Planta Med 2002; 68(4): 311-315
DOI: 10.1055/s-2002-26749
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

Anti-Inflammatory Triterpenes from Pistacia terebinthus Galls

Eva M. Giner-Larza1 , Salvador Máñez1 , Rosa M. Giner1 , M. Carmen Recio1 , José M. Prieto1 , Miguel Cerdá-Nicolás2 , José Luis Ríos1
  • 1Departament de Farmacologia, Facultat de Farmàcia, Universitat de València, Burjassot, Valencia, Spain
  • 2Departament de Patologia, Facultat de Medicina, Universitat de Valencia, Valencia, Spain
Weitere Informationen

Publikationsverlauf

June 25, 2001

September 30, 2001

Publikationsdatum:
02. Mai 2002 (online)

Abstract

From the galls of Pistacia terebinthus we obtained an extract that proved to be effective against chronic and acute inflammation. Now we report on the isolation and identification of three triterpenes: two tirucallane-type lanostanoids and one oleanane, which we have identified as masticadienonic acid (1), masticadienolic acid (2), and morolic acid (3), respectively. All of them showed effectiveness on the mouse ear inflammation induced by repeated applications of 12-O-tetradecanoylphorbol 13-acetate and on the phospholipase A2-induced foot paw edema. The pharmacological activity of the compounds was ratified by a histological study of the ear samples. In addition, they inhibited leukotriene B4 production in rat polymorphonuclear leukocytes stimulated with calcium ionophore A 23 187.

Abbreviations

DMSO:dimethyl sulfoxide

EPP:ethyl phenylpropiolate

HPLC-DAD:high performance liquid chromatography-diode
array detection

HTAB:hexadecyltrimethylammonium bromide

5-LOX:5-lipoxygenase

LTB4:leukotriene B4

MPLC:medium pressure liquid chromatography

MTT:3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
bromide

PGB2:prostaglandin B2

PLA2:phospholipase A2

PMNL:polymorphonuclear leukocytes

TMB:tetramethylbenzidine

TPA:12-O-tetradecanoylphorbol 13-acetate

VLC:vacuum liquid chromatography

References

  • 1 Giner-Larza E M, Máñez S, Recio M C, Giner R M, Ríos J L. A review on the pharmacology of lanostanes and related tetracyclic triterpenes.  Research Advances in Phytochemistry. 2000;  1 65-81
  • 2 Safayhi H, Sailer E R. Anti-inflammatory actions of pentacyclic triterpenes.  Planta Medica. 1997;  63 487-93
  • 3 Giner E M, Máñez S, Recio M C, Giner R M, Cerdá-Nicolás M, Ríos J L. In vivo studies on the anti-inflammatory activity of pachymic and dehydrotumulosic acids.  Planta Medica. 2000;  66 221-7
  • 4 Ríos J L, Recio M C, Máñez S, Giner R M. Studies in Natural Products Chemistry: Bioactive Natural Products. Natural triterpenoids as anti-inflammatory agents. In: Atta-Ur-Rahman editor Vol. 22, part C. Amsterdam; Elsevier 2000: 93-143
  • 5 Ansari H, Ali M, Qadry J S. Three new tetracyclic triterpenoids from galls of Pistacia integerrima Stew.  Die Pharmazie. 1993;  48 215-17
  • 6 Caputo R, Mangoni L. Acidi triterpenici dalle galle di Pistacia terebinthus .  Gazzeta Chimica Italiana. 1970;  100 317-25
  • 7 Monaco P, Caputo R, Palumbo G, Mangoni L. Neutral triterpenes from galls of Pistacia terebinthus .  Phytochemistry. 1973;  12 939-42
  • 8 Ansari S H, Ali M. Analgesic and anti-inflammatory activity of tetracyclic triterpenoids from Pistacia integerrima galls.  Fitoterapia. 1996;  68 103-5
  • 9 Giner-Larza E M, Máñez S, Giner-Pons R M, Recio M C, Ríos J L. On the anti-inflammatory and anti-phospholipase A2 activity of extracts from lanostane-rich species.  Journal of Ethnopharmacology. 2000;  73 61-9
  • 10 Neves P CA, Neves M CA, Bella Cruz A, Sant’ana A EG, Yunes R A, Calixto J B. Differential effects of Mandevilla velutina compounds on paw oedema induced by phospholipase A2 and phospholipase C.  European Journal of Pharmacology. 1993;  243 213-9
  • 11 Brattsand R, Thalén A, Roempke K, Källström L, Gruvstad E. Influence of 16α,17α-acetal substitution and steroid nucleus fluorination on the topical to systemic activity ratio of glucocorticoids.  Journal of Steroid Biochemistry. 1982;  16 779-86
  • 12 Stanley P L, Steiner S, Havens M, Tramposch K M. Mouse skin inflammation induced by multiple topical applications of 12-O-tetradecanoylphorbol 13-acetate.  Skin Pharmacology. 1991;  4 262-71
  • 13 De Young L M, Kheifets J B, Ballaron S J, Young J M. Oedema and cell infiltration in the phorbol ester-treated mouse ear oedema are temporally separate and can be differentially modulated by pharmacological agents.  Agents and Actions. 1989;  26 335-41
  • 14 Armed Forces Institute of P athology. Advanced Laboratory Methods in Histology and Pathology. Mikel U V, editor Washington; 1994: 254
  • 15 Mossman T. Rapid colorimetric assay for cellular growth and survival: Applications to proliferation and cytotoxic assays.  Journal of Immunological Methods. 1983;  65 55-63
  • 16 Safayhi H, Sailer E R, Ammon H P. Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-β-boswellic acid.  Molecular Pharmacology. 1995;  47 1212-6
  • 17 Konno C, Saito T, Oshima Y, Hikino H, Kabuto C. Structure of methyl adenophorate and triphyllol, triterpenoids of Adenophora triphylla var. japonica roots.  Planta Medica. 1981;  42 268-74
  • 18 Mahato S B, Kundu A P. 13C-NMR spectra of pentacyclic triterpenoids A compilation and some salient features.  Phytochemistry. 1994;  37 1517-75
  • 19 Cirino G, Peers S H, Wallace J L, Flower R J. A study of phospholipase A2-induced oedema in rat paw.  European Journal of Pharmacology. 1989;  166 505-10
  • 20 Cirino G, Peers S H, Flower R, Browning J L, Pepinsky R B. Human recombinant lipocortin 1 has acute local anti-inflammatory properties in the rat paw oedema test.  Proceedings of the National Academy of Sciences USA. 1989;  86 3428-32
  • 21 Marshall L A, Chang J Y, Calhoun W, Yu J, Carlson R P. Preliminary studies on phospholipase A2-induced mouse edema as a model to evaluate anti-inflammatory agents.  Journal of Cellular Biochemistry. 1989;  40 147-55
  • 22 Jain M K, Yu B Z, Rogers J M, Smith A E, Boger E TA, Ostrander R L, Rheingold A L. Specific competitive inhibitor of secreted phospholipase A2 from berries of Schinus terebinthifolius .  Phytochemistry. 1995;  39 537-47
  • 23 Máñez S, Recio M C, Giner R M, Ríos J L. Effect of selected triterpenoids on chronic dermal inflammation.  European Journal of Pharmacology.. 1997;  334 103-5

Prof. Dr. J. L. Ríos

Departament de Farmacologia

Facultat de Farmàcia

Universitat de València

Avda. Vicent Andrés Estellés s/n

46100 Burjassot, Spain

Telefon: /Fax: +34-963-864-973.

eMail: riosjl@uv.es