nach oben

Erschienen in:

2020 | OriginalPaper | Buchkapitel

Pharmacophore Mapping of Natural Products for Pancreatic Lipase Inhibition

verfasst von : Matheus Gabriel de Oliveira, Waléria Ramos Nogueira de Souza, Ricardo Pereira Rodrigues, Daniel F. Kawano, Leonardo Luiz Borges, Vinicius Barreto da Silva

Erschienen in: Emerging Research in Science and Engineering Based on Advanced Experimental and Computational Strategies

Verlag: Springer International Publishing

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

The use of pancreatic lipase (LP) inhibitors to reduce the absorption of dietary fats has become one of the pharmacological approaches adopted for the treatment of obesity. Since natural products continue to play a significant role in drug discovery and development the search for natural compounds with PL inhibitory activity is an interesting approach to provide new lead compounds for drug discovery and to guide dietary trends in order to prevent or treat obesity. The consumption of Myrciaria genus plant species is also related to increased HDL cholesterol and improved triglycerides excretion in animal models. In addition, extracts of species from Myrciaria genus are related to in vitro inhibitory activity against PL. Hence it is important to identify which chemical markers from Myrciaria genus species are structurally related to PL inhibitory activity. Ligand-based pharmacophore modeling is one of the most applied approaches in medicinal chemistry in order to detect molecular features related to molecules that are able to modulate a particular biological target. Some Myrciaria genus chemical markers including polyphenols, glycosides and lactonic derivatives share molecular features found in classic PL inhibitors. Such phytomolecules from Myrciaria species are a starting point to develop novel therapeutic options for obesity with PL inhibitory activity.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Vorheriges Kapitel Design of Inhibitors of the Human Fibroblast Activation Protein α as a Strategy to Hinder Metastasis and Angiogenesis

Nächstes Kapitel Theoretical Insights About the Chemical Dependent Role of Exchange-Correlation Functionals: A Case Study

Newman, D.J., Cragg, G.M.: Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75(3), 311–335 (2012)CrossRef

Haustedt, L.O., Mang, C., Siems, K., Schiewe, H.: Rational approaches to natural-product-based drug design. Curr. Opin. Drug Discov. Devel. 9(4), 445–462 (2006)

Baker, D.D., Chu, M., Oza, U., Rajgarhia, V.: The value of natural products to future pharmaceutical discovery. Nat. Prod. Rep. 24(6), 1225–1244 (2007)CrossRef

Grabowski, K., Baringhaus, K.H., Shneider, G.: Scaffold diversity of natural products: inspiration for combinatorial library design. Nat. Prod. Rep. 25(5), 892–904 (2008)CrossRef

Haustedt, L.O.; Siems, K.: The role of natural products in drug discovery: examples of marketed drugs. In: Werngard, C., Peter, H. (eds.) Small molecule medicinal chemistry: strategies and technologies, p. 381. Wiley (2015)

Rollinger, J.M., Langer, T., Stuppner, H.: Strategies for efficient lead structure discovery from natural products. Curr. Med. Chem. 13(13), 1491–1507 (2006)CrossRef

Al-Masri, I.M.: Pancreatic lipase inhibition by papaverine: investigation by simulated molecular docking and subsequent in vitro evaluation. Jordan. J. Pharmacol. 6(3), 271–279 (2013)

Tsai, A.G., Williamson, D.F., Glick, H.A.: Direct medical cost of overweight and obesity in the USA: a quantitative systematic review. Obes. Rev. 12(1), 50–61 (2011)CrossRef

Calle, E.E., Rodriguez, C., Walker-Thurmond, K., Thun, M.J.: Overweight, obesity, and mortality from cancer in a prospectively studied cohort of U.S. adults. N. Engl. J. Med. 348(17), 1625–1638 (2003)CrossRef

10.

Carrière, F., Renou, C., Ransac, S., Lopez, V., De Caro, J., Ferrato, F., De Caro, A., Fleury, A., Sanwald-Ducray, P., Lengsfeld, H., Beglinger, C., Hadvary, P., Verger, R., Laugier, R.: Inhibition of gastrointestinal lipolysis by orlistat during digestion of test meals in healthy volunteers. Am. J. Physiol. Gastrointest. Liver Physiol. 281(1), G16–G28 (2001)CrossRef

11.

Myoda, T., Fujimura, S., Park, B., Nagashima, T., Nakagawa, J., Nishizawa, M.: Exotic fruits reference guide. J. Food Agric. Environ. 8, 304–307 (2010)

12.

Dastmalchi, K., Flores, G., Wu, S.B., Ma, C., Dabo, A.J., Whalen, K., Reynertson, K.A., Foronjy, R.F., D’Armiento, J.M., Kennelly, E.J.: Edible Myrciaria vexator fruits: bioactive phenolics for potential COPD therapy. Bioorgan. Med. Chem. 20(14), 4549–4555 (2012)CrossRef

13.

Lenquiste, S.A., Batista, A.G., Marinele, R.S., Dragano, N.R.V., Maróstica, M.R.: Freeze-dried jaboticaba peel added to high-fat diet increases HDL-cholesterol and improves insulin resistance in obese rats. Food Res. Int. 49, 153–160 (2012)CrossRef

14.

Batista, G.B., Lenquiste, S.A., Moldenhauer, C., Godoy, J.T., Reis, S.M.P.M., Junior, M.R.M.: Jaboticaba (Myrciaria jaboticaba (Vell.) Berg.) peel improved triglycerides excretion and hepatic lipid peroxidation in high-fat-fed rats. Rev. Nutr. 25, 571–581 (2013)CrossRef

15.

Alezandro, M.R., Granato, D., Genovese, M.L.: Análises químicas, propriedades funcionais e controle de qualidade de alimentos e bebidas: uma abordagem teórico-prática. Food Res. Int. 54, 650–659 (2013)CrossRef

16.

Ewas, A.F., Maghrabi, I.A., Namarneh, A.I.: Advances in molecular modeling and docking as a tool for modern drug discovery. Der Pharma Chem. 6, 211–228 (2014)

17.

Sanders, M.P.A., McGuire, R., Roumen, L., Esch, I.J.P., Vlieg, J., Klomp, J.P.G., Graaf, C.: From the protein’s perspective: the benefits and challenges of protein structure-based pharmacophore modeling. Med. Chem. Commun. 3, 28–38 (2012)CrossRef

18.

Harvey, A.L.: Natural products in drug discovery. Drug Disc. Today 13, 894–901 (2008)CrossRef

19.

Baker, D.D., Chu, M., Oza, U., Rajgarhia, V.: The value of natural products to future pharmaceutical discovery. Nat. Prod. Rep. 24, 1225–1244 (2007)CrossRef

20.

Strohl, W.R.: The role of natural products in a modern drug discovery program. Drug Disc. Today 5, 39–41 (2000)CrossRef

21.

Harvey, A.: Strategies for discovering drugs from previously unexplored natural products. Drug Disc. Today 5, 294–299 (2000)CrossRef

22.

Newman, D.J., Cragg, G.M.: Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod. 79(3), 629–661 (2016)CrossRef

23.

WHO: National policy on traditional medicine and regulation of herbal medicines: report of a WHO global survey. World Health Organization, Geneva, Switzerland (2005)

24.

Balunas, M.J., Kinghorn, A.D.: Drug discovery from medicinal plants. Life Sci. 78, 431–441 (2005)CrossRef

25.

Sharma, S.B., Gupta, R.: Drug development from natural resource: a systematic approach. Mini. Rev. Med. Chem. 15, 52–57 (2015)CrossRef

26.

Ghorbani, A., Naghibi, F., Mosaddegh, M.: Ethnobotany, ethnopharmacology and drug discovery. Iran. J. Pharm. Sci. 2, 109–118 (2006)

27.

Haustedt, L.O., Mang, C., Siems, K., Schiewe, H.: Rational approaches to natural-product-based drug design. Curr. Opin. Drug Disc. Dev. 9, 445–462 (2006)

28.

Wolfender, J.-L., Marti, G., Thomas, A., Bertrand, S.: Current approaches and challenges for the metabolite profiling of complex natural extracts. J. Chromatogr. A 1382, 136–164 (2015)CrossRef

29.

Cheng, F., Li, W., Liu, G., Tang, Y.: In silico ADMET prediction: recent advances, current challenges and future trends. Curr. Topics Med. Chem. 13, 1273–1289 (2013)CrossRef

30.

Ertl, P., Roggo, S., Schuffenhauer, A.: Natural product-likeness score and its application for prioritization of compound libraries. J. Chem. Inf. Model. 48, 68–74 (2008)CrossRef

31.

Patwardhan, B., Vaidya, A.D.B., Chorghade, M., Joshi, S.P.: Reverse pharmacology and systems approaches for drug discovery and development. Curr. Bioact. Compd. 4(4), 1–12 (2008)CrossRef

32.

Mukherjee, P.K., Harwansh, R.K., Bahadur, S., et al.: Metabolomics of medicinal plants—a versatile tool for standardization of herbal products and quality evaluation of ayurvedic formulations. Curr. Sci. 111, 1624–1630 (2016)CrossRef

33.

Lenz, M., Richter, T., Mühlhauser, I.: The morbidity and mortality associated with overweight and obesity in adulthood: a systematic review. Dtsch. Arztebl. Int. 106, 641–648 (2009)

34.

Peeters, A., Barendregt, J.J., Willekens, F., et al.: Obesity in adulthood and its consequences for life expectancy: a life-table analysis. Ann. Intern. Med. 138, 24–32 (2003)CrossRef

35.

World Health Organization: Obesity and Overweight (2014). http://www.who.int/mediacentre/factsheets/fs311/en/

36.

World Health Organization: Obesity and Overweight (2016). https://www.who.int/gho/ncd/risk_factors/overweight/en/

37.

GBD 2015 Obesity Collaboration: Health effects of overweight and obesity in 195 countries over 25 years. N. Engl. J. Med. 377, 13–27 (2017)CrossRef

38.

Flegal, K.M., Kit, B.K., Orpana, H., Graubard, B.I.: Association of all-cause mortality with overweight and obesity using standard body mass index categories: a systematic review and meta-analysis. JAMA 309, 71–82 (2013)CrossRef

39.

Racette, S.B., Deusinger, S.S., Deusinger, R.H.: Obesity: overview of prevalence, etiology, and treatment. Phys. Ther. 83(3), 276–288 (2003)CrossRef

40.

Kaila, B., Raman, M.: Obesity: a review of pathogenesis and management strategies. Can. J. Gastroenterol. 22(1), 61–68 (2008)CrossRef

41.

Jensen, M.D., Ryan, D.H., Apovian, C.M., et al.: 2013 AHA/ACC/TOS guideline for the management of overweight and obesity in adults: a report of the American College of Cardiology/American Heart Association Task Force on practice guidelines and the obesity society. Circulation 129(Suppl 2), S102–S138 (2014)CrossRef

42.

Yanovski, S.Z., Yanovski, J.A.: Long-term drug treatment of obesity. A systematic and clinical review. JAMA 311, 74–86 (2014)MATHCrossRef

43.

Joo, J.K., Lee, K.S.: Pharmacotherapy for obesity. J. Menopausal Med. 20(3), 90–96 (2014)CrossRef

44.

Srivastava, G., Apovian, C.M.: Current pharmacotherapy for obesity. Nat. Rev. Endocrinol. 14(1), 12–24 (2018)CrossRef

45.

Xu, P.F., Dai, S., Wang, J., et al.: Preventive obesity agent montmorillonite adsorbs dietary lipids and enhances lipid excretion from the digestive tract. Sci. Rep. 6, 19659 (2016)CrossRef

46.

Drew, B.S., Dixon, A.F., Dixon, J.B.: Obesity management: update on orlistat. Vasc. Health Risk Manag. 3, 817–821 (2007)

47.

Wang, H., Eckel, R.: Lipoprotein lipase: from gene to obesity. Am. J. Physiol. Endocrinol. Metab. 297, E271–E288 (2009)CrossRef

48.

Mead, J.R., Irvine, S.A., Ramji, D.P.: Lipoprotein lipase: structure, function, regulation, and role in disease. J. Mol. Med. (Berl.) 80, 753–769 (2002)CrossRef

49.

Winkler, F.K., D’Arcy, A., Hunziker, W.: Structure of human pancreatic lipase. Nature 343, 771–774 (1990)CrossRef

50.

Lowe, M.E.: Structure and function of pancreatic lipase and colipase. Annu. Rev. Nutr. 17, 141–158 (1997)CrossRef

51.

Bacha, A.B., Karray, A., Daoud, L., Bouchaala, E., Ali, M.B., Gargouri, Y., Ali, Y.B.: Biochemical properties of pancreatic colipase from the common stingray Dasyatis pastinaca. Lipids Health Dis. 10, 69 (2011). https://doi.org/10.1186/1476-511x-10-69CrossRef

52.

Tsujita, T., Matsuura, Y., Okuda, H.: Studies on the inhibition of pancreatic and carboxylester lipases by protamine. J. Lipid Res. 37(7), 1481–1487 (1996)

53.

Brownlee, I.A., Forster, D.J., Wilcox, M.D., Dettmar, P.W., Seal, C.J., Pearson, J.P.: Physiological parameters governing the action of pancreatic lipase. Nutr. Res. Rev. 23, 146–154 (2010)CrossRef

54.

Buchholz, T., Melzig, M.F.: Polyphenolic compounds as pancreatic lipase inhibitors. Planta Med. 81, 771–783 (2015)CrossRef

55.

Li, F., Li, W., Fu, H., Zhang, Q., Koike, K.: Pancreatic lipase-inhibiting triterpenoid saponins from fruits of Acanthopanax senticosus. Chem. Pharm. Bull. (Tokyo) 55, 1087–1089 (2007)CrossRef

56.

Subandi, Zakiyaturrodliyah, L., Brotosudarmo, T.H.P.: Saponin from purple eggplant (Solanum melongena L.) and their activity as pancreatic lipase inhibitor. IOP Conf. Ser. Mater. Sci. Eng. 509, 012139 (2019)CrossRef

57.

Peng, Y.A.N.G., Yanqin, L.I.: Inhibitory effect of flavonoids and fagopyritols from buckwheat on pancreatic lipase. Food Sci. 36(11), 60–63 (2015)

58.

Rahim, A.T.M.A., Takahashi, Y., Yamaki, K.: Mode of pancreatic lipase inhibition activity in vitro by some flavonoids and non-flavonoid polyphenols. Food Res. Int. 75, 289–294 (2015)CrossRef

59.

Birari, R., Roy, S.K., Singh, A., Bhutani, K.: Pancreatic lipase inhibitory alkaloids of Murraya koenigii leaves. Nat. Prod. Commun. 4, 1089–1092 (2009)

60.

Sridhar, S.N.C., Mutya, S., Paul, A.T.: Bis-indole alkaloids from Tabernaemontana divaricata as potent pancreatic lipase inhibitors: molecular modelling studies and experimental validation. Med. Chem. Res. 26, 1268–1278 (2017)CrossRef

61.

Matsumoto, M., Hosokawa, M., Matsukawa, N., HagioM, Shinoki A., Nishimukai, M., et al.: Suppressive effects of the marine carotenoids, fucoxanthin and fucoxanthinolon triglyceride absorption in lymph ductcannulatedrats. Eur. J. Nutr. 49, 243–249 (2010)CrossRef

62.

Ninomiya, K., Matsuda, H., Shimoda, H., Nishida, N., Kasajima, N., Yoshino, T., et al.: Carnosic acid, a newclass of lipid absorption inhibitor from sage. Bioorg. Med. Chem. Lett. 14, 1943–1946 (2004)CrossRef

63.

Ahn, J.H., Shin, E.J., Liu, Q., Kim, S.B., Choi, K.M., Yoo, H.S., Hwang, B.Y., Lee, M.K.: Lignan derivatives from Fraxinus rhynchophylla and inhibitory activity on pancreatic lipase. Nat. Prod. Sci. 18, 116–120 (2012)

64.

Camlofski, A.M.: Caracterização do fruto de Cerejeira ‘Eugenia Involocrata DC’ visando seu aproveitamento tecnológico. Dissertation, Universidade Estadual de Ponta Grossa, Ponta Grossa (2008)

65.

IPNI: The International Plant Name Index (http://www.ipni.org/). In: The Royal Botanic Gardens. The Harvard University Herbaria; Australian National Herbarium, Kew (2012)

66.

Mattos, J.R.: Jaboticabeiras. Instituto de Pesquisas de Recursos Naturais Renováveis. Porto Alegre, AP (1983)

67.

Donadio, L.C.: Jabuticaba (Myrciaria jaboticaba (Vell.) Berg). Jaboticabal, Funep (2000)

68.

Jham, G.N., Fernandes, S.A., Garcia, C.F., Palmquist, D.: Comparison of GC and HPLC for quantification of organic acids in two jaboticaba (Myrciaria) fruit varieties. Quim. Nova 30(7), 1529–1534 (2007)CrossRef

69.

Balerdi, C.F., Rafie, R., Crane, J.: Jaboticaba (Myrciaria cauliflora Berg.) a delicious fruit with an excellent market potential. Proc. Fla. Sta. Hortic. Soc. 119(1), 66–68 (2006)

70.

Ascheri, D.P.R., Ascheri, J.L.R., Carvalho, C.W.P.: Caracterização da farinha de bagaço de jabuticaba e propriedades funcionais dos extrusados. Ciênci. Tecnol. Aliment. 26(4), 897–905 (2006)CrossRef

71.

Oliveira, A.L., Neto, E.A.B., Fenerich, E.J., Alonso, C.O., Azevedo, J.S.A., Neto, P.O.: Efeito da aplicação pré-colheita de cálcio na qualidade dos frutos de jabuticaba. In: XX Congresso Brasileiro de Fruticultura. Vitória (2008)

72.

Leite, A.V., Malta, L.G., Riccio, M.F., Eberlin, M.N., Pastore, G.M., Maróstica Júnior, M.R.: Antioxidant potential of rat plasma by administration of freeze-dried jaboticaba peel (Myrciaria jaboticaba Vell Berg). J. Food Chem. 59, 2277–2283 (2011)CrossRef

73.

Hagiwara, A., Miyashita, K., Nakanishi, T., Sano, M., Tamano, S., Kadota, T., Koda, T., Nakamura, M., Imaida, K., Ito, N., Shirai, T.: Pronounced inhibition by a natural anthocyanin, purple corn color, of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-associated colorectal carcinogenesis in male F344 rats pretreated with 1,2-dimethylhydrazine. Cancer Lett. 171(1), 17–25 (2001)CrossRef

74.

Kapadia, G.J., Balasubramanian, V., Tokuda, H., Iwashima, A., Nishino, H.: Inhibition of 12-O-tetradecanoylphorbol-13-acetate induced Epstein-Barr virus early antigen activation by natural colorants. Cancer Lett. 115(2), 173–178 (1997)CrossRef

75.

Wang, C.J., Wang, J.M., Lin, W.L., Chu, C.Y., Chou, F.P., Tseng, T.H.: Protective effect of Hibiscus anthocyanins against tert-butyl hydroperoxide-induced hepatic toxicity in rats. Food Chem. Toxicol. 38(5), 411–416 (2000)CrossRef

76.

Kong, J.M., Chia, L.S., Goh, N.K., Chia, T.F., Brouillard, R.: Analysis and biological activities of anthocyanins. Phytochemistry 64(5), 923–933 (2003)CrossRef

77.

Katsube, N., Iwashita, K., Tsushida, T., Yamaki, K., Kobori, T.: Induction of apoptosis in cancer cells by Bilberry (Vaccinium myrtillus) and the anthocyanins. J. Agric. Food Chem. 51(1), 68–75 (2003)CrossRef

78.

Tsuda, T., Horio, F., Uchida, K., Aoki, H., Osawa, T.: Dietary cyanidin 3-O-b-D-glucoside-rich purple corn color prevents obesity and ameliorates hyperglycemia in mice. J. Nutr. 133, 2125–2130 (2003)CrossRef

79.

Wang, J., Mazza, G.: Effects of anthocyanins and other phenolic compounds on the production of tumor necrosis factor alpha in LPS/IFN-gamma-activated RAW. J. Agric. Food Chem. 50, 4183–4189 (2002)CrossRef

80.

DeFuria, J., Bennett, G., Strissel, K.J., Perfield II, J.W., Milbury, P.E., Greenberg, A.S., Obin, M.S.: Dietary blueberry attenuates whole-body insulin resistance in high fat-fed mice by reducing adipocyte death and its inflammatory sequelae. J. Nutr. 139(8), 1510–1516 (2009)CrossRef

81.

Prior, R.L., Wu, X., Gu, L., Hager, T., Hager, A., Wilkes, S., Howard, L.: Purified berry anthocyanins but not whole berries normalize lipid parameters in mice fed an obesogenic high fat diet. Mol. Nutr. Food Res. 53(11), 1406–1418 (2009)CrossRef

82.

Prior, R.L., Wilkes, S., Rogers, T., Khanal, R.C., Wu, X., Hager, T.J., Hager, A., Howard, L.: Dietary black raspberry anthocyanins do not alter development of obesity in mice fed an obesogenic high-fat diet. J. Agric. Food Chem. 58(7), 3977–3983 (2010)CrossRef

83.

Souza-Moreira, T.M., Severi, J.A., Santos, E., Silva, V.Y.A., Vilegas, W., Salgado, H.R.N., Pietro, R.C.L.R.: Chemical and antidiarrheal studies of Plinia cauliflora. J. Med. Food 14(12), 1590–1596 (2011)CrossRef

84.

Boari Lima, A.J., Duarte Corrêa, A., Carvalho Alves, A.P., Patto Abreu, C.M., Dantas-Barros, A.M.: Caracterização química do fruto jabuticaba (Myrciaria cauliflora Berg) e de suas frações. Arch. Latinoam. Nutr. 58(4), 416–421 (2008)

85.

Reynertson, K.A., Wallace, A.M., Adachi, S., Gil, R.R., Yang, H., Basile, M.J., D’Armiento, J., Weinstein, I.B., Kennelly, E.J.: Bioactive depsides and anthocyanins from Jaboticaba (Myrciaria cauliflora) Kurt. J. Nat. Prod. 69, 1228–1230 (2006)CrossRef

86.

87.

Akter, M.S., Oh, S., Eun, J.-B., Ahmed, M.: Nutritional compositions and health promoting phytochemicals of camu-camu (Myrciaria dubia) fruit: a review. Food Res. Int. 44(7), 1728–1732 (2011)CrossRef

88.

Lenquiste, S.A., Batista, Â.G., Marineli, R.D.S., Dragano, N.R.V., Maróstica, M.R.: Freeze-dried jaboticaba peel added to high-fat diet increases HDL-cholesterol and improves insulin resistance in obese rats. Food Res. Int. 49(1), 153–160 (2012)CrossRef

89.

Diniz, D.N., Macêdo-Costa, M.R., Pereira, M.S.V., Pereira, J.V., Higino, J.S.: Efeito antifúngico in vitro do extrato da folha e do caule de Myrciaria cauliflora Berg. sobre microrganismos orais. Rev. Odontol. UNESP 39, 151–156 (2010)

90.

Inoue, T., Komoda, H., Uchida, T., Node, K.: Tropical fruit camu-camu (Myrciaria dubia) has anti-oxidative and anti-inflammatory properties. J. Cardiol. 52(2), 127–132 (2008)CrossRef

91.

Myoda, T., Fujimura, S., Park, B., Nagashima, T., Nakagawa, J., Nishizawa, M.: Antioxidative and antimicrobial potential of residues of camu-camu juice production. J. Food Agric. Environ. 8(2), 304–307 (2010)

92.

Ueda, H., Kuroiwa, E., Tachibana, Y., Kawanishi, K., Ayala, F., Moriyasu, M.: Aldose reductase inhibitors from the leaves of Myrciaria dubia (H. B. & K.) McVaugh. Phytomedicine 11(7–8), 652–656 (2004)CrossRef

93.

Silva, F.C., Arruda, A., Ledel, A., Dauth, C., Romao, N.F., Viana, R.N., de Barros Falcao Ferraz, A., Picada, J.N., Pereira, P.: Antigenotoxic effect of acute, subacute and chronic treatments with Amazonian camu-camu (Myrciaria dubia) juice on mice blood cells. Food Chem. Toxicol. 50(7), 2275–2281 (2012)CrossRef

94.

Yu, W., MacKerell Jr., A.D.: Computer-aided drug design methods. Methods Mol. Biol. 1520, 85–106 (2017). https://doi.org/10.1007/978-1-4939-6634-9_5CrossRef

95.

Kore, P., Mutha, M., Antre, R., Oswal, R., Kshirsagar, S.: Computer-aided drug design: an innovative tool for modeling. Open J. Med. Chem. 2(4), 139–148 (2012)CrossRef

96.

Yang, S.-Y.: Pharmacophore modeling and applications in drug discovery: challenges and recent advances. Drug Discov. Today 15, 444–450 (2010)CrossRef

97.

Langer, T.: Pharmacophores in drug research. Mol. Inf. 29, 470–475 (2010)CrossRef

98.

Kutlushina, A., Khakimova, A., Madzhidov, T., Polishchuk, P.: Ligand-based pharmacophore modeling using novel 3D pharmacophore signatures. Molecules 23, 3094 (2018)CrossRef

99.

Che, J., Wang, Z., Sheng, H., et al.: Ligand-based pharmacophore model for the discovery of novel CXCR1 antagonists as anti-cancer metastatic agents. R Soc Open Sci. 5(7), 180176 (2018). Published 4 Jul 2018CrossRef

100.

Mendez, D., Gaulton, A., Bento, A.P., Chambers, J., De Veij, M., Félix, E., Magariños, M.P., Mosquera, J.F., Mutowo, P., Nowotka, M., et al.: ChEMBL: towards direct deposition of bioassay data. Nucl. Acids Res. 47, D930–D940 (2019)CrossRef

101.

Kim, S., Thiessen, P.A., Bolton, E.E., et al.: PubChem substance and compound databases. Nucl. Acids Res. 44(D1), D1202–D1213 (2016)CrossRef

102.

Gilson, M.K., Liu, T., Baitaluk, M., Nicola, G., Hwang, L., Chong, J.: BindingDB in 2015: a public database for medicinal chemistry, computational chemistry and systems pharmacology. Nucl. Acids Res. 44(D1), D1045–D1053 (2016)CrossRef

103.

Wishart, D.S., Feunang, Y.D., Guo, A.C., et al.: DrugBank 5.0: a major update to the DrugBank database for 2018. Nucl. Acids Res. 46(D1), D1074–D1082 (2018)CrossRef

104.

Leach, A.R., Gillet, V.J., Lewis, R.A., Taylor, R.: Three-dimensional pharmacophore methods in drug discovery. J. Med. Chem. 53, 539–558 (2010)CrossRef

105.

Dassault Systèmes BIOVIA: Discovery Studio v. 4.0, Dassault Systèmes, San Diego (2012)

106.

Dixon, S.L., Smondyrev, A.M., Knoll, E.H., Rao, S.N., Shaw, D.E., Friesner, R.A.: PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. J. Comput. Aided Mol. Des. 20, 647–671 (2006)CrossRef

107.

Wolber, G., Langer, T.: LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J. Chem. Inf. Model. 45, 160–169 (2005). https://doi.org/10.1021/ci049885eCrossRef

108.

Schneidman-Duhovny, D., Dror, O., Inbar, Y., Nussinov, R., Wolfson, H.J.: PharmaGist: a webserver for ligand-based pharmacophore detection. Nucleic Acids Res. 36(Web server issue), W223–W228 (2008)CrossRef

109.

Hu, B., Lill, M.A.: Exploring the potential of protein-based pharmacophore models in ligand pose prediction and ranking. J. Chem. Inf. Model. 53(5), 1179–1190 (2013)CrossRef

110.

Rose, P.W., Prlić, A., Altunkaya, A., et al.: The RCSB protein data bank: integrative view of protein, gene and 3D structural information. Nucl. Acids Res. 45(D1), D271–D281 (2017)

111.

Hecker, E.A., Duraiswami, C., Andrea, T.A., Diller, D.J.: Use of catalyst pharmacophore models for screening of large combinatorial libraries. J. Chem. Inf. Comput. Sci. 42, 1204–1211 (2002)CrossRef

112.

Wolber, G., Langer, T.: LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J. Chem. Inf. Model. 45(1), 160–169 (2005)CrossRef

113.

Liu, X., Ouyang, S., Yu, B., Liu, Y., Huang, K., Gong, J., Zheng, S., Li, Z., Li, H., Jiang, H.: PharmMapper server: a web server for potential drug target identification using pharmacophore mapping approach. Nucl. Acids Res. 38, W609–W614 (2010)CrossRef

114.

Rohilla, A., Khare, G., Tyagi, A.K.: Virtual screening, pharmacophore development and structure based similarity search to identify inhibitors against IdeR, a transcription factor of Mycobacterium tuberculosis. Sci. Rep. 7, 4653 (2017)CrossRef

115.

Yadav, D., Paliwal, S., Yadav, R., Pal, M., Pandey, A.: Identification of novel HIV 1-protease inhibitors: application of ligand and structure based pharmacophore mapping and virtual screening. PLoS ONE 7(11), e48942 (2012)CrossRef

116.

Kumar, A., Zhang, K.Y.J.: Hierarchical virtual screening approaches in small molecule drug discovery. Methods. Epub 27 July 2014

117.

Alqahtani, S.: In silico ADME–Tox modeling: progress and prospects. Exp. Opin. Drug Metab. Toxicol. 13(11), 1147–1158 (2017)CrossRef

118.

Kaur, P., Chamberlin, A.R., Poulos, T.L., Sevrioukova, I.F.: Structure-based inhibitor design for evaluation of a CYP3A4 pharmacophore model. J. Med. Chem. 59(9), 4210–4220 (2016)CrossRef

119.

Kratz, J.M., Schuster, D., Edtbauer, M., Saxena, P., Mair, C.E., Kirchebner, J., et al.: Experimentally validated hERG pharmacophore models as cardiotoxicity prediction tools. J. Chem. Inf. Model. 54(10), 2887–2901 (2014)CrossRef

120.

Liu, T., Lin, Y., Wen, X., Jorissen, R.N., Gilson, M.K.: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucl. Acids Res. 35, D198–D201 (2007)CrossRef

121.

Kim, S., Thiessen, P.A., Bolton, E.E., Chen, J., Fu, G., Gindulyte, A.: Nucl. Acids Red. 78, 1–12 (2015)

122.

ACD/ChemSketch (Freeware) 2017.2.1. Advanced Chemistry Development, Inc

123.

Discovery Studio Client, v2.5.0.9164. Accelrys Software Inc

124.

Schneidman-Duhovny, D., Dror, O., Inbar, Y., Nussinov, R., Wolfson, H.J.: PharmaGist: a webserver for ligand-based pharmacophore detection. Nucl. Acids Res. 36, W223–W228 (2008)CrossRef

125.

Lunagariya, N.A., Patel, N.K., Jagtap, S.C., Bhutani, K.K.: Inhibitors of pancreatic lipase: state of the art and clinical perspectives. Excli J. 13, 897–921 (2014)

126.

Sharma, N.K., Ahirwar, D.: A review on herbal medicinal plants for the treatment of obesity. J. Harm. Res. 2, 01–33 (2013)

127.

Sukhdev, S., Singh, K.S.: Therapeutic role of phytomedicines on obesity: importance of herbal pancreatic lipase inhibitors. Int. Res. J. Med. Sci. 1(9), 15–26 (2013)

128.

Wu, S.B.A., Dastmalchi, K., Long, C.L., Kennelly, E.J.: Metabolite profiling of jaboticaba (Myrciaria cauliflora) and other dark-colored fruit juices. J. Agric. Food Chem. 60, 7513–7525 (2012)CrossRef

129.

Hussein, S.A.M., Hashem, A.N.M., Seliem, M.A., Lindequist, U., Nawwar, M.A.M.: Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry 64, 883–889 (2003)CrossRef

130.

Einbond, L.S., Reynertson, K.A., Luo, X.D., Basile, M.J., Kennelly, E.J.: Anthocyanin antioxidants from edible fruits. Food Chem. 1(84), 23–28 (2004)CrossRef

131.

Vidigal, M.C.T.R., Minim, V.P.R., Carvalho, N.B., Milagres, M.P., Gonçalves, A.C.A.: Effect of a health claim on consumer acceptance of exotic Brazilian fruit juices: Açaí (Euterpe oleracea Mart.), camu-camu (Myrciaria dubia), Cajá (Spondias lutea L.) and Umbu (Spondias tuberosa Arruda). Food Res. Int. 44(7), 1988–1996 (2011)CrossRef

132.

Chirinos, R., Galarza, J., Betalleluz-Pallardel, I., Pedreschi, R., Campos, D.: Antioxidant compounds and antioxidant capacity of Peruvian camu camu (Myrciara dubia [H.B.K.] McVaugh) fruit at different maturity stages. Food Chem. 120, 1019–1024 (2010)CrossRef

133.

Akter, M.S., Oh, S., Eun, J.B., Ahmed, M.: Nutritional compositions and health promoting phytochemicals of camu-camu (Myrciaria dubia) fruit: a review. Food Res. Int. 44, 1728–1732 (2011)CrossRef

134.

Tietbohl, L.A.C., Lima, B.G., Fernandes, C.P., Santos, M.G., Silva, F.E.B., Denardin, E.L.G., Bachinski, R., Alves, G.G., Silva-Filho, M.V., Rocha, L.: Comparative study and anticholinesterasic evaluation of essential oils from leaves, stems and flowers of Myrciaria floribunda (H. West ex Willd.) O. Berg. Lat. Am. J. Pham. 31(4), 637–641 (2012)

135.

Apel, M.A., Sobral, M., Zuanazzi, J.A., Henriques, A.T.: Essential oil composition of four Plini species (Myrtaceae). Flavour Frag. J. 21, 565–567 (2006)CrossRef

136.

Sergent, T., Vanderstraeten, J., Winand, J., Beguin, P., Schneider, Y.J.: Phenolic compounds and plant extracts as potential natural anti-obesity substances. Food Chem. 135(1), 68–73 (2012)CrossRef

137.

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. 53(11), 4593–4598 (2005)CrossRef

138.

Hu, B., Cui, F., Yin, F., Zeng, X., Sun, Y., Li, Y.: Coffeoylquinic acids competitively inhibit pancreatic lipase through binding to the catalytic triad. Int. J. Biol. Macromol. 80, 529–535 (2015)CrossRef

139.

Bentley, D., Young, A.M., Rowell, L., Gross, G., Tardio, J., Carlile, D.: Evidence of a drug-drug interaction linked to inhibition of ester hydrolysis by orlistat. J. Cardiovasc. Pharmacol. 60(4), 390–396 (2012)CrossRef

140.

King, A.R., Lodola, A., Carmi, C., Fu, J., Mor, M., Piomelli, D.: A critical cysteine residue in monoacylglycerol lipase is targeted by a new class of isothiazolinone-based enzyme inhibitors. Br. J. Pharmacol. 157(6), 974–983 (2009)CrossRef

Titel: Pharmacophore Mapping of Natural Products for Pancreatic Lipase Inhibition
verfasst von: Matheus Gabriel de Oliveira
Waléria Ramos Nogueira de Souza
Ricardo Pereira Rodrigues
Daniel F. Kawano
Leonardo Luiz Borges
Vinicius Barreto da Silva
Verlag: Springer International Publishing
Buch: Emerging Research in Science and Engineering Based on Advanced Experimental and Computational Strategies
Print ISBN: 978-3-030-31402-6

Electronic ISBN: 978-3-030-31403-3

Copyright-Jahr: 2020
DOI: https://doi.org/10.1007/978-3-030-31403-3_12

Premium Partner

Marktübersichten

Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.

Zur Marktübersicht