Effect of the Method of Preparation on the Composition and Cytotoxic Activity of the Essential Oil of Pituranthos tortuosus
Loading...
Date
2011
Authors
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
Zeitschrift für Naturforschung
Series Info
Z. Naturforsch.;66
Doi
Scientific Journal Rankings
Abstract
The aerial parts of Pituranthos tortuosus (Desf.) Benth and Hook (Apiaceae), growing
wild in Egypt, yielded 0.8%, 0.6%, and 1.5% (v/w) of essential oil when prepared by hydrodistillation
(HD), simultaneous hydrodistillation-solvent (n-pentane) extraction (Lickens-
Nickerson, DE), and conventional volatile solvent extraction (preparation of the “absolute”,
SE), respectively. GC-MS analysis showed that the major components in the HD sample
were β-myrcene (18.81%), sabinene (18.49%), trans-iso-elemicin (12.90%), and terpinen-
4-ol (8.09%); those predominent in the DE sample were terpinen-4-ol (29.65%), sabinene
(7.38%), γ-terpinene (7.27%), and β-myrcene (5.53%); while the prominent ones in the SE
sample were terpinen-4-ol (15.40%), dill apiol (7.90%), and allo-ocimene (4E,6Z) (6.00%).
The oil prepared in each case was tested for its cytotoxic activity on three human cancer cell
lines, i.e. liver cancer cell line (HEPG2), colon cancer cell line (HCT116), and breast cancer
cell line (MCF7). The DE sample showed the most potent activity against the three human
cancer cell lines (with IC50 values of 1.67, 1.34, and 3.38 μg/ml against the liver, colon, and
breast cancer cell lines, respectively). Terpinen-4-ol, sabinene, γ-terpinene, and β-myrcene
were isolated from the DE sample and subjected to a similar evaluation of cytotoxic potency;
signifi cant activity was observed.
Description
MSA Google Scholar
Keywords
University of Pituranthos tortuosus
Citation
Abdel-Ghani A. and Hafez S. S. (1995), GC-MS analysis and antimicrobial activity of essential oil of Pituranthos tortuosus (Desf.). Qatar. Univ. Sci. J. 15, 23 – 26. Abdel-Kader M. S. (2003), New ester and furanocoumarins from the roots of Pituranthos tortuosus. J. Braz. Chem. Soc. 14, 48 – 51. Abdel-Mogib M., Ayyad S. N., Metwally M. A., and Dawidar A. M. (1992), Lactones from Pituranthos tortuosus. Pak. J. Sci. Ind. Res. 35, 93. Abdelwahed A., Hayder N., Kilani S., Mahmoud A., Chibani J., Hammami M., Chekir-Ghedira L., and Ghedira K. (2006), Chemical composition and antimicrobial activity of essential oils from Tunisian Pituranthos tortuosus (Coss.) Maire. Flav. Fragr. J. 21, 129 – 133. Abdullaev F. I., Luna R. R., Roitenburd B. V., and Espinosa A. J. (2000), Pattern of childhood cancer mortality in Mexico. Arch. Med. Res. 31, 526 – 531. Adams R. P. (2004), Identifi cation of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy. Allured Publishing Press, Carol Stream, IL, pp. 41 – 415. Ait M’Barek L., Ait Mouse H., Jaafari A., Aboufatima R., Benharref A., and Kamal M. (2007), Cytotoxic effect of essential oil of thyme (Thymus broussonettii) on the IGR-OV1 tumor cells resistant to chemotherapy. Brazil. J. Med. Biol. Res. 40, 1537 – 1544. Babu T. D., Kuttan G., and Padikkala J. (1995), Cytotoxic and anti-tumour properties of certain taxa of Umbelliferae with special reference to Centella asiatica (L.) Urban. J. Ethnopharmacol. 48, 53 – 57. Bakkali F., Averbeck S., Averbeck D., and Idaomar M. (2008), Biological effects of essential oils – A review. Food Chem. Toxicol. 46, 446 – 475. Calcabrini A., Stringaro A., Toccacieli L., Meschini S., Marra M., Colone M., Salvatore G., Mondellow F., Arancia G., and Molinari A. (2004), Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma. J. Invest. Dermatol. 122, 349 – 360. Gupta M., Mazumder U. K., Kumar R. S., and Kumar T. S. (2004), Antitumor activity and antioxidant role of Bauhinia racemosa against Ehrlich ascites carcinoma in Swiss albino mice. Acta Pharmacol. Sin. 25, 1070 – 1076. Hasheminejad G. and Caldml J. (1994), Genotoxicity of the alkenylbenzenes α- and β-asarone, myristicin and elemicin as determined by the UDS assay in cultured rat hepatocytes. Food Chem. Toxicol. 32, 223 – 231. Hou J., Sun T., Hu J., Chen S., Cai X., and Zou G. (2006), Chemical composition, cytotoxic and antioxidant activity of the leaf essential oil of Photinia serrulata. Food Chem. 103, 355 – 358. Hursting S. D., Fischer S. M., Wargovich M. J., and Digiovanni J. (1999), Nutritional modulation of the carcinogenesis process. In: Nutrition Oncology ( Heber D. and Blackburn G., eds.). Academic Press, San Diego, CA, pp. 91 – 104. Karber G. (1931), Determination of LD50. Arch. Exp. Pathol. Pharmakol. 162, 480. Koedam A., Scheffer J. C. S., and Svendsen A. B. (1979), Comparison of isolation procedures for essential oils. Z. Lebensm. Unters. Forsch. 168, 106 – 111. Mahran G. H., Ahmed M. S., Seida A. A., and Amarquaye A. A. (1989), A phytochemical investigation of Pituranthos tortuosus (Desf.) Benth and Hook. Bull. Fac. Pharm. 27, 87 – 89. Mitic-Culafi c D., Zegura B., Nikolic B., Vukovic-Gacic B., Knezevic-Vukcevic J., and Filipic M. (2009), Protective effect of linalool, myrcene and eucalyptol against t-butyl hydroperoxide induced genotoxicity in bacteria and cultured human cells. Food Chem. Toxicol. 47, 260 – 266 Pae H. O., Oh H., Yun Y. G., Oh G. S., Jang S., Hwang K. M., Kwon T. O., Lee H. S., and Chung H. T. (2002), Imperatorin, a furanocoumarin from Angelica dahurica (Umbelliferae), induces cytochrome c-dependent apoptosis in human promyelocytic leukaemia, hl-60 cells. Pharmacol. Toxicol. 91, 40 – 48. Pietras R. J. and Weinberg O. K. (2005), Antiangiogenic steroids in human cancer therapy. Evid Bas. Complement. Alternat. Med. 2, 49 – 57. Singab A. N., Khalifa T., Mahran G. H., Okada Y., Matsumaru Y., Nishino H., and Okuyama T. (1998), A new fl avonoid glycoside from Pituranthos tortuosus (Desf.) Benth and Hook. Nat. Med. 52, 191 – 194. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J. T., Bokesch H., Kenney S., and Boyd M. R. (1990), New colorimetric cytotoxicity assay for cytotoxic-drug screening. J. Natl. Canc. Inst. 82, 1107 – 1112. Sylvestre M., Legault J., Dufour D., and Pichette A. (2005), Chemical composition and anticancer activity of leaf essential oil of Myrica gale L. Phytomedicine 12, 299 – 304. Sylvestre M., Pichette A., Longtin A., Nagau F., and Legault J. (2006), Essential oil analysis and anticancer activity of leaf essential oil of Croton fl avens L. from Guadeloupe. J. Ethnopharmacol. 103, 99 – 102. Täckholm V. (1974) Student’s Flora of Egypt, 2nd ed. Cooperative Printing Company, Beirut, p. 388. Tao L., Zhou L., Zheng L., and Yao M. (2006), Elemene displays anti-cancer ability on laryngeal cancer cells in vitro and in vivo. Cancer Chemother. Pharmacol. 58, 24 – 34. Usta J., Kreydiyyeh S., Knio K., Barnabe P., Bou- Moughlabay Y., and Dagher S. (2009), Linalool decreases HepG2 viability by inhibiting mitochondrial complexes I and II, increasing reactive oxygen species and decreasing ATP and GSH levels. Chemico- Biolog. Interact. 180, 39 – 46. Wagner H., Baldt S., and Zgainski E. M. (1984), Plant Drug Analysis. Springer, Berlin, pp. 215 – 220. Wang G., Li X., Huang F., Zhao J., Ding H., Cunningham C., Coad J. E., Flynn D. C., Reed E., and Li Q. Q. (2005), Antitumor effect of β-elemene in non-small lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death. Cell Mol. Life Sci. 62, 881 – 893. Wattenberg L. W. (1990), Inhibition of carcinogenesis by minor nutrient constituents of the diet. Proc. Nutr. Soc. 49, 173 – 183. Wattenberg L. W. (1992), Inhibition of carcinogenesis by minor dietary constituents. Cancer Res. 52, 2085s – 2091s. Xiao J. B., Chen X. Q., Zhang Y. W., Jiang X. Y., and Xu M. (2006), Cytotoxicity of Marchantia convoluta leaf extracts to human liver and lung cancer cells. Braz. J. Med. Biol. Res. 39, 731 – 738. Yim D., Singh R. P., Agarwal C., Lee S., Chi H., and Agarwal R. (2005), A novel cytotoxic agent, decursin, induces g1 arrest and apoptosis in human prostate carcinoma cells. Cancer Res. 65, 1035 – 1044.