡介………………………………………………………………….126

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