HPTLC simultaneous quantification of triterpene acids for quality control of Plantago major L. and evaluation of their cytotoxic and antioxidant activities

Industrial Crops and Products

Volumn 60, Issue , 2014, Pages 239-246

  Kartini, ^a,b   Piyaviriyakul, S ^c   Siripong, P ^c   Vallisuta, O ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

^b UNIVERSITY OF SURABAYA   (Indonesia)

^c NATIONAL CANCER INSTITUTE   (Thailand)

Author keywords

Antioxidant; Cytotoxic; HPTLC; Oleanolic acid; Simultaneous analysis; Ursolic acid

Indexed keywords

ANTIOXIDANTS; CARBOXYLIC ACIDS; CELL CULTURE; CHROMATOGRAPHY; CYTOTOXICITY; METHANOL; ORGANIC SOLVENTS; PLANTS (BOTANY);

CYTOTOXIC; HPTLC; OLEANOLIC ACIDS; SIMULTANEOUS ANALYSIS; URSOLIC ACID;

EXTRACTION;

ANTIOXIDANT; BIOACTIVITY; BIOASSAY; CHEMICAL ANALYSIS; CHROMATOGRAPHY; METHANOL; PLANT COMMUNITY; PROVENANCE; SEED; TERPENE;

EID: 84903850416     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2014.06.020     Document Type: Article

References (50)

1. 2-induced oxidative stress in astrocytes primary cultures. Neurosci. Lett. 2008, 442:224-227.
2. Brand-Williams W., Cuvelier M.E., Berset C. Use of a free radical method to evaluate antioxidant activity. LWT - Food Sci. Technol. 1995, 28:25-30.
3. Caligiani A., Malavasi G., Palla G., Marseglia A., Tognolini M., Bruni R. A simple GC-MS method for the screening of betulinic, corosolic, maslinic, oleanolic and ursolic acid contents in commercial botanicals used as food supplement ingredients. Food Chem. 2013, 136:735-741.
4. Chen Z., Bertin R., Froldi G. EC50 estimation of antioxidant activity in DPPH assay using several statistical programs. Food Chem. 2013, 138:414-420.
5. Chiang L.-C., Chiang W., Chang M.-Y., Ng L.-T., Lin C.-C. Antileukemic activity of selected natural products in Taiwan. Am. J. Chin. Med. 2003, 31:37-46.
6. Chiang L.C., Chiang W., Chang M.Y., Lin C.C. In vitro cytotoxic, antiviral and immunomodulatory effects of Plantago major and Plantago asiatica. Am. J. Chin. Med. 2003, 31:225-234.
7. Chiang L.C., Ng L.T., Chiang W., Chang M.Y., Lin C.C. Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. Planta Med. 2003, 69:600-604.
8. de Padua L.S., Bunyapraphatsara N. Plant Resources of South-East Asia 1999, Prosea Foundation, Bogor.
9. Galvez M., Martin-Cordero C., Houghton P.J., Ayuso M.J. Antioxidant activity of methanol extracts obtained from Plantago species. J. Agric. Food Chem. 2005, 53:1927-1933.
10. Galvez M., Martin-Cordero C., Lopez-Lazaro M., Cortes F., Ayuso M.J. Cytotoxic effect of Plantago spp. on cancer cell lines. J. Ethnopharmacol. 2003, 88:125-130.
11. Ghopur H., Usmanova S.K., Ayupbek A., Aisa H. A new chromone from seeds of Cydonia oblonga. Chem. Nat. Compd. 2012, 48:562-564.
12. Jager S., Trojan H., Kopp T., Laszczyk M.N., Scheffler A. Pentacyclic triterpene distribution in various plants - rich sources for a new group of multi-potent plant extracts. Molecules 2009, 14:2016-2031.
13. Janicsák G., Veres K., Kállai M., Máthé I. Gas chromatographic method for routine determination of oleanolic and ursolic acids in medicinal plants. Chromatographia 2003, 58:295-299.
14. Jin L., Xue H.-Y., Jin L.-J., Li S.-Y., Xu Y.-P. Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes. Eur. J. Pharmacol. 2008, 582:162-167.
15. Karamac M., Kosinska A., Pegg R.B. Comparison of radical-scavenging activities for selected phenolic acids. Pol. J. Food Nutr. Sci. 2005, 14:165-170.
16. Kolak U., Boǧa M., Uruşak E.A., Ulubelen A. Constituents of Plantago major subsp. intermedia with antioxidant and anticholinesterase capacities. Turkish J. Chem. 2011, 35:637-645.
17. Kontogianni V.G., Exarchou V., Troganis A., Gerothanassis I.P. Rapid and novel discrimination and quantification of oleanolic and ursolic acids in complex plant extracts using two-dimensional nuclear magnetic resonance spectroscopy - comparison with HPLC methods. Anal. Chim. Acta 2009, 635:188-195.
18. Lee T.-H., Juang S.-H., Hsu F.-L., Wu C.-Y. Triterpene acids from the leaves of Planchonella duclitan (Blanco) Bakhuizan. J. Chin. Chem. Soc. 2005, 52:1275-1280.
19. Li S., Han Q., Qiao C., Song J., Cheng C.L., Xu H. Chemical markers for the quality control of herbal medicines: an overview. Chin. Med. 2008, 3:7.
20. Liu J. Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 1995, 49:57-68.
21. Liu J. Oleanolic acid and ursolic acid: research perspectives. J. Ethnopharmacol. 2005, 100:92-94.
22. Martelanc M., Vovk I., Simonovska B. Separation and identification of some common isomeric plant triterpenoids by thin-layer chromatography and high-performance liquid chromatography. J. Chromatogr. A 2009, 1216:6662-6670.
23. Ozaslan M., Didem Karagoz I., Kalender M.E., Kilic I.H., Sari I., Karagoz A. In vivo antitumoral effect of Plantago major L. extract on Balb/C mouse with Ehrlich ascites tumor. Am. J. Chin. Med. 2007, 35:841-851.
24. Özgen U., Mavi A., Terzi Z., Kazaz C., Aşçi A., Kaya Y., Seçen H. Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp. sipyleus var. sipyleus. Rec. Nat. Prod. 2011, 5.
25. Pollier J., Goossens A. Oleanolic acid. Phytochemistry 2012, 77:10-15.
26. Ringbom T., Segura L., Noreen Y., Perera P., Bohlin L. Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalyzed prostaglandin biosynthesis. J. Nat. Prod. 1998, 61:1212-1215.
27. Rivelli D.P., Silva V.V., Ropke d.C.D., Miranda D.V., Almeida R.L., Sawada T.C.H., Barros S.B.d.M. Simultaneous determination of chlorogenic acid, caffeic acid and caffeine in hydroalcoholic and aqueous extracts of Ilex paraguariensis by HPLC and correlation with antioxidant capacity of the extracts by DPPH reduction. Revista Brasileira de Ciências Farmacêuticas 2007, 43:215-222.
28. Ruffa M.J., Ferraro G., Wagner M.L., Calcagno M.L., Campos R.H., Cavallaro L. Cytotoxic effect of Argentine medicinal plant extracts on human hepatocellular carcinoma cell line. J. Ethnopharmacol. 2002, 79:335-339.
29. Samuelsen A.B. The traditional uses, chemical constituents and biological activities of Plantago major L. A review. J. Ethnopharmacol. 2000, 71:1-21.
30. Sánchez-Moreno C. Methods used to evaluate the free radical scavenging activity in foods and biological systems. Food Sci. Technol. Int. 2002, 8:121-137. (review).
31. 13C NMR resonances of oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn. Reson. Chem. 2003, 41:636-638.
32. Shanmugam M.K., Dai X., Kumar A.P., Tan B.K., Sethi G., Bishayee A. Ursolic acid in cancer prevention and treatment: molecular targets, pharmacokinetics and clinical studies. Biochem. Pharmacol. 2013, 85:1579-1587.
33. Silva M.G., Vieira I.G., Mendes F.N., Albuquerque I.L., dos Santos R.N., Silva F.O., Morais S.M. Variation of ursolic acid content in eight Ocimum species from northeastern Brazil. Molecules 2008, 13:2482-2487.
34. Stenholm A., Goransson U., Bohlin L. Bioassay-guided supercritical fluid extraction of cyclooxygenase-2 inhibiting substances in Plantago major L. Phytochem. Anal. 2013, 24:176-183.
35. Szakiel A., Mroczek A. Distribution of triterpene acids and their derivatives in organs of cowberry (Vaccinium vitis-idaea L.) plant. Acta Biochim. Pol. 2007, 54:733-740.
36. Tarvainen M., Suomela J.-P., Kallio H., Yang B. Triterpene acids in Plantago major: identification, quantification and comparison of different extraction methods. Chromatographia 2010, 71:279-284.
37. Thani W., Vallisuta O., Siripong P., Ruangwises N. Anti-proliferative and antioxidative activities of Thai noni/Yor (Morinda citrifolia Linn.) leaf extract. Southeast Asian J. Trop. Med. Public Health 2010, 41:482-489.
38. Tistaert C., Dejaegher B., Heyden Y.V. Chromatographic separation techniques and data handling methods for herbal fingerprints: a review. Anal. Chim. Acta 2011, 690:148-161.
39. Vasconcelos M.A., Royo V.A., Ferreira D.S., Crotti A.E., Andrade e Silva M.L., Carvalho J.C., Bastos J.K., Cunha W.R. In vivo analgesic and anti-inflammatory activities of ursolic acid and oleanoic acid from Miconia albicans (Melastomataceae). Z. Naturforsch. C 2006, 61:477-482.
40. Wang C., Liu H., Zhang B., Guo H. Determination of oleanolic and ursolic acid in Chinese herbs using HPLC and γ-CD as mobile phase modifier. J. Sep. Sci. 2011, 34:3023-3028.
41. Wang H., Wang Z., Guo W. Comparative determination of ursolic acid and oleanolic acid of Macrocarpium officinalis (Sieb. et Zucc.) Nakai by RP-HPLC. Ind. Crops Prod. 2008, 28:328-332.
42. Wang X., Li X., Li H. Reassessment of antioxidant activity of baicalein in vitro. Asian J. Pharm. Biol. Res. 2011, 1(2):186-194.
43. Wilairat R., Kijjoa A., Pinto M., José Nascimento M.S., Silva A.M., Eaton G., Herz W. Constituents of Schisandra verruculosa and their cytotoxic effect on human cancer cell lines. Pharm. Biol. 2006, 44:411-415.
44. Wojciak-Kosior M. Separation and determination of closely related triterpenic acids by high performance thin-layer chromatography after iodine derivatization. J. Pharm. Biomed. Anal. 2007, 45:337-340.
45. Wójciak-Kosior M., Sowa I., Kocjan R., Nowak R. Effect of different extraction techniques on quantification of oleanolic and ursolic acid in Lamii albi flos. Ind. Crops Prod. 2013, 44:373-377.
46. Xia E.-Q., Wang B.-W., Xu X.-R., Zhu L., Song Y., Li H.-B. Microwave-assisted extraction of oleanolic acid and ursolic acid from Ligustrum lucidum Ait. Int. J. Mol. Sci. 2011, 12:5319-5329.
47. Yang Z.-G., Li H.-R., Wang L.-Y., Li Y.-H., Lu S.-G., Wen X.-F., Wang J., Daikonya A., Kitanaka S. Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities. Chem. Pharm. Bull. 2007, 55:15-18.
48. Yin M.C., Chan K.C. Nonenzymatic antioxidative and antiglycative effects of oleanolic acid and ursolic acid. J. Agric. Food Chem. 2007, 55:7177-7181.
49. Zacchigna M., Cateni F., Faudale M., Sosa S., Loggia R.D. Rapid HPLC analysis for quantitative determination of the two isomeric triterpenic acids, oleanolic acid and ursolic acid, in Plantago major. Sci. Pharm. 2009, 77:79-86.
50. Zhang X.-G., Han T., Zhang Q.-Y., Zhang H., Huang B.-K., Xu L.-L., Qin L.-P. Chemical fingerprinting and hierarchical clustering analysis of Centella asiatica from different locations in China. Chromatographia 2009, 69:51-57.