Antiproliferative effects of pinostrobin and 5,6-dehydrokavain isolated from leaves of Alpinia zerumbet

Revista Brasileira de Farmacognosia - Tập 27 - Trang 592-598 - 2017
Walter A. Roman Junior1,2, Denise B. Gomes1, Barbara Zanchet1, Amanda P. Schönell2, Kriptsan A.P. Diel2, Thais P. Banzato3, Ana L.T.G. Ruiz3, João E. Carvalho3,4, Angelita Neppel5, Andersson Barison5, Cid Aimbiré M. Santos6
1Programa de Pós-graduação em Ciências da Saúde, Universidade Comunitária da Região de Chapecó, Chapecó, SC, Brazil
2Grupo de Pesquisa em Fitoquímica e Farmacologia de Produtos Naturais, Universidade Comunitária da Região de Chapecó, Chapecó, SC, Brazil
3Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas, Divisão de Farmacologia e Toxicologia, Universidade Estadual de Campinas, Campinas, SP, Brazil
4Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Campinas, SP, Brazil
5Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil
6Laboratório de Farmacognosia, Departamento de Farmácia, Universidade Federal do Paraná, Curitiba, PR, Brazil

Tài liệu tham khảo

Almeida, 1993 Almeida, 2005, Câncer e agentes antineoplásicos ciclo-celular específicos e ciclo-celular não específicos que interagem com o DNA: uma introdução, Quim. Nova, 28, 118, 10.1590/S0100-40422005000100021 Apaya, 2016, Phytomedicine polypharmacology: cancer therapy through modulating the tumor microenvironment and oxylipin dynamics, Pharmacol. Ther., 162, 58, 10.1016/j.pharmthera.2016.03.001 Bevilaqua, 2016, Involvement of the catecholaminergic system on the antidepressant-like effects of Alpinia zerumbet in mice, Pharm. Biol., 54, 151, 10.3109/13880209.2015.1025287 Brandão, 2010, Química e farmacologia de quimioterápicos antineoplásicos derivados de plantas, Quim. Nova, 33, 1359, 10.1590/S0100-40422010000600026 Chompoo, 2011, Advanced glycation end products inhibitors from Alpinia zerumbet rhizomes, Food Chem., 12, 709, 10.1016/j.foodchem.2011.04.034 Correa, 2010, Alpinia zerumbet (Pers.) B.L. Burtt & R.M. Sm (Zingiberaceae): levantamento de publicações nas áreas farmacológica equímica para o período de 1987 a 2008, Rev. Bras. Pl. Med., 12, 113, 10.1590/S1516-05722010000100016 Costa-Lotufo, 2010, Contribuição dos produtos naturais como fonte de novos fármacos anticâncer: estudos no Laboratório Nacional de Oncologia Experimental da Universidade Federal do Ceará, Rev. Virtual. Quim., 2, 47 Elkady, 2016, Harmal extract induces apoptosis of HCT116 human colon cancer cells, mediated by inhibition of nuclear factor-(B and activator protein-1 signaling pathways and induction of cytoprotective genes, Asian Pac. J. Cancer Prev., 17, 1947, 10.7314/APJCP.2016.17.4.1947 Elzaawely, 2007, Antioxidant activity and contents of essential oil and phenolic compounds in flowers and seeds of Alpinia zerumbet (Pers.) B.L. Burtt & R.M. Sm, Food Chem., 104, 1648, 10.1016/j.foodchem.2007.03.016 Fouche, 2008, In vitro anticancer screening of South African plants, J. Ethnopharmacol., 119, 455, 10.1016/j.jep.2008.07.005 García-Lafuente, 2009, Flavonoids as anti-inflammatory agents: implications in cancer and cardiovascular disease, Inflamm. Res., 58, 537, 10.1007/s00011-009-0037-3 George, 2017, Plant flavonoids in cancer chemoprevention: role in genome stability, J. Nutr. Biochem., 45, 1, 10.1016/j.jnutbio.2016.11.007 Ghil, 2013, Antiproliferative activity of Alpinia officinarum extract in the human breast cancer cell line MCF-7, Mol. Med. Rep., 7, 1288, 10.3892/mmr.2013.1305 Harvey, 2015, The re-emergence of natural products for drug discovery in the genomics era, Nat. Rev. Drug Discov., 14, 111, 10.1038/nrd4510 Hema, 2009, Flavonoids and other constituents from the rhizomes of Alpinia calcarata, Biochem. Syst. Ecol., 37, 52, 10.1016/j.bse.2009.01.001 Itokawa, 1981, Phenolic compouds from the rhizomes of Alpinia speciosa, Phytochemistry, 20, 2503, 10.1016/0031-9422(81)83082-8 Iwashina, 2000, The structure and distribution of the flavonoids in plants, J. Plant Res., 113, 287, 10.1007/PL00013940 Krishna, 1973, Cardamonin and alpinetin from the seeds of Alpinia speciosa, Phytochemistry, 12, 238, 10.1016/S0031-9422(00)84672-5 Kristo, 2016, Protective role of dietary berries in cancer, Antioxidants, 5, 37, 10.3390/antiox5040037 Kumagai, 2016, 5,6-Dehydrokawain from Alpinia zerumbet promotes osteoblastic MC3T3-E1 cell differentiation I recommend a short morphological description of A. zerumbet, Biosci. Biotechnol. Biochem., 7, 1425, 10.1080/09168451.2016.1153959 Kuster, 1999, Determination of kava-pyrones in Alpinia zerumbet leaves, J. High Resolut. Chromatogr., 22, 129, 10.1002/(SICI)1521-4168(19990201)22:2<129::AID-JHRC129>3.0.CO;2-R Lahlou, 2003, Antihypertensive effects of the essential oil of Alpinia zerumbet and its main constituent, terpinen-4-ol, in DOCA-salt hypertensive conscious rats, Fundam. Clin. Pharmacol., 17, 323, 10.1046/j.1472-8206.2003.00150.x Laranja, 1991, Evaluation of acute administration of natural products with potential diuretic effects, in humans, Mem. Inst. Oswaldo Cruz, 86, 237, 10.1590/S0074-02761991000600053 Le Bail, 2000, Effects of pinostrobin on estrogen metabolism and estrogen receptor transactivation, Cancer Lett., 156, 37, 10.1016/S0304-3835(00)00435-3 Lee, 2005, Cytotoxicity of plants from Malaysia and Thailand used traditionally to treat cancer, J. Ethnopharmacol., 100, 237, 10.1016/j.jep.2005.01.064 Lin, 2008, Alpinia zerumbet potentially elevates high-density lipoprotein cholesterollevel in hamsters, J. Agric. Food Chem., 56, 4435, 10.1021/jf800195d Lorenzi, 2002 Lorenzi, 2008 Markham, 1978, Carbon-13 NMR studies of flavonoids. III. Naturally occurring flavonoid glycosides and their acylated derivatives, Tetrahedron, 34, 1389, 10.1016/0040-4020(78)88336-7 McGuire, 2016, World Cancer Report 2014. Geneva, Switzerland: World Health Organization, International Agency for Research on Cancer, WHO Press, 2015, Adv. Nutr., 7, 418, 10.3945/an.116.012211 Mendonça, 1991, Pharmacological and toxicological evaluation of Alpinia speciosa, Mem. Inst. Oswaldo Cruz, 86, 93, 10.1590/S0074-02761991000600023 Mohamad, 2004, DPPH free radical scavenger components from the fruits of Alpinia rafflesiana Wall. ex. Bak. (Zingiberaceae), Z. Naturforsch., 59, 11 Monks, 1991, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst., 83, 757, 10.1093/jnci/83.11.757 Mpalatinos, 1998, Biologically active flavonoids and kava pyrones from the aqueous extract of Alpinia zerumbet, Phytother. Res., 12, 442, 10.1002/(SICI)1099-1573(199809)12:6<442::AID-PTR320>3.0.CO;2-Y Newman, 2016, Natural products as sources of new drugs over the period 1981–2014, J. Nat. Prod., 79, 629, 10.1021/acs.jnatprod.5b01055 Pinto, 2009, Endothelium-dependent vasorelaxant effects of the essential oil from aerial parts of Alpinia zerumbet and its main constituent 1,8-cineole in rats, Phytomedicine, 16, 1151, 10.1016/j.phymed.2009.04.007 Prakash, 2013, Anticancer potential of plants and natural products: a review, Am. J. Pharmacol. Sci., 1, 104 Pugialli, 1993, Chemotaxonomy of superorder Zingiberiflorae (sensu Dahlgren) I. Flavonoids, Acta Bot. Bras., 7, 135, 10.1590/S0102-33061993000200009 Ramirez, 2013, Antifungal activity of raw extract and flavanons isolated from Piper ecuadorense from Ecuador, Rev. Bras. Farmacogn., 23, 370, 10.1590/S0102-695X2013005000012 Rowe, 2011, Toxicokinetics of kava, Adv. Pharmacol. Sci., 1, 1 Saboo, 2014, An organized assessment of species of plants of Alpinia genera, belonging to family Zingiberaceae, Am. J. Ethnomed., 2, 102 Samarghandian, 2014, Antiproliferative activity and induction of apoptotic byethanolic extract of Alpinia galanga rhizhome in human breast carcinoma cell line, BMC Complement. Altern. Med., 14, 1, 10.1186/1472-6882-14-192 Sayre, 2012, Stereospecific analytical method development and preliminary in vivo pharmacokinetic characterization of pinostrobin in the rat, Biomed. Chromatogr., 27, 548, 10.1002/bmc.2834 Sayre, 2015, Pre-clinical pharmacokinetic and pharmacodynamic characterization of selected chiral flavonoids: pinocembrin and pinostrobin, J. Pharm. Pharm. Sci., 4, 368, 10.18433/J3BK5T Sharma, 2014, Cell cycle inhibitory activity of Piper longum against A549 cell line and its protective effect against metal-induced toxicity in rats, Indian J. Biochem. Biophys., 51, 358 Sharma, 2016, Medicinal attributes of major phenylpropanoids present in cinnamon, BMC Complement. Altern. Med., 16, 156, 10.1186/s12906-016-1147-4 Siegel, 2016, Cancer statistics, CA Cancer J. Clin., 66, 7, 10.3322/caac.21332 Siekmann, 2013, The antiproliferative effect of pinostrobin on human umbilical vein endothelial cells (HUVEC), Eur. Rev. Med. Pharmacol. Sci., 17, 668 Smolarz, 2006, Pinostrobin – an anti-leukemic flavonoid from Polygonumla pathifolium L. ssp. nodosum (Pers.) Dans, Z. Naturforsch., 61, 64, 10.1515/znc-2006-1-212 Sukardiman, 2000, Cytotoxic mechanism of flavonoid from Temu Kunci (Kaempferia pandurata) in cell culture of human mammary carcinoma, Clin. Hemorheol. Microcirc., 23, 185 Topcul, 2014, Endpoint of cancer treatment: targeted therapies, Asian Pac. J. Cancer Prev., 15, 4395, 10.7314/APJCP.2014.15.11.4395 Victório, 2009, Vasodilator activity of extracts of field Alpinia purpurata (Vieill) K. Schum and A. zerumbet (Pers.) Burtt et Smith cultured in vitro, Braz. J. Pharm. Sci., 45, 507, 10.1590/S1984-82502009000300017 Xuan, 2015, Dihydro-5,6-dehydrokavain (DDK) from Alpinia zerumbet: its isolation, synthesis, and characterization, Molecules, 20, 16306, 10.3390/molecules200916306