title: Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera.
abstract: BACKGROUND
  Bursera copallifera (Burseraceae) releases a resin known as "copal ancho" which has been used, since pre-Colombian times, as ceremonially burned incense and to treat tooth ache, tumors, arthritis, cold, cough, and various inflammatory conditions; however, its anti-inflammatory potential is poorly studied. The aim of the present study was to isolate, quantify, and to investigate the anti-inflammatory activity of triterpene compounds isolated from the copal resin of B. copallifera.
  
  
  METHODS
  The constituents present in the total resin of B. copallifera were obtained by successive chromatographic procedures, and quantitative analysis was performed by High Performance Liquid Chromatography (HPLC). Anti-inflammatory effects of the isolated triterpenes were investigated to determine their inhibitory effects on phorbol ester 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema in mice, viability and nitric oxide (NO) production inhibition on lipopolysaccharide (LPS)-activated RAW 264.7 macrophages, and inhibition of cyclooxygenase (COX)-1, COX-2 and secretory Phospholipase A2(sPLA2) activities in vitro.
  
  
  RESULTS
  Quantitative phytochemical analysis of the copal resin showed the presence of six pentacyclic triterpenes of which, 3-epilupeol (59.75 % yield) and α-amyrin (21.1 % yield) are the most abundant. Among the isolated triterpenes, 3-epilupeol formiate (Inhibitory Concentration 50 % (IC50) = 0.96 μmol), α.amyrin acetate (IC50= 1.17 μmol), lupenone (IC50= 1.05 μmol), and 3-epilupeol (IC50= 0.83 μmol) showed marked inhibition of the edema induced by TPA in mice. α-amyrin acetate and 3-epilupeol acetate, at 70 μM, also inhibited the activity of COX-2 by 62.85 and 73.28 % respectively, while α-amyrin and 3-epilupeol were the best inhibitors of the production of NO in LPS-activated RAW 264.7 cells with IC50values of 15.5 and 8.98 μM respectively, and did not affected its viability. All compounds moderately inhibited the activity of PLA2.
  
  
  CONCLUSIONS
  This work supports the folk use of B. copallifera and provides the basis for future investigations about the therapeutic use of this resin in treating inflammation.
authors: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: Antonio
authors: A
authors: Romero-Estrada
authors: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: Amalia
authors: A
authors: Maldonado-Magaña
authors: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: Judith
authors: J
authors: González-Christen
authors: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: Silvia Marquina
authors: SM
authors: Bahena
authors: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: María Luisa
authors: ML
authors: Garduño-Ramírez
authors: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
authors: Verónica
authors: V
authors: Rodríguez-López
authors: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, Cuernavaca, Morelos, 62209, Mexico. lalvarez@uaem.mx.
authors: Laura
authors: http://orcid.org/0000-0001-7464-9898
authors: L
authors: Alvarez
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D031233:Bursera / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D004487:Edema / Q000139:chemically induced / Q000378:metabolism; D007249:Inflammation; D008297:Male; D051379:Mice; D009569:Nitric Oxide / Q000378:metabolism; D053978:Pentacyclic Triterpenes / Q000737:chemistry / Q000494:pharmacology*; D010703:Phorbol Esters / Q000633:toxicity; D000067996:RAW 264.7 Cells; D012116:Resins, Plant / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D053978:Pentacyclic Triterpenes; D010703:Phorbol Esters; D012116:Resins, Plant; D009569:Nitric Oxide
keywords: B. copallifera; COX-2 inhibition; Copal ancho; Inflammation; NO inhibition; Pentacyclic triterpenes