Caffeoylated phenylpropanoid glycosides from Brandisia hancei inhibit advanced glycation end product formation and aldose reductase in vitro and vessel dilation in larval zebrafish in vivo

Planta Medica

Volumn 79, Issue 18, 2013, Pages 1705-1709

  Yu, Song Yi ^a   Lee, Ik Soo ^a   Jung, Seung Hyun ^a   Lee, Yun Mi ^a   Lee, Yu Ri ^a   Kim, Joo Hwan ^b   Sun, Hang ^c   Kim, Jin Sook ^a  

^a Korea Institute of Oriental Medicine (KIOM)   (South Korea)

^b Gachon University   (South Korea)

^c KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

advanced glycation end product; Brandisia hancei; diabetic vascular complications; phenylpropanoid glycoside; rat lens aldose reductase; Scrophulariaceae; zebrafish

Indexed keywords

ACTEOSIDE; ADVANCED GLYCATION END PRODUCT; ALCOHOL; ALDEHYDE REDUCTASE; AMINOGUANIDINE; BRANDIOSIDE; GLUCOSE; GLYCOSIDE; ISOACTEOSIDE; PHELIPOSIDE; POLIUMOSIDE; QUERCETIN; TETRAMETHYLENEGLUTARIC ACID; UNCLASSIFIED DRUG;

ADULT; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOASSAY; BRANDISIA HANCEI; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFECT; DRUG ISOLATION; ENZYME ASSAY; ENZYME INHIBITION; IC 50; IN VITRO STUDY; IN VIVO STUDY; LARVA; LENS; MEDICINAL PLANT; NONHUMAN; PLANT LEAF; PLANT STEM; RAT; RETINA BLOOD VESSEL; VASODILATATION; ZEBRA FISH;

BRANDISIA HANCEI; DANIO RERIO; RATTUS; SCROPHULARIACEAE;

ALDEHYDE REDUCTASE; ANIMALS; DIABETIC ANGIOPATHIES; DISEASE MODELS, ANIMAL; FLAVONOIDS; GLUCOSE; GLYCOSIDES; GLYCOSYLATION END PRODUCTS, ADVANCED; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; OROBANCHACEAE; PLANT EXTRACTS; PLANT LEAVES; PLANT STEMS; PROPANOLS; RATS; RATS, SPRAGUE-DAWLEY; RETINAL VESSELS; ZEBRAFISH;

EID: 84890986090     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0033-1351101     Document Type: Article

References (32)

1. Wei M., Gaskill S. P., Hanffner S. M., Stern M. P. Effect of diabetes and level of glycemia on all-cause and cardiovascular mortality. The San Antonio Heart Study. Diabet Care: 1998; 21 1167 1172 (Pubitemid 28368527)
2. Laakso M. Hyperglycemia and cardiovascular disease in type 2 diabetes. Diabetes: 1999; 48 937 942 (Pubitemid 29226337)
3. Nishikawa T., Edelstein D., Du X. L., Yamagishi S., Matsumura T., Kaneda Y., Yorek M. A., Beebe D., Oates P. J., Hammes H. P., Giardino I., Brownlee M. Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage. Nature: 2000; 404 787 790 (Pubitemid 30212409)
4. Brownlee M. Biochemistry and molecular cell biology of diabetic complications. Nature: 2001; 414 813 820 (Pubitemid 34000785)
5. Takenaka K., Yamagishi S., Matsui T., Nakamura K., Imaizumi T. Role of advanced glycation end products (AGEs) in thrombogenic abnormalities in diabetes. Curr Neurovasc Res: 2006; 3 73 77
6. Morrison A. D., Clements R. S., Winegord A. I. Effects of elevated glucose concentrations on the metabolism of the aortic wall. J Clin Invest: 1972; 51 3114 3123
7. Kinoshita J. H. A thirty year journey in the polyol pathway. Exp Eye Res: 1990; 50 567 573 (Pubitemid 20191282)
8. Yabe-Nishimura C. Aldose reductase in glucose toxicity: a potential target for the prevention of diabetic complications. Pharmacol Rev: 1998; 50 21 33 (Pubitemid 28158840)
9. Reddy V. P., Beyaz A. Inhibitors of the Maillard reaction and AGE breakers as therapeutics for multiple diseases. Drug Discov Today: 2006; 11 646 654
10. He Z. D., Wang D. Z., Yang C. R. Phenylpropanoid glycosides from Brandisia hancei. Acta Bot Yunn: 1990; 12 439 446
11. He Z. D., Yang C. R. Brandioside, a phenylpropanoid glycoside from Brandisia hancei. Phytochemistry: 1991; 30 701 702
12. Kong L. D., Wolfender J. L., Cheng C. H., Hostettmann K., Tan R. X. Xanthine oxidase inhibitors from Brandisia hancei. Planta Med: 1999; 65 744 746
13. He Z. D., Huang Y., Yao X., Lau C. W., Law W. I., Chen Z. Y. Purification of phenylethanoids from Brandisia hancei and the antiproliferative effects on aortic smooth muscle. Planta Med: 2001; 67 520 522 (Pubitemid 32800416)
14. Lee Y. M., Kim Y. S., Kim J. H., Kim J. S. Screening of herbal medicines from China with inhibitory activity on advanced glycation end products (AGEs) formation (VI). Korean J Pharmacogn: 2011; 42 161 168
15. Li L., Rong T., Zhiqiang L., Shuying L., Raymond Y., Zhihong F. Isolation and purification of acteoside and isoacteoside from Plantago psyllium L. by high-speed counter-current chromatography. J Chromatogr A: 2005; 1063 161 169 (Pubitemid 40075543)
16. Andary C., Privat G., Wylde R. Pheliposide and arenarioside, two new heterosidic esters isolated from caffeic acid of Orobanche arenaria. J Nat Prod: 1985; 48 778 783 (Pubitemid 16185153)
17. Jang D. S., Yoo N. H., Kim N. H., Lee Y. M., Kim C. S., Kim J., Kim J. H., Kim J. S. 3,5-Di- O -caffeoyl-epi-quinic acid from the leaves and stems of Erigeron annuus inhibits protein glycation, aldose reductase, and cataractogenesis. Biol Pharm Bull: 2010; 33 329 333
18. Brownlee M., Vlassara H., Kooney A., Ulrich P., Cerami A. Aminoguanidine prevents diabetes-induced arterial wall protein cross-linking. Science: 1986; 232 1629 1632 (Pubitemid 16095602)
19. Kohda H., Tanaka S., Yamakoa Y., Yahara S., Nohara T., Tanimoto T., Tanaka A. Studies on lens-aldose-reductase inhibitor in medicinal plants. II. Active constituents of Monochasma savatierii Franch. Et Maxim. Chem Pharm Bull: 1989; 37 3153 3154 (Pubitemid 20056118)
20. Stitt A. W., Li Y. M., Gardiner T. A., Bucala R., Archer D. B., Vlassara H. Advanced glycation end products (AGEs) co-localize with AGE receptors in the retinal vasculature of diabetic and of AGE-infused rats. Am J Pathol: 1997; 150 523 531 (Pubitemid 27073782)
21. Stitt A., Gardiner T. A., Alderson N. L., Canning P., Frizzell N., Duffy N., Boyle C., Januszewski A. S., Chachich M., Baynes J. W., Thorpe S. R. The AGE inhibitor pyridoxamine inhibits development of retinopathy in experimental diabetes. Diabetes: 2002; 51 2826 2832 (Pubitemid 34970937)
22. Gardiner T. A., Anderson H. R., Stitt A. W. Inhibition of advanced glycation end products protects against retinal capillary basement membrane expansion during long-term diabetes. J Pathol: 2003; 201 328 333 (Pubitemid 37258944)
23. Alvarez Y., Chen K., Reynolds A. L., Waghorne N., OÊConnor J. J., Kennedy B. N. Predominant cone photoreceptor dysfunction in a hyperglycaemic model of non-proliferative diabetic retinopathy. Dis Model Mech: 2010; 3 236 245
24. Matsuda H., Morokawa T., Toguchida I., Yoshikawa M. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull: 2002; 50 788 795 (Pubitemid 41694896)
25. Matsuda H., Wang T., Managi H., Yoshikawa M. Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. Bioorg Med Chem: 2003; 11 5317 5323 (Pubitemid 37464658)
26. Lee J., Jang D. S., Kim N. H., Lee Y. M., Kim J., Kim J. S. Galloyl glucoses from the seeds of Cornus officinalis with inhibitory activity against protein glycation, aldose reductase, and cataractogenesis ex vivo. Biol Pharm Bull: 2011; 34 443 446
27. Jang D. S., Lee G. Y., Kim Y. S., Lee Y. M., Kim C. S., Yoo J. L., Kim J. S. Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase. Biol Pharm Bull: 2007; 30 2207 2210 (Pubitemid 350097056)
28. de la Fuente J. A., Manzanaro S. Aldose reductase inhibitors from natural sources. Nat Prod Rep: 2003; 20 243 251 (Pubitemid 36453609)
29. Fujita T., Ohira K., Miyatake K., Nakana Y., Nakayama M. Inhibitory effects of perillosides A and C, and related monoterpene glycosides on aldose reductase and their structure activity relationships. Chem Pharm Bull: 1995; 43 920 926
30. Kurkin V. A. Phenylpropanoids from medicinal plants: distribution, classification, structural analysis, and biological activity. Chem Nat Compd: 2003; 39 123 153
31. Pan J., Yuan C., Lin C., Jia Z., Zheng R. Pharmacological activities and mechanism of natural phenyl propanoid glycosides. Pharmazie: 2003; 58 767 775 (Pubitemid 37462457)
32. Laporta O., Perez-Fons L., Balan K., Paper D., Cartagena V., Micol V. Bifunctional antioxidative oligosaccharides with antiinflammatory activity for joint health. Agro Food Ind Hi Tech: 2004; 15 30 33 (Pubitemid 39662319)