Download PDF
Planta Med 2013; 79(18): 1705-1709
DOI: 10.1055/s-0033-1351101
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Song Yi Yu   *
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
,
Ik-Soo Lee   *
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
,
Seung-Hyun Jung
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
,
Yun Mi Lee
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
,
Yu-Ri Lee
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
,
Joo-Hwan Kim
2   Department of Life Science, Kyungwon University, Seongnam, Republic of Korea
,
Hang Sun
3   Laboratory of Biodiversity and Biogeography, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, Peopleʼs Republic of China
,
Jin Sook Kim
1   KM-Based Herbal Drug Development Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon, Republic of Korea
› Author Affiliations
Further Information

Publication History

received 11 June 2013
revised 21 October 2013

accepted 27 October 2013

Publication Date:
28 November 2013 (online)

Also available at
    Permissions and Reprints

Abstract

In our continuing efforts to identify effective naturally sourced agents for diabetic complications, five caffeoylated phenylpropanoid glycosides, acteoside (1), isoacteoside (2), poliumoside (3), brandioside (4), and pheliposide (5) were isolated from the 80 % EtOH extract of Brandisia hancei stems and leaves. These isolates (1–5) were subjected to an in vitro bioassay evaluating their inhibitory activity on advanced glycation end product formation and rat lens aldose reductase activity. All tested compounds exhibited significant inhibition of advanced glycation end product formation with IC50 values of 4.6–25.7 µM, compared with those of aminoguanidine (IC50 = 1056 µM) and quercetin (IC50 = 28.4 µM) as positive controls. In the rat lens aldose reductase assay, acteoside, isoacteoside, and poliumoside exhibited greater inhibitory effects on rat lens aldose reductase with IC50 values of 0.83, 0.83, and 0.85 µM, respectively, than those of the positive controls, 3,3-tetramethyleneglutaric acid (IC50 = 4.03 µM) and quercetin (IC50 = 7.2 µM). In addition, the effect of acteoside on the dilation of hyaloid-retinal vessels induced by high glucose in larval zebrafish was investigated. Acteoside reduced the diameters of high glucose-induced hyaloid-retinal vessels by 69 % at 10 µM and 81 % at 20 µM, compared to the high glucose-treated control group. These results suggest that B. hancei and its active components might be beneficial in the treatment and prevention of diabetic vascular complications.

Key words

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

* These two authors contributed equally to this work.


 

  • References

  • 1 Wei M, Gaskill SP, Hanffner SM, Stern MP. Effect of diabetes and level of glycemia on all-cause and cardiovascular mortality. The San Antonio Heart Study. Diabet Care 1998; 21: 1167-1172
    CrossrefPubMedSearch in Google Scholar
  • 2 Laakso M. Hyperglycemia and cardiovascular disease in type 2 diabetes. Diabetes 1999; 48: 937-942
    CrossrefPubMedSearch in Google Scholar
  • 3 Nishikawa T, Edelstein D, Du XL, Yamagishi S, Matsumura T, Kaneda Y, Yorek MA, Beebe D, Oates PJ, Hammes HP, Giardino I, Brownlee M. Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage. Nature 2000; 404: 787-790
    CrossrefPubMedSearch in Google Scholar
  • 4 Brownlee M. Biochemistry and molecular cell biology of diabetic complications. Nature 2001; 414: 813-820
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 6 Morrison AD, Clements RS, Winegord AI. Effects of elevated glucose concentrations on the metabolism of the aortic wall. J Clin Invest 1972; 51: 3114-3123
    CrossrefPubMedSearch in Google Scholar
  • 7 Kinoshita JH. A thirty year journey in the polyol pathway. Exp Eye Res 1990; 50: 567-573
    CrossrefPubMedSearch in Google Scholar
  • 8 Yabe-Nishimura C. Aldose reductase in glucose toxicity: a potential target for the prevention of diabetic complications. Pharmacol Rev 1998; 50: 21-33
    PubMedSearch in Google Scholar
  • 9 Reddy VP, Beyaz A. Inhibitors of the Maillard reaction and AGE breakers as therapeutics for multiple diseases. Drug Discov Today 2006; 11: 646-654
    CrossrefPubMedSearch in Google Scholar
  • 10 He ZD, Wang DZ, Yang CR. Phenylpropanoid glycosides from Brandisia hancei . Acta Bot Yunn 1990; 12: 439-446
    PubMedSearch in Google Scholar
  • 11 He ZD, Yang CR. Brandioside, a phenylpropanoid glycoside from Brandisia hancei . Phytochemistry 1991; 30: 701-702
    CrossrefPubMedSearch in Google Scholar
  • 12 Kong LD, Wolfender JL, Cheng CH, Hostettmann K, Tan RX. Xanthine oxidase inhibitors from Brandisia hancei . Planta Med 1999; 65: 744-746
    Thieme ConnectPubMedSearch in Google Scholar
  • 13 He ZD, Huang Y, Yao X, Lau CW, Law WI, Chen ZY. Purification of phenylethanoids from Brandisia hancei and the antiproliferative effects on aortic smooth muscle. Planta Med 2001; 67: 520-522
    Thieme ConnectPubMedSearch in Google Scholar
  • 14 Lee YM, Kim YS, Kim JH, Kim JS. Screening of herbal medicines from China with inhibitory activity on advanced glycation end products (AGEs) formation (VI). Korean J Pharmacogn 2011; 42: 161-168
    PubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 17 Jang DS, Yoo NH, Kim NH, Lee YM, Kim CS, Kim J, Kim JH, Kim JS. 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 20 Stitt AW, Li YM, Gardiner TA, Bucala R, Archer DB, 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
    PubMedSearch in Google Scholar
  • 21 Stitt A, Gardiner TA, Alderson NL, Canning P, Frizzell N, Duffy N, Boyle C, Januszewski AS, Chachich M, Baynes JW, Thorpe SR. The AGE inhibitor pyridoxamine inhibits development of retinopathy in experimental diabetes. Diabetes 2002; 51: 2826-2832
    CrossrefPubMedSearch in Google Scholar
  • 22 Gardiner TA, Anderson HR, Stitt AW. Inhibition of advanced glycation end products protects against retinal capillary basement membrane expansion during long-term diabetes. J Pathol 2003; 201: 328-333
    CrossrefPubMedSearch in Google Scholar
  • 23 Alvarez Y, Chen K, Reynolds AL, Waghorne N, OʼConnor JJ, Kennedy BN. Predominant cone photoreceptor dysfunction in a hyperglycaemic model of non-proliferative diabetic retinopathy. Dis Model Mech 2010; 3: 236-245
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 26 Lee J, Jang DS, Kim NH, Lee YM, Kim J, Kim JS. 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
    CrossrefPubMedSearch in Google Scholar
  • 27 Jang DS, Lee GY, Kim YS, Lee YM, Kim CS, Yoo JL, Kim JS. Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase. Biol Pharm Bull 2007; 30: 2207-2210
    CrossrefPubMedSearch in Google Scholar
  • 28 de la Fuente JA, Manzanaro S. Aldose reductase inhibitors from natural sources. Nat Prod Rep 2003; 20: 243-251
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 30 Kurkin VA. Phenylpropanoids from medicinal plants: distribution, classification, structural analysis, and biological activity. Chem Nat Compd 2003; 39: 123-153
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar