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DOI: 10.1055/s-2003-45109
Pangelin, an Antimycobacterial Coumarin from Ducrosia anethifolia
Publikationsverlauf
Received: March 10, 2003
Accepted: June 19, 2003
Publikationsdatum:
02. Dezember 2003 (online)
Abstract
The aerial parts of Ducrosia anethifolia afforded the monoterpene glucoside 8-debenzoylpaeoniflorin (1) and the prenylated furanocoumarin pangelin {5-[2′′(R)-hydroxy-3′′-methyl-3′′-butenyloxy]furocoumarin} (2). Their structures were determined by extensive 1- and 2-dimensional NMR studies. Compound 2 demonstrated activity against a panel of fast growing mycobacteria, namely Mycobacterium fortuitum, M. aurum, M. phlei and M. smegmatis and minimum inhibitory concentration (MIC) values ranged from 64 - 128 μg/mL. Whilst compounds 1 and 2 have previously been reported as an antihyperglycaemic component from Paeonia lactiflora, and as a constituent of Angelica pancici, respectively, this is the first report of the full 1H- and 13C-NMR data for these natural products.
References
- 1 Cantrell C L, Franzblau S G, Fischer N H. Antimycobacterial plant terpenoids. Planta Medica. 2001; 67 685-94
- 2 Newton S M, Lau C, Wright C W. A review of antimycobacterial natural products. Phytotherapy Research. 2000; 14 303-22
- 3 Newton S M, Lau C, Gurcha S S, Besra G S, Wright C W. The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis . Journal of Ethnopharmacology. 2002; 79 57-67
- 4 Raviglione M C, Gupta R, Dye C M, Espinal M A. The burden of drug-resistant tuberculosis and mechanisms for its control. Annals of the New York Academy of Science. 2001; 953 88-97
- 5 Fujita N, Utani A, Matsumoto F, Matsushima H, Kakuta M, Hatamochi A, Shinkai H. Levofloxacin alone efficiently treated a cutaneous Mycobacterium fortuitum infection. Journal of Dermatology. 2002; 29 452-54
- 6 Gillespie S H, Morrissey I, Everett D. A comparison of the bactericidal activity of quinolone antibiotics in a Mycobacterium fortuitum model. Journal of Medical Microbiology. 2001; 50 565-70
- 7 Janssen A M, Scheffer J J, Baerheim Svendsen A, Aynehchi Y. The essential oil of Ducrosia anethifolia (DC.) Boiss. Chemical composition and antimicrobial activity. Pharmaceutisch Weekblad Science. 1984; 6 157-60
- 8 Kaneda M, Itaka Y, Shibata S. Chemical studies on the oriental plant drugs - XXXII The absolute structures of paeoniflorin, albiflorin, oxypaeoniflorin and benzoylpaeoniflorin isolated from Chinese paeony root. Tetrahedron. 1972; 28 4309-17
- 9 Yamasaki K, Kaneda M, Tanaka O. Carbon-13 NMR spectral assignments of paeoniflorin homologues with the aid of spin-lattice relaxation time. Tetrahedron Letters. 1976; 44 3965-68
- 10 Hsu F, Lai C, Cheng J. Antihyperglycaemic effects of paeoniflorin and 8-debenzylpaeoniflorin, glucosides from the root of Paeonia lactiflora . Planta Medica. 1997; 63 323-25
- 11 Adebajo A C, Reisch J. Minor furocoumarins of Murraya koenigii . Fitoterapia. 2000; 71 334-7
- 12 Ognyanov I, Botcheva D. Pangeline and angeloylpangeline - two new furocoumarins in the roots of Angelica pancici Vandas. Comptes Rendus de l’Academie Bulgare des Sciences. 1971; 24 315-8
- 13 Schinkovitz A, Gibbons S, Stavri M, Cocksedge M J, Bucar F. Ostruthin: An antimycobacterial coumarin from the roots of Peucedanum ostruthium Koch. Planta Medica. 2003; 69 369-71
- 14 Al-Yayha M A, Muhammad I, Mirza H H, El-Feraly F S. Antibacterial constituents from the rhizomes of Ferula communis . Phytotherapy Research. 1998; 12 335-9
- 15 Chatterji M, Unniraman S, Mahadevan1 S, Nagaraja V. Effect of different classes of inhibitors on DNA gyrase from Mycobacterium smegmatis . Journal of Antimicrobial Chemotherapy. 2001; 48 479-85
Dr. Simon Gibbons
Centre for Pharmacognosy and Phytotherapy
The School of Pharmacy
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