Chemical Analysis and Antimicrobial Studies on Three Species of Ferulago from Greece

Abstract

The chemical composition of the essential oils of the flowering parts and of the hexane extracts of the leaves, of three species of the genus Ferulago (Apiaceae) from Greece, i.e., F. thyrsiflora, F. sylvatica and F. nodosa, was analysed by GC and GC-MS. Manoyl oxide isomers and lupanine, were identified in the hexane extracts of F. thyrsiflora. Dillapiole, was identified in all hexane extracts. Ent-3β-hydroxy-13-epi-manoyl oxide was identified and isolated from the essential oil of F. thyrsiflora. All these compounds are new reports for the genus Ferulago and are useful chemotaxonomic markers. Chemical data of F. thyrsiflora is presented for the first time. The essential oils and the extracts were investigated for their antimicrobial activity against Gram-positive and Gram-negative microorganisms.

References

• 1 Bernardi  L.. Tentamen revisions generis Ferulago. .  Boissiera. 1979;;  30 1-182
• 2 Tomkovich  L P,, Pimenov  M G.. Botanico-geographical analysis of the genus Ferulago W. D. J. Koch (Umbelliferae).  Feddes Repert.. 1989;;  100 (3 - 4) 119-29
• 3 Kabadas  D.. Botanical and Phytochemical Lexikon, Vol H (124),. Athens,; 1956: 4082
• 4 Doganca  S,, Ulubele  A,, Tuzlaci  E.. 1-Acetylhydroquinone 4-galactoside from Ferulago aucheri. .  Phytochemistry. 1991;;  30 2803-5
• 5 Miski  M,, Moubasher  H A,, Mabry  T J.. Sesquiterpene aryl esters from Ferulago antiochia. .  Phytochemistry. 1990;;  29 881-6
• 6 Giuseppe  R,, Cannizzo  S,, Amico  V,, Bizzini  M,, Piattelli  M.. Chemical constituents of Ferulago nodosa. .  J. Nat. Prod.. 1994;;  57 1731-3
• 7 Lemmich  J,, Pedersen  P A,, Said  M S,, Nielsen  B E.. Constituents of umbelliferous plants.  Acta. Chem. Scand.. 1971;;  25 995-9
• 8 Chalchat  J C,, Garry  R Ph,, Gorunovic  M S,, Bogavac  P M.. Composition of the essential oil of Ferulago sylvatica (Besser) Reichenb. (Apiaceae).  Pharmazie. 1992;;  47 802-3
• 9 Lienert  D,, Anklam  E,, Panne  U.. Gas chromatography-mass spectral analysis of roots of Echinaceae species and classification by multivariate data analysis.  Phytochem. Anal.. 1998;;  9 88-9
• 10 Demetzos  C,, Mitaku  S,, Couladi  M,, Harvala  C,, Kokkinopoulos  D.. Natural metabolites of ent-13-epi-manoyl oxide and other cytotoxic diterpenes from the resin Ladano of Cistus creticus.  Planta Medica. 1994;;  60 590-1
• 11 Adams  P R.. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Corporation, Carol Sream, Illinois; 1995
• 12 National Committee for Clinical Laboratory Standards.. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. National Committee for Clinical Laboratory Standards, Wayne, Pa. Vol. 15,: 14-7-A3 1995
• 13 Panter  K E,, Keeler  R F,, Bunch  T D.. Congenital skeletal malformations and cleft palate induced in goats by ingestion of Lupinus, Conium and Nicotiana species.  Toxicon. 1990;;  28 377-1385
• 14 Betz  J M,, Andrzejewski  D,, Troy  A,, Casey  R E,, Obermeyer  W R,, Page  S W, et al.. Gas chromatography determination of toxic quinolizidine alkaloids in Blue Cohosh, Caulophyllum thalictroides (L.) Michx.  Phytochem. Anal.. 1998;;  9 232-6
• 15 Anastassaki  T,, Demetzos  C,, Perdetzoglou  D,, Gazouli  M,, Loukis  A,, Harvala  A.. Analysis of labdane-type diterpenes from Cistus creticus (i.e subsp. creticus and subsp. eriocephalus) by GC and GC-MS.  Planta Medica. 1999;;  65 735-9
• 16 Van den Dool  H,, Kratz  P DA.. Generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography.  J. Chromatog.. 1963;;  11 463-71