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. 2016 Apr 30;25(2):561–566. doi: 10.1007/s10068-016-0078-7

Anti-inflammatory effect of birsonimadiol from seeds of Byrsonima crassifolia

Rosa Martha Pérez Gutiérrez 1,
PMCID: PMC6049191  PMID: 30263306

Abstract

The new compound identified as 16α,23α-dihydroxy-3β,28β,30α-triacetoxy-olean-12-ene, named birsonimadiol (BIR) was isolated from Byrsonima crassifolia seeds using activity-guided fractionation and structural elucidation was achieved based on extensive analysis of spectroscopic data. Effects of BIR on acute and chronic phases of inflamation were studied in edema induced using formaldehyde, 12-O-tetradecanoylphorbol-acetate (TPA)-induced ear edema (meloperoxidase activity), and histamine, carrageenan, cotton pellet granuloma, and adjuvant-induced arthritis. Anti-inflammatory activities of BIR were indicated based on reduction of edema levels induced in models of inflammation. Anti-inflammatory activities were also investigated in murine macrophage RAW264.7 cells. BIR suppressed production of nitric oxide (NO) and prostaglandin E2 (PGE2), decreased gene expression of cyclooxygenase-2 (COX-2), inhibited tumor necrosis factor (TNF)-α, and protein secretion of interleukin IL-6. Triterpene was an effective topical anti-inflammatory agent in experimental models of acute and chronic dermatitis and can be used in inflammatory disorders.

Keywords: anti-inflammatory, cytokines, triterpenoid, Byrsonima crassifolia

References

  • 1.Yamamoto Y, Gaynor RB. Therapeutic potential of the NF-kB pathway in the treatment of inflammation and cancer. J. Clin. Invest. 2001;107:135–142. doi: 10.1172/JCI11914. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 2.Bejar E, Malone MH. Pharmacological and chemical screening of Byrsonima crassifolia, a medicinal tree from Mexico. Part I. J. Ethnopharmacol. 1993;39:141–158. doi: 10.1016/0378-8741(93)90029-5. [DOI] [PubMed] [Google Scholar]
  • 3.Alves GL, Franco MRB. Headspace gas chromatography-mass spectrometry of volatile compounds in murici (Byrsonima crassifolia) J. Chromatogr. A. 2003;985:297–301. doi: 10.1016/S0021-9673(02)01398-5. [DOI] [PubMed] [Google Scholar]
  • 4.Geiss F, Heinrich M, Hunkler D, Rimpler H. Proanthocyanidins with (+)-epicatechin units from Byrsonima crassifolia bark. Phytochemistry. 1995;39:635–643. doi: 10.1016/0031-9422(94)00934-L. [DOI] [Google Scholar]
  • 5.Rastrelli L, De Tommasi N, Berger I, Caceres A, Saravia A, De Simona F. Glycolipids from Byrsonima crassifolia. Phytochemistry. 1997;45:647–650. doi: 10.1016/S0031-9422(96)00842-4. [DOI] [Google Scholar]
  • 6.Cifuentes CM, Gomez-Serranillos MP, Iglesias I, Villar del Fresno AM. Neuropharmacological profile of ethnomedicinal plants of Guatemala. J. Etnopharmacol. 2001;76:223–228. doi: 10.1016/S0378-8741(01)00235-5. [DOI] [PubMed] [Google Scholar]
  • 7.Silva EM, Souza JNS, Rogez H, Rees JF, Larondelle Y. Antioxidant activities and polyphenolic contents of fifteen selected plant species from the Amazonian region. Food Chem. 2007;101:1012–1018. doi: 10.1016/j.foodchem.2006.02.055. [DOI] [Google Scholar]
  • 8.Martinez-Vazquez M, Gonzalez-Esquinca AR, Cazares LL, Moreno GMN, Garcia-Argaer AN. Antimicrobial activity of Byrsonima crassifolia (L.) H.B.K. J. Ethnopharmacol. 1999;66:79–82. doi: 10.1016/S0378-8741(98)00155-X. [DOI] [PubMed] [Google Scholar]
  • 9.Berger I, Barrientos AC, Cáceres A, Hernández M, Rastrelli L, Passreiter CM, Kubelka W. Plants used in Guatemala for the treatment of protozoal infections: Activity of extracts and fractions of five Guatemalan plants against Trypanosoma cruzi. J. Ethnopharmacol. 1998;62:107–115. doi: 10.1016/S0378-8741(98)00011-7. [DOI] [PubMed] [Google Scholar]
  • 10.Perez-Gutierrez RM, Muñiz-Ramirez A, Gomez YG, Bautista-Ramirez E. Antihyperglycemic, antihyperlipidemic and antiglycation of Byrsonima crassifolia fruits. Plant Food. Hum. Nutr. 2010;18:2071–2078. doi: 10.1007/s11130-010-0181-5. [DOI] [PubMed] [Google Scholar]
  • 11.Muñiz-Ramirez A, Perez-Gutierrez RM, Flores-Cotera LB. Evaluation of antiinflammatory activity hexane extract of Byrsonima crassifolia. Altern. Ther. Health M. 2013;19:26–36. [PubMed] [Google Scholar]
  • 12.Perez-Gutierrez RM, Muñiz-Ramírez A. Inhibitory activities of guaianolides from the seeds of Byrsonima crassifolia against protein glycation in vitro. Med. Chem. 2015;5:5–10. [Google Scholar]
  • 13.Gepdiremen A, Mshvildadze Y, Suleyman H, Elias R. Acute and chronic antiinflammatory effects of Hedera cochica in rats. J. Ethnopharmacol. 2004;94:191–195. doi: 10.1016/j.jep.2004.06.001. [DOI] [PubMed] [Google Scholar]
  • 14.Axel V, Wolff MS, Paul DVM, Smith PD. Office of laboratory animal welfare compliance at the institutional and programmatic level. Lab Animal. 1994;23:28–29. [Google Scholar]
  • 15.Aluja AS. Laboratory Animals and Official Mexican Norms. 1999;138:295–298. [PubMed] [Google Scholar]
  • 16.Correa CR, Calixto JB. Evidence for participation of B1 and B2 kinin receptors in formalin-induced nociceptive response in the mouse. Brit. J. Pharmacol. 1993;110:193–198. doi: 10.1111/j.1476-5381.1993.tb13791.x. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 17.Swingle KF, Shidernan FE. Phases of the inflammatory response to subcutaneous implantation of cotton pellet and their modification by certain anti-inflammatory agents. J. Pharmacol. Exp. Ther. 1972;183:226–234. [PubMed] [Google Scholar]
  • 18.Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods. 1983;65:55–63. doi: 10.1016/0022-1759(83)90303-4. [DOI] [PubMed] [Google Scholar]
  • 19.Sandoval-Chacon M, Thompson JH, Zhang XJ, Liu X, Mannick EE, Sadowska-Krowicka H, Charbonnet RM, Clark DA, Miller MJ. Antiinflammatory actions of cat’s claw: The role of NF-kappaB. Aliment. Pharm. Ther. 1998;12:1279–1289. doi: 10.1046/j.1365-2036.1998.00424.x. [DOI] [PubMed] [Google Scholar]
  • 20.Hsu C, Fang S, Huang H, Yen G. Anti-inflammatory effects of triterpenes and steroid compounds isolated from the stem bark of Hiptage benghalensis. J. Funct. Foods. 2015;12:420–427. doi: 10.1016/j.jff.2014.12.009. [DOI] [Google Scholar]
  • 21.Li MM, Su XQ, Sun J, Gu YF, Huang Z, Zeng KW, Zhang Q, Zhao YF, Ferreira D, Zjawiony JK, Li J, Tu PF. Anti-inflammatory ursane-and oleanane-type triterpenoids from Vitex negundo v ar. cannabifolia. J. Nat. Prod. 2014;77:2248–2254. doi: 10.1021/np500509q. [DOI] [PubMed] [Google Scholar]
  • 22.Bisoli E, Garcez WS, Hamerski L, Tieppo C, Garcez FR. Bioactive pentacyclic triterpenes from the stems of Combretum laxum. Molecules. 2008;13:2717–2728. doi: 10.3390/molecules13112717. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 23.Perianayagam JB, Sharma SK, Pillai KK. Anti-inflammatory activity of Trichodesma indicum root extract in experimental animals. J. Ethnopharmacol. 2006;104:410–414. doi: 10.1016/j.jep.2005.08.077. [DOI] [PubMed] [Google Scholar]
  • 24.Vasudevan M, Parle M. Pharmacological actions of Thespesia populnea relevant to Alzheimer’s disease. Phytomedicine. 2006;13:677–687. doi: 10.1016/j.phymed.2006.01.007. [DOI] [PubMed] [Google Scholar]
  • 25.Burnouf-Radosevich M, Norman ED, England R. Gas chromatography-mass spectrometry of oleanane-and ursane-type triterpenes-application to Chenopodium quinoa triterpenes. Phytochemistry. 1985;24:2061–2066. doi: 10.1016/S0031-9422(00)83122-2. [DOI] [Google Scholar]
  • 26.Zhang Z, Koike K, Jia Z, Nikaido T, Guo D, Zheng J. Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis. Chem. Pharm. Bull. 1999;47:388–393. doi: 10.1248/cpb.47.388. [DOI] [PubMed] [Google Scholar]
  • 27.Lavaud C, Crublet ML, Pouny I, Litaudon M, Sevenet T. Triterpenoid saponins from the stems of Elattostachys apetala. Phytochemistry. 2001;57:469–478. doi: 10.1016/S0031-9422(01)00063-2. [DOI] [PubMed] [Google Scholar]
  • 28.Yang JH, Wang YS, Huang R, Luo SD, Zhang HB, Li L. Newpolyoxygenated triterpenoids from Stachyurus himalaicus var. himalaicus. Helv. Chim. Acta. 2006;89:2830–2835. doi: 10.1002/hlca.200690254. [DOI] [Google Scholar]
  • 29.Ricciotti E, Garret A F, Gerald MD. Prostaglandins and inflammation. Arterioscl. Throm. Vas. 2011;31:986–1000. doi: 10.1161/ATVBAHA.110.207449. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 30.Raval ND, Ravishankar B, Ashok BK. Anti-inflammatory effect of Chandrashura (Lepidium sativum Linn.) an experimental study. Ayu. 2013;34:302–304. doi: 10.4103/0974-8520.123132. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 31.Patil CR, Gadekar AR, Patel PN, Rambhade A, Surana SJ, Gaushal MH. Dual effect of Toxicodendron pubescens on carrageenan induced paw edema in rats. Homeopathy. 2009;8:88–91. doi: 10.1016/j.homp.2009.01.003. [DOI] [PubMed] [Google Scholar]
  • 32.Parra-Delgado H, Ruiz GG, Camacho AN, Martínez-Vázquez M. Antiinflammatory activity of some extracts and isolates from Leonotis nepetaefolia on TPA-induced edema model. Rev. Soc. Quím. Méx. 2004;48:293–295. [Google Scholar]
  • 33.Bradley PP, Christensen RD, Rothstein G. Cellular and extracelular myeloperoxidase in pyogenic inflammation. Blood. 1982;60:618–622. [PubMed] [Google Scholar]
  • 34.Dubois RN, Abramson SB, Crofford L, Gupta RA, Simon LS, Van De Putte LB, Lipsky PE. Cyclooxygenase in biology and disease. FASEB J. 1998;12:1063–1073. [PubMed] [Google Scholar]

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