Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC

Canadian Journal of Physiology and Pharmacology

Volumn 85, Issue 9, 2007, Pages 865-871

  Jovel, Eduardo M ^a   Xi, Ling Zhou ^a   Dong, Sheng Ming ^a   Wahbe, Tanya R ^a   Towers, G H Neil ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

1,2,3,4,6 penta O galloyl D glucoside; And 1,6 digalloyl D glucoside; Catechin gallate; Euscaphic acid; L ascorbic acid (vitamin C); Maslinic acid; Quercetin; Quercetin 3 O glucoside; Tormentic acid; Ursolic acid

Indexed keywords

ASCORBIC ACID; CATECHIN; GALLIC ACID; GLUCOSIDE; MASLINIC ACID; PLANT EXTRACT; QUERCETIN; ROSA NUTKANA EXTRACT; TORMENTIC ACID; UNCLASSIFIED DRUG; URSOLIC ACID;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; DRUG SYNTHESIS; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ROSA NUTKANA; ROSACEAE; SPECTROPHOTOMETER;

ANTI-BACTERIAL AGENTS; ASCORBIC ACID; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT; GLUCOSIDES; METHICILLIN RESISTANCE; MICROBIAL SENSITIVITY TESTS; PLANT EXTRACTS; QUERCETIN; ROSACEA; STAPHYLOCOCCUS AUREUS;

EID: 36549029203     PISSN: 00084212     EISSN: None     Source Type: Journal    
DOI: 10.1139/Y07-053     Document Type: Article

References (46)

1. Aktan, S., and Sagdic, O. 2004. Dried rose (Rosa damascena Mill.) Dreg.: An alternative litter material in broiler production. S. Afr. J. Anim. Sci. 34: 75-79.
2. Barnes, S., and Prasain, J. 2005. Current progress in the use of traditional medicines and nutraceuticals. Curr. Opin. Plant Biol. 8: 324-328. doi:10.1016/j.pbi.2005.03.010.
3. B.C. Conservation Data Centre. 2007. Species Summary: Rosa nutkana var. hispida. B.C. Species and Ecosystems Explorer [online]. B.C. Ministry of Environment. Available from http://srmapps.gov.bc.ca/apps/eswp/ [accessed 7 September 2007].
4. Beninger, C.W., and Hosfield, G.L. 2003. Antioxidant activity of extracts, condensed tannin fractions and pure flavonoids from Phaseolus vulgaris L. seed coat color genotypes. J. Agric. Food Chem. 51: 7879-7883. doi:10.1021/jf0304324.
5. Chen, L. 1991. Polyphenols from leaves of Euphorbia hirta L. Zhongguo Zhongyao Zazhi, 16: 38-39.
6. Chen, F.Z., Peng, S.L., Ding, L.H., He, Y.Q., and Wang, M.K. 2001. Chemical constituents from fruit of Rosa bella. Zhongguo Zhongyao Zazhi, 26: 549-551.
7. Choi, J., Lee, K.T., Ha, J., Yun, S.Y., Ko, C.D., Jung, H.J., and Park, H.J. 2003. Antinociceptive and antiinflammatory effects of Niga-ichigoside F1 and 23-hydroxytormentic acid obtained from Rubus coreanus. Biol. Pharm. Bull. 26: 1436-1441. doi:10.1248/bpb.26.1436.
8. Dong, H., Chen, S.X., Hini, R.M., and Xu, H.X. 1998. Effects of tannins from Geum japonicum on the catalytic activity of thrombin and factor Xa of blood coagulation cascade. J. Nat. Prod. 61: 1356-1360. doi:10.1021/np9801458.
9. 13C) ascorbic acid: synthesis and NMR characterization. Carbohydr. Res. 284: 135-143. doi:10.1016/0008-6215(96)00008-0.
10. Duarte, T.L., and Lunec, J. 2005. When is an antioxidant not an antioxidant? A review of novel actions and reactions of vitamin C. Free Radic. Res. 39: 671-686. doi:10.1080/10715760500104025.
11. Erdelyi, K., Kiss, A., Bakondi, E., Bai, P., Szabo, C., Gergely, P., Erdodi, F., and Virag, L. 2005. Gallotannin inhibits the expression of chemokines and inflammatory cytokines in A549 cells. Mol. Pharmacol. 68: 895-904.
12. Funatogawa, K., Hayashi, S., Shimomura, H., Yoshida, T., Hatano, T., Ito, H., and Hirai, Y. 2004. Antibacterial activity of hydrolysable tannins derived from medicinal plants against Helicobacter pylori. Microbiol. Immunol. 48: 251-261.
13. Gamez, E.J.C., Luyengi, L., Lee, S.K., Zhu, L., Zhou, B., Fong, H.H.S., Pezzuto, J.M., and Kinghorn, A.D. 1998. Antioxidant flavanoid glycosides from Daphniphyllum calycinum. J. Nat. Prod. 61: 706-708. doi:10.1021/np9800203.
14. Guo, Q.L., and Yang, J.S. 2005. Studies on chemical constituents in fruit of Rubus chingii. Zhongguo Zhongyao Zazhi, 30: 198-200.
15. Hagerman, A.E., Riedl, K.M., Jones, G.A., Sovik, K.N., Ritchard, N.T., Hartzfield, P.W., and Riechel, T.L. 1998. High molecular weight plant polyphenols (tannins) as biological antioxidants. J. Agric. Food Chem. 46: 1887-1892. doi:10.1021/jf970975b.
16. Hartzen, S.H., Frimodt-Moller, N., and Thomsen, V.F. 1991. The antibacterial activity of a siderophore. 2. The influence of deferoxamine alone and combined with ascorbic acid on the activity of antibiotics against Staphylococcus aureus. APMIS 99: 879-886.
17. Hashidoko, Y. 1996. The phytochemistry of Rosa rugosa. Phytochemistry (Oxf.), 43: 535-549.
18. Iwashina, T., Kitajima, J., and Kato, T. 2005. An analysis of flavanoid compounds in leaves of Japonolirion (Petrosaviaceae). J. Plant Res. 118: 31-36. doi:10.1007/s10265-005-0194-6.
19. Juang, L.J., and Sheu, S.J. 2005. Chemical identification of the sources of commercial Fructus chebulae. Phytochem. Anal. 16: 246-251. doi:10.1002/pca.823.
20. Jung, H.J., Nam, J.H., Choi, J., Lee, K.T., and Park, H.J. 2005. 19α-hydroxyursane-type triterpenoids: antinociceptive anti-inflammatory principles of the roots of Rosa rugosa. Biol. Pharm. Bull. 28: 101-104. doi:10.1248/bpb.28.101.
21. Kakegawa, H., Matsumoto, H., Endo, K., Satoh, T., Nonaka, G., and Nishioka, I. 1985. Inhibitory effects of tannins on hyaluronidase activation and on the degranulation from rat mesentery mast cells. Chem. Pharm. Bull. (Tokyo), 33: 5079-5082.
22. Klinkenberg, B. 2007. E-Flora BC: Electronic atlas of the plants of British Columbia. [online]. Lab for Advanced Spatial Analysis, Department of Geography, and the UBC Herbarium, University of British Columbia, Vancouver, Canada. Available from www.eflora.bc.ca [accessed 7 September 2007].
23. Kuhnlein, H.V., Receveur, O., Soueida, R., and Egeland, G.M. 2004. Arctic Indigenous peoples experience the nutrition transition with changing dietary patterns and obesity. J. Nutr. 134: 1447-1453.
24. Lianou, P.E., Fortis, A.A., and Papavassilliou, J.T. 2003. The effect of the low concentrations of ascorbic acid in microbial adherence in vitro. Int. J. Vitam. Nutr. Res. 73: 245-250. doi:10.1024/0300-9831.73.4.245.
25. Marian, M., and Matkovics, B. 1982. Potentiation of biological activities of daunomycin and adriamycin by ascorbic acid and dimethylsulfoxide. Experientia, 38: 573-574. doi:10.1007/BF02327056.
26. Mavi, A., Terzi, Z., Ozgen, U., Yildim, A., and Coskum, M. 2004. Antioxidant properties of some medicinal plants: Prangos ferulacea (Apiaceae), Sedum sempervivoides (Crassulaceae), Malva neglecta (Malvaceae), Cruciata taurica (Rubiaceae), Rosa pimpenellifolia (Rosaceae), Galium verum subsp. verum (Rubiaceae), Urtica dioica (Urticaceae). Biol. Pharm. Bull. 27: 702-705. doi:10.1248/bpb.27.702.
27. McCutcheon, A.R., Robert, T.E., Gibbons, E., Ellis, S.M., Babiuk, L.A., Hancock, R.E.W., and Towers, G.H.N. 1995. Antiviral screening of British Columbia medicinal plants. J. Ethnopharmacol. 49: 101-110.
28. Ming, D.S., Lopez, A., Hillhouse, B.J., French, C.J., Hudson, J.B., and Towers, G.H.N. 2002. Bioactive constituents from Iryanthera megistophylla. J. Nat. Prod. 65: 1412-1416. doi:10.1021/np0201691.
29. Moerman, D. 1998. Native American ethnobotany. Timber Press, Portland, Oregon.
30. Oh, G.S., Pae, H.O., Choi, B.M., Lee, H.S., Kim, I.K., Yun, Y.G., Kim, J.D., and Chung, H.T. 2004. Penta-O-galloyl-beta-D-glucose inhibits phorbol myristate acetate-induced interleukin-8 [correction of intereukin-8] gene expression in human monocytic U937 cells through its inactivation of nuclear factor-kappaB. Int. Immunopharmacol. 4: 377-386. doi:10.1016/j.intimp.2003.10.010.
31. Ozkan, G., Sagdic, O., Baydar, N.G., and Baydar, H. 2004. Antioxidant activities of Rosa damascena flower extracts. Food Sci. Technol. Int. 10: 277-281. doi:10.1177/1082013204045882.
32. Owen, R.W., Haubner, R., Hull, W.E., Erben, G., Spiegelhaider, B., Bartsch, H., and Haber, B. 2003. Isolation and structure elucidation of the major individual polyphenols in carob fibre. Food Chem. Toxicol. 41: 1727-1738.
33. Paveto, C., Guida, M., Esteva, M.I., Martino, V., Coussio, J., Flawia, M.M., and Torres, H.N. 2004. Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins. Antimicrob. Agents Chemother. 48: 69-74. doi:10.1128/AAC48.1.69-74.2004.
34. Plaper, A., Golob, M., Hafner, I., Oblak, M., Solmajer, T., and Jerala, R. 2003. Characterization of quercetin binding site on DNA gyrase. Biochem. Biophys. Res. Commun. 306: 530-536. doi:10.1016/S0006-291X(03)01006-4.
35. Rukachaisirikul, V., Naklue, W., Sukpondma, Y., and Phongpaichit, S. 2005. An antibacterial biphenyl derivative from Garcinia bancana MIQ. Chem. Pharm. Bull. (Tokyo), 53: 342-343.
36. Shiota, S., Shimizu, M., Sugiyama, J., Morita, Y., Mizushima, T., and Tsuchiya, T. 2004. Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of betalactams against methicillin-resistant Staphylococcus aureus. Microbiol. Immunol. 48: 67-73.
37. Stapleton, P.D., Shah, S., Anderson, J.C., Hara, Y., Hamilton-Miller, J.M.T., and Taylor, P.W. 2004. Modulation of β-lactam resistance in Staphylococcus aureus by catechins and gallates. Int. J. Antimicrob. Agents, 23: 462-467.
38. Taylor, R.S., Manandhar, N.P., and Towers, G.H.N. 1995. Screening of selected medicinal plants of Nepal for antimicrobial activities. J. Ethnopharmacol. 46: 153-159. doi:10.1016/0378-8741(95)01242-6.
39. Tripoli, E., Giammanco, M., Tabacchi, G., Di Majo, D., Giammanco, S., and La Guardia, M. 2005. The phenolic compounds of olive oil: Structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 18: 98-112. doi:10.1079/NRR200495.
40. Turner, N.J., and Reed, A. 1994. Ethnobotanical contributions. In Plants of Coastal British Columbia including Washington, Oregon & Alaska. Edited by A. Mackinnon and J. Pojar. Lone Pine Publishing, Vancouver, British Columbia.
41. Turner, N.J., and Szczawinski, A.F. 1979. Edible wild fruits and nuts of Canada. Edible wild plants of Canada No. 3. National Museum of Natural Sciences, National Museums of Canada, Ottawa.
42. Turner, N.J., Bouchard, R., and Kennedy, D.I.D. 1980. Ethnobotany of the Okanagan-Colville Indians of British Columbia and Washington. British Columbia Provincial Museum Occasional Paper No. 21, Victoria, British Columbia.
43. Turner, N.J., Thompson, L.C., Thompson, M.T., and York, A.Z. 1990. Thompson Ethnobotany. Knowledge and usage of plants by the Thompson Indians of British Columbia. Royal British Columbia Museum, Memoir No. 3. Victoria, British Columbia.
44. van Asbeck, B.S., Marcelis, J.H., Marx, J.J., Struyvenberg, A., Van Kats, J.H., and Verhoef, J. 1983. Inhibition of bacterial multiplication by iron chelator deferoxamine: potentiating effect of ascorbic acid. Eur. J. Clin. Microbiol. 2: 426-431. doi:10.1007/BF02013899.
45. VanderJagt, T.J., Ghattas, R., VanderJagt, D.J., Crossey, M., and Glew, R.H. 2002. Comparison of the total antioxidant content of 30 widely used medicinal plants of New Mexico. Life Sci. 70: 1035-1040. doi:10.1016/S0024-3205(01)01481-3.
46. Yi, O., Jovel, E.M., Towers, G.H., Wahbe, T.R., and Cho, D. 2007. Antioxidant and antimicrobial activities of native Rosa sp. from British Columbia, Canada. Int. J. Food Sci. Nutr. 58: 178-189. doi:10.1080/09637480601121318.