簡易檢索 / 詳目顯示

研究生: 莊育修
Chuang, Yu-Hsiu
論文名稱: 冬瓜子之成分研究
The constituents of the seeds of Benincasa hispida
指導教授: 吳天賞
Wu, Tian-Shung
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2011
畢業學年度: 99
語文別: 中文
論文頁數: 86
中文關鍵詞: 冬瓜屬冬瓜子三酸甘油酯
外文關鍵詞: Benincasa, Benincasa hispida, triglyceride
相關次數: 點閱:38下載:11
分享至:
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報
  • 由冬瓜子(Benincasa hispida)分離得到40個化合物,其中25個經光譜分析,確認其化學結構,分別為1,3-dilinoleoyl-2-olein (18)、squalene (25)、β-sitosterol (26) & stigmasterol (27)、β-sitosteryl laurate (28)、Δ7-sitosteryl laurate (29)、α-spinasteryl laurate (30)、cussoracoside C (31)、(2E, 4E)-dihydrophaseic acid (32)、(2Z, 4E)-dihydrophaseic acid (33)、cucumegastigmane I (34)、dehydrovomifoliol (35)、cyclo(Gly- L-Leu) (36)、cyclo(Gly- L-Phe) (37)、N5-(4-methoxyphenyl) methyl-L-glutamine (38)、vanillin (39)、4-hydroxybenzyl alcohol (40)、(E)-ferulic acid (41)、trans-coniferyl aldehyde (42)、erythro-guaiacylglycerol (43)、dihydroconiferyl alcohol (44)、trans-coniferyl alcohol (45)、glabrol (46)、(2S)-liquiritigenin-4’-methyl ether (47)、hyaloserin (48)。上述化合物的結構乃是利用1維和2維核磁共振光譜,質譜,紫外光譜以及紅外線光譜決定,並與文獻所報導的物理性質和光譜數據進行比對得到確認。另有15個未知化合物結構尚待確定。

    Forty compounds were isolated from the seeds of Benincasa hispida. Among them, twenty five known compounds were identified their structures as 1,3-dilinoleoyl-2-olein (18), squalene (25), β-sitosterol (26) & stigmasterol (27), β-sitosteryl laurate (28), Δ7-sitosteryl laurate (29), α-spinasteryl laurate (30), cussoracoside C (31), dehydrovomifoliol (32), cucumegastigmane I (33), (2E, 4E)-dihydrophaseic acid (34), (2Z, 4E)-dihydrophaseic acid (35), cyclo(Gly- L-Leu) (36), cyclo(Gly- L-Phe) (37), N5-(4-methoxyphenyl) methyl- L-glutamine (38), vanillin (39), 4-hydroxybenzyl alcohol (40), (E)-ferulic acid (41), trans-coniferyl aldehyde (42), erythro-guaiacylglycerol (43), dihydroconiferyl alcohol (44), trans-coniferyl alcohol (45), glabrol (46), (2S)-liquiritigenin-4'-methyl ether (47) and hyaloserin (48) by 1H-, 13C-, 2D-NMR, MS, UV and IR spectral analyses. The structures were identified by comparison of their physical and spectral data with those reported in the literature. In addition, fifteen unknown compounds have to further identify their structures by spectral and chemical methods.

    Abstract...I 中文摘要...II 誌謝...III 第一章 緒論...1 第一節 前言...1 第二節 植物形態...2 第二章 冬瓜屬植物之藥理研究回顧...4 第三章 冬瓜屬植物之成分研究回顧...6 第四章 冬瓜子成分之萃取與分離...9 第五章 化學構造研究...17 第一節 Cussoracoside C (31)之構造解析...17 第二節 (2E, 4E)-Dihydrophaseic acid (32)之構造解析...21 第三節 (2Z, 4E)-Dihydrophaseic acid (33)之構造解析...27 第四節 Cucumegastigmane I (34)之構造解析...31 第五節 Dehydrovomifoliol (35)之構造解析...37 第六節 Cyclo(Gly-L-Leu) (36)之構造解析...39 第七節 Cyclo(Gly-L-Phe) (37)之構造解析...44 第八節 trans-Coniferyl aldehyde (42)之構造解析...49 第九節 Glabrol (46)之構造解析...51 第十節 (2S)-Liquiritigenin-4’-methyl ether (47)之構造解析...53 第十一節 Hyaloserin (48)之構造解析...55 第十二節 其他化合物之構造解析...61 第六章 結論...62 第七章 實驗部分...63 第一節 本實驗所使用之儀器...63 第二節 冬瓜子之萃取與分離...65 第三節 光譜數據...68 參考文獻...82

    1.國家中醫藥管理局中華本草編委會,中華本草精選本,上海科學技術出版社,上海,1998;pp 1189-1191。
    2.Girdhar, S.; Wanjari, M. M.; Prajapati, S. K.; Girdhar, A., Evaluation of anti-compulsive effect of methanolic extract of Benincasa hispida Cogn. fruit in mice. Acta Pol. Pharm. 2010, 67, 417-421.
    3.Qadrie, Z. L.; Hawisa, N. T.; Khan, M. W.; Samuel, M.; Anandan, R., Antinociceptive and anti-pyretic activity of Benincasa hispida (thunb.) Cogn. in Wistar albino rats. Pak. J. Pharm. Sci. 2009, 22, 287-290.
    4.Moon, M. K.; Kang, D. G.; Lee, Y. J.; Kim, J. S.; Lee, H. S., Effect of Benincasa hispida Cogniaux on high glucose-induced vascular inflammation of human umbilical vein endothelial cells. Vascul. Pharmacol. 2009, 50, 116-122.
    5.Shetty, B. V.; Arjuman, A.; Jorapur, A.; Samanth, R.; Yadav, S. K.; Valliammai, N.; Tharian, A. D.; Sudha, K.; Rao, G. M., Effect of extract of Benincasa hispida on oxidative stress in rats with indomethacin induced gastric ulcers. Indian J. Physiol. Pharmacol. 2008, 52, 178-182.
    6.Roy, C.; Ghosh, T. K.; Guha, D., The antioxidative role of Benincasa hispida on colchicine induced experimental rat model of alzheimer’s disease. Biog. Amines 2007, 21, 42-55.
    7.Lee, K. H.; Choi, H. R.; Kim, C. H., Anti-angiogenic effect of the seed extract of Benincasa hispida Cogniaux. J. Ethnopharmacol. 2005, 97, 509-513.
    8.Huang, H. Y.; Huang, J. J.; Tso, T. K.; Tsai, Y. C.; Chang, C. K., Antioxidant and angiotension-converting enzyme inhibition capacities of various parts of Benincasa hispida (wax gourd). Nahrung 2004, 48, 230-233.
    9.Grover, J. K.; Adiga, G.; Vats, V.; Rathi, S. S., Extracts of Benincasa hispida prevent development of experimental ulcers. J. Ethnopharmacol. 2001, 78, 159-164.
    10.Wang, W.; Wang, W. X.; Sun, B. H.; Zhao, D. Z.; Gao, P., Effect of haidonghua powder (HDHP) on hypothalamic obesity in rats. Zhongguo Zhong Yao Za Zhi 2000, 25, 490-492.
    11.Grover, J. K.; Rathi, S. S.; Vats, V., Preliminary study of fresh juice of Benincasa hispida on morphine addiction in mice. Fitoterapia 2000, 71, 707-709.
    12.Yoshizumi, S.; Murakami, T.; Kadoya, M.; Matsuda, H.; Yamahara, J.; Yoshikawa, M., Medicinal foodstuffs. XI. Histamine release inhibitors from wax gourd, the fruits of Benincasa hispida Cogn. Yakugaku Zasshi 1998, 118, 188-192.
    13.Chandrasekar, B.; Mukherjee, B.; Mukherjee, S. K., Blood sugar lowering potentiality of selected Cucurbitaceae plants of Indian origin. Indian J. Med. Res. 1989, 90, 300-305.
    14.Akihisa, T.; Kimura, Y.; Kasahara, Y.; Kumaki, K.; Thakur, S.; Tamura, T., 7-Oxodihydrokarounidol-3-benzoate and other triterpenes from the seeds of Cucurbitaceae. Phytochemistry 1997, 46, 1261-1266.
    15.Akihisa, T.; Yasukawa, K.; Kimura, Y.; Takido, M.; Kokke, W. C.; Tamura, T., Five D:C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii Maxim. and their anti-inflammatory effects. Chem. Pharm. Bull. 1994, 42, 1101-1105.
    16.Harinantenaina, L.; Kasai, R.; Yamasaki, K., Ent-kaurane diterpenoid glycosides from the leaves of Cussonia racemosa, a Malagasy endemic plant. Chem. Pharm. Bull. 2002, 50, 268-271.
    17.Limited, S. R., The absolute configuration of phaseic and dihydrophaseic acids Phytochemistry 1975, 14, 1145-1053.
    18.ÇalIs, I.; Kuruüzüm-Uz, A.; Lorenzetto, P. A.; Rüedi, P., (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits. Phytochemistry 2002, 59, 451-457.
    19.Masamune, T.; Anetai, M.; Fukuzawa, A.; Takasugi, M.; Matsue, H.; Kabayashi, K.; Ueno, S.; Katsui, N., Glycinoeclepins, natural hatching stimuli for the soybean cyst nematode, Heterodera glycines. I. Isolation. Bull. Chem. Soc. Jpn. 1987, 60, 981-999.
    20.Kai, H.; Baba, M.; Okuyama, T., Two new megastigmanes from the leaves of Cucumis sativus. Chem. Pharm. Bull. 2007, 55 , 133-136.
    21.Netting, A. G.; Milborrow, B. V.; Duffield, A. M., Determination of abscisic acid in Eucalyptus haemastoma leaves using gas chromatography/mass spectrometry and deuterated internal standards. Phytochemistry 1982, 21, 385-389.
    22.Julian, W.; Snow, M.; Thomas, M.; Hooker, Jr., Contribution of side-chain chromophores to the optical activity of proteins. Model compound studies. III. Alanyl-p-hydroxyphenylglycine diketopiperazine. J. Am. Chem. Soc. 1975, 97, 3506-3511.
    23.Kanzaki, H.; Mizuta, N.; Nitoda, T.; Kawazu, K., Novel diketopiperazine metabolism in a microorganism: two-step hydrolysis of cyclo(Gly-Leu) to amino acids and preliminary characterization of cyclo(Gly-Leu) hydrolase and dipeptidase. J. Biosci. Bioeng. 2000, 89, 602-605.
    24.Ren, H.; Gu, Q.; Cui, C.; Zhu, W., The cytotoxic constituents from marine-derived streptomyces 3320#. J. Ocean Univ. China 2006, 5, 75-81.
    25.Miyazawa, M.; Hisama, M., Antimutagenic activity of phenylpropanoids from clove (Syzygium aromaticum). J. Agric. Food Chem. 2003, 51, 6413-6422.
    26.Mabry, T. J.; Markham, K. R.; Thomas, M. B., The systematic identification of flavonoids. Springer Verlag New York, 1970.
    27.Hanawa, F.; Tahara, S.; Mizutani, J., Flavonoids produced by Iris pseudacorus leaves treated with cupric chloride. Phytochemistry 1991, 30, 2197-2198.
    28.Saitoh, T.; Kinoshita T.; Shibata S., New isoflavan and flavanone from licorice root. Chem. Pharm. Bull. 1976, 24, 752-755.
    29.Achenbach, H.; Stöcker, M.; A. Constenla, M., Flavonoid and other constituents of Bauhinia manca. Phytochemistry 1988, 27, 1835-1841.
    30.Agrawal, P. K.; Rastogi, R. P.; Osterdahl, B. G., 13C NMR spectral analysis of dihydrobenzofuran lignans. Org. Mag. Reson. 1983, 21, 119-121.
    31.Kim, T. H.; Ito, H.; Hayashi, K.; Hasegawa, T.; Machiguchi, T.; Yoshida, T., Aromatic constituents from the heartwood of Santalum album L. Chem. Pharm. Bull. 2005, 53, 641-644.
    32.de Trimarco, J. T.; de Riscala, E. C.; Catalán, C. A. N.; Griffin, C. L.; Herz, W., Sesquiterpene lactones and a neolignan from Hyaloseris andrade-limae. Biochem. Syst. Ecol. 2004, 32, 1063-1067.
    33.Ramsewak, R. S.; Nair, M. G.; Murugesan, S.; Mattson, W. J.; Zasada, J., Insecticidal fatty acids and triglycerides from Dirca palustris. J. Agric. Food Chem. 2001, 49, 5852-5856.
    34.He, H. P.; Cai, Y.; Sun, M.; Corke, H., Extraction and purification of squalene from Amaranthus grain. J. Agric. Food Chem. 2002, 50, 368-372.
    35.Wu, T. S.; Lin, D. M.; Shi, L. S.; Damu, A. G.; Kuo, P. C.; Kuo, Y. H., Cytotoxic anthraquinones from the stems of Rubia wallichiana Decne. Chem. Pharm. Bull. 2003, 51, 948-950.
    36.Hiermann, A., Uber inhaltsstoffe von sabalfruchten und deren prufung auf entzundungshemmende wirkung. Arch. Pharm. 1989, 322, 111-114.
    37.Inouye, Y.; Wakahoi, T.; Satoh, S., N5-(4-methoxyphenyl) methyl-glutamine in xylem sap from squash root. Phytochemistry 1999, 51, 425-428.
    38.Ito, J.; Chang, F. R.; Wang, H. K.; Park, Y. K.; Ikegaki, M.; Kilgore, N.; Lee, K. H., Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 2001, 64, 1278-1281.
    39.Taguchi, H.; Yosioka, I.; Yamasaki K., Studies on the constituents of Gastrodia elata blume. Chem. Pharm. Bull. 1981, 29, 55-62.
    40.Tan, J.; Bednarek, P.; Liu, J.; Schneider, B.; Svatos, A.; Hahlbrock, K., Universally occurring phenylpropanoid and species-specific indolic metabolites in infected and uninfected Arabidopsis thaliana roots and leaves. Phytochemistry 2004, 65, 691-699.
    41.Okuyama, E.; Fujimori, S.; Yamazaki, M.; Deyama, T., Pharmacologically active components of viticis fructus (Vitex rotundifolia). II. The components having analgesic effects. Chem. Pharm. Bull. 1998, 46, 655-662.
    42.Suga, T.; Ohta, S.; Munesada, K.; Ide, N.; Kurokawa, M.; Shimizu, M.; Ohta, E., Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris. Phytochemistry 1993, 33, 1395-1401.
    43.Yao, C. S.; Lin, M.; Wang, L., Isolation and biomimetic synthesis of anti-inflammatory stilbenolignans from Gnetum cleistostachyum. Chem. Pharm. Bull. 2006, 54, 1053-1057.

    下載圖示 校內:2021-12-31公開
    校外:2021-12-31公開
    QR CODE