African Journal of
Pharmacy and Pharmacology

  • Abbreviation: Afr. J. Pharm. Pharmacol.
  • Language: English
  • ISSN: 1996-0816
  • DOI: 10.5897/AJPP
  • Start Year: 2007
  • Published Articles: 2288

Full Length Research Paper

Cubebin and semisynthetic dibenzyl butyrolactone derivatives: Biological activities

Pereira C.C. S. S.
  • Pereira C.C. S. S.
  • Faculty of Pharmaceutical Sciences, University of Campinas, Campinas, São Paulo, Brazil.
  • Google Scholar
Perazzo, F. F.
  • Perazzo, F. F.
  • Departamento de Ciências Exatas e da Terra, Diadema, University Federal of São Paulo, São Paulo, Brazil.
  • Google Scholar
Souza G. H. B.
  • Souza G. H. B.
  • Department of Pharmacy, University Federal of Ouro Preto, School of Pharmacy, Ouro Preto, Minas Gerais, Brazil. 4ABC Foundation School of Medicine, Santo André, São Paulo, Brazil.
  • Google Scholar
Fonseca, F. L. A.
  • Fonseca, F. L. A.
  • Departamento de Ciências Exatas e da Terra, Diadema, University Federal of São Paulo, São Paulo, Brazil.
  • Google Scholar
Rosa P. C. P
  • Rosa P. C. P
  • Faculty of Pharmaceutical Sciences, University of Campinas, Campinas, São Paulo, Brazil.
  • Google Scholar


  •  Received: 18 November 2015
  •  Accepted: 17 June 2016
  •  Published: 08 July 2016

References

 

Aboul-Eneim HY, Kladna A, Kruk I (2011). Radical scavenging ability of some compounds isolated from Piper cubeba towards free radicals. Luminescence 26:202-207.
Crossref

 

Aas JA, Griffen AL, Dardis SR, Lee AM, Olsen I, Dewhirst FE (2008). Bacteria of dental caries in primary and permanent teeth in children and young adults. J. Clin. Microbiol. 46:1407-1417.
Crossref

 
 

Achike FI, Kwan CY (2003). Nitric oxide, human diseases and the herbal products that affect the nitric oxide signalling pathway. Clin. Exp. Pharmacol. Physiol. 30:605-615.
Crossref

 
 

Barbosa FJM (2004). Lignanas, Neolignanas E Seus Análogos. In: Simões CMO, Schenkel EP, Gosmann G, Mello JCP, Mentz LA, Petrovick PR (Org.). Farmacognosia: da planta ao medicamento, 5ª ed. Editora da UFRGS/Editora da UFSC, Porto Alegre/Florianópolis, Brasil pp. 557-575.

 
 

Barbosa LC, Furtado RA, Bertanha HCC, Tomazella IM, Costa ES, Bastos JK, Silva MLA, Tavares DC (2014). Chemopreventive Effects of (−)-Hinokinin against 1,2- Dimethylhydrazine-Induced Genotoxicity and Preneoplastic Lesions in Rat Colon. J. Nat. Prod. 77:2312-2315.
Crossref

 
 

Bastos JK, Albuquerque S, Silva MLA (1999). Evaluation of the trypanocidal activity of lignans isolated from the leaves of Zanthoxylum naranjillo. Planta Medica 65:541-544.
Crossref

 
 

Bastos JK, Carvalho JC, De Souza GH, Pedrazzi AH, Sarti SJ (2001). Antiinflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb. J. Ethnopharmacol. 75:279-282.
Crossref

 
 

Bates PA (2007). Transmission of Leishmania metacyclic promastigotes by phle- botominesa nd flies. Int. J. Parasitol. 37(10):1097–106. .
Crossref

 
 

Blumenthal EEA, Da Silva MS, Yoshida M (1997). Lignoids, flavonoids and polyketides of Virola surinamensis. Phytochemistry 46(4):745-749.
Crossref

 
 

Bodiwala HS, Singh G, Singh R, Dey CS, Sharma SS, Bhutani KK, Singh IP (2007). Antileishmanial amides and lignans from Piper cubeba and Piper retrofractum. J. Natural Med. 61:418-421.
Crossref

 
 

Carvalho PB, Ferreira EI (2001). Leishmaniasis phytotherapy. Nature's leadership against an ancient disease. Fitoterapia 72:599–618.
Crossref

 
 

Carvalho MTM, Rezende KCS, Evora PRB, Bastos JK, Cunha WR, Silva MLA, Celotto AC (2013). The Lignan (-)-Cubebin Inhibits Vascular Contraction and Induces Relaxation Via Nitric Oxide Activation in Isolated Rat Aorta. Phytother. Res. Res. 27:1784–1789
Crossref

 
 

Chan-Bacab MJ, Pena-Rodrigues LM (2001). Plant natural products with leishmanicidal activity. Nat. Prod. Rep. 18:674–688
Crossref

 
 

Coimbra H, Dos S, Royo V, De A, De Souza VA, Pereira AC, De Souza GHB, Da Silva R, Donate PM, Silva MLA, Cunha WR, Carvalho JCT, Bastos JK (2004). Analgesic and anti-inflammatory activities of (-)-o benzyl cubebin, a (-)-cubebin derivative ,obtainned by partial syntesis. Boll. Chim. Farmac. - Anno 143 - n. 2 Marzo 2004.

 
 

Coura JC (2009). Present situation and new strategies for Chaga's disease chemotherapy – a proposal. Mem. Inst. Oswaldo Cruz. 104:549-554.
Crossref

 
 

De Pascoli IC, Nascimento IR, Lopes LM (2006). Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens. Phytochemistry 67(7):735-742.
Crossref

 
 

De Rezende AAA, Silva MLA, Tavares DC, Cunha WR, Rezende KCS, Bastos JK, Lehmann M, De Andrade HHR, Guterres ZR, Silva LP, Spano MA (2011). The effect of the dibenzylbutyrolactolic lignan (-)-cubebin on doxorubicin mutagenicity and recombinogenicity in wing somatic cells of Drosophila melanogaster. Food Chem. Toxicol. 49:1235-1241.
Crossref

 
 

De Rezende AAA, Munari CC, De Oliveira PF, Ferreira NH, Tavares DC, Silva MLA, Rezende KCS, Spano MA (2013). A comparative study of the modulatory effects of (-)-cubebin on the mutagenicity/recombinogenicity induced by different chemical agents. Food Chem.Toxicol. 55:645-652.
Crossref

 
 

De Souza VA, Silva R, Pereira AC, Royo VA, Saraiva J, Montanheiro M, Souza GHB, Filho AAS, Grando MD, Donate PM, Bastos JK, Albuquerque S,Silva MLA (2005). Trypanocidal activity of (_)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi. Bioorganic Medicinal Chem. Letters 15:303-307.
Crossref

 
 

Edelstein B (2006). The dental caries pandemic and disparities prob¬lem. BMC Oral. Health. 15:(Suppl 1)S2.
Crossref

 
 

Esperandim VR, Ferreira DS, Saraiva J, Silva MLA, Costa EV, Pereira AC, Bastos JK, Albuquerque S (2010). Reduction of parasitism tissue by treatment of mice chronically infected with Trypanosoma cruzi with lignano lactones. Parasitol. Res. 107:525-530.
Crossref

 
 

Esperadim VR, Ferreira DS, Rezende KCS, Cunha WR, Saraiva J, Bastos JK, Silva MLA, Albuquerque S (2013). Evaluation of the in vivo therapeutic properties of cubebin and hinokinin against Trypanosoma cruzi. Experimental Parasitol. 133:442-446.
Crossref

 
 

Featherstone JDB (2004). The continuum of dental caries-evidence for a dynamic disease process. J. Dent. Res. 83:39-42.
Crossref

 
 

Hardman JG, Molinoff PB, Gilman AG (1996). Goodman e Gilman: As bases farmacológicas da terapêutica. 9a ed. Rio de Janeiro: McGraw-Hill. pp. 453-454.

 
 

Hoiby JS, Ciofu NO, Johansen HK (2011). The clinical impact of bacterial biofilms. Int. J. Oral. Sci. 3:55-65.
Crossref

 
 

Impotence (1992). NIH Consens Statement. 10:1.

 
 

Junqueira APF, Perazzo FF, Souza GHB, Maistro EL (2007). Clastogenicity of Piper cubeba (Piperaceae) seed extract in an in vivo mammalian cell system. Genetics Molecular Biol. 30:656-663.
Crossref

 
 

Mainenti P, Rosa LEB (2008). Carcinogênese química experimental em glândulas salivares – revisão da literatura. Revista Brasileira de Cancerologia. 54(2):167-174.

 
 

Moncayo A, Ortiz Yanine MI (2006). An update on Chaga's disease human American trypanosomiasis. Ann. Trop. Med. Parasitol. 100:663-677.
Crossref

 
 

Murray HW, Berman JD, Davies CR, Saravia NG (2005). Advances in leishmaniasis. Lancet 366(9496):1561-77.
Crossref

 
 

Parkington HC Coleman HA, Tare M (2004). Prostacyclin and endothelium-dependent hyperpolarization. Pharmacol. Res. 49:509-514.
Crossref

 
 

Pessuto MB, Da Costa IC, De Souza AB, Nicoli FM, De Melo JCP, Petereit F, Luftmann H (2009). Atividade antioxidante de extratos e taninos condensados das folhas de Maytenus ilicifolia Mart. es Reiss. Química Nova 32(2):412-416.
Crossref

 
 

Rao CBS (1978). Chemistry of lignans, University Press, Andhra Pradesh, India, p. 213.

 
 

Rajalekshmi DS, Kabeer FA, Madhusoodhanan AR, Bahulayan AK, Prathapan R, Prakasan N, Varughese S, Nair MS (2016). Anticancer activity studies of cubebin isolated from Piper cubeba and its synthetic derivatives. Bioorganic Med. Chem. Lett. 26:1767-1771.
Crossref

 
 

Rassi Jr A, Rassi A, Marin-Neto JA (2010). Chagas's disease. Lancet 375 :1388-1402.
Crossref

 
 

Ready PD (2014). Epidemiology of visceral leishmaniasis. Clin. Epidemiol. 6:147–54.
Crossref

 
 

Reitz PR (1960). Flora ilustrada Catarinense, first Ed. Santa Catarina, Brazil, pp. 13-14.

 
 

Rodrigues ER (2002). Estudos pré-clínicos de possíveis efeitos adversos da cubebina. Ribeirão Preto. (Tese Doutorado – Faculdade de Ciências Farmacêuticas de Ribeirão Preto – USP).

 
 

Saleem M, Kim HJ, Alic MS, Lee YS (2007). An update on management of Chagas cardiomyopathy. Expert review of anti-infective therapy. Englant, 5:727-743.

 
 

Salman SM, Rubeiz NG, Kibbi AG (1999). Cutaneous leishmaniasis: clinical features and diagnosis. Clin. Dermatol. 17(3):291-296.
Crossref

 
 

Saraiva J, Vega C, Rolon M, Da Silva R, Silva MLA, Donate PM, Bastos JK, Gomez-Barrio A, De Albuquerque S (2007). In vitro and in vivo activity of lignan lactones derivatives against Trypanosoma cruzi. Parasitol. Res. 100:791-795.
Crossref

 
 

Saraiva J, Siqueira CM, Silva CHTP, Barreto VB, Tudella VG, Silva R, Andrade ESML, Dorta DJ, Bastos JK, Uyemura SA, De Albuquerque S, Curti C (2009). Cubebin and derivatives as inhibitors of mitochondrial complex I.Proposed interaction with subunit B8. J. Enzyme Inhib. Med. Chem. 24:599-606.
Crossref

 
 

Selwitz RH, Ismail AI, Pitts NB (2007). Dental caries. The Lancet. 369:51-59.
Crossref

 
 

Silva R, Souza GHB, Silva AA, Souza VA, Pereira AC, Royo VA, Silva MLA, Donate PM, Araújo ALSM, Carvalho JCT, Bastos JK (2005). Synthesis and biological activity evaluation of lignin lactones derived from (-)-cubebin. Bioorganic Med. Chem. Lett. 15:1033-1037.
Crossref

 
 

Silva ML, Coimbra HS, Pereira AC, Almeida VA, Lima TC, Costa ES, Vinholis AH, Royo VA, Silva R, Filho AA, Cunha WR, Furtado NA, Martins CH, Carvalho TC, Bastos JK (2007). Evaluation of Piper cubeba extract, (-)-cubebinand its semi-synthetic derivatives against oral pathogens. Phytother. Res. 21:420-422.
Crossref

 
 

Silva MLA, Cicarelli RMB, Pauletti PM, Luz PP, Rezende KCS, Januario AH, Da Silva R, Pereira AC, Bastos JK, De Albuquerque S, Magalhaes LG, Cunha WR (2011). Trypanosoma cruzi: evaluation of (-)-cubebin derivatives activity in the messenger RNAs processing. Parasitol. Res. 109:445-451.
Crossref

 
 

Simões CMO, Schenkel EP, Gosmann G, Mello JCP De Mentz LA, Petrovick PR (1999). Farmacognosia: da Planta ao medicamento. Porto Alegre/Florianópolis: Ed. Universidade / UFRGS / Ed.da UFSC, p. 821.

 
 

Sinigaglia M, Lehmann M, Barumgardt P, Amaral VS, Dihl RR, Reguly ML, De Andrade HHR (2006). Vanillin as a modulator agent in SMART test: inhibitionin the steps that precede N-methyl-N-nitrosourea-, N-ethyl-N-nitrosourea-,ethylmethanesulphonate- and bleomycin-genotoxicity. Mutat. Res. 607:225-230.
Crossref

 
 

Souza GHB, Da Silva Filho AA, Pereira AC, De A, Royo VE, Silva MLA, Da Silva MLA, Da Silva R, Donate PM, Carvalho JCT, Bastos JK (2004). Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl,(-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-)-cubebin. II Farmaco 59:55-61.
Crossref

 
 

Souza VA, Silva R, Pereira AC, Royo VA, Saraiva J, Montanheiro M, Souza GHB, Filho AA, Da S, Grando MD, Donate MD, Bastos JK, Albuquerme S, Silva MLA (2005). Trypanocidal activity of ()-cubebin derivatives against freeamastigote forms of Trypanosomacruzi. Bioorganic Med. Chem. Lett. 15:303-307.
Crossref

 
 

Stutz A, Golenbock DT, Latz E (2009). Science in medicine: Inflammasomes: too big to miss. The Journal of Clinical Investigation 119(12):3502-3511.
Crossref

 
 

Tanzer JM, Livingston J, Thompson AM (2001).The micro-biology of primary dental caries in humans. J. Dent. Educ. 65:128-137.

 
 

Usia T, Watabe T, Kadota S, Tezuka Y (2005). Metabolite-cytochrome P450 complex formation by methylenedioxyphenyl lignans of Piper cubeba:mechanism-based inhibition. Life Sci. 76:2381-2391.
Crossref

 
 

Usia T, Iwata H, Hiratsuka A, Watabe T, Kadota S, Tezuka Y (2006). CYP3A4 and CYP2D6 inhibitory activities of Indonesian medicinal plants. Phytomedicine 13:67-73.
Crossref

 
 

Vainio H, Magee P, Mcgregor D, Mcmichael AJ (1992). Mechanisms of carcinogenesis in risk identification. Lyon: International Agency for Research on Cancer. pp. 8-54.

 
 

Vasconcelos SML, Goulart MOF, Moura JBF, Manfredini V, Benfato MS, Kubota LT (2007). Espécies reativas de oxigênio e de nitrogênio, antioxidantes e marcadores de danos oxidativos em sangue humano: principais métodos analíticos para sua determinação. Química Nova 30(5):1323-1338.
Crossref

 
 

Yam J, Kreuter M, Drewe J (2008). Piper cubeba targets multiple aspects of the androgen-signalling pathway. A potential phytotherapy against prostate cancer growth? Planta Medica 74:33-38.
Crossref