Nat Prod Sci.  2017 Dec;23(4):274-280. 10.20307/nps.2017.23.4.274.

Phenolic Compounds from the Leaves of Homonoia riparia and their Inhibitory Effects on Advanced Glycation End Product Formation

Affiliations
  • 1KM Convergence Research Division, Korea Institute of Oriental Medicine, Daejeon 34054, Republic of Korea. jskim@kiom.re.kr
  • 2Division of Marine-Bio Research, National Marine Biodiversity Institute of Korea, Seocheon-gun 33662, Republic of Korea.

Abstract

In a search for novel treatments for diabetic complications from natural resources, we found that the ethyl acetate-soluble fraction from the 80% ethanol extract of the leaves of Homonoia riparia has a considerable inhibitory effect on advanced glycation end product (AGE) formation. Bioassay-guided isolation of this fraction resulted in identification of 15 phenolic compounds (1 - 15). These compounds were evaluated in vitro for inhibitory activity against the formation of AGE. The majority of tested compounds, excluding ethyl gallate (15), markedly inhibited AGE formation, with ICâ‚…â‚€ values of 2.2 - 89.9 µM, compared with that of the positive control, aminoguanidine (ICâ‚…â‚€ = 962.3 µM). In addition, the effects of active isolates on the dilation of hyaloid-retinal vessels induced by high glucose (HG) in larval zebrafish was investigated; (-)-epigallocatechin-3-O-gallate (6), corilagin (7), and desmanthine-2 (11) significantly decreased HG-induced dilation of hyaloid-retinal vessels compared with the HG-treated control group.

Keyword

Homonoia riparia; Euphorbiaceae; Advanced glycation end product; Zebrafish; Diabetic complication

MeSH Terms

Diabetes Complications
Ethanol
Euphorbiaceae
Glucose
In Vitro Techniques
Natural Resources
Phenol*
Zebrafish
Ethanol
Glucose
Phenol

Figure

  • Fig. 1 The chemical structures of isolated compounds (1 – 15) from the leaves of H. riparia.

  • Fig. 2 Effects of compounds 6, 7, and 11 on dilation of hyaloidretinal vessels in a high-glucose (HG)-induced diabetic retinopathy model. Hyaloid-retinal vessels of flk:EGFP transgenic zebrafish from the following groups: (A) untreated normal (NOR); (B) HG-treated control (HG); HG-treated specimens receiving (C) 10 µM, and (D) 20 µM compound 6; HG-treated specimens receiving (E) 10 µM, and (F) 20 µM compound 7; HG-treated specimens receiving (G) 10 mM, and (H) 20 mM compound 11. (I) Data are displayed as mean artificial units (AU) for vessel diameters. The diameters of hyaloid-retinal vessels were measured at locations proximal to the optic disc (red circle). Scale bar = 50 µm. The hyaloid vessel diameter of each lens was measured three times and the experiment was performed in triplicate. ###p < 0.001 vs. NOR, *p < 0.05 vs. HG, **p < 0.01 vs. HG, ***p < 0.001 vs. HG.


Reference

1. Harvey A. IDrugs. 2010; 13:70–72.
2. Carlson EE. ACS Chem Biol. 2010; 5:639–653.
3. Siddiqui S, Verma A, Rather AA, Jabeen F, Meghavansi MK. Adv Biol Res. 2009; 3:188–195.
4. Warrier PK, Nambiar VPK, Ramankutty C. Indian Medicinal Plants: A compendium of 500 species, vol. 3. Chennai: Orient Longman Ltd.;1994. p. 172.
5. Parveen N, Singh MP, Khan NU. J Indian Chem Soc. 1988; 65:815–816.
6. Viswanadh GS, Atchuta Ramaiah P, Laatsch H, Maskey R. J Trop Med Plant. 2006; 7:267–273.
7. Yang SM, Liu XK, Qing C, Wu DG, Zhu DY. Acta Pharm Sin. 2007; 42:292–296.
8. Lee I, Kim J, Kim YS, Yoo NH, Kim CS, Jo K, Kim JH, Bach TT, Kim JS. J Nat Prod. 2012; 75:1312–1318.
9. Shin DI, Kim J. Korean J Pharmacogn. 1991; 22:207–210.
10. Dai D, He J, Sun R, Zhang R, Aisa H, Abliz Z. Anal Chim Acta. 2009; 632:221–228.
11. Kim HJ, Woo ER, Park H. J Nat Prod. 1994; 57:581–586.
12. Kim YK, Kim YS, Choi SU, Ryu SY. Arch Pharm Res. 2004; 27:44–47.
13. Zhou T, Chen B, Fan G, Chai Y, Wu Y. J Chromatogr A. 2006; 1116:97–101.
14. Lee SH, Kim SY, Kim JJ, Jang TS, Chung SR. Korean J Pharmacogn. 1999; 30:397–403.
15. Okuda T, Yoshida T, Nayeshiro H. Chem Pharm Bull. 1977; 25:1862–1869.
16. Sotnikova OM, Litvinenko VI. Chem Nat Compd. 1968; 4:42–43.
17. Chung SK, Kim YC, Takaya Y, Terashima K, Niwa M. J Agric Food Chem. 2004; 52:4664–4668.
18. Nicollier G, Thompson AC. Flavonoids of Desmanthus illinoensis. J Nat Prod. 1983; 46:112–117. http://pubs.acs.org/doi/pdf/10.1021/np50025a011.
Article
19. Fukunaga T, Nishiya K, Kajikawa I, Watanabe Y, Suzuki N, Takeya K, Itokawa H. Chem Pham Bull. 1988; 36:1180–1184.
20. Park WY. Korean J Pharmacogn. 1996; 27:212–218.
21. Sato Y, Oketani H, Singyouchi K, Ohtsubo T, Kihara M, Shibata H, Higuti T. Biol Pharm Bull. 1997; 20:401–404.
22. Brownlee M, Vlassara H, Kooney A, Ulrich P, Cerami A. Science. 1986; 232:1629–1632.
23. Morimitsu Y, Yoshida K, Esaki S, Hirota A. Biosci Biotechnol Biochem. 1995; 59:2018–2021.
24. Lou H, Yuan H, Yamazaki Y, Sasaki T, Oka S. Planta Med. 2001; 67:345–349.
Article
25. Stitt A, Gardiner TA, Alderson NL, Canning P, Frizzell N, Duffy N, Boyle C, Januszewski AS, Chachich M, Baynes JW, Thorpe SR. Diabetes. 2002; 51:2826–2832.
26. Hammes HP, Weiss A, Fuhrer D, Krämer HJ, Papavassilis C, Grimminger F. Diabetologia. 1996; 39:251–255.
27. Brownlee M. Nature. 2001; 414:813–820.
28. Takenaka K, Yamagishi S, Matsui T, Nakamura K, Imaizumi T. Curr Neurovasc Res. 2006; 3:73–77.
29. Reddy VP, Beyaz A. Drug Discov Today. 2006; 11:646–654.
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