Synthetic and natural lipase inhibitors

Mini-Reviews in Medicinal Chemistry

Volumn 18, Issue 8, 2018, Pages 672-683

  Białecka Florjańczyk, Ewa ^a   Fabiszewska, Agata Urszula ^a   Krzyczkowska, Jolanta ^a   Kuryłowicz, Alina ^b  

^a WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

^b MOSSAKOWSKI MEDICAL RESEARCH CENTRE   (Poland)

Author keywords

Biochemistry; Inhibitor; Lipase; Obesity; Orlistat; lactone

Indexed keywords

ENZYME INHIBITOR; PEPTIDE; PHOSPHONIC ACID DERIVATIVE; PLANT EXTRACT; POLYPHENOL; SAPONIN; TETRAHYDROLIPSTATIN; BORONIC ACID DERIVATIVE; FATTY ACID; LACTONE; SURFACTANT; TRIACYLGLYCEROL LIPASE;

DIETARY FIBER; DRUG EFFICACY; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME STRUCTURE; HUMAN; HYDROLYSIS; LIPID ABSORPTION; LIPOLYSIS; NONHUMAN; OBESITY; REVIEW; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; METABOLISM; PATHOLOGY; SYNTHESIS;

ANIMALS; BORONIC ACIDS; ENZYME INHIBITORS; FATTY ACIDS; HUMANS; LACTONES; LIPASE; OBESITY; ORGANOPHOSPHONATES; PLANT EXTRACTS; SURFACE-ACTIVE AGENTS;

EID: 85046264862     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/1389557516666160630123356     Document Type: Review

References (109)

1. Hasan, F.; Shah, A.A.; Hameed, A. Industrial applications of microbial lipases. Enz. Microb. Technol., 2006, 39(2), 235-251.
2. Schmid, R.D.; Verger, R. Lipases: interfacial enzymes with attractive applications. Angew. Chem., Int. Ed. Engl., 1998, 37, 1608-1633.
3. Jaeger, K.E.; Reetz, M.T. Microbial lipases form versatile tools for biotechnology. Trends Biotechnol., 1998, 16(9), 396-403.
4. Sharma, R.; Chisti, Y.; Banerjee, U.Ch. Production, purification, characterization and application of lipases. Biotechnol. Adv., 2001, 19(8), 627-662.
5. Barros, M.; Fleuri, L.F.; Macedo, G.A. Seed lipase: sources, applications and properties - a review. Braz. J. Chem. Eng., 2010, 27(1), 15-29.
6. Nagarajan, S. New tools for exploring “old friends - microbial lipases”. Appl. Biochem. Biotechnol., 2012, 168(5), 1163-1196.
7. Gupta, R.; Gupta, N.; Rathi, P. Bacterial lipases: an overview of production, purification and biochemical properties. Appl. Microbiol. Biotechnol., 2004, 64(6), 763-781.
8. Treichel, H.; de Oliveira, D.; Mazutti, M.A.; Di Luccio, M.; Oliveira, J.V. A review on microbial lipases production. Food Bioproces. Technol., 2010, 3(2), 182-196.
9. Grillitsch, K.; Daum, G. Triacylglicerol lipases of the yeast. Front. Biol., 2011, 6(3), 219-230.
10. Singh, A.K.; Mukhopadhyay, M. Overview of fungal lipase: A review. Appl. Biochem. Biotechnol., 2012, 166(2), 486-520.
11. Jaeger, K.E.; Eggert, T. Lipases for biotechnology. Curr. Opin. Biotechnol., 2002, 13(4), 390-397.
12. Reis, P.; Holmberg, K.; Watzke, H.; Leser, M.E.; Miller, R. Lipases at interfaces: A review. Adv. Coll. Interface Sci., 2009, 147-148, 237-250.
13. Patel, R.N. Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coordination Chem. Rev., 2008, 252, 659-701.
14. Chávez-Flores, D.; Salvador, J.M. Commercially viable resolution of ibuprofen. Biotechnol J., 2009, 4(8), 1222-1224.
15. González-Sabín, J.; Gotor, V.; Rebolledo, F. Chemoenzymatic Preparation of optically active trans-cyclohexane-1,2-diamine derivatives: An efficient synthesis of the analgesic U-(−)-50,488. Chem. Eur. J., 2004, 10, 5788-5794.
16. Gupta, R.; Kumari, A.; Syal, P.; Singh, Y. Molecular and functional diversity of yeast and fungal lipases: Their role in biotechnology and cellular physiology. Progr. Lipid Res., 2015, 57, 40-54.
17. Ramesh, N.; Patel, R.N., Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr. Opin. Biotechnol., 2001, 12(6), 587-604.
18. Fickers, P.; Marty, A.; Nicaud, J.-M. The lipases from Yarrowia lipolytica: genetics, production, regulation, biochemical characterization and biotechnological applications. Biotechnol. Adv., 2011, 29(6), 632-644.
19. Adamczak, M.; Bednarski, W. Lipazy - narzędzie w biotechnologii tłuszczów i olejów. Biotechnologia, 1994, 4(27), 140-153.
20. Ollis, D.L.; Cheah, E.; Cygler, M.; Dijkstra, B.; Frolow, F.; Franken, S.M.; Harel, M.; Remington, S.J.; Silman, I.; Schrag, J.; Sussman, J.L.; Verschueren, K.H.G.; Goldman, A. The alpha/beta hydrolase fold. Protein Eng., 1992, 5(3), 197-211.
21. Brady, L.; Brzozowski, A.M.; Derewenda, Z.S.; Dodson, E.; Dodson, G.; Tolley, S.; Turkenburg, J.P.; Christiansen, L.; Huge-Jensen, B.; Norskov, L.; Thim, L.; Menge, U. A serine protease triad forms the catalytic center of a triacylglycerol lipase. Nature, 1990, 343(6260), 767-770.
22. Pleiss, J.; Fischer, M.; Peiker, M.; Thiele, C.; Schmid, R.D. Lipase engineering database: Understanding and exploiting sequencestructure-function relationships. J. Mol. Catal. B Enzym., 2000, 10(5), 491-508.
23. Aloulou A., Rodriguez J.A., Fernandez S., Van Oosterhout D., Puccinelli D., Carriere F. Exploring the specific features of interfacial enzymology based on lipase studies. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids, 2006, 1761, 995-1013.
24. Bordes, F.; Barbe, S.; Escalier, P.; Mourey, L.; André, I.; Marty, A.; Tranier, S. Exploring the conformational states and rearrangements of Yarrowia lipolytica lipase. Biophys. J., 2010, 99(7), 2225-2234.
25. Rehm, S.; Trodler, P.; Pleiss, J. Solvent-induced lid opening in lipases: a molecular dynamics study. Protein Sci., 2010, 19(11), 2122-2130.
26. Arpigny, J.L.; Jaeger, K.E. Bacterial lipolytic enzymes: classification and properties. Biochem. J., 1999, 343(1), 177-183.
27. Bornscheuer, U.T. Microbial carboxyl esterases: classification, properties and application in biocatalysis. FEMS Microbiol. Rev., 2002, 26(1), 73-81.
28. Widmann, M.; Juhl, P.B.; Pleiss, J. Structural classification by the Lipase Engineering Database: a case study of Candida antarctica lipase A. BMC Genom., 2010, 11, 123.
29. Messaoudi, A.; Belguith, H.; Ghram, I.; Hamida, J.B. LIPABASE: a database for 'true' lipase family enzymes. Int. J. Bioinform. Res. Appl., 2011, 7(4), 390-401.
30. Chapus, C.; Sémériva, M. Mechanism of pancreatic lipase action 2. Catalytic properties of modified lipases. Biochemistry, 1976, 15(23), 4988-4991.
31. Verger, R. Interfacial activation of lipases: facts and artefacts. Trends Biotechnol., 1997, 15(1), 32-38.
32. Verger, R.; de Haas, G.H. Interfacial enzyme kinetics of lipolysis. Annu. Rev. Biophys. Bioeng., 1976, 5, 77-117.
33. Tsujita, T.; Takaichi, H.; Takaku, T.; Sawai, T.; Yoshida, N.; Hiraki, J. Inhibition of lipase activities by basic polysaccharide. J. Lipid Res., 2007, 48, 358-365.
34. Schweitzer-Stenner, R. (Ed.); Uversky, V. (Series Ed.) Protein and Peptide Folding, Misfolding, and Non-Folding. J. Wiley, 2012, ISBN: 978-0-470-59169-7.
35. Li, Y.; McClements, D.J. Inhibition of lipase-catalyzed hydrolysis of emulsified triglyceride oils by low-molecular weight surfactants under simulated gastrointestinal conditions. Eur. J. Pharm. Biopharm., 2011, 79(2), 423-431.
36. Delorme, V.; Dhouib, R.; Canaan, S.; Fotiadu, F.; Carrière, F.; Cavalier, J.-F. Effects of surfactants on lipase structure, activity, and inhibition. Pharm. Res., 2011, 28, 1831.
37. Cavalier, J.-F.; Buono, G.; Verger, R. Covalent inhibition of digestive lipases by chiral phosphonates. Acc. Chem. Res., 2000, 33(9), 579-589.
38. Björkling, F.; Dahl, A.; Patkar, S.; Zundel, M. Inhibition of lipases by phosphonates. Bioorg. Med. Chem., 1994, 2, 697-705.
39. Gargouri, Y.; Ransac, S.; Verger, R. Covalent inhibition of digestive lipases. An in vitro study. Biochim. Biophys. Acta, 1997, 1344, 6-37.
40. Marguet, F.; Cudrey, C.; Verger, R.; Buono, G. Digestive lipases: Inactivation by phosphonates. Biochim. Biophys. Acta, 1994, 1210, 157-166.
41. Cavalier, J.-F.; Ransac, S.; Verger, R.; Buono, G. Inhibition of human gastric and pancreatic lipases by chiral alkylphosphonates. A kinetic study with 1,2-didecanoyl-sn-glycerol monolayer. Chem. Phys. Lipids., 1999, 100(1-2), 3-31.
42. Marguet, F.; Cavalier, J.-F.; Verger, R.; Buono, G. New synthesis of sn-1,2 and sn-2,3-O-diacylglycerols. - Application to the synthesis of enantiopure phosphonates analogous to triglycerides: A new class of inhibitor of lipases. Eur. J. Org. Chem., 1999, 1671-1678.
43. Mannesse, M. L. M.; Boots, J. W. P.; Dijkman, R.; Slotboom, A. J.; Vanderhijden, H. T. W. V.; Egmond, M. R.; Verheij, H. M.; de Haas, G. H. Phosphonate analogues of triacylglycerols are potent inhibitors of lipases. Biochim. Biophys. Acta, 1995, 1259, 56-64.
44. Garner, C.W. Boronic acid inhibitors of porcine pancreatic lipase. J. Biol. Chem., 1980, 255, 5064-5068.
45. Raghavendra, M.P.; Prakash, V. Phenylboronic acid-a potent inhibitor of lipase from Oryza sativa. J. Agric. Food Chem., 2002, 50, 6037-6041.
46. Constantinou-Kokotou, V.; Magrioti, V.; Verger, R. Sterically hindered triacylglycerol analogues as potent inhibitors of human digestive lipases. Chem. Eur. J., 2004, 10, 1133-1140.
47. Magrioti, V.; Verger, R.; Constantinou-Kokotou, V. Triacylglycerols based on 2-(N-tert-butoxycarbonylamino)oleic acid are potent inhibitors of pancreatic lipase. J. Med. Chem., 2004, 47(2), 288-291.
48. Chiou, A.; Markidis, T.; Constantinou-Kokotou, V.; Verger, R.; Kokotos, G. Synthesis and study of a lipophilic α-keto amide inhibitor of pancreatic lipase. Org. Lett., 2000, 2(3), 347-350.
49. Chiou, A.; Verger, R.; Kokotos, G. Synthetic routes and lipaseinhibiting activity of long-chain alpha-keto amides. Lipids, 2001, 36(5), 535-542.
50. Kokotos, G.; Verger, R.; Chiou, A. Synthesis of 2-Oxo amide triacylglycerol analogues and study of their inhibition effect on pancreatic and gastric lipases. Chem. Eur. J., 2000, 6(22), 4211-4217.
51. Kotsovolou, S.; Chiou, A.; Verger, R.; Kokotos, G. Bis-2-oxo amide triacylglycerol analogues: a novel class of potent human gastric lipase inhibitors. J. Org. Chem., 2001, 66(3), 962-967.
52. Kotsovolou, S.; Verger, R.; Kokotos, G. Synthesis of lipophilic aldehydes and study of their inhibition effect on human digestive lipases. Org. Lett., 2002, 4(16), 2625-2628.
53. Kokotos, G.; Kotsovolou, S.; Verger, R. Novel trifluoromethyl ketones as potent gastric lipase inhibitors. Chembiochemistry, 2003, 4(1), 90-95.
54. Böttcher, T.; Sieber, S.A. β-lactams and β-lactones as activitybased probes in chemical biology. Med. Chem. Commun., 2012, 3, 408-417.
55. Hadváry, P.; Sidler, W.; Meister, W.; Vetter, W.; Wolfer, H. The lipase inhibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase. J. Biol. Chem., 1991, 266(4), 2021-2027.
56. Bénarouche, V.; Point, F.; Carrière, J.-F.; Cavalier, J.-F. Using the reversible inhibition of gastric lipase by Orlistat for investigating simultaneously lipase adsorption and substrate hydrolysis at the lipid-water interface. Biochimie, 2014, 102, 145-153.
57. Tiss, A.; Lengsfeld, H.; Carrière, F.; Verger, R. Inhibition of human pancreatic lipase by tetrahydrolipstatin: Further kinetic studies showing its reversibility. J. Mol. Cat. B., 2009, 58, 41-47.
58. Potthoff, A.P.; Haalck, L.; Spener, F. Inhibition of lipases from Chromobacterium viscosum and Rhizopus oryzae by tetrahydrolipstatin. Biochim. Biophys. Acta, 1998, 1389(2), 123-131.
59. Weibel, E.; Hadvary, P.; Hochuli, E.; Kupfer, E.; Lengsfeld, H. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. J. Antibiot., 1987, 40(8), 1081-1085.
60. Mutoh, M.; Nakada, N.; Matsukuma, S.; Ohshima, S.; Yoshinri, K.; Watanabe, J.; Arisawa, M. Panclicins, novel pancreatic lipase inhibitors I. Taxonomy, fermentation, isolation and biological activity. J. Antibiot., 1994, 47, 1369-1384.
61. Nonaka, Y.; Ohtaki, H.; Ohtsuka, E.; Kocha, T.; Fukuda, T.; Takeuchi, T.; Aoyagi, T. Effects of ebelactone B, a lipase inhibitor, on intestinal fat absorption in the rat. J. Enzyme Inhib., 1996, 10(1), 57-63.
62. Paterson, I.; Hulme, A.N. Total synthesis of (-)-ebelactone A and B. J. Org. Chem., 1995, 60(11), 3288-3300.
63. Welles, J.S.; Trejo, W.H.; Principe, P.A.; Sykes, R.B. Obafluorin, a novel β -lactone produced by Pseudomonas fluorescens. Taxonomy, fermentation and biological properties. J. Antibiot., 1984, 37(7), 802-803.
64. Liu, D.-Z.; Wang, F.; Lian, T.-G.; Tang, J.-G., Steglich, W.; Zhu, H.-J.; Liu J.-K. Vibralactone: A lipase inhibitor with an unusual fused β-lactone produced by cultures of the Basidiomycete Boreostereum Vibrans. Org. Lett., 2006, 8(25), 5749-5752.
65. Barbier, P.; Schneider, F. Synthese of tetrahydrolipstatin and absolute configuration of tetrahydrolipstatin and lipstatin. Helv. Chim. Acta, 1987, 70, 196-202.
66. Mulzer, M.; Tiegs, B.J.; Wang, Y.; Coates G.W.; O'Doherty, G. Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols. J. Am. Chem. Soc., 2014, 136(30), 10814-10820.
67. Mineeva, I.V. Asymmetric synthesis of valilactone. Russ. J. Org. Chem., 2014, 50, 100-104.
68. Slanc, P.; Doljak, B.; Kreft, S.; Lunder, M.; Janes, D.; Strukelj, B. Screening of selected food and medicinal plant extracts for pancreatic lipase inhibition. Phytother. Res., 2009, 23(6), 874-877.
69. Ibrahim, S.R.M.; Mohamed, G.A.; Banjar, Z.M.; Kamal, H.K.M. Natural antihyperlipidemic agents: Current status and future perspectives. Phytopharmacology, 2013, 4(3), 492-531.
70. de la Garza, A.L.; Milagro, F.I.; Boque, N.; Campión, J.; Martínez, J.A. Natural inhibitors of pancreatic lipase as new players in obesity treatment. Planta Med., 2011, 77(8), 773-785.
71. Sharma, N.; Sharma, V.K.; Seo, S.-Y. Screening of some medicinal plants for anti-lipase activity. J. Ethnopharmacol., 2005, 97(3), 453-456.
72. Han, L.; Li, W.; Narimatsu, S.; Liu, L.; Fu, H.; Okuda, H.; Koike, K. Inhibitory effects of compounds isolated from fruit of Juglans mandshurica on pancreatic lipase. J. Nat. Med., 2007, 61, 184-186.
73. Gondoin, A.; Grussu, D.; Stewart, D.; McDougall, G.J. White and green tea polyphenols inhibit pancreatic lipase in vitro. Food Res. Int., 2010, 43(5), 1537-1544.
74. Bitou, N.; Ninomiya, M.; Tsujita, T.; Okuda, H. Screening of lipase inhibitors from marine algae. Lipids, 1999, 34, 441-445.
75. Yun, J.W. Possible anti-obesity therapeutics from nature--a review. Phytochemistry, 2010, 71(14-15), 1625-1641.
76. Gholamhoseinian, A.; Shahouzehi, B.; Sharifi-far, F. Inhibitory effect of some plant extracts on pancreatic lipase. Int. J. Pharmacol., 2010, 6, 18-24.
77. Moreno, D.A.; Ilic, N.; Poulev, A.; Brasaemle, D.L.; Fried, S.K.; Raskin, I. Inhibitory effects of grape seed extract on lipases. Nutrition, 2003, 19(10), 876-879.
78. Kim, H.Y.; Kang, M.H. Screening of Korean medicinal plants for lipase inhibitory activity. Phytother. Res., 2005, 19(4), 359-361.
79. Han, L.K.; Kimura, Y.; Kawashima, M. Anti-obesity effects in rodents of dietary teasaponin, a lipase inhibitor. Int. J. Obesity, 2001, 25, 1459-1464.
80. Moreno, D.A.; Ilic, N.; Poulev, A.; Raskin, I. Effects of Arachis hypogaea nutshell extract on lipid metabolic enzymes and obesity parameters. Life Sci., 2006, 78, 2797-2803.
81. Nakai, M.; Fukui, Y.; Asami, S.; Toyoda-Ono, Y.; Iwashita, T.; Shibata, H.; Mitsunaga, T.; Hashimoto, F.; Kiso, Y. Inhibitory effects of oolong tea polyphenols on pancreatic lipase in vitro. J. Agric. Food Chem., 2005, 53(11), 4593-4598.
82. Koo, S.I.; Noh, S.K. Green tea as inhibitor of the intestinal absorption of lipids: potential mechanism for its lipid-lowering effect. J. Nutr. Biochem., 2007, 18(3), 179-183.
83. Shishikura, Y.; Khokhar, S.; Murray, B.S. Effect of tea polyphenols on emulsification of olive oil in a small intestine model system. J. Agric. Food Chem., 2006, 54, 1906-1913.
84. Nakayama, T.; Ishii, T.; Uekusa, Y.; Kato, K.; Kumazawa, S. I Interaction of tea catechins with phospholipids - roles in their tastes and biological activities. J. Food Drug Anal., 2012, 20, 305-308.
85. Uekusa, Y.; Kamihira, M.; Sugimoto, I.O.; Ishii, T.; Kumazawa, S.; Nakamura, K.; Tanji, K.; Naito, A.; Nakayama, T. Interaction of epicatechin gallate with phospholipid membranes as revealed by solid-state NMR spectroscopy. Biochim. Biophys. Acta-Biomembranes, 2011, 1808(6), 1654-1660.
86. Wu, X.; He, W.; Yao, L.; Zhang, H.; Liu, Z.; Wang, W.; Ye, Y.; Cao, J. Characterization of binding interactions of (−)-epigallocatechin-3-gallate from green tea and lipase. J. Agric. Food Chem., 2013, 61(37), 8829-8835.
87. Kwon, C.S.; Sohn, H.Y.; Kim, S.H.; Kim, J.H.; Son, K.H.; Lee, J.S.; Lim, J.K.; Kim, J.S. Anti-obesity effect of Dioscorea nipponica Makino with lipase-inhibitory activity in rodents. Biosci. Biotechnol. Biochem., 2003, 67(7), 1451-1456.
88. Murakami, T.; Nakamura, J.; Matsuda, H.; Yoshikawa, M. Bioactive saponins and glycosides. XV. Saponin constituents with gastroprotective effect from the seeds of tea plant, Camellia sinensis L. var. assamica Pierre, cultivated in Sri Lanka: structures of assamsaponins A, B, C, D, and E. Chem. Pharm. Bull. (Tokyo), 1999, 47(12), 1759-64.
89. Kimura, H.; Ogawa, S.; Katsube, T.; Jisaka, M.; Yokota, K. Antiobese effects of novel saponins from edible seeds of Japanese horse chestnut (Aesculus turbinata BLUME) after treatment with wood ashes. J. Agric. Food Chem., 2008, 56(12), 4783-4788.
90. Yoshizumi, K.; Hirano, K.; Ando, H.; Hirai, Y.; Ida, Y.; Tsuji, Y.; Tanaka, T.; Satouchi, K.; Terao, J. Lupane-type saponins from leaves of Acanthopanax sessiliflorus and their inhibitory activity on pancreatic lipase. J. Agric. Food Chem., 2006, 54(2), 335-341.
91. Ruiz, C.; Falcocchio, S.; Xoxi, E.; Villo, L.; Nicolosi, G.; Pastor, F.I.J.; Diaz, P.; Saso, L. Inhibition of Candida rugosa lipase by saponins, flavonoids and alkaloids. J. Mol. Catal. B, Enzymatic, 2006, 40(3-4).
92. Sheng, L.; Qian, Z.; Zheng, S.; Xi, L. Mechanism of hypolipidemic effect of crocin in rats: crocin inhibits pancreatic lipase. Eur. J. Pharmacol., 2006, 543(1-3), 116-122.
93. Han, L.K.; Kimura, Y.; Kawashima, M. Anti-obesity effects in rodents of dietary teasaponin, a lipase inhibitor. Int. J. Obesity, 2001, 25, 1459-1464.
94. Gholamhoseinian, A.; Shahouzehi, B.; Sharifi-far, F. Inhibitory effect of some plant extracts on pancreatic lipase. Int. J. Pharmacol., 2010, 6, 18-24.
95. Tsujita, T.; Takaichi, H.; Takaku, T.; Aoyama, S.; Hiraki, J. Antiobese action of e-polylysine, a potent inhibitor of pancreatic lipase. J. Lipid Res., 2006, 47, 1852-1858.
96. Tsujita, T., Matsuura, Y.; Okuda, H. Studies on the inhibition of pancreatic and carboxylester lipases by protamine. J. Lipid Res., 1996, 37, 1481-1487.
97. Tsujita, T.; Sumiyoshi, M.; Takaku, T.; Momsen, W.E.; Lowe, M.E.; Brockman, H.L. Inhibition of lipases by e-polylysine. J. Lipid Res., 2003, 44, 2278-2286.
98. Tsujita, T.; Takaichi, H.; Takaku, T.; Sawai, T.; Yoshida, N.; Hiraki J. Inhibition of lipase activities by basic polysaccharide. J Lipid Res., 2007, 48(2), 358-365.
99. McClendon, K.S.; Riche, D.M.; Uwaifo, G.I. Orlistat: current status in clinical therapeutics. Expert Opin. Drug Saf., 2009, 8(6), 727-744.
100. Sjöström, L.; Rissanen, A.; Andersen, T.; Boldrin, M.; Golay, A.; Koppeschaar, H.P.; Krempf, M. Randomised placebo-controlled trial of orlistat for weight loss and prevention of weight regain in obese patients. European Multicentre Orlistat Study Group. Lancet, 1998, 352, 167-172.
101. Davidson, M.H.; Hauptman, J.; DiGirolamo, M.; Foreyt, J.P.; Halsted, C.H.; Heber, D.; Heimburger, D.C.; Lucas, C.P.; Robbins, D.C.; Chung, J.; Heymsfield, S.B. Weight control and risk factor reduction in obese subjects treated for 2 years with orlistat: a randomized controlled trial. JAMA, 1999, 281, 235-242.
102. Yanovski, S.Z.; Yanovski, J.A. Long-term drug treatment for obesity: a systematic and clinical review. JAMA, 2014, 311(1), 74-86.
103. Olszanecka-Glinianowicz, M.; Dąbrowski, P.; Kocełak, P.; Janowska, J.; Smertka, M.; Jonderko, K.; Chudek, J. Long-term inhibition of intestinal lipase by orlistat improves release of gut hormones increasing satiety in obese women. Pharmacol. Rep., 2013, 65(3), 666-671.
104. Sumithran, P.; Proietto, J. Benefit-risk assessment of orlistat in the treatment of obesity. Drug Saf., 2014, 37(8), 597-608.
105. Gras, J. Cetilistat for the treatment of obesity. Drugs Today (Barc), 2013, 49(12), 755-759.
106. Courtney, A.E.; O'Rourke, D.M.; Maxwell, A.P. Rapidly progressive renal failure associated with successful pharmacotherapy for obesity. Nephrol. Dial. Transplant, 2007, 22, 621-623.
107. Singh, A.; Sarkar, S.R.; Gaber, L.W.; Perazella, M.A. Acute oxalate nephropathy associated with orlistat, a gastrointestinal lipase inhibitor. Am. J. Kidney Dis., 2007, 49, 153-157.
108. Padwal, R.; Li, S.K.; Lau, D.C.W. Long-term pharmacotherapy for overweight and obesity: A systematic review and meta-analysis of randomized controlled trials. Int. J. Obesity, 2003, 27(12), 1437-1446.
109. Gillman, M.W.; Poston, L.; Maternal Obesity, Cambridge University Press, Cambridge, UK, 2012.