Planta Med 2014; 80(02/03): 209-214
DOI: 10.1055/s-0033-1360302
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Sphaeralcic Acid and Tomentin, Anti-inflammatory Compounds Produced in Cell Suspension Cultures of Sphaeralcea angustifolia

Juanita Pérez-Hernández
1   Centro de Investigación Biomédica del Sur (CIBIS), Instituto Mexicano del Seguro Social (IMSS), Xochitepec, Morelos, México
4   Departamento de Biotecnología, Universidad Autónoma Metropolitana Unidad Iztapalapa (UAM-Iztapalapa), Ciudad de México, México
,
Manasés González-Cortazar
1   Centro de Investigación Biomédica del Sur (CIBIS), Instituto Mexicano del Seguro Social (IMSS), Xochitepec, Morelos, México
,
Silvia Marquina
2   Centro de Investigaciones Químicas (CIQ), Universidad Autónoma del Estado de Morelos (UAEM), Cuernavaca, Morelos, México
,
Maribel Herrera-Ruiz
1   Centro de Investigación Biomédica del Sur (CIBIS), Instituto Mexicano del Seguro Social (IMSS), Xochitepec, Morelos, México
,
Mariana Meckes-Fischer
3   Unidad de Investigación Médica en Farmacología de Productos Naturales, Instituto Mexicano del Seguro Social (UIMFPN-IMSS), Hospital de Pediatría, Centro Médico Nacional Siglo XXI (CMN-SXXI), Ciudad de México, México.
,
Jaime Tortoriello
1   Centro de Investigación Biomédica del Sur (CIBIS), Instituto Mexicano del Seguro Social (IMSS), Xochitepec, Morelos, México
,
Francisco Cruz-Sosa
4   Departamento de Biotecnología, Universidad Autónoma Metropolitana Unidad Iztapalapa (UAM-Iztapalapa), Ciudad de México, México
,
María del Pilar Nicasio-Torres
1   Centro de Investigación Biomédica del Sur (CIBIS), Instituto Mexicano del Seguro Social (IMSS), Xochitepec, Morelos, México
› Author Affiliations
Further Information

Publication History

received 10 September 2013
revised 12 December 2013

accepted 30 December 2013

Publication Date:
31 January 2014 (online)

Abstract

Sphaeralcea angustifolia, an endangered plant species in Mexico, is employed to treat inflammatory processes and as a wound healing remedy. Scopoletin (1) was reported as one of the main bioactive compounds in this plant. Here, we isolated and identified compounds with anti-inflammatory properties from the suspension-cultured cells of S. angustifolia. The CH2Cl2 : CH3OH extract of the cells exhibited anti-inflammatory properties in acute inflammation models. Two compounds were isolated, 5-hydroxy-6,7-dimethoxycoumarin, named tomentin (2), and 2-(1,8-dihydroxy-4-isopropyl-6-methyl-7-methoxy)-naphthoic acid, denominated as sphaeralcic acid (3). Their structures were determined by spectroscopic and spectrometric analyses. The anti-inflammatory effects of both compounds were also evaluated. At a dose of 45 mg/kg, compound 2 inhibited the formation of λ-carrageenan footpad edema at 58 %, and compound 3 at 66 %. Local application of compound 2 (225 mM per ear) or 3 (174 mM per ear) inhibited the phorbol ester-induced auricular edema formation by 57 % or 86 %, respectively. The effect of compound 3 was dose-dependent and the ED50 was 93 mM.

Supporting Information

 
  • References

  • 1 Martínez M. Catálogo de nombres vulgares y científicos de plantas mexicanas. Mexico: Fondo de la Cultura Económica, Ediciones Botas; 1979: 429
  • 2 Aguilar A, Camacho JR, Chino S, Jácquez P, López ME. Herbario medicinal del instituto mexicano del seguro social. Mexico: Instituto Mexicano del Seguro Social; 1994: 140 251
  • 3 Calderón-Rzedowski G, Rzedowski J. Flora fanerogámica del Valle de México. Pátzcuaro, Michoacán, México: Instituto de Ecología, A. C. y Comisión Nacional para el Conocimiento y Uso de la Biodiversidad; 2001: 393-395 406–408
  • 4 García-Rodríguez RV, Chamorro-Cevallos G, Siordia G, Jiménez-Arellanes A, Chávez-Soto MA, Meckes-Fischer M. Sphaeralcea angustifolia (Cav.) G. Don extract, a potential phytomedicine to treat chronic inflammation. Bol Latinoam Caribe Plant Med Aromat 2012; 11: 454-463
  • 5 Juárez-Ciriaco M, Román-Ramos R, González-Márquez H, Meckes-Fischer M. Efecto de Sphaeralcea angustifolia sobre la expresión de citocinas pro y antiinflamatorias. Lab Ciencia con Noticias Técnicas de Laboratorio 2008; 2: 21-23
  • 6 Meckes M, David-Rivera AD, Nava-Aguilar V, Jiménez A. Activity of some Mexican medicinal plant extracts on carrageenan-induced rat paw edema. Phytomedicine 2004; 11: 446-451
  • 7 Osti-Castillo MR, Torres-Valencia JM, Villagómez-Ibarra JR, Castelán-Pelcastre I. Estudio químico de cinco plantas mexicanas de uso común en la medicina tradicional. Bol Latinoam Caribe Plant Med Aromat 2010; 9: 359-367
  • 8 Stafford AM. Plant cell cultures as a source of bioactive small molecules. Curr Opin Drug Discov Dev 2002; 5: 296-303
  • 9 Vanisree M, Lee CY, Lo SF, Nalawade SM, Lin CY, Tsay HS. Studies on the production of some important secondary metabolites from medicinal plants by plant tissue cultures. Bot Bull Acad Sin 2004; 45: 1-22
  • 10 Morris CJ. Carrageenan-induced paw edema in the rat and mouse. Inflammation Protocols, Vol. 225. University of Bath. Bath, UK: Springer Protocols; 2003: 115-121
  • 11 Gepdiremen A, Mshvildadze V, Süleyman H, Elias R. Acute anti-inflammatory activity of four saponins isolated from ivy: alpha-hederin, derasaponin-C, hederacolchiside-E and hederacolchiside-F in carrageenan-induced rat paw edema. Phytomedicine 2005; 12: 440-444
  • 12 Gábor M. Mouse ear inflammation models and their pharmacological applications. Budapest: Akadémiai Kiadó; 2000
  • 13 Pan R, Gao XH, Li Y, Xia YF, Dai Y. Anti-arthritic effect of scopoletin, a coumarin compound occurring in Erycibe obtusifolia Benth stems, is associated with decreased angiogenesis in synovium. Fundam Clin Pharmacol 2010; 24: 477-490
  • 14 Okada Y, Tsuzuki Y, Narimatsu K, Sato H, Ueda T, Hozumi H, Sato S, Hokari R, Kurihara C, Komoto S, Watanabe C, Tomita K, Kawaguchi A, Nagao S, Miura S. 1,4-dihydroxy-2-naphthoic acid from Propionibacterium freudenreichii reduces inflammation in interleukin-10-deficient mice with colitis by suppressing macrophage-derived proinflammatory cytokines. J Leukoc Biol 2013; 94: 473-480
  • 15 Mok CF, Xie CM, Sham KW, Lin ZX, Cheng CH. 1,4-dihydroxy-2-naphthoic acid induces apoptosis in human keratinocyte: potential application for psoriasis treatment. Evid Based Complement Alternat Med 2013; 2013: 792840
  • 16 Burnett AR, Thompson RH. Naturally occurring quinines. Part XIII. Anthraquinones and related naphthalenic compounds in Galium spp. in Asperula odorata . J Chem Soc C 1968; 854-857
  • 17 González AG, Barroso JT, Cardona RJ, Medina JM, Rodríguez-Luis F. Química de las Rubíaceas. II. Componentes de la “Putoria calábrica” Perss. An Quim 1977; 73: 538-545
  • 18 Schmeda-Hirschmann G, Papastergiou F. Naphthoquinone derivatives and lignans from the Paraguayan crude drug “Tayï Pytá” (Tabebuia heptaphylla, Bignoniaceae). Z Naturforsch C 2003; 58: 495-501
  • 19 Hammoda HM, Aboul Ela MA, El-Lakany AM, El-Hanbali O, Zaki CS, Ghazy NM. New constituents of Artemisia monosperma Del. Pharmazie 2008; 63: 611-614
  • 20 Ludy CP, Hernández-Rodríguez P. Importancia química de Jatropha curcas y sus aplicaciones biológicas, farmacológicas e industriales. Rev Cubana Plant Med 2012; 17: 194-209
  • 21 Ravindranath N, Ravinder Reddy M, Ramesh C, Ramu R, Prabhakar A, Jagadeesh B, Das B. New lathyrane and podocarpane diterpenoids from Jatropha curcas . Chem Pharm Bull 2004; 52: 608-611
  • 22 Murashige T, Skoog F. A revised medium for rapid growth and bioassay with tobacco tissue culture. Plant Physiol 1962; 15: 473-497
  • 23 Gupta M, Mazumder UK, Kumar RS, Sambath R, Gomathi P, Rajeshwar Y, Kakoti BB, Selven VT. Anti-inflammatory, analgesic and antipyretic effects of methanolextract from Bauhinia racemosa stembark in animal models. J Ethnopharmacol 2005; 98: 267-273
  • 24 Boeris MA, Toso RE, Skliar MI. Actividad antiinflamatoria de Salpichroa origanifolia . Acta Farm Bonaerense 2004; 23: 138-141
  • 25 Payá M, Ferrándiz ML, Sanz MJ, Bustos G, Blasco R, Ríos JL, Alcaraz MJ. Study of the antioedema activity of some seaweed and sponge extracts from the Mediterranean coast in mice. Phytother Res 1993; 7: 159-162