Toxic essential oils. Part IV: The essential oil of Achillea falcata L. as a source of biologically/pharmacologically active trans-sabinyl esters

Food and Chemical Toxicology

Volumn 80, Issue , 2015, Pages 114-129

  Radulović, Niko S ^a   Mladenović, Marko Z ^a   Randjelovic, Pavle J ^a   Stojanović, Nikola M ^a   Dekić, Milan S ^a,b   Blagojević, Polina D ^a  

^a UNIVERSITY OF NI   (Serbia)

^b State University of Novi Pazar   (Serbia)

Author keywords

Acetylcholinesterase inhibitory activity; Achillea falcata L.; Acute toxicity; Antinociceptive activity; Essential oil; Trans Sabinol

Indexed keywords

4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL 2 METHYLBUTANOIC ACID; 4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL 2 METHYLPROPANOIC ACID; 4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL ACETIC ACID; 4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL BUTANOIC ACID; 4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL FORMIC ACID; 4 METHYLENE 1 [1 METHYLETHYL]BICYCLO[3.1.0]HEXAN 3 YL PROPANOIC ACID; ABSINTHOL; BENZALDEHYDE; CAMPHOR; CHOLINESTERASE INHIBITOR; CRESOL; DODECANE; ESSENTIAL OIL; EUGENOL; FURFURAL; GUAIACOL; HEXANOL; ISOPENTYL ALCOHOL; ISOPHORONE; LINALOOL; PARA CYMENE; PENTANOL; PHYSOSTIGMINE; PINENE; RIVASTIGMINE; TERPINOLENE; THYMOL; TRIDECANE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANILLIN; TERPENE; VEGETABLE OIL;

ACHILLEA; ACHILLEA FALCATA; ACUTE TOXICITY; ANIMAL EXPERIMENT; ANTINOCICEPTION; AREA UNDER THE CURVE; ARTEMIA SALINA; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOT PLATE TEST; HYDROLYSIS; INFRARED SPECTROSCOPY; ION CURRENT; LETHALITY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; MOLECULAR DOCKING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TAIL IMMERSION TEST; WRITHING TEST; CHEMICAL STRUCTURE; CHEMISTRY;

ACHILLEA FALCATA; ARTEMIA SALINA; ASTERACEAE; MUS;

ACHILLEA; CHOLINESTERASE INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT OILS; TERPENES;

EID: 84925709760     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2015.03.001     Document Type: Article

References (50)

1. Aburjai T., Hudaib M. Antiplatelet, antibacterial and antifungal activities of Achillea falcata extracts and evaluation of volatile oil composition. Pharmacogn. Mag 2006, 2:188-195.
2. Aburjai T., Hudaib M., Tayyema R., Yousef M., Qishawi M. Ethnopharmacological survey of medicinal herbs in Jordan, the Ajloun Heights region. J. Ethnopharmacol 2007, 110:294-304.
3. Adams R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry 2007, Allured Books, Carol Stream, IL. fourth ed.
4. Adhami H.R., Linder T., Kaehlig H., Schuster D., Zehl M., Krenn L. Catechol alkenyls from Semecarpus anacardium: acetylcholinesterase inhibition and binding mode predictions. J. Ethnopharmacol 2012, 139:142-148.
5. Akhila J.S., Deepa S., Alwar M.C. Acute toxicity studies and determination of median lethal dose. Curr. Sci 2007, 93:917-920.
6. Alzweiri M., Al Sarhan A., Mansi K., Hudaib M., Aburjai T. Ethnopharmacological survey of medicinal herbs in Jordan, the Northern Badia region. J. Ethnopharmacol 2011, 137:27-35.
7. Bar-On P., Millard C.B., Harel M., Dvir H., Enz A., Sussman J.L., et al. Kinetic and structural studies on the interaction of cholinesterases with the anti-Alzheimer drug rivastigmine. Biochemistry 2002, 41:3555-3564.
8. Bittencourt S.C., De Lima T.C.M., Morato G.S. Antinociceptive effects of clebopride in the mouse. Gen. Pharmacol 1995, 26:1083-1087.
9. Bruno M., Rosselli S., Raccuglia R.A., Maggio A., Senatore F., Apostolides A.N., et al. Terpenoids and flavones from Achillea falcata (Asteraceae). Rev. Soc. Quim. Mex 2003, 47:130-131.
10. Burrows G.E., Tyrl R.J. Toxic Plants of North America 2012, John Wiley & Sons, Oxford, UK. second ed.
11. Casares R. Juniperus sabina. Food Cosmet. Toxicol 1964, 2:680-681.
12. Cégiéla-Carlioz P., Bessière J.-M., David B., Mariotte A.-M., Gibbons S., Dijoux-Franca M.-G. Modulation of multi-drug resistance (MDR) in Staphylococcus aureus by Osha (Ligusticum porteri L., Apiaceae) essential oil compounds. Flavour Fragr. J. 2005, 20:671-675.
13. Collier H.O.J., Dinneen L.C., Johnson C.A., Schneider C. The abdominal constriction response and its suppression by analgesic drugs in the mouse. Br. J. Pharmacol. Chemother 1968, 32:295-310.
14. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03 2004, Gaussian, Inc., Wallingford CT.
15. Ghantous A., Nasser N., Saab I., Darwiche N., Saliba N. Structure-activity relationship of seco-tanapartholides isolated from Achillea falcata for inhibition of HaCaT cell growth. Eur. J. Med. Chem 2009, 44:3794-3797.
16. Hackett D., Buckett W.R. Drug effects in a novel biphasic writhing syndrome induced by acetylcholine in mice. Eur. J. Pharmacol 1975, 30:280-287.
17. Hayamizu K., Yamamoto O. The relative sign of the long range spin-spin coupling constants in formic acid esters. J. Mol. Spectrosc 1967, 23:121-130.
18. Herrick-Davis S., Chippari S., Luttinger D., Ward S.J. Evaluation of adenosine agonists as potential analgesics. Eur. J. Pharmacol 1989, 162:365-369.
19. Hofer O., Greger H., Robien W., Werner A. Carbon-13 NMR and proton lanthanide-induced shifts of naturally occurring alkamides with cyclic amide moieties. Amides from Achillea falcata. Tetrahedron 1986, 42:2707-2716.
20. Judzentiene A., Budiene J., Gircyte R., Masotti V., Laffont-Schwob I. Toxic activity and chemical composition of Lithuanian wormwood (Artemisia absinthium L.) essential oils. Rec. Nat. Prod 2012, 6:180-183.
21. Karaalp C., Yurtman A.N., Yavasoglu N., Karabay U. Evaluation of antimicrobial properties of Achillea L. flower head extracts. Pharm. Biol 2009, 47:86-91.
22. Konyahoglu S., Karamenderes C. Screening of total flavonoid, phenol contents and antioxidant capacities of some Achillea L. species growing in Turkey. Acta Pharm. Turc 2004, 46:163-170.
23. Konyalioglu S., Karamenderes C. The protective effects of Achillea L. species native in Turkey against H(2)O(2)-induced oxidative damage in human erythrocytes and leucocytes. J. Ethnopharmacol 2005, 102:221-227.
24. Kürkçüoglu M., Demirci B., Tabanca N., Özek T., Başer K.H.C. The essential oil of Achillea falcata L. Flavour Fragr. J. 2003, 18:192-194.
25. Law N.M., Bharucha A.E., Undale A.S., Zinsmeister A.R. Cholinergic stimulation enhances colonic motor activity, transit, and sensation in humans. Am. J. Physiol. Gastrointest. Liver Physiol 2001, 281:G1228-G1237.
26. Le Bars D., Gozariu M., Cadden S.W. Animal models of nociception. Pharmacol. Rev 2001, 53:597-652.
27. Mack L., Gros P., Burkhardt J., Seifert K. Elicitors of tansy volatiles from cotton leaf worm larval oral secretion. Phytochemistry 2013, 96:158-169.
28. Medeiros L.B.P., Rocha M.S., de Lima S.G., de Sousa Júnior G.R., Citó A.M.G.L., da Silva D., et al. Chemical constituents and evaluation of cytotoxic and antifungal activity of Lantana camara essential oils. Rev. Bras. Farmacogn 2012, 22:1259-1267.
29. Millard C.B., Kryger G., Ordentlich A., Greenblatt H.M., Harel M., Raves M.L., et al. Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level. Biochemistry 1999, 38:7032-7039.
30. Narayanan C.R., Sarma M.R. Deshielding effect on neighboring protons on the esterification of a hydroxyl group. Tetrahedron Lett 1968, 9:1553-1556.
31. Norin T., Strömberg S., Weber M. Lanthanide-induced shifts in proton magnetic resonance; studies on the conformations of Thujane derivatives. Acta Chem. Scand 1973, 27:1579-1585.
32. Pages N., Fournier G., Baduel C., Turt N., Rusnac M. Sabinyl acetate, the main component of Juniperus sabina L'Herit. essential oil, is responsible for antiimplantation effect. Phytother. Res 1996, 10:438-440.
33. Radulović N.S., Dekić M.S., Randjelović P.J., Stojanović N.M., Zarubica A.R., Stojanović-Radić Z.Z. Toxic essential oils: anxiolytic, antinociceptive and antimicrobial properties of the yarrow Achillea umbellata Sibth. et Sm. (Asteraceae) volatiles. Food Chem. Toxicol 2012, 50:2016-2026.
34. Radulović N.S., Dordević N.D., Denić M., Pinheiro M.M., Fernandes P.D., Boylan F. A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity. Food Chem. Toxicol 2012, 50:274-279.
35. Radulović N.S., Blagojević P.D., Randjelović P.J., Stojanović N.M. The last decade of antinociceptive alkaloids: structure, synthesis, mechanism of action and prospect. Curr. Top. Med. Chem 2013, 13:2134-2170.
36. Radulović N.S., Mladenović M.Z., Blagojević P.D., Stojanović-Radić Z.Z., Ilic-Tomic T., Senerovic L., et al. Toxic essential oils. Part III: identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.). Food Chem. Toxicol 2013, 62:554-565.
37. Radulović N.S., Randjelović P.J., Stojanović N.M., Blagojević P.D., Stojanović-Radić Z.Z., Ilić I.R., et al. Toxic essential oils. Part II: chemical, toxicological, pharmacological and microbiological profiles of Artemisia annua L. volatiles. Food Chem. Toxicol 2013, 58:37-49.
38. Radulović N.S., Zlatković D.B., Randjelović P.J., Stojanović N.M., Novaković S.B., Akhlaghi H. Chemistry of spices: bornyl 4-methoxybenzoate from Ferula ovina (Boiss.) Boiss. (Apiaceae) induces hyperalgesia in mice. Food Funct 2013, 4:1751-1758.
39. Rnjan N., Andreasen K.F., Kumar S., Hyde-Volpe D., Arya D.P. Aminoglycoside binding of Oxytricha nova telomeric DNA. Biochemistry 2010, 49:9891-9903.
40. Saikali M., Ghantous A., Halawi R., Talhouk S.N., Saliba N.A., Darwiche N. Sesquiterpene lactones isolated from indigenous Middle Eastern plants inhibit tumor promoter-induced transformation of JB6 cells. BMC Complement. Altern. Med 2012, 12:1-10.
41. Salla M., Fakhoury I., Saliba N., Darwiche N., Gali-Muhtasib H. Synergistic anticancer activities of the plant-derived sesquiterpene lactones salograviolide A and iso-seco-tanapartholide. J. Nat. Med 2013, 67:468-479.
42. Sanner M.F. Python: a programming language for software integration and development. J. Mol. Graph. Model 1999, 17:57-61.
43. Senatore F., Napolitano F., Arnold N.A., Bruno M., Herz W. Composition and antimicrobial activity of the essential oil of Achillea falcata L. (Asteraceae). Flavour Fragr. J. 2005, 20:291-294.
44. Sorgeloos P., Remiche-Van der Wielen C., Persoone G. The use of Artemia nauplii for toxicity test: a critical analysis. Ecotoxicol. Environ. Saf. 1978, 2:249-255.
45. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker L., et al. Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein. Science 1991, 253:872-879.
46. Tohme R., Al Aaraj L., Ghaddar T., Gali-Muhtasib H., Saliba N.A., Darwiche N. Differential growth inhibitory effects of highly oxygenated guaianolides isolated from the Middle Eastern indigenous plant Achillea falcata in HCT-116 colorectal cancer cells. Molecules 2013, 18:8275-8288.
47. Trott O., Olson A.J. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem 2010, 31:455-461.
48. Van den Dool H., Kratz P.D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr 1963, 11:463-471.
49. Whittle B.A. The use of changes in capillary permeability in mice to distinguish between narcotic and nonnarcotic analgesics. Br. J. Pharmacol. Chemother 1964, 22:246-253.
50. Zetler G. Apomorphine separates the antinociceptive effects of cholecystokinin octapeptide and ceruletide from those of morphine. Eur. J. Pharmacol 1983, 92:151-154.