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Constituents of the Fruits of Rumex japonicus with Inhibitory Activity on Aldose Reductase

  • Kim, Jong-Min (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Jang, Dae-Sik (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Lee, Yun-Mi (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Lee, Ga-Young (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Kim, Jin-Sook (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine)
  • Published : 2008.02.29

Abstract

Five anthraquinones, emodin (1), ${\omega}$-hydroxyemodin (2), chrysophanol-8-O-${\beta}$-D-glucoside (3), emodin-8-O-${\beta}$-D-glucoside (4), and physcion-8-O-${\beta}$-D-glucoside (5), and five flavonoids, kaempferol-3-O-${\beta}$-D-glucoside (6), quercetin (7), quercitrin (8), isoquercitrin (9), and (+)-catechin (10), were isolated from the EtOAc-soluble extract of the fruits of Rumex japonicus. The structures of 1-10 were identified by spectroscopic methods including NMR studies. This is the first report on the isolation of compounds 3-5 from this plant. The isolates were subjected to in vitro bioassays to evaluate their inhibitory activities on the rat lens aldose reductase (RLAR), among which two anthraquinones (1 and 4), and five flavonols (5-9) showed significant activities on RLAR.

Keywords

References

  1. Amani SA, Maitland DJ, and Soliman GA (2006) Hepatoprotective activity of Schouwia thebica webb. Bioorg Med Chem Lett 16, 4624-4628 https://doi.org/10.1016/j.bmcl.2006.06.011
  2. Aritomi M, Kiyota I, and Mazaki T (1965) Flavonoid constituents in leaves of Rumex acetosa and R. japonicus. Chem Pharm Bull 13, 1470-1471 https://doi.org/10.1248/cpb.13.1470
  3. Bae K (2000) In Medicinal Plants of Korea, pp. 92, Kyo- Hak Publishing Co., Seoul
  4. Beyer-Mears A and Cruz E (1985) Reversal of diabetic cataract by sorbinil, an aldose reductase inhibitor. Diabetes 34, 15-21 https://doi.org/10.2337/diab.34.1.15
  5. Choe SG, Hwang BY, Kim MS, Oh GJ, Lee KS, and Ro JS (1998) Chemical components of Rumex acetosella L. Kor J Pharmacog 29, 209-216
  6. Hwang SW, Ha TJ, Lee JR, Lee J, Nam SH, Park KH, and Yang MS (2004) Isolation of anthraquinone derivatives from the root of Rumex japonicus H. J Korean Soc Appl Biol Chem 47, 274-278
  7. Jang DS, Kim JM, Kim JH, and Kim JS (2005) 24-norursane type triterpenoids from the stems of Rumex japonicus. Chem Pharm Bull 53, 1594-1596 https://doi.org/10.1248/cpb.53.1594
  8. Jang DS, Kim JM, Lee YM, Kim YS, Kim J-H, and Kim JS (2006) A new inhibitor of advanced glycation end products (AGEs) isolated from the roots of Pueraria lobata. Chem Pharm Bull 54, 1315-1317 https://doi.org/10.1248/cpb.54.1315
  9. Jang DS, Kim JM, Lee YM, You JL, Kim YS, Kim J-H, and Kim JS (2006) Flavonols from Houttuynia cordata with protein glycation and aldose reductase inhibitory activity. Nat Prod Sci 12, 210-213
  10. Kim DK, Choi SU, Ryu SY, Lee KR, and Zee OP (1998) Cytotoxic constituents of Rumex japonicus. Yakhak Hoeji 42, 233-237
  11. Kim HY and Oh JH (1999) Screening of Korean forest plants for rat lens aldose reductase inhibition. Biosci Bio-technol Biochem 63, 184-188 https://doi.org/10.1271/bbb.63.184
  12. Koyama J, Morita I, Kawanishi K, Tagahara K, and Kobayashi N (2003) Capillary electrophoresis for simultaneous determination of emodin, chrysophanol, and their 8-$\beta$-D-glucosides, Chem Pharm Bull 51, 418-420 https://doi.org/10.1248/cpb.51.418
  13. Lee C-H, Kim S-I, Lee K-B, Yoo Y-C, Ryu S-Y, and Song K-S (2003) Neuraminidase inhibitors from Reynoutria elliptica. Arch Pharm Res 26, 367-374 https://doi.org/10.1007/BF02976693
  14. Lee JH, Ku CH, Baek N-I, Kim S-H, Park HW, and Kim DK (2004) Phytochemical constituents from Diodia teres, Arch Pharm Res 27, 40-43 https://doi.org/10.1007/BF02980043
  15. Li YP, Takamiyagi A, Ramzi ST, and Nonaka S (2000) Inhibitory effect of Rumex japonicus Houtt on the porphyrin photooxidative reaction. J Dermatology 27, 761- 768 https://doi.org/10.1111/j.1346-8138.2000.tb02278.x
  16. Matsuda H, Morikawa T, Toguchida I, and Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50, 788-795 https://doi.org/10.1248/cpb.50.788
  17. Nishina A, Kubota K, and Osawa T (1993) Antimicrobial components, trachrysone and 2-methoxystypandrone, in Rumex japonicus Houtt. J Agric Food Chem 41, 1772- 1775 https://doi.org/10.1021/jf00034a047
  18. Yabe-Nishimura C (1998) Aldose reductase in glucose toxicity: a potential target for the prevention of diabetic complications. Pharmacol Rev 50, 21-33
  19. Yokozawa T, Kashiwada Y, Hattori M, and Chung HY (2002) Study on the components of Luobuma with peroxynitrite- scavenging activity. Biol Pharm Bull 25, 748-752 https://doi.org/10.1248/bpb.25.748
  20. Zee OP, Kim DK, Kwon HC, and Lee KR (1998) A new epoxynaphthoquinol from Rumex japonicus. Arch Pharm Res 21, 485-486 https://doi.org/10.1007/BF02974649
  21. Zhang X, Thuong PT, Jin WY, Su ND, Sok DE, Bae K, and Kang SS (2005) Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis. Arch Pharm Res 28, 22-27 https://doi.org/10.1007/BF02975130

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