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.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
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)
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)
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)
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)
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)
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)
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)
Myoda, T., Fujimura, S., Park, B., Nagashima, T., Nakagawa, J., Nishizawa, M.: Exotic fruits reference guide. J. Food Agric. Environ. 8, 304–307 (2010)
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)
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)
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)
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)
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)
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)
Harvey, A.L.: Natural products in drug discovery. Drug Disc. Today 13, 894–901 (2008)
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)
Strohl, W.R.: The role of natural products in a modern drug discovery program. Drug Disc. Today 5, 39–41 (2000)
Harvey, A.: Strategies for discovering drugs from previously unexplored natural products. Drug Disc. Today 5, 294–299 (2000)
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)
WHO: National policy on traditional medicine and regulation of herbal medicines: report of a WHO global survey. World Health Organization, Geneva, Switzerland (2005)
Balunas, M.J., Kinghorn, A.D.: Drug discovery from medicinal plants. Life Sci. 78, 431–441 (2005)
Sharma, S.B., Gupta, R.: Drug development from natural resource: a systematic approach. Mini. Rev. Med. Chem. 15, 52–57 (2015)
Ghorbani, A., Naghibi, F., Mosaddegh, M.: Ethnobotany, ethnopharmacology and drug discovery. Iran. J. Pharm. Sci. 2, 109–118 (2006)
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)
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)
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)
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)
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)
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)
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)
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)
World Health Organization: Obesity and Overweight (2014). http://www.who.int/mediacentre/factsheets/fs311/en/
World Health Organization: Obesity and Overweight (2016). https://www.who.int/gho/ncd/risk_factors/overweight/en/
GBD 2015 Obesity Collaboration: Health effects of overweight and obesity in 195 countries over 25 years. N. Engl. J. Med. 377, 13–27 (2017)
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)
Racette, S.B., Deusinger, S.S., Deusinger, R.H.: Obesity: overview of prevalence, etiology, and treatment. Phys. Ther. 83(3), 276–288 (2003)
Kaila, B., Raman, M.: Obesity: a review of pathogenesis and management strategies. Can. J. Gastroenterol. 22(1), 61–68 (2008)
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)
Yanovski, S.Z., Yanovski, J.A.: Long-term drug treatment of obesity. A systematic and clinical review. JAMA 311, 74–86 (2014)
Joo, J.K., Lee, K.S.: Pharmacotherapy for obesity. J. Menopausal Med. 20(3), 90–96 (2014)
Srivastava, G., Apovian, C.M.: Current pharmacotherapy for obesity. Nat. Rev. Endocrinol. 14(1), 12–24 (2018)
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)
Drew, B.S., Dixon, A.F., Dixon, J.B.: Obesity management: update on orlistat. Vasc. Health Risk Manag. 3, 817–821 (2007)
Wang, H., Eckel, R.: Lipoprotein lipase: from gene to obesity. Am. J. Physiol. Endocrinol. Metab. 297, E271–E288 (2009)
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)
Winkler, F.K., D’Arcy, A., Hunziker, W.: Structure of human pancreatic lipase. Nature 343, 771–774 (1990)
Lowe, M.E.: Structure and function of pancreatic lipase and colipase. Annu. Rev. Nutr. 17, 141–158 (1997)
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-10-69
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)
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)
Buchholz, T., Melzig, M.F.: Polyphenolic compounds as pancreatic lipase inhibitors. Planta Med. 81, 771–783 (2015)
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)
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)
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)
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)
Birari, R., Roy, S.K., Singh, A., Bhutani, K.: Pancreatic lipase inhibitory alkaloids of Murraya koenigii leaves. Nat. Prod. Commun. 4, 1089–1092 (2009)
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)
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)
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)
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)
Camlofski, A.M.: Caracterização do fruto de Cerejeira ‘Eugenia Involocrata DC’ visando seu aproveitamento tecnológico. Dissertation, Universidade Estadual de Ponta Grossa, Ponta Grossa (2008)
IPNI: The International Plant Name Index (http://www.ipni.org/). In: The Royal Botanic Gardens. The Harvard University Herbaria; Australian National Herbarium, Kew (2012)
Mattos, J.R.: Jaboticabeiras. Instituto de Pesquisas de Recursos Naturais Renováveis. Porto Alegre, AP (1983)
Donadio, L.C.: Jabuticaba (Myrciaria jaboticaba (Vell.) Berg). Jaboticabal, Funep (2000)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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. Bioorg. Med. Chem. 20(14), 4549–4555 (2012)
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)
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)
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)
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)
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)
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)
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)
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_5
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)
Yang, S.-Y.: Pharmacophore modeling and applications in drug discovery: challenges and recent advances. Drug Discov. Today 15, 444–450 (2010)
Langer, T.: Pharmacophores in drug research. Mol. Inf. 29, 470–475 (2010)
Kutlushina, A., Khakimova, A., Madzhidov, T., Polishchuk, P.: Ligand-based pharmacophore modeling using novel 3D pharmacophore signatures. Molecules 23, 3094 (2018)
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 2018
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)
Kim, S., Thiessen, P.A., Bolton, E.E., et al.: PubChem substance and compound databases. Nucl. Acids Res. 44(D1), D1202–D1213 (2016)
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)
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)
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)
Dassault Systèmes BIOVIA: Discovery Studio v. 4.0, Dassault Systèmes, San Diego (2012)
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)
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/ci049885e
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)
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)
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)
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)
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)
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)
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)
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)
Kumar, A., Zhang, K.Y.J.: Hierarchical virtual screening approaches in small molecule drug discovery. Methods. Epub 27 July 2014
Alqahtani, S.: In silico ADME–Tox modeling: progress and prospects. Exp. Opin. Drug Metab. Toxicol. 13(11), 1147–1158 (2017)
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)
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)
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)
Kim, S., Thiessen, P.A., Bolton, E.E., Chen, J., Fu, G., Gindulyte, A.: Nucl. Acids Red. 78, 1–12 (2015)
ACD/ChemSketch (Freeware) 2017.2.1. Advanced Chemistry Development, Inc
Discovery Studio Client, v2.5.0.9164. Accelrys Software Inc
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)
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)
Sharma, N.K., Ahirwar, D.: A review on herbal medicinal plants for the treatment of obesity. J. Harm. Res. 2, 01–33 (2013)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 Springer Nature Switzerland AG
About this chapter
Cite this chapter
de Oliveira, M.G., de Souza, W.R.N., Rodrigues, R.P., Kawano, D.F., Borges, L.L., da Silva, V.B. (2020). Pharmacophore Mapping of Natural Products for Pancreatic Lipase Inhibition. In: La Porta, F., Taft, C. (eds) Emerging Research in Science and Engineering Based on Advanced Experimental and Computational Strategies. Engineering Materials. Springer, Cham. https://doi.org/10.1007/978-3-030-31403-3_12
Download citation
DOI: https://doi.org/10.1007/978-3-030-31403-3_12
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-31402-6
Online ISBN: 978-3-030-31403-3
eBook Packages: EngineeringEngineering (R0)