Abstract
The therapeutic activities of flavonoids from natural plant sources were investigated. The ethanol extracts from the aerial parts of Cirsium japonicum var. maackii (CJM) were tested for aldose reductase inhibition (ARI). Additionally, stepwise polarity fractions and flavonoids from CJM were evaluated for ARI. The ethyl acetate (EtOAc) fraction from CJM showed significant inhibitory effects. The compounds in the EtOAc fraction were identified as the flavonoids-cirsimaritin (1), hispidulin (2), and cirsimarin (3). Based on an ARI assay, the EtOAc fraction and hispidulin (2) exhibited good AR inhibitory activity (IC50 values of 0.21 μg/mL and 0.77 μM, respectively). An HPLC quantitative analysis of different parts of CJM showed that the aerial part collected in the spring season (CJL1) contains the highest total flavonoid content. These results serve as a basis for maximizing the flavonoid yield and for the efficient usage of various parts of CJM. Our results also suggest that CJM could be a useful ARI material for the treatment of various diabetic complications.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs13765-017-0302-z/MediaObjects/13765_2017_302_Fig1_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs13765-017-0302-z/MediaObjects/13765_2017_302_Fig2a_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs13765-017-0302-z/MediaObjects/13765_2017_302_Fig2b_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs13765-017-0302-z/MediaObjects/13765_2017_302_Fig3a_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs13765-017-0302-z/MediaObjects/13765_2017_302_Fig3b_HTML.gif)
Similar content being viewed by others
References
Alberti KGMM, Zimmet PF (1998) Definition, diagnosis and classification of diabetes mellitus and its complications. Part 1: diagnosis and classification of diabetes mellitus. Provisional report of a WHO consultation. Diabet Med 15:539–553
Guariguata L, Whiting DR, Hambleton I, Beagley J, Linnenkamp U, Shaw JE (2014) Global estimates of diabetes prevalence for 2013 and projections for 2035. Diabetes Res Clin Pract 103:137–149
Shaw JE, Sicree RA, Zimmet PZ (2010) Global estimates of the prevalence of diabetes for 2010 and 2030. Diabetes Res Clin Pract 87:4–14
Dyck PJ, Kratz KM, Karnes JL, Litchy WJ, Klein R, Pach JM, Wilson DM, O’brien PC, Melton L (1993) The prevalence by staged severity of various types of diabetic neuropathy, retinopathy, and nephropathy in a population-based cohort: the Rochester diabetic neuropathy study. Neurology 43:817
Goldin A, Beckman JA, Schmidt AM, Creager MA (2006) Advanced glycation end products. Circulation 114:597–605
Lee AY, Chung SS (1999) Contributions of polyol pathway to oxidative stress in diabetic cataract. FASEB J 13:23–30
Oka M, Kat N (2001) Aldose reductase inhibitors. J Enzym Inhib 16:465–473
Jung HA, Kim YS, Choi JS (2009) Quantitative HPLC analysis of two key flavonoids and inhibitory activities against aldose reductase from different parts of the Korean thistle, Cirsium maackii. Food Chem Toxicol 47:2790–2797
Mok SY, Lee SL, Kim HM, Lee JM, Lee DG, Ahn YH, Park CG, Cho EJ, Lee S (2011) Inhibition of rat lens aldose reductase by flavonoids from dandelions. Nat Prod Sci 17:130–134
Kim HM, Lee DG, Lee S (2015) Plant-derived molecules from Saussurea grandifolia as inhibitors of aldose reductase. J Korean Soc Appl Biol Chem 58:365–371
Liu S, Zhang J, Li D, Liu W, Luo X, Zhang R, Li L, Zhao J (2007) Anticancer activity and quantitative analysis of flavone of Cirsium japonicum DC. Nat Prod Res 21:915–922
Liu S, Luo X, Li D, Zhang J, Qiu DL, Liu W, She L, Yang Z (2006) Tumor inhibition and improved immunity in mice treated with flavone from Cirsium japonicum DC. Int Immunopharmacol 6:1387–1393
Genzera M, Pocher A, Stuppner H (2005) Differentiation of Cirsium japonicum and C. setosum by TLC and HPLC-MS. Phytochem Anal 16:205–209
Thao NTP, Cuong TD, Hung TM, Lee JH, Na M, Son JK, Jung HJ, Fang Z, Woo MH, Choi JS, Min BS (2011) Simultaneous determination of bioactive flavonoids in some selected Korean thistles by high-performance liquid chromatography. Arch Pharm Res 34:455–461
Zhang Z, Jia P, Zhang X, Zhang Q, Yang H, Shi H, Zhang L (2014) LC–MS/MS determination and pharmacokinetic study of seven flavonoids in rat plasma after oral administration of Cirsium japonicum DC. extract. J Ethnopharmacol 158:66–75
Yoo SK, Bae YM (2012) Phylogenetic and chemical analyses of Cirsium pendulum and Cirsium setidens inhabiting Korea. J Life Sci 22:1120–1125
Jung HA, Jin SE, Min BS, Kim BW, Choi JS (2012) Anti-inflammatory activity of Korean thistle Cirsium maackii and its major flavonoid, luteolin 5-O-glucoside. Food Chem Toxicol 50:2171–2179
Liao Z, Wu Z, Wu M (2012) Cirsium japonicum flavones enhance adipocyte differentiation and glucose uptake in 3T3-L1 cells. Biol Pharm Bull 35:855–860
Sato S, Kador PF (1990) Inhibition of aldehyde reductase by aldose reductase inhibitors. Biochem Pharmacol 40:1033–1042
Hyun HB, Shrestha S, Boo KH, Kim Cho S (2015) Evaluation of antioxidant potential of ethyl acetate fraction of Rosmarinus officinalis L. and its major components. J Korean Soc Appl Biol Chem 58:715–722
Park JC, Lee JH, Choi JW (1995) Isolation and biological activity of flavone glycosides from the aerial part of Cirsium japonicum var. ussuriense in Korea. J Korean Soc Food Nutr 24:906–910
Chung AK, Kwon HC, Choi SZ, Min YD, Lee SO, Lee WB, Yang MC, Lee KH, Nam JH, Kwak JH, Lee KR (2002) Norisoprenoids from Cirsium rhinoceros. Korean J Pharmacogn 33:81–84
Kim SJ, Kim GH (2003) Identification for flavones in different parts of Cirsium japonicum. J Food Sci Nutr 8:330–335
Jung M, Park M, Lee HC, Kang YH, Kang ES, Kim SK (2006) Antidiabetic agents from medicinal plants. Curr Med Chem 13:1203–1218
Jeong DM, Jung HA, Choi JS (2008) Comparative antioxidant activity and HPLC profiles of some selected Korean thistles. Arch Pharm Res 31:28–33
Nazaruk J, Jakoniuk P (2005) Flavonoid composition and antimicrobial activity of Cirsium rivulare (Jacq.) All. flowers. J Ethnopharmacol 102:208–212
Varma SD, Mikuni I, Kinoshita JH (1975) Flavonoids as inhibitors of lens aldose reductase. Science 188:1215–1216
Shimizu M, Ito T, Terashima S, Hayashi T, Arisawa M, Morita N, Kurokawa S, Ito K, Hashimoto Y (1984) Inhibition of lens aldose reductase by flavonoids. Phytochemistry 23:1885–1888
Matsuda H, Morikawa T, Toguchida I, Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50:788–795
Kowluru RA, Kennedy A (2001) Therapeutic potential of anti-oxidants and diabetic retinopathy. Expert Opin Investig Drugs 10:1665–1676
Okada Y, Miyauchi N, Suzuki K, Kobayashi T, Tsutsui C, Mayuzumi K, Nishibe S, Okuyama T (1995) Search for naturally occurring substances to prevent the complications of diabetes. II. Inhibitory effect of coumarin and flavonoid derivatives on bovine lens aldose reductase and rabbit platelet aggregation. Chem Pharm Bull 43:1385–1387
Yin J, Heo SI, Wang MH (2008) Antioxidant and antidiabetic activities of extracts from Cirsium japonicum roots. Nutr Res Pract 2:247–251
Jiang XL, Fan CL, Ye WC (2006) Studies on the chemical constituents of Cirsium japonicum DC. Chin Trad Herb Drugs 37:510–512
Acknowledgments
This research was supported by the Ministry of Agriculture, Food and Rural Affairs (MAFRA), through the 2015 Healthy Local Food Branding Project of the Rural Resources Complex Industrialization Support Program.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, J., Rodriguez, J.P., Lee, K.H. et al. Determination of flavonoids from Cirsium japonicum var. maackii and their inhibitory activities against aldose reductase. Appl Biol Chem 60, 487–496 (2017). https://doi.org/10.1007/s13765-017-0302-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13765-017-0302-z