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

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.

Key words

Magydaris tomentosa - Apiaceae - coumarins - (+)-meranzin hydrate - antibacterial activity - anticoagulant activity

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