Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

In vitro Free Radical Scavenging and Hepatoprotective Compound from Sanguisorbae Radix

  • An, Ren-Bo (College of Pharmacy, Wonkwang University,College of Pharmacy, Yanbian University) ;
  • Tian, Yu-Hua (College of Pharmacy, Wonkwang University) ;
  • Oh, Hyun-Cheol (MCBI & College of Natural Sciences, Silla University) ;
  • Kim, Youn-Chul (College of Pharmacy, Wonkwang University)
  • Published : 2005.09.01
Download PDF
⟨ Previous Next ⟩

Abstract

In the course of searching for hepatoprotective agents from natural products, four compounds were isolated from the MeOH extract of Sanguisorbae Radix, as guided by their DPPH free radical scavenging activity. The structures were determined as 4,5-dimethoxy-3-hydroxybenzoic acid methyl ester (1), (+)-gallocatechin (2), methyl $6-O-galloyl-{\beta}-D-glucopyranoside$ (3), and pomolic acid $3-O-[{\alpha}-L-arabinopyranoside]-28-O-[{\beta}-D-glucopyranosyl]$ ester (ziyu-glycoside I) (4). Compounds 2 and 3 showed significant DPPH free radical scavenging effects, exhibiting $IC_{50}$ values of 11.4 and $13.0\;{\mu}M$, respectively. L-Ascorbic acid was used as a positive control and exhibited the $IC_{50}$ value of $50.3\;{\mu}M$. In evaluation of the hepatoprotective activity of the isolated compounds on drug-induced cytotoxicity, compound 2 showed the significant hepatoprotective effect with the $EC_{50}$ value of $91.84\;{\pm}\;11.0\;{\mu}M$ on tacrine-induced cytotoxicity in Hep G2 cells, while silybin, a positive control, exhibited $EC_{50}$ value of $122.4\;{\pm}\;12.5\;{\mu}M$.

Keywords

References

  1. Bastow, K.F., Bori, I.D., Fukushima, Y., Kashiwada, Y., Tanaka, T., Nonaka, G., Nishioka, I., and Lee, K.H., Inhibition of DNA topoisomerases by sanguiin H-6, a cytotoxic dimeric ellagitannin from Sanguisorba dfficinalis. Planta Med, 59, 240-245 (1993) https://doi.org/10.1055/s-2006-959659
  2. Chang, H.-M. and But, P.P.-H., Pharmacology and Applications of Chinese Materia Medica, World Scientific, Singapore, pp. 468-473 (1986)
  3. Cheng, D. and Cao, X., Pomolic acid derivatives from the root of Sanguisorba officinalis. Phytochemistry, 31, 1317-1320 (1992) https://doi.org/10.1016/0031-9422(92)80499-5
  4. Foo, L.Y., Lu, Y., Molan, A.L., Woodfield, D.R., and McNabb, W.C., The phenols and prodelphinidins of white clover flowers. Phytochemistry, 54, 539-548 (2000) https://doi.org/10.1016/S0031-9422(00)00124-2
  5. Halliwell, B., Free radicals, antioxidants and human disease: curiosity, cause or consequence? Lancet, 344, 721-724 (1994) https://doi.org/10.1016/S0140-6736(94)92211-X
  6. Jeong, C.S., Suh, I.O., Hyun, J.E., and Lee, E.B., Screening of hepatoprotective activity of medicinal plant extracts on carbon tetrachloride-induced hepatotoxicity in rats. Nat. Prod Sci., 9, 87-90 (2003)
  7. Kappus, H., Lipid peroxidation: mechanisms, enzymology & biological relevance. In Sies II (ed.). Oxidative Stress. Academic Press, London, pp. 273-310 (1985)
  8. Kim, T.G, Kang, S.Y., Jung, K.K., Kang, J.H., Lee, E., Han, H.M., and Kim, S.H., Antiviral activities of extracts isolated from Terminalis chebula Retz., Sanguisorba officinalis L., Rubus coreanus Miq. and Rheum palmatum L. against hepatitis B virus. Phytother. Res., 15, 718-720 (2001) https://doi.org/10.1002/ptr.832
  9. Lee, S.Y. and Chung, S.H., Anxiolytic activities of Sanguisorbae Radix. Yakhak Hoeji, 38, 733-741 (1994)
  10. Masaki, H., Sakaki, S., Atsumi, T., and Sakurai, H., Activeoxygen scavenging activity of plant extracts. Biol. Pharm. Bull., 18, 162-166 (1995) https://doi.org/10.1248/bpb.18.162
  11. Oh, H., Kim, D.H., Cho, J.H., and Kim, Y.C., Hepatoprotective and free radical scavenging activities of phenolie petrosins and flavonoids isolated from Equisetum arvense. J. Ethnopharmacol., 95, 421-424 (2004) https://doi.org/10.1016/j.jep.2004.08.015
  12. Osseni, R.A., Debbasch, C., Christen, M.-O., Rat, P., and Warnet, J.-M., Tacrine-induced reactive oxygen species in a human liver cell line: the role of anethole dithiolethione as a scavenger. Toxicol. In Vitro, 13, 683-688 (1999) https://doi.org/10.1016/S0887-2333(99)00050-8
  13. Park, K.H., Koh, D., Kim, K., Park, J, and Lim, Y., Antiallergic activity of a disaccharide isolated from Sanguisorba officinalis., 18, 658-662 (2004) https://doi.org/10.1002/ptr.1545
  14. Song, E.K., Cho, H., Kim, J.S., Kim, N.Y., An, N.H., Kim, J.A., Lee, S.H., and Kim, Y.C., Diarylheptanoids with free radical scavenging and hepatoprotective activity in vitro from Curcuma longa. Planta Med., 67, 876-877 (2001) https://doi.org/10.1055/s-2001-18860
  15. Tanaka, T., Nonaka, G., and Nishioka, I., Tannins and related compounds. XVI. Isolation and characterization of six methyl glucoside gallates and a gallic acid glucoside gallate from Sanguisorba officinalis L. Chem. Pharm. Bull., 32, 117-121 (1984) https://doi.org/10.1248/cpb.32.117
  16. Tsukahara, K., Moriwaki, S., Fujimura, T., and Takema, Y., Inhibitory effect of an extract of Sanguisorba officinalis L. on ultraviolet-B-induced photodamage of rat skin. Biol. Pharm. Bull., 24, 998-1003 (2001) https://doi.org/10.1248/bpb.24.998
  17. Watkins, P.B., Zimmerman, H.J., Knapp, M.J., Gracon, S.I., and Lewis, K.W., Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease. J. Am. Med. Assoc., 271, 992-998 (1994) https://doi.org/10.1001/jama.271.13.992
  18. Wenjuan, Q., Xiue, W., Junjie, Z., Fukuyama, Y., Yamada, T., and Nakagawa, K., Triterpenoid glycosides from leaves of Ilex cornuta. Phytochemistry, 25, 913-916 (1986) https://doi.org/10.1016/0031-9422(86)80026-7
  19. Wipf, P., and Weiner, W.S., Enantioselective synthesis and photoracemization studies of (+)-2-cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester, an advanced intermediate of a dihydrofolate reductase inhibitor. J. Org. Chem., 64, 5321-5324 (1999) https://doi.org/10.1021/jo990352s