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化学进展 2016, Vol. 28 Issue (6): 814-828 DOI: 10.7536/PC150917 前一篇   后一篇

• 综述与评论 •

鹅去氧胆酸及其衍生物的制备和应用

胡祥正1,2*, 王建敏1   

  1. 1. 天津科技大学食品工程与生物技术学院 天津 300457;
    2. 天津科技大学化工与材料学院 天津 300457
  • 收稿日期:2015-09-01 修回日期:2015-12-01 出版日期:2016-06-15 发布日期:2016-03-23
  • 通讯作者: 胡祥正 E-mail:huxzh@tust.edu.cn
  • 基金资助:
    天津市科技计划项目(No.14ZXCXSY00109, 14RCHZSY00159)资助

Preparation and Application of Chenodeoxycholic Acid and Its Derivatives

Hu Xiangzheng1,2*, Wang Jianmin1   

  1. 1. College of Food Engineering and Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, China;
    2. College of Chemical Engineering and Materials Science, Tianjin University of Science and Technology, Tianjin 300457, China
  • Received:2015-09-01 Revised:2015-12-01 Online:2016-06-15 Published:2016-03-23
  • Supported by:
    The work was supported by the Tianjin Science and Technology Project Funds (No. 14ZXCXSY00109, 14RCHZSY00159)
鹅去氧胆酸是天然的初级胆汁酸,是鸡、鸭和鹅等家禽胆汁中的主要有机成分,具有杀菌、抗炎和溶解胆结石等作用,是临床上治疗胆固醇结石的药物之一,也是合成临床上治疗胆结石疾病用量最大的药物熊去氧胆酸的原料。鹅去氧胆酸在医药方面的应用价值促使其制备方法逐步完善。近年来,关于鹅去氧胆酸衍生物的研究越来越多,相关研究也延伸到生物医药、分子识别和功能材料等多个领域,尤其在生物医药领域,鹅去氧胆酸衍生物显示出广阔的应用前景。本文系统地综述了鹅去氧胆酸的提取、合成与化学修饰方法,以及鹅去氧胆酸衍生物的合成、性质及应用,并展望了其发展前景。
Chenodeoxycholic acid as a natural primary bile acid is one of the main organic compounds in the bile of chicken, duck, goose and so on. It has the function of sterilization, anti-inflammatory and dissolution of gallstones. In clinical practice, chenodeoxycholic acid is the drug for treatment of cholesterol gallstones. Ursodeoxycholic acid is the largest amount of drug for the treatment of gallstone disease, and chenodeoxycholic acid is the raw material for the synthetic of ursodeoxycholic acid. The application value in medicine promotes the preparation methods of chenodeoxycholic acid gradually improved. In recent years, great progress has been made in the research of chenodeoxycholic acid derivatives. Study on application of chenodeoxycholic acid has been extended to biological medicine, molecular recognition, functional materials and other fields. In particular, chenodeoxycholic acid derivatives show broad application prospects in the field of biological medicine. This paper provides an overview of the methods of extraction, synthesis and chemical modification of chenodeoxycholic acid according to chenodeoxycholic acid related research progress. Meanwhile, synthesis methods, properties and applications of chenodeoxycholic acid derivatives are also reviewed. The development prospects of chenodeoxycholic acid and its derivatives is also prospected.

Contents
1 Introduction
2 The preparation of chenodeoxycholic acid
2.1 The extraction of chenodeoxycholic acid from bile
2.2 Chemical synthesis of chenodeoxycholic acid
3 The synthesis of chenodeoxycholic acid derivatives
3.1 Synthesis of derivatives modified at 6-position
3.2 Synthesis of derivatives modified at 3,7-position
3.3 Synthesis of derivatives modified at 24-position carboxyl
3.4 Synthesis of derivatives modified at other positions
4 Conclusion

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[1] Hofmann A F. Hepatology, 2009, 49(5): 1403.
[2] Thistle J L, Schoenfield L J. The New England Journal of Medicine, 1971, 284(4): 177.
[3] 李培锋(Li P F), 关红(Guan H), 哈斯苏荣(Hasi S R), 曹金山(Cao J S).中兽医医药杂志(Journal of Traditional Chinese Veterinary Medicine), 2002, (1): 7.
[4] Begum S F, Panati K, Narasimha V R, Narala V R. Biochemical and Biophysical Research Communications, 2015, 463(4): 600.
[5] Yan Z, Dong J, Qin C, Zhao C, Miao L, He C. Mediators of Inflammation, 2015, 1.
[6] Yahalom G, Tsabari R, Molshatzki N, Ephraty L, Cohen H, Hassin-Baer S. Clinical Neuropharmacology, 2013, 36(3): 78.
[7] Pierre G, Setchell K, Blyth J, Preece M A, Chakrapani A, Mckiernan P. Journal of Inherited Metabolic Disease, 2009, 31 (Suppl 2): 241.
[8] Shihabudeen M S, Roy D, James J, Thirumurugan K. Molecular and Cellular Endocrinology, 2015, 414: 19.
[9] Yee S B, Yeo W J, Park B S, Kim J Y, Baek S J, Kim Y C, Seo S Y, Lee S H, Kim J H, Suh H, Kim N D, Lim Y J,Yee S B. International Journal of Oncology, 2005, 27(3): 653.
[10] Leverrier A, Bero J, Frédérich M, Quetin-Leclercq J, Palermo J. European Journal of Medicinal Chemistry, 2013, 66: 355.
[11] Chong H S, Chen Y, Kang C S, Sun X, Wu N. Bioorganic & Medicinal Chemistry Letters, 2015, 25: 1082.
[12] 刘雁红(Liu Y H), 胡祥正(Hu X Z).天津科技大学学报 (Journal of Tianjin University of Science & Technology), 2009, (3): 43.
[13] 张能荣(Zhang N R). 生化药物杂志(Chinese Journal of Biochemical Pharmaceutics), 1986, (3): 44.
[14] 李培锋(Li P F), 哈斯苏荣(Hasi S R), 关红(Guan H), 曹金山(Cao J S). 内蒙古农业大学学报(自然科学版)(Journal of Inner Mongolia Agricultural University(Natural Science Edition)), 2000, (4): 68.
[15] 高玉琼(Gao Y Q), 刘建华(Liu J H), 单友谅(Shan Y L), 徐章雄(Xu Z X). 中国生化药物杂志 (Chinese Journal of Biochemical Pharmaceutics), 1996, (1): 17.
[16] 潘现军(Pan X J), 张晓梅(Zhang X M). 河北医药 (Hebei Medical Journal), 2006, (2): 147.
[17] 陆进(Lu J), 杜守颖(Du S Y), 赵丽瑞(Zhao L R), 张薇(Zhang W). 中国中药杂志(China Journal of Chinese Materia Medica), 2004, (5): 34.
[18] Knez Z, Markocic E, Leitgeb M, Primozic M, Hrncic M K, Skerget M. Energy, 2014, 77: 235.
[19] Scalia S, Williams J R, Shim J H, Law B, Morgan E D. Chromatographia, 1998, 48(11/12): 785.
[20] Wan J, He J, Cao X. Journal of Industrial and Engineering Chemistry, 2012, 18(1): 65.
[21] Pietro A, Tiziano S, Fausto G, Andrea F. EP 1903050A2, 2008.
[22] Kandrac J, Kevresan S, Gu J K, Mikov M, Fawcett J P, Kuhajda K. European Journal of Drug Metabolism and Pharmacokinetics, 2006, 31(3): 157.
[23] Shimada K, Mitamura K, Higashi T. Journal of Chromatography A, 2001, 935(1): 141.
[24] Kawai S. Zeitschrft fuer Physiologische Chemie, 1933, 214: 71.
[25] Plattner P A, Heusser H. Helvetica Chimica Acta, 1944, 27 (1): 748.
[26] Huang M. Journal of the American Chemical Society, 1948, 70(8): 2802.
[27] FieserL F. Experientia, 1950, 6(8): 312.
[28] Anderson I G, Haslewood G A D, Wiggins H S, Wootton I D P. Nature, 1952, 169(4302): 621.
[29] Sato Y, Ikekawa N. Journal of Organic Chemistry, 1959, 24 (9): 1367.
[30] lida I, Chang F. Journal of Organic Chemistry, 1981, 46: 2786.
[31] Takahaski K. Jap 88856, 1974.
[32] Nakada F. Steriods, 1963, 2(1): 45.
[33] Chen C H. Synthesis, 1976, (2): 125.
[34] 王鍾麒(Wang Z Q), 姜立中(Jiang L Z), 周维善(Zhou W S), 龚逸民(Gong Y M), 钱涌(Qian Y). 中国科学(Science China Chemistry), 1991, (7): 680.
[35] 张飞(Zhang F), 赵静国(Zhao J G), 赵蒙浩(Zhao M H). 化学与生物工程(Chemistry & Bioengineering), 2014, (1): 47.
[36] Shaik F B, Prasad D V R, Narala V R. Inflammation Research, 2015, 64(1): 9.
[37] Gioiello A, Cerra B, Mostarda S, Guercini C, Pellicciari R, Macchiarulo A. Current Topics in Medicinal Chemistry, 2014, 14(19): 2159.
[38] Maloney P R, Parks D J, Haffner C D, Fivush A M, Chandra G, Plunket K D, Creech K L, Moore L B, Wilson J G, Lewis M C, Jones S A, Willson T M. Journal of Medicinal Chemistry, 2000, 43(16): 2971.
[39] Lindor K D. Current Opinion in Gastroenterology, 2011, 27(3): 285.
[40] Pellicciari R, Fiorucci S, Camaioni E, Clerici C, Costantino G, Maloney P R, Morelli A, Parks D J, Willson T M. Journal of Medicinal Chemistry, 2002, 45(17): 3569.
[41] Steiner A, Waenerlundpoulsen H, Jolibois E, Rewolinski M, Gross R, Sharp E, Dubas-fisher F, Eberlin A. WO 192097A1, 2013.
[42] Yu D, Mattern D L, Forman B M. Steroids, 2012, 77(13): 1335.
[43] Gioiello A, Macchiarulo A, Carotti A, Filipponi P, Costantino G, Rizzo G, Adorini L, Pellicciari R. Bioorganic & Medicinal Chemistry, 2011, 19: 2650.
[44] Sepe V, Ummarino R, D'Auria M V, Chini M G, Bifulco G, Renga B, D'Amore C, Debitus C, Fiorucci S, Zampella A. Journal of Medicinal Chemistry, 2012, 55(1): 84.
[45] Yu D D, Forman B M. US 0062526A1, 2009.
[46] Pellicciari R. US 7138390 B2, 2006.
[47] Ferrari M, Pellicciari R. WO 122977A2, 2006.
[48] Xue C H, Mu Q M, Chen S H. Chinese Chemical Letters, 2001, 12(5): 413.
[49] Li L, Mu Q M, Yang Z X, Zhao Z G, Yan Q, Chen S H. Chinese Journal of Organic Chemistry, 2003, 23(5): 452.
[50] Xue C H, Hu R, Mu Q M, Li F, Chen S H, Lu D, Gan Y. Acta Chimica Sinica, 2000, 58 (6): 717.
[51] Xue C H, Mu Q M, Chen S H. Acta Chimica Sinica, 2002, 60 (2): 355.
[52] 赵志刚(Zhao Z G), 张佩玉(Zhang P Y), 杨祖幸(Yang Z X), 陈淑华(Chen S H). 有机化学(Chinese Journal of Organic Chemistry), 2005, (6): 679.
[53] 刘兴利(Liu X L), 赵志刚(Zhao Z G), 陈淑华(Chen S H).化学研究与应用(Chemical Research and Application), 2007, (3): 330.
[54] 石治川(Shi Z C), 赵志刚(Zhao Z G), 李晖(Li H),谭炯(Tan J). 有机化学(Chinese Journal of Organic Chemistry), 2014, (3): 572.
[55] 赵志刚(Zhao Z G), 王晓红(Wang X H), 石治川(Shi Z C), 程玉宇(Chen Y Y). 有机化学(Chinese Journal of Organic Chemistry), 2014, (6): 1110.
[56] Shi Z, Zhao Z, Liu M, Wang X. Comptes Rendus Chimie, 2013, 16 (11): 977.
[57] Bai X, Barne C, Dias J R. Tetrahedron Letters, 2009, 50(5): 503.
[58] 黄燕敏(Huang Y M), 姚秋翠(Yao Q C), 刘志平(Liu Z P), 甘春芳(Gan C F), 郑嘉桦(Zheng J H), 盛海兵(Sheng H B), 石海信(Shi H X), 崔建国(Cui J G). 有机化学(Chinese Journal of Organic Chemistry), 2015, 35: 2168.
[59] 黄燕敏(Huang Y M), 崔建国(Cui J G), 姚秋翠(Yao Q C), 甘春芳(Gan C F), 林启福(Lin Q F). CN 103044518A, 2013.
[60] García L G, Antonela Z M, Simonetti L, Longhi S A, Baldessari A. Bioorganic & Medicinal Chemistry, 2015, 23 (15): 4804.
[61] 何秀玲(He X L), 关红(Guan H), 李培锋(Li P F). 畜牧与饲料科学(Animal Husbandry and Feed Science), 2008, (3): 57.
[62] 吴慧(Wu H), 高柳滨(Gao L B). 药学进展(Progress in Pharmaceutical Sciences), 2015, (3): 227.
[63] Im E O, Choi Y H, Paik K J, Suh H, Jin Y, Kim K W, Yoo Y H, Kim N D. Cancer Letters, 2001, 163(1): 83.
[64] Im E, Choi S H, Suh H, Choi Y H, Yoo Y H, Kim N D. Cancer Letters, 2005, 229(1): 49.
[65] Yee S B, Song Y S, Jeong S H, Lee H S, Seo S Y, Kim J H, Suh H, Kim N D, Yoo Y H. Oncology Reports, 2007, 17 (4): 919.
[66] Park S E, Lee S W, Hossain M A, Kim M Y, Kim M, Ahn E Y, Park Y C, Suh H, Kim G, Choi Y H, Kim N D. Cancer Letters, 2008, 270(1): 77.
[67] Liu H, Qin C K, Han G Q, Xu H W, Ren W H, Qin C Y. Cancer Letters, 2008, 270(2): 242.
[68] Pellicciari R, Gioiello A, Costantino G, Bahman M S, Rizzo G, Meyer U, Derek J P, Entrena G A, Fiorucci S. Journal of Medicinal Chemistry, 2006, 49(14): 4208.
[69] El Kihel L, Clément M, Bazin M A, Descamps G, Khalid M, Rault S. Bioorganic & Medicinal Chemistry, 2008, 16 (18): 8737.
[70] Brossard D, El Kihel L, Clément M, Sebbahi W, Khalid M, Roussakis C, Rault S. European Journal of Medicinal Chemistry, 2010, 45(7): 2912.
[71] 韦英亮(Wei Y L), 姚秋翠(Yao Q C), 杨春晖(Yang C H), 黄燕敏(Huang Y M), 甘春芳(Gan C F), 崔建国(Cui J G). 化学研究与应用(Chemical Research and Application), 2015, (2): 139.
[72] Siless G E, Knott M E, Derita M G, Zacchino S A, Puricelli L, PalermoJ A. Steroids, 2012, 77 (1/2): 45.
[73] 崔建国(Cui J G), 刘亮(Liu L), 甘春芳(Gan C F), 肖琦(Xiao Q), 黄燕敏(Huang Y M). 化学进展(Progress in Chemistry), 2014, (Z1): 320.
[74] 张盈(Zhang Y), 杨硕(Yang S), 李灵芝(Li L Z). 中国新药杂志(Chinese Journal of New Drugs), 2013, (8): 923.
[75] Tolle-Sander S, Lentz K A, Maeda D Y, Coop A, Polli J E. Molecular Pharmaceutics, 2004, 1(1): 40.
[76] Balakrishnan A, Polli J E. Molecular Pharmaceutics, 2006, 3(3): 223.
[77] Laird M, Gidal B. Annals of Pharmacotherapy, 2000, 34(1): 802.
[78] Cundy K C, Branch R, Rogan T C, Dias T, Estrada T, Hold K, Koller K, Liu X, Mann A, Panuwat M. Journal of Pharmacology & Experimental Therapeutics, 2004, 311(1): 315.
[79] Richter A, Anton S E, Koch P, Dennett S L. Clinical Therapeutics, 2003, 25(8): 2307.
[80] Rais R, Fletcher S, Polli J E. Journal of Pharmaceutical Sciences, 2011, 100(3): 1184.
[81] Balakrishnan A, Wring S A, Polli J E. Pharmaceutical Research, 2006, 23(7): 1451.
[82] Balakrishnan A, Wring S A, Coop A, Polli J E. Molecular Pharmaceutics, 2006, 3(3): 282.
[83] 李庆勇(Li Q Y), 高洋(Gao Y), 祖元刚(Zu Y G), 张宝友(Zhang B Y), 何乌娜(He W N), 赵腾飞(Zhao T F), 邓晓秋(Deng X Q),朱翅楚(Zhu C C). CN 101967172A, 2011.
[84] Wu X, Chen H, Sun J, Peng Y, Liang Y, Wang G, Wu J, Zhang P. Journal of Chromatography B, 2010, 878(23): 2067.
[85] Liang D, Zhou Q, Zhang J, Gong W, Xu C, Li B, Wang Y, Li J. Steroids, 2012, 77(13): 1381.
[86] 周庆(Zhou Q), 张久亮(Zhang J L), 王奕(Wang Y). 医药导报(Herald of Medicine), 2015, (4): 467.
[87] Hagey L R, Schteingart C D, Ton-Nu H T, Hofmann A F. Journal of Lipid Research, 2002, 43: 685.
[88] Genta K, Takashi I, Takaaki G, Nariyasu M, Junichi G, Toshio N, Hagey L R, Schteingart C D, Hofmann A F. Journal of Lipid Research, 2006, 47: 1.
[89] Hofmann A F, Hagey L R. Cellular & Molecular Life Sciences, 2008, 65(16): 2461.
[90] Iida T, Hikosaka M, Kakiyama G, Shiraishi K, Schteingart C D, Hagey L R, Ton-Nu H T, Hofmann A F, Mano N, Goto J. Chemical & Pharmaceutical Bulletin, 2002, 50(10): 1327.
[91] Omura K, Ohsaki A, Zhou B A, Kushida M, Mitsuma T, Kobayashi A, Hagey L R, Hofmann A F, Iida T. Lipids, 2014, 49(11): 1169.
[92] Genta K, Takashi I, Atsushi Y, Takaaki G, Nariyasu M, Junichi G, Toshio N, Hagey L R, Hofmann A F. Journal of Lipid Research, 2004, 45(3): 567.
[93] Xiao W, Zhang B, Cong Y. Colloid & Polymer Science, 2008, 286(3): 267.
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