Planta Med 2006; 72(6): 575-578
DOI: 10.1055/s-2006-931557
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Phytochemical and Pharmacological Studies on the Acetonic Extract of Marrubium globosum ssp. libanoticum

Daniela Rigano1 , Armando Grassia1 , Francesca Borrelli2 , Gabriella Aviello2 , Franco Piozzi3 , Maurizio Bruno3 , Nelly Apostolides Arnold4 , Raffaele Capasso2 , Felice Senatore1
  • 1Department of Chemistry of Natural Products, University of Naples Federico II, Naples, Italy
  • 2Department of Experimental Pharmacology, University of Naples Federico II, Naples, Italy
  • 3Department of Organic Chemistry, University of Palermo, Palermo, Italy
  • 4Faculty of Agronomic Sciences, University of Saint Esprit, Kaslik (Beyrouth), Lebanon
Further Information

Publication History

Received: June 7, 2005

Accepted: December 2, 2005

Publication Date:
24 April 2006 (online)

Abstract

A new natural labdane diterpene, marrulibanoside, was isolated from the acetonic extract of aerial parts of M. globosum Montbr. et Auch. ex Benth. ssp. libanoticum Boiss. (Lamiaceae). Its structure was determined by spectroscopic methods such as 1D and 2D NMR and mass spectrometry. Pharmacological studies have shown that the extract of M. globosum exerts anti-inflammatory effects in the rat paw oedema induced by carrageenin resulting in reduced paw swelling. This activity, which seems due to marrulibanoside, is a consequence of iNOS and COX-2 activities inhibition.

References

  • 1 Mabberley D J. The Plant Book. 2nd Edition Cambridge; Cambridge University Press 1997
  • 2 Girre L. Infusions et plantes de santé en France. Tours; Ed. Ouest-France 2000: 60
  • 3 Karioti A, Skaltsa H, Heilmann J, Sticher O. Acylated flavonoids and phenylpropanoid glycosides from Marrubium velutinum .  Phytochemistry. 2003;  64 655-60
  • 4 Sahpaz S, Garbacki N, Tits M, Bailleul F. Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare .  J Ethnopharmacol. 2002;  79 389-92
  • 5 Sahpaz S, Hennebelle T, Bailleul F. Marruboside, a new phenylethanoid glycoside from Marrubium vulgare .  Nat Prod Lett. 2002;  16 195-9
  • 6 Karioti A, Heilmann J, Skaltsa H. Secondary metabolites from Marrubium vellutinum growing wild in Greece.  Z Naturforsch B. 2005;  60 328-32
  • 7 Citoglu G S, Aksit F. Occurrence of marrubiin and ladanein in Marrubium trachyticum from Turkey.  Biochem Syst Ecol. 2002;  30 885-6
  • 8 Michelis F, Tiligada E, Skaltsa H, Lazari D, Skaltsounis A L, Delitheos D. Effects of the flavonoid pilloin isoleted from Marrubium cylleneum on mitogen-induced lymphocyte transformation.  Pharm Biol. 2002;  40 245-8
  • 9 Iida A, Tanaka Y, Mihara T, Tabata M, Honda G, Shinghu T. et al . Marrubinones A and B, new labdane diterpenoids from Marrubium astracanicum .  Chem Pharm Bull. 1995;  43 1454-7
  • 10 Hatam N AR, Porzel A, Seifer K. Polyodonine, a prefuranic labdane diterpene from Marrubium polydon .  Phytochemistry. 1995;  40 1575-6
  • 11 Sagitdinova G B, Makhmudov M K, Tashkhodzhaev B, Maltsev I I. Labdanoids of Marrubium anisodon .  Khim Prir Soedin Engl Edition. 1996;  32 43-6
  • 12 Karioti A, Heilmann J, Skatsa H. Labdane diterpenes from Marrubium velutinum and Marrubium cylleneum .  Phytochemistry. 2005;  66 1060-6
  • 13 Takeda Y, Yanagihara K, Masuda T, Otsuka H, Honda G, Takaishi Y. et al . Labdane diterpenoids from Marrubium globosum subsp. globosum .  Chem Pharm Bull. 2000;  48 1234-5
  • 14 Laonigro G, Lanzetta R, Parrilli M, Adinolfi M, Mangoni L. The configuration of the diterpene spiroethers from Marrubium vulgare and from Leonotis leonurus .  Gazz Chim Ital. 1979;  109 145-50
  • 15 Marzocco S, Di Paola R, Serraino I, Sorrentino R, Meli R, Mattaceraso G. et al . Effect of methylguanidine in carrageenan-induced acute inflammation in the rats.  Eur J Pharmacol. 2004;  484 341-50
  • 16 De Jesus R AP, Cechinel-Filho V, Oliveira A E, Schlemper V. Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare .  Phytomedicine. 2000;  7 111-5
  • 17 Meyre-Silva C, Yunes R A, Schlemper V, Campos-Buzzi F, Cechinel-Filho V. Analgesic potential of marrubiin derivatives, a bioactive diterpene present in Marrubium vulgare (Lamiaceae).  Farmaco. 2005;  60 321-6
  • 18 Borrelli F, Maffia P, Pinto L, Ianaro A, Russo A, Capasso F. et al . Phytochemical compounds involved in the anti-inflammatory effect of propolis extract.  Fitoterapia. 2002;  73 53-63
  • 19 Marotta P, Sautebin L, Di Rosa M. Modulation of the induction of nitric oxide synthase by eicosanoids in the murine macrophage cell line J774.  Br J Pharmacol. 1992;  107 640-1

Prof. Maurizio Bruno

Dipartimento di Chimica Organica ”E. Paternò”

Università di Palermo

Viale delle Scienze

Parco d’Orleans II

90128 Palermo

Italy

Phone: +39-091-596-905

Fax: +39-091-596-825

Email: bruno@dicpm.unipa.it