Planta Med 2007; 73(2): 116-120
DOI: 10.1055/s-2006-951772
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Antibacterial and Anticoagulant Activities of Coumarins Isolated from the Flowers of Magydaris tomentosa

Sergio Rosselli1 , Antonella Maggio1 , Gabriella Bellone1 , Carmen Formisano2 , Adriana Basile3 , Carla Cicala4 , Alessio Alfieri4 , Nicola Mascolo4 , Maurizio Bruno1
  • 1Dipartimento di Chimica Organica, Università degli Studi di Palermo, Palermo, Italy
  • 2Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli ”Federico II”, Napoli, Italy
  • 3Dipartimento di Biologia Vegetale, Università degli Studi di Napoli ”Federico II”, Napoli, Italy
  • 4Dipartimento di Farmacologia Sperimentale, Università degli Studi di Napoli ”Federico II”, Napoli, Italy
Further Information

Publication History

Received: July 27, 2006

Accepted: October 30, 2006

Publication Date:
24 November 2006 (online)

Abstract

The phytochemical investigation of the acetone and methanol extracts of the flowers of Magydaris tomentosa (Desf.) DC afforded six known coumarins as well as (+)-meranzin hydrate (7), not previously reported as a natural product. The antibacterial activity of umbelliprenin (1), osthol (2), imperatorin (3), citropten (4) and (+)-meranzin hydrate (7) was tested against Gram-positive and Gram-negative bacteria. All coumarins (1 - 7) isolated in this study inhibited growth of all bacterial strains tested (MIC between 16 and 256 μg/mL), the most active being imperatorin (3) (MICs between 32 and 128 μg/mL) and citropten (4) (MICs between 16 and 256 μg/mL). The anticoagulant activity of compounds 1 - 4 and 7 was also evaluated.

References

  • 1 Pignatti S. Flora d’Italia, Vol. 2. Bologna; Ed Agricole 1982: 211
  • 2 Cerri R, Pintore G, Dessi G, Asproni B, Piseddu G, Sini S. Isolation, characterization and pharmacological activity of Magydaris pastinacea glucosides.  Farmaco. 1995;  50 841-8
  • 3 Cerri R, Dessi G, Manconi P M, Serra D, Pau A. Glycosides of the Magydaris pastinacea L.  Pharmacol Res Commun. 1988;  20 109-12
  • 4 Camarda L, Di Stefano V, Lentini F, Mazzola P. Coumarins from the fruits of Magydaris pastinacea .  Fitoterapia. 1996;  67 282
  • 5 De Pascual Teresa J, Grande C, Grande M. Chemical components of Umbelliferae. Magydardiendiol, diterpenoid with a new skeleton from Magydaris panacifolia (Umbelliferae).  Tetrahedron Lett. 1978;  19 4563-6
  • 6 Nagano H, Masunaga Y, Matsuo Y, Shiota M. Synthesis of 2,6-dimethyl-6-(8-methyl-4-methylene-7-nonenyl)-2-cyclohexene-1-methanols from α-santonin.  Bull Chem Soc Jpn. 1987;  60 707-11
  • 7 Bruno M, Lamartina L, Lentini F, Pascual C, Savona G. Bonandiol: a new irregular, monocyclic diterpene from Bonannia greca (L.) Halacsy (Umbelliferae).  Tetrahedron Lett. 1984;  25 4287-90
  • 8 Pinar M. Coumarins of Magydaris panacifolia, Cachrys sicula, Cachrys libanotis and Lafuentea rotundifolia.  Anal Quim. 1977;  73 599-600
  • 9 Erricson H M, Sherris J C. Antibiotic sensitivity testing: report of an international collaborative study.  Acta Pathol Microbiol Scand [B] Microbiol Immunol. 1971;  217 1-90
  • 10 Ieven M, Dirk A, Vanden Berghe V, Francis M, Vlietinck A, Lammens E. Screening of higher plants for biological activities I. Antimicrobial activity.  Planta Med. 1979;  36 311-21
  • 11 Basile A, Spagnuolo V, Giordano S, Sorrentino C, Castaldo Cobianchi R. Effect of α-D-galacturonides in Nephrolepis sp.  Int J Antimicrob Agents. 1997;  8 131-4
  • 12 Kir'yalov N P. The structure of cocanikine and umbelliprenin, components of the neutral part of oil from Ferula cocanica.  Tr Akad Nauk SSSR Inst Botan. 5;  1961 7-14
  • 13 Iranshahi M, Amin G -R, Jalalizadeb H, Shafiee A. New germacrane derivative from Ferula persica .  Pharm Biol. 2003;  41 431-3
  • 14 Chatteryee A, Baneryi J, Basa S C. Loctonic constituents of Prangos pabularia Lindl. (Umbelliferae).  Tetrahedron. 1972;  28 5175-82
  • 15 Steck W, Mazurek M. Identification of natural coumarins by NMR spectroscopy.  Lloydia. 1972;  35 418-39
  • 16 Sharma Y N, Zaman A, Kindwai A R. Chemical examination of Heracleum candicans. Isolation and stucture of a new furocoumarin-heraclenin.  Tetrahedron. 1964;  20 87-90
  • 17 Kuznetsova G A, Abyshev A Z. Natural (-)-7-methoxy-8-(β,γ-dihydroxyisopentyl)coumarin.  Khim Prirodn Soedin. 1965;  1 283-8
  • 18 Ceccherelli P, Curini M, Marcotullio M C, Madruzzza G. Tortuoside, a new natural coumarin glucoside from Seseli tortuosum .  J Nat Prod. 1990;  53 536-8
  • 19 Basile A, Sorbo S, Giordano S, Lavitola A, Castaldo Cobianchi R. Antibacterial activity in Pleurochaete squarrosa extract (Bryophyta).  Int J Antimicrob Agents. 1998;  10 169-72
  • 20 Basile A, Vuotto M L, Ielpo M TL, Moscatiello V, Ricciardi L, Giordano S. et al . Antibacterial activity in Rhynchostegium riparioides (Hedw.) Card. Extract (Bryophyta).  Phytoter Res. 1998;  12 146-8
  • 21 Basile A, Giordano S, López-Sáez J A, Castaldo Cobianchi R. Antibacterial activity of pure flavonoids isolated from mosses.  Phytochemistry. 1999;  52 1479-82
  • 22 Vuotto M L, Basile A, Moscatiello V, De Sole P, Castaldo Cobianchi R, Laghi E. et al . Antimicrobial and antioxidant activities of Feijoa sellowiana fruit.  Int J Antimicrob Agents. 1999;  13 97-201
  • 23 Kazuo S, Kaku S, Hirayama F, Koshio H, Matsumoto Y, Kawasaki T. et al . Antithrombotic effect of YM-75 466 is separated from its effect on bleeding time and coagulation time.  Eur J Pharmacol. 1998;  352 59-63

Prof. Dr. Maurizio Bruno

Dipartimento di Chimica Organica

Università degli Studi di Palermo

Viale delle Scienze

Parco d’Orleans II

90128 Palermo

Italy

Phone: +39-091-596-905

Fax: +39-091-596-905

Email: bruno@dicpm.unipa.it

    >