The genus Caesalpinia L. (Caesalpiniaceae): Phytochemical and pharmacological characteristics

Molecules

Volumn 17, Issue 7, 2012, Pages 7887-7902

  Baldim Zanin, João L ^a   De Carvalho, Bianca A ^a   Martineli, Paloma Salles ^a   Dos Santos, Marcelo Henrique ^a   Lago, João Henrique G ^b   Sartorelli, Patrícia ^b   Viegas, Cláudio ^a   Soares, Marisi G ^a  

^a FEDERAL UNIVERSITY OF ALFENAS   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Biological activity; Caesalpinia; Phenolic derivatives; Terpenoids

Indexed keywords

ANTIINFECTIVE AGENT; ENZYME INHIBITOR; PHENOL DERIVATIVE; PLANT EXTRACT; TRITERPENE;

CAESALPINIA; CHEMISTRY; ISOLATION AND PURIFICATION; PHYTOTHERAPY; REVIEW;

ANTI-INFECTIVE AGENTS; CAESALPINIA; ENZYME INHIBITORS; PHENOLS; PHYTOTHERAPY; PLANT EXTRACTS; TRITERPENES;

EID: 84864625051     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17077887     Document Type: Article

References (65)

1. Rates, S.M.K. Plants as source of drugs. Toxicon 2000, 39, 603-613.
2. Pinto, A.C.; Silva, D.H.S.; Bolzani, V.S.; Lopes, N.P.; Epifanio, R.A. Produtos naturais: Atividade, desafios e perspectivas. Quim. Nova 2002, 25, 45-61.
3. Niero, R.; Malheiros, A.; Bittencourt, C.M.S.; Biavatti, M.W.; Leite, S.N.; Cechinel-Filho, V. Aspectos químicos e biológicos de plantas medicinais e considerações sobre fitoterápicos. In Ciências Farmacêuticas: Contribuição ao desenvolvimento de novos fármacos e medicamentos; Bresolin, T.M.B., Cechinel Filho, V., Eds.; Univali: Itajaí, Brazil, 2003; pp. 10-56.
4. Elisabetsky, E. Sociopolitical, economical and ethical issues in medicinal plant research. J. Ethnopharmacol. 1991, 32, 235-239.
5. Pinto, A.C. O Brasil dos viajantes e exploradores e a Química de Produtos Naturais Brasileira. Quim Nova 1995, 18, 608-615.
6. Srinivas, K.V.N.S.; Rao, Y.K.; Das, I.M.B.; Krishna, K.V.S.R.; Kishore, K.H.; Murty, U.S.N. Flavanoids from Caesalpinia pulcherrima. Phytochemistry 2003, 63, 789-793. (Pubitemid 36903592)
7. Nagumo, S.; Whasiyama, M.; Sasaki, Y.; Hosokawa, T. Anti-inflammatory constituents of Sappan lignum. Biol. Pharm. Bull. 2009, 32, 941-944.
8. Udenigwe, C.C.; Ata, A.; Samarasekera, R. Glutathione S-transferase inhibiting chemical constituents of Caesalpinia bonduc. Chem. Pharm. Bull. 2007, 55, 442-445. (Pubitemid 46513410)
9. Hemalatha, K.; Kiran, A.S.; Bannappa, U.; Satyanarayana, D. Analgesic activity of Caesalpinia sappan heartwood. Pharm. Biol. 2007, 45, 360-362. (Pubitemid 46911983)
10. Carvalho, J.C.T.; Teixeira, J.R.M.; Souza, P.J.C.; Bastos, J.K.; Filho, D.S.; Sarti, S.J. Preliminary studies of analgesic and anti-inflammatory properties of Caesalpinia ferrea crude extract. J. Ethnopharmacol. 1996, 53, 175-178. (Pubitemid 26306229)
11. Shukla, S.; Mehta, A.; Mehta, P.; Vyas, S.P.; Shukla, S.; Bajpai, V.K. Studies on anti-inflammatory, antipyretic and analgesic properties of Caesalpinia bonducella F. seed oil in experimental animal models. Food Chem. Toxicol. 2010, 48, 61-64.
12. Archana, P.; Tandan, S.K.; Chandra, S.; Lal, J. Antipyretic and analgesic activities of Caesalpinia bonducella seed kernel extract. Phytother. Res. 2005, 19, 376-381. (Pubitemid 41285002)
13. Devi, R.A.; Tandan, S.K.; Kumar, D.; Dudhgaonkar S.P.; Lal, J. Analgesic activity of Caesalpinia bonducella flower extract. Pharm. Biol. 2008, 46, 668-672.
14. Jabbar, A.; Zaman, M.A.; Iqbal, Z.; Yassen, M.; Shamin, A. Antihelmintic activity of Chenopodium album (L.) and Caesalpinia crista (L.) against trichostrongylid nematodes of sheep. J. Ethnopharmacol. 2007, 114, 86-91. (Pubitemid 47444511)
15. Shukla, S.; Mehta, A.; John, J.; Singh, S.; Mehta, P.; Vyas, S.P. Antioxidant activity and total phenolic content of ethanolic extract of Caesalpinia bonducella seeds. Food Chem. Toxicol. 2009, 47, 1848-1851.
16. Roengsumran, S.; Limsuwankesorn, S.; Ngamrojnavanich, N.; Petson, A.; Chaichantipyuth, C.; Ishikawa, T. Cassane diterpenoid from Caesalpinia major. Phytochemistry 2000, 53, 841-844. (Pubitemid 30233109)
17. Das, B.; Trirupathi, P.; Ravikanth, B.; Kumar, R.A.; Sarma, A.L.S.; Basha, S.J. Isolation, synthesis, and bioactivity of homoisoflavonoids from Caesalpinia pulcherrima. Chem. Pharm. Bull. 2009, 57, 1139-1141.
18. Sudhakar, M.; Rao, C.V.; Rao, P.M.; Raju, D.B.; Venkateswarlu, Y. Antimicrobial activity of Caesalpinia pulcherrima, Euphorbia hirta and Asystasia gangeticum. Fitoterapia 2006, 77, 378-380. (Pubitemid 44056189)
19. Saeed, M.A.; Sabir, A.W. Antibacterial activity of Caesalpinia bonducella seeds. Fitoterapia 2001, 72, 807-809. (Pubitemid 33033201)
20. Dickson, R.A.; Houghton, P.J.; Hylands, P.J. Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana. Phytochemistry 2007, 68, 1436-1441. (Pubitemid 46661923)
21. Woldemichael, G.M.; Singh, M.P.; Maiese, W.M.; Timmermann, B.N. Constituents of antibacterial extract of Caesalpinia paraguaiensis Burk. Z. Naturforsch 2003, 58c, 70-75. (Pubitemid 36251155)
22. Ragasa, C.Y.; Hofileña, J.G.; Rideout, J.A. New furanoid diterpenes from Caesalpinia pulcherrima. J. Nat. Prod. 2002, 65, 1107-1110. (Pubitemid 34976486)
23. Sgariglia, M.A.; Soberón, J.R.; Sampietro, E.N.; Quiroga, E.N.; Vattuone, M.A. Isolation of antibacterial components from infusion of Caesalpinia paraguaiensis bark. A bio-guided phytochemical study. Food Chem. 2011, 126, 395-404.
24. Vattuone, M.A.; Martínez, R.H.; Corzo, A.G. Actividad antibacteriana de extractos de hojas de Caesalpinia paraguaiensis, Par Burk, "Guayacán". Quebracho 2008, 15, 37-41.
25. Lee, H.; Lim, M.; Jeon, J.; Jeong, E.; Lee, C. Antimicrobial activity of 5-hidroxy-1, 4- naphtoquinine isolated from Caesalpinia sappan toward intestinal bacteria. Food Chem. 2007, 100, 1254-1258. (Pubitemid 44062215)
26. Jeong, G.S.; Lee, D.S.; Kwon, T.; Lee, H.; An, R.; Kim, Y. Cytoprotective constituents of the heartwood of Caesalpinia sappan on glutamate-induced oxidative damage in HT22 cells. Biol. Pharm. Bull. 2009, 32, 945-949.
27. Lee, Y.M.; Jeong, G.S.; Lim, H.D.; An, R.B.; Kim, Y.C.; Kim, E.C. Isoliquiritigenin 2″-methyl ether induces growth inhibition and apoptosis in oral cancer cells via hemeoxygenase-1. Toxicol. In Vitro 2010, 24, 776-782.
28. Choi, B.M.; Lee, J.; Gao, S.S.; Eun, S.Y.; Kim, Y.; Ryu, S.; Choi, Y.; Park, R.; Kwon, D.Y.; Kim, B. Brazilin and the extract from Caesalpinia sappan L. protect oxidative injury through the expression on heme oxygenase-1. BioFactor 2007, 30, 149-157. (Pubitemid 352038451)
29. Du, L.; Xing, D.; Su, H.; Lin, H.; Zhang, H.; Shen, J. Brazilein protects the brain against focal cerebral ischemia reperfusion injury correlating to inflammatory response suppression. Eur. J. Pharmacol. 2007.558, 88-95. (Pubitemid 46328876)
30. Yen, C.; Nakagawa-Got, K.; Hwang, T.; Wu, P.; Morris-Natschke, S.L.; Lai, W.; Bastow, K.F.; Chang, F.; Wu Y.; Lee, K. Antitumor agents. 27: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents. Bioorg. Med. Chem. Lett. 2010, 20, 1037-1039.
31. Nakamura, S.E.; Kurosaki, F.; Arisawa, M.; Mukainaka, T.; Okuda, M.; Tokuda, H.; Nishino, H.; Pastore, F.J. Cancer chemopreventive effects of constituents of Caesalpinia ferrea and related compounds. Cancer Lett. 2002, 177, 119-124. (Pubitemid 34127912)
32. Bacchi, E.M.; Sertié, J.A.A. Antiulcer action of Styrax camporum and Caesalpinia ferrea in rats. Planta Med. 1994, 60, 118-120. (Pubitemid 24120892)
33. Bacchi, E.M.; Sertié, J.A.A.; Villa, N.; Katz, H. Antiulcer action and toxicity of Styrax camporum and Caesalpinia ferrea. Planta Med. 1995, 61, 204-207.
34. Jiang, R.W.; Ma, S.; But, P.P.; Mak, T.C.W. New antiviral cassane furanoditerpenes from Caesalpinia minax. J. Nat. Prod. 2001, 64, 1266-1272. (Pubitemid 33029204)
35. Jiang, T.; But, P.P.H.; Ma, S.; Ye, W.; Chan, S.; Mak, T.C.W. Structure and antiviral properties of macrocaesalmin, a novel cassane furanoditerpenoid lactone from the seeds of Caesalpinia minax Hance.Tetrahedron Lett. 2002, 43, 2415-2418. (Pubitemid 34230467)
36. Hong, C.H.; Hur, S.K.; Oh, O.J.; Kim, S.S.; Nam, K.A.; Lee, S.K. Evaluation of natural products on inhibition of inducible cyclooxygenase (COX-2) and nitric oxide synthase (iNOS) in cultured mouse macrophage cells. J. Ethnopharmacol. 2002, 83, 153-159. (Pubitemid 36164741)
37. Jun, H.; Xiaoling, Y.; Wei, W.; Hao, W.; Lei, H.; Li, J.D. Antioxidant activity in vitro of three constituents from Caesalpinia sappan L. Tsinghua Sci. Technol. 2008, 13, 474-479.
38. Sampaio, F.C.; Pereira, M.S.V.; Dias, C.S.; Costa, V.C.O.; Conde, N.C.O.; Buzalaf, M.A.R. In vitro antimicrobial activity of Caesalpinia ferrea Martius fruits against oral pathogens. J. Ethnopharmacol. 2009, 124, 289-294.
39. Menezes, I.A.C.; Moreira, I.J.A.; Carvalho, A.A.; Antoniolli, A.R.; Santos, M.R.V. Cardiovascular effects of the aqueous extract from Caesalpinia ferrea: Involvement of ATP-sensitive potassium channels. Vascul. Pharmacol. 2007, 47, 41-47. (Pubitemid 46839070)
40. Hu, L.; Liu, G.; Ma, L.; Li, D. Cassane diterpene-lactones from the seed of Caesalpinia minax Hance. Chem. Biodiv. 2006, 3, 1260-1265. (Pubitemid 46017354)
41. Yodsaoue, O.; Karalai, C.; Ponglimanont, C.; Tewthkul, S.; Chantrapromma, C. Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk. Phytochemistry 2010, 71, 1756-1764.
42. Srinivasan, R.; Chandrasekar, M.J.N.; Nanjan, M.J.; Suresh, B. Antioxidant activity of Caesalpinia digyna root. J. Ethnopharmacol. 2007, 113, 284-291. (Pubitemid 47243784)
43. Cavalheiro, M.G.; Farias, D.F.; Fernandes, G.S.; Nnunes, E.P.; Cavalcanti, F.S.; Vasconcelos, I.M.; Melo, V.M.M.; Ccarvalho, A.F.U. Atividades biológicas e enzimáticas do extrato aquoso de sementes de Caesalpinia ferrea Mart., Leguminosae. Rev. Bras. Farmacogn. 2009, 19, 586-591.
44. Cheenpracha, S.; Srisuwan, R.; Karalai, C.; Ponglimanont, C.; Chantrapromma, S.; Chantrapromma, K.; Fun, H.; Anjum, S.; Rahman, A. New diterpenoids from stems and roots of Caesalpinia crista. Tetrahedron 2005, 61, 8656-8662. (Pubitemid 41111450)
45. Laekeman, G.M.; Kuria, K.A.M.; Coster, S.; Muriuki, G.; Masengo, W.; Kibwage, I.; Hoogmartens, J. Antimalarial activity of Ajuda remota Benth (Labiatae) and Caesalpinia volkensii Harms (Caesalpiniaceae): In vitro confirmation of ethnopharmacological use. J. Ethnopharmacol. 2001, 74, 141-148. (Pubitemid 32141096)
46. Halliwell, B.; Gutteridge, J.M.C. Free Radicals in Biology and Medicine; Oxford University Press: Oxford, UK, 1999.
47. Silva, B.A.; Ferreres, F.; Malva, J.O.; Dias, A.C.P. Phytochemical and antioxidant characterization of Hypericum perforatum alcoholic extracts. Food Chem. 2005, 90, 157-167. (Pubitemid 39298798)
48. Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Antioxidant properties of phenolic compounds. Trends Plant Sci. 1997, 2, 152-159. (Pubitemid 27158898)
49. Anagnostopulou, M.A.; Kefalas, P.; Papageorgiou, V.P.; Assimepoulou, A.N.; Boskou, D. Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis). Food Chem. 2006, 94, 19-25. (Pubitemid 40922877)
50. Arif, T.; Mandal, T.K.; Kumar, N.; Bhosale, J.D.; Hole, A.; Sharma, G.L.; Padhi, M.M.; Lavekar, G.S.; Dabur, R. In vitro and in vivo antimicrobial activities of seeds of Caesalpinia bonduc (Lin.) Roxb. J. Ethnopharmacol. 2009, 123, 177-180.
51. Zhang, Q.; Liu, X.; Liang, J.; Min, Z. Chemical constituents from the stem of Caesalpinia decapetala. Chin. J. Nat. Med. 2008, 6, 168-172.
52. Rao, V.C.; Damu, G.L.V.; Sudhakar, D.; Siddiah, V.; Rao, V.M. New efficient synthesis and bioactivity of homoisoflavonoids. Arkivoc 2008, 11, 285-294.
53. Mandal, S.; Hazra, B.; Sarkar, R.; Biswas, S.; Mandal, N. Assessment of the antioxidant and reactive oxygen species scavening activity of methanolic extract of Caesalpinia crista leaf. eCAM 2009, doi:10.1093/ecam/nep072.
54. Bulbovas, P.; Moraes, R.M.; Rinaldi, M.C.S.; Cunha, A.L.; Delitti, W.B.C.; Domingos, M. Leaf antioxidant fluctuations and growth responses in saplings of Caesalpinia echinata Lam. (brazilwood) under an urban stressing environment. Ecotoxicol. Environ. Saf. 2010, 73, 664-670.
55. Kannur, D.M.; Hukkeri, V.I.; Akki, K.S. Antidiabetic activity of Caesalpinia bonducella seed extracts in rats. Fitoterapia 2006, 77, 546-549. (Pubitemid 44738281)
56. Chakrabarti, S.; Biswas, T.K.; Rokeya, B.; Ali, L.; Mosihuzzaman, M.; Nahar, N.; Khan, A.K.A.; Mukherjee, B. Advanced studies on the hypoglycemic effect of Caesalpinia bonducella F in type 1 and 2 diabetes in Long Evans rats. J. Ethnopharmacol. 2003, 84, 41-46. (Pubitemid 36034234)
57. Kannur, D.M.; Hukkeri, V.I.; Akki, K.S. Adaptogenic activity of Caesalpinia bonduc seed extracts in rats. J. Ethnopharmacol. 2006, 108, 327-331. (Pubitemid 44693101)
58. Muruganantham, N.; Basavaraj, K.H.; Dhanabal, S.P.; Praveen, T.K.; Shamasundar, N.M.; Rao, K.S. Screening of Caesalpinia bonduc leaves for antipsoriatic activity. J. Ethnopharmacol. 2011, 133, 897-901.
59. Yadav, P.P.; Arora, A.; Bid, H.K.; Konwar, R.T.; Kanojiva, S. New cassane butenolide hemiketal diterpenes from the marine creeper Caesalpinia bonduc and their proliferative activity. Tetrahedron Lett. 2007, 48, 7194-7198. (Pubitemid 47361277)
60. Yadav, P.P.; Maurya, R.; Sarkar, J.; Arora, A.; Kanojiya, S.; Sinha, S.; Srivasava, M.N.; Raghubir, R. Cassane diterpenes from Caesalpinia bonduc. Phytochemistry 2009, 70, 256-261.
61. Saravanan, K.S.; Saraswathy, G.R.; Periyanayagam, K.; Ismail, M.; Betanabhatla, K.S.; Athimoolam, J. In vitro antifilarial activity of Caesalpinia bonduc (l) Roxb. against microfilariae of Wuchereria bancrofti and macrofilariae of Setaria digitata. Pharmacologyonline 2008, 2, 550-559.
62. Zamblé, A.; Martin-Nizard, F.; Sahpaz, S.; Hennebelle, T.; Staels, B.; Bordet, R.; Duriez, P.; Brunet, C.; Bailleul, F. Vasoactivity, antioxidant and aphrodisiac properties of Caesalpinia benthamiana roots. J. Ethnopharmacol. 2008, 116, 112-119.
63. Moon, H.; Chung, I.; Seo, S.; Kang, E. Protective Effects of 3″-deoxy-4-O-methylepisappanol from Caesalpinia sappan against glutamate-induced neurotoxicity in primary cultured rat cortical cells. Phytother. Res. 2010, 24, 463-465.
64. Jiang, R.; But, P.P.H.; Ma, S.; Ma, T.C.W. Furanoditerpenoid lactones from the seeds of Caesalpinia minax Hance. Phytochemistry 2001, 57, 517-521. (Pubitemid 32479745)
65. Nguyen, M.T.T.; Awale, S.; Tezuka, Y.; Tran, Q.L.; Kadota, S. Neosappanone, A, a xanthine oxidase (XO) inhibitory dimeric methanodibenzoxocinone with a new carbon skeleton form Caesalpinia sappan. Tetrahedron Lett. 2004, 45, 8519-8522. (Pubitemid 39369904)