Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents

Molecules

Volumn 17, Issue 9, 2012, Pages 11173-11184

  Sandoval Montemayor, Nallely E ^a   García, Abraham ^a   Elizondo Treviño, Elizabeth ^a   Garza González, Elvira ^b   Alvarez, Laura ^c   Del Rayo Camacho Corona, María ^a  

^a UNIVERSIDAD AUTÓNOMA DE NUEVO LEÓN   (Mexico)

^b Medicina UANL   (Mexico)

^c CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

Citrus aurantifolia; Coumarins; Fatty acids; GC MS analysis; Multidrug resistant; Mycobacterium tuberculosis

Indexed keywords

BERGAMOTTIN; CITRAL; COUMARIN DERIVATIVE; ETHAMBUTOL; ISONIAZID; ISOPIMPINELLIN; LINOLEIC ACID; OLEIC ACID; PALMITIC ACID; PLANT EXTRACT; PSORALEN DERIVATIVE; STREPTOMYCIN; TERPENE; TUBERCULOSTATIC AGENT;

ARTICLE; CHEMISTRY; DRUG EFFECT; ISOLATION AND PURIFICATION; LIME (FRUIT); MICROBIAL SENSITIVITY TEST; MULTIDRUG RESISTANCE; MYCOBACTERIUM TUBERCULOSIS;

ANTITUBERCULAR AGENTS; CITRUS AURANTIIFOLIA; COUMARINS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; ETHAMBUTOL; ISONIAZID; LINOLEIC ACID; MICROBIAL SENSITIVITY TESTS; MONOTERPENES; MYCOBACTERIUM TUBERCULOSIS; OLEIC ACID; PALMITIC ACID; PLANT EXTRACTS; PSORALENS; STREPTOMYCIN;

EID: 84866915162     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules170911173     Document Type: Article

References (47)

1. World Health Organization Home Page. Available online: http://http://www.who.int/tb/publications/2011/factsheet-tb-2011.pdf (accessed on 20 July 2012).
2. Tripathi, R.P.; Tewari, N.; Dwivedi, N.; Tiwari, V.K. Fighting tuberculosis: An old disease with new challenges. Med. Res. Rev. 2005, 25, 93-131.
3. Copp, B.R. Antimycobacterial natural products. Nat. Prod. Rep. 2003, 20, 535-557.
4. Okunade, A.L.; Elvin-Lewis, M.P.F.; Lewis, W.H. Natural antimycobacterial metabolites: Current status. Phytochemistry 2004, 65, 1017-1032.
5. Nayyar, A.; Jain, R. Recent advances in new structural classes of anti-tuberculosis agents. Curr. Med. Chem. 2005, 12, 1873-1886.
6. Copp, B.R.; Pearce, A.N. Natural product growth inhibitors of Mycobacterium tuberculosis. Nat. Prod. Rep. 2007, 24, 278-297.
7. García, A.; Bocanegra-García, V.; Palma-Nicolás, J.P.; Rivera, G. Recent advances in antitubercular natural products. Eur. J. Med. Chem. 2012, 49, 1-23.
8. Camacho-Corona, M.R.; Ramírez-Cabrera, M.A.; González- Santiago, O.; Garza-González, E.; Palacios, I.P.; Luna-Herrera, J. Activity against drug resistant-tuberculosis strains of plants used in Mexican traditional medicine to treat tuberculosis and other respiratory diseases. Phytother. Res. 2008, 22, 82-85.
9. Camacho-Corona, M.R.; Favela-Hernández, J.M.J.; González-Santiago, O.; Garza-González, E.; Molina-Salinas, G.M.; Said-Fernández, S.; Delgado, G.; Luna-Herrera, J. Evaluation of some plant-derived secondary metabolites against sensitive and multidrug-resistant Mycobacterium tuberculosis. J. Mex. Chem. Soc. 2009, 53, 71-75.
10. Favela-Hernández, J.M.J.; García, A.; Garza- González, E.; Rivas-Galindo, V.M.; Camacho-Corona, M.R. Antibacterial and antimycobacterial lignans and flavonoids from Larrea tridentata. Phytother. Res. 2012, doi:10.1002/ptr.4660.
11. Esquivel-Ferriño, P.C.; Favela-Hernández, J.M.; Garza-González, E.; Waksman, N.; Ríos, M.Y.; Camacho-Corona, M.R. Antimycobacterial activity of constituents from Foeniculum vulgare var. dulce grown in México. Molecules 2012, 17, 8471-8482.
12. Nicolosi, E.; Deng, Z.N.; Gentile, A.; La Malfa, S.; Continella, G.; Tribulato, E. Citrus phylogeny and genetic origin of important species as investigated by molecular markers. Theor. Appl. Genet. 2000, 100, 1155-1166.
13. Morton, J. Mexican Lime. In Fruits of Warm Climates, 1st ed.; J.F. Morton: Miami, FL, USA, 1987; pp. 168-172.
14. Apraj, V.; Thakur, N.D.; Bhagwat, A.; Mallya, R.; Sawant, L.; Pandita, N. Pharmacognostic and phytochemical evaluation of Citrus aurantifolia (Christm) Swingle peel. Pharmacogn. J. 2011, 3, 70-76.
15. Feger, W.; Brandauer, H.; Ziegler, H. Sesquiterpene hydrocarbons of cold-pressed lime oils. Flav. Frag. J. 2000, 15, 281-284.
16. Johann, S.; Smania, A.; Pizzolatti, M.G.; Schripsema, J.; Braz-Filho, R.; Branco, A. Complete 1H and 13C-NMR assignments and antifungal activity of two 8-hydroxy flavonoids in mixture. An. Acad. Bras. Cienc. 2007, 79, 215-222.
17. Piccinelli, A.L.; Garcia, M.M.; Armenteros, D.M.; Alfonso, M.A.; Arevalo, A.C.; Campone, L.; Rastrelli, L. HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. J. Agric. Food. Chem. 2008, 56, 1574-1581.
18. Jiwajinda, S.; Santisopasri, V.; Ohigashi, H. Coumarin-related compounds as plant growth inhibitors from two rutaceous plants in thailand. Biosci. Biotechnol. Biochem. 2000, 64, 420-423.
19. Afolayan, A.J.; Asekun, O.T. Comparative study of the chemical profiles of the essential oils of ripe and rotten fruits of Citrus aurantifolia Swingle. Nat. Prod. Commun. 2008, 3, 1133-1136.
20. Chisholm, G.M.; Wilson, M.A.; Gaskey, G.M. Characterization of aroma volatiles in the key lime essential oils (Citrus aurantifolia Swingle). Flav. Frag. J. 2003, 18, 106-115.
21. Jafari, S.; Esfahani, S.; Fazeli, M.R.; Jamalifar, H.; Samadi, M.; Samadi, N.; Najarian-Toosi, A.; Shams-Ardekani, M.R.; Khanavi, M. Antimicrobial activity of lime essential oil against food-borne pathogens isolated from cream-filled cakes and pastries. Int. J. Biol. Chem. 2011, 5, 258-265.
22. Tundis, R.; Loizzo, M.R.; Bonesi, M.; Menichini, F.; Mastellone, V.; Colica, C.; Menichini, F. Comparative study on the antioxidant capacity and cholinesterase inhibitory activity of Citrus aurantifolia Swingle, C. aurantium L., and C. bergamia Risso and Poit. peel essential oils. J. Food. Sci. 2012, 77, H40-H46.
23. Taur, D.J.; Kulkarni, V.B.; Patil, R.Y.; Patil, R.N. Anthelmintic activity of Ocimum sanctum and Citrus aurantifolia oils. Pharmacologyonline 2009, 3, 495-499.
24. Gharagozloo, M.; Doroudchi, M.; Ghaderi, A. Effects of Citrus aurantifolia concentrated extract on the spontaneous proliferation of MDA-MB-453 and RPMI-8866 tumor cell lines. Phytomedicine 2002, 9, 475-477.
25. Shalaby, N.M.M.; Abd-Alla, H.I.; Ahmed, H.H.; Basoudan, N. Protective effect of Citrus sinensis and Citrus aurantifolia against osteoporosis and their phytochemical constituents. J. Med. Plants Res. 2011, 5, 579-588.
26. Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Isolation of furanocoumarins from bergamot fruits as HL-60 differentiation-inducing compounds. J. Agric. Food Chem. 1999, 47, 4073-4078.
27. Miyake, Y.; Hiramitsu, M. Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel. J. Food Sci. Technol. 2011, 48, 635-639.
28. Shiota, H. Volatile components in the peel oil from fingered citron (Citrus medica L. var. sarcodactylis Swingle). Flav. Frag. J. 1990, 5, 33-37.
29. Hongwei, Y.; Bogang, L.; Changsong, L.; Guolin, Z. Chemical Study on Evodia vestita. Chin. J. Appl. Environ. Biol. 2010, 16, 72-75.
30. Miyazawa, M.; Tsukamoto, T.; Anzai, J.; Ishikawa, Y. Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster. J. Agric. Food Chem. 2004, 52, 4401-4405.
31. Evans, F.E.; Fu, P.P.; Cairns, T. Long-range coupling constants for structural analysis of complex polycyclic aromatic hydrocarbons by high-field proton magnetic resonance spectrometry. Anal. Chem. 1981, 53, 558-560.
32. Craske, J.D.; Suryadi, N.; Wootton, M.A. Comparison of the peel oil components of Australian native lime (Microcitrus australe) and Mexican lime (C. aurantifolia Swingle). J. Sci. Food Agric. 2005, 85, 522-525.
33. Chamblee, T.S.; Clark, B.C. Analysis and chemistry of distilled lime oil (Citrus aurantifolia Swingle). J. Essent. Oil Res. 1997, 9, 267-274.
34. Bourgaud, E.; Hehn, A.; Larbat, R.; Doerper, S.; Gontier, E.; Kellner, S.; Matern, U. Biosynthesis of coumarins in plants: A major pathway still to be unraveled for cytochrome P450 enzymes. Phytochem. Rev. 2006, 5, 293-308.
35. Ngwendson, J.N.; Bedir, E.; Efange, S.M.; Okunji, C.O.; Iwu, M.M.; Schuster, B.G.; Khan, I.A. Constituents of Peucedanum zenkeri seeds and their antimicrobial effects. Pharmazie 2003, 58, 587-589.
36. Abbaskhan, A.; Choudhary, M.I.; Ghayur, M.N.; Parween, Z.; Shaheen, F.; Gilani, A.U.; Maruyama, T.; Iqbal, K.; Tsuda, Y. Biological activities of Indian celery, Seseli diffusum (Roxb. Ex Sm.) Sant. & Wagh. Phytother. Res. 2012, 26, 783-786.
37. Guo, S.; Li, S.; Peng, Z.; Ren, X. Isolation and identification of active constituents of Toddalia asiatica in cardiovascular system. Zhong Yao Cai 1998, 21, 515-516.
38. Kleiner, H.E.; Vulimiri, S.V.; Starost, M.F.; Reed, M.J.; DiGiovanni, J. Oral administration of the citrus coumarin, isopimpinellin, block DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz(a)anthracene in SECAR mice. Carcinogenesis 2002, 23, 1667-1675.
39. Chiou, W.F.; Huang, Y.L.; Chen, C.F.; Chen, C.C. Vasorelaxing effect of coumarins from Cnidium monnieri on rabbit corpus cavernosum. Planta Med. 2001, 67, 282-284.
40. Hudson, J.B.; Miki, N.; Towers, G.H. Isopimpinellin is not phototoxic to viruses and cells. Planta Med. 1987, 53, 306-307.
41. Ivie, G.W.; Beier, R.C. Isopimpinellin is not phototoxic in a chick skin assay. Photochem. Photobiol. 1996, 63, 306-307.
42. Olguín-Reyes, S.; Camacho-Carranza, R.; Hernández-Ojeda, S.; Elinos-Baez, M.; Espinosa-Aguirre, J.J. Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Food Chem. Toxicol. 2012, 50, 3094-3099.
43. Miyake, Y.; Murakami, A.; Sugiyama, Y.; Isobe, M.; Koshimizu, K.; Ohigashi, H. Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation. J. Agric. Food Chem. 1999, 47, 3151-3157.
44. Saravanakumar, D.E.M.; Folb, P.I.; Campbell, B.W.; Smith, P. Antimycobacterial activity of the red alga Polysiphonia virgata. Pharm. Biol. 2008, 46, 254-260.
45. Hirsch, I.W.; Barchet, H.M. Significance of medium lengh fatty acids and their salts in the prophylaxis of tuberculosis. Deutsche Zeitschrift fuer Verdauung und Stoffwechselkrankheiten. 1955, 15, 214-218.
46. Zhing, C.J.; Yoo, J.S.; Lee, T.G.; Cho, H.Y.; Kim, Y.H.; Kim, W.G. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Lett. 2005, 579, 5157-5162.
47. Adams, R.P. Identification of Essential Oils Components by Gas Chromatography/Mass Spectrometry, 4th ed.; Allured Business Media: Carol Stream, IL, USA, 2007; pp. 1-804.