Ferulagone: A New Monoterpene Ester from Ferulago thirkeana Essential Oil

Abstract

Essential oil obtained by micro-distillation and hydrodistillation of the endemic Ferulago thirkeana (Boiss.) Boiss. (Apiaceae) was analysed by GC/MS. An unknown component isolated from the essential oil was characterized by chromato-spectral techniques (1D-, 2D-NMR, HRMS, IR and UV) as (1S)-2,6,6-trimethyl-4-oxobicyclo[3.1.1]hept-2-enyl(2E)-2-methylbut-2-enoate (= ferulagone or 1-angeloyloxyverbenone) (1). Biological activities of the essential oil and the purified major component (1) were tested against various human pathogenic microorganisms resulting in moderate inhibition (62.5 - 125 μg/ml).

References

• 1 Davis P H. Flora of Turkey and The East Aegean Islands. Vol. 4 University Press Edinburgh; 1972: 453-71
• 2 Davis P H, Mill R R, Tan K. Flora of Turkey and The East Aegean Islands. Vol. 10 University Press Edinburgh; 1988: 301
• 3 Güner A, Özhatay N, Ekim T, Başer K HC. Flora of Turkey and The East Aegean Islands. Vol. 11 University Press Edinburgh; 2000
• 4 Akalin E. Pharmaceutical Botanical Investigation of Ferulago Species Growing in Western Turkey. Ph.D Thesis, Istanbul Univ. Istanbul; 1999
• 5 Baytop T. Türkiye’de Tıbbi Bitkiler ile Tedavi - Geçmişte ve Bugün (Therapy with Medicinal Plants in Turkey - Past and Present). 2nd Ed; Nobel Tip Basimevi Istanbul; 1999: 348-9
• 6 Başer K HC, Koyuncu M, Vural M. Composition of the essential oil of Ferulago trachycarpa (Fenzl) Boiss.  Journal of Essential Oil Research. 1998;  10 665-6
• 7 Başer K HC, Demirci B, Duman H. Composition of the essential oil of Ferulago asparagifolia Boiss. from Turkey.  Journal of Essential Oil Research. 2001;  13 134-5
• 8 Başer K HC, Demirci B, Özek T, Akalin E, Özhatay N. Micro-distilled volatile compounds from Ferulago species growing in Western Turkey. Pharmaceutical Biology 2002 (in print)
• 9 Demirci F, Işcan G, Güven K, Kirimer N, Demirci B, Başer K HC. Antimicrobial activities of Ferulago essential oils.  Zeitschrift für Naturforschung C. 2000;  55 886-9
• 10 Demetzos C, Perdetzoglou D, Gazouli M, Tan K, Economakis C. Chemical analysis and antimicrobial studies on three species of Ferulago from Greece.  Planta Medica. 2000;  66 560-3
• 11 Chang C WJ, Flament I, Matson J A, Nishida T, Ohloff G, Wherli F W,. et al .The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy, In: Progress in the Chemistry of Organic Natural Products. Eds: Zechmeister L, Herz W, Grisebach, Kirby WG Springer Verlag New York; 1979 Vol. 36: 1
• 12 Bates R B, Thalacker V P. Nuclear magnetic resonance spectral parameters in bicyclo-[3.1.1]heptanes: α-pinene, myrtenal, and verbenone.  Journal of Organic Chemistry. 1968;  33 1730-5
• 13 But P P-H, Hon P -M, Cao H, Chan T WD, Wu B -M, Mak T CW,. et al . Sesquiterpene lactones from Elephantopus scaber .  Phytochemistry. 1997;  44 113-6
• 14 Banerjee S, Schmeda-Hirschmann G, Castro V, Schuster A, Jakupovic J, Bohlmann F. Further Sesquiterpene lactones from Elephantopus mollis and Centratherum punctatum .  Planta Medica. 1986;  52 29-32
• 15 Başer K HC, Demirci B, Demirci F, Bedir E, Weyerstahl P, Marschall H,. et al . A new bisabolene derivative from the essential oil of Prangos uechtritzii Boiss. & Hausskn. Fruits.  Planta Medica. 2000;  67 674-7
• 16 Koneman E W, Allen S D, Janda W M, Schreckenberger P C, Winn W C. Color Atlas and Textbook of Diagnostic Microbiology. Lippincott-Raven Pub Philadelphia; 1997: 785-856
• 17 Rahalison L, Hamburger M, Monod M, Hostettmann K, Frenk E. Antifungal tests in phytochemical investigations: comparison of bioautographic methods using phytopathogenic and human pathogenic fungi.  Planta Medica. 1994;  60 41-4