DOI QR코드

DOI QR Code

Antidiabetic Activities of Korean Red Pine (Pinus densiflora) Inner Bark Extracts

  • Min, Hee-Jeong (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Kim, Eun-Ji (Regional Strategic Industry Innovation Center, Hallym University) ;
  • Shinn, Seong-whan (Department of Advanced Materials and Chemical Engineering, Halla university) ;
  • Bae, Young-Soo (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University)
  • Received : 2019.05.16
  • Accepted : 2019.07.15
  • Published : 2019.07.25

Abstract

This study was carried out to investigate the potential of Korean red pine (Pinus densiflora) inner bark extracts as an antidiabetic agent. The ethyl acetate soluble fraction of the bark extracts was chromatographed on a Sephadex LH-20 column to yield five compounds, which structures were elucidated by NMR spectroscopy. The isolated compounds were (+)-catehin, (-)-epicatechin, taxifolin, taxifolin-3'-O-${\beta}$-D-(+)-glucose and $\tilde{n}$-courmaric acid. The antidiabetic activity of the different fractions, including the crude extracts and isolated compounds, was evaluated by ${\beta}$-cells insulin secretion and glucose uptake in skeletal muscle cells. The insulin secretion was 128% for taxifolin at $25{\mu}g/mL$. However, the other samples had no effect on this test. For the glucose uptake activity assay, $1{\mu}M$ insulin and 2 mM metformin were used as controls. Both the crude extract and taxifolin showed relatively low activity values, but the other samples yielded glucose uptake values over 260%. ${\rho}$-courmaric acid showed the highest uptake (270%). The results confirmed that Korean red pine extracts may be used as a hypoglycemic agent.

Keywords

HMJGBP_2019_v47n4_498_f0001.png 이미지

Fig. 1. Chemical structures of isolated compounds.

HMJGBP_2019_v47n4_498_f0002.png 이미지

Fig. 2. Effects of crude on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0003.png 이미지

Fig. 3. Effects of EtOAc soluble fraction on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0004.png 이미지

Fig. 5. Effects of (+)-catechin on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0005.png 이미지

Fig. 6. Effects of (-)-epicatechin on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0006.png 이미지

Fig. 10. Insulin secretion of HIT-T15 treated with the crude.

HMJGBP_2019_v47n4_498_f0007.png 이미지

Fig. 12. Insulin secretion of HIT-T15 treated with the H2O soluble fraction.

HMJGBP_2019_v47n4_498_f0008.png 이미지

Fig. 14. Insulin secretion of HIT-T15 treated with (-)-epicatechin.

HMJGBP_2019_v47n4_498_f0009.png 이미지

Fig. 16. Insulin secretion of HIT-T15 treated with taxifolin-3′-O-β-D-(+)-glucose.

HMJGBP_2019_v47n4_498_f0010.png 이미지

Fig. 11. Insulin secretion of HIT-T15 treated with the EtOAc soluble fraction.

HMJGBP_2019_v47n4_498_f0011.png 이미지

Fig. 13. Insulin secretion of HIT-T15 treated with (+)-catechin.

HMJGBP_2019_v47n4_498_f0012.png 이미지

Fig. 15. Insulin secretion of HIT-T15 treated with taxifolin.

HMJGBP_2019_v47n4_498_f0013.png 이미지

Fig. 17. Insulin secretion of HIT-T15 treated with ρ-coumaric acid.

HMJGBP_2019_v47n4_498_f0014.png 이미지

Fig. 18. Effects of crude on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0015.png 이미지

Fig. 19. Effects of EtOAc soluble fraction on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0016.png 이미지

Fig. 20. Effects of H2O soluble fraction on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0017.png 이미지

Fig. 21. Effects of (+)-catechin on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0018.png 이미지

Fig. 26. Glucose uptake activities of the crude.

HMJGBP_2019_v47n4_498_f0019.png 이미지

Fig. 28. Glucose uptake activities of the H2O soluble fraction.

HMJGBP_2019_v47n4_498_f0020.png 이미지

Fig. 30. Glucose uptake activities of (-)-epicatechin.

HMJGBP_2019_v47n4_498_f0021.png 이미지

Fig. 32. Glucose uptake activities of taxifolin-3′-O-β-D-(+)-glucose.

HMJGBP_2019_v47n4_498_f0022.png 이미지

Fig. 27. Glucose uptake activities of the EtOAc soluble fraction.

HMJGBP_2019_v47n4_498_f0023.png 이미지

Fig. 29. Glucose uptake activities of (+)-catechin.

HMJGBP_2019_v47n4_498_f0024.png 이미지

Fig. 31. Glucose uptake activities of taxifolin.

HMJGBP_2019_v47n4_498_f0025.png 이미지

Fig. 33. Glucose uptake activities of ρ-coumaric acid.

HMJGBP_2019_v47n4_498_f0026.png 이미지

Fig. 4. Effects of H2O soluble fraction on the viability of HIT -T15 cells.

HMJGBP_2019_v47n4_498_f0027.png 이미지

Fig. 7. Effects of taxifolin on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0028.png 이미지

Fig. 8. Effects of taxifolin-3′-O-β-D-(+)-glucose on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0029.png 이미지

Fig. 9. Effects of ρ-coumaric acid on the viability of HIT-T15 cells.

HMJGBP_2019_v47n4_498_f0030.png 이미지

Fig. 22. Effects of (-)-epicatechin on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0031.png 이미지

Fig. 23. Effects of taxifolin on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0032.png 이미지

Fig. 24. Effects of taxifolin-3′-O-β-D-(+)-glucose on the viability of L6 cells.

HMJGBP_2019_v47n4_498_f0033.png 이미지

Fig. 25. Effects of ρ-coumaric acid on the viability of L6 cells.

Table 1. Weight of each fraction of Korean red pine inner bark extracts

HMJGBP_2019_v47n4_498_t0001.png 이미지

Table 2. Weight of the isolated compounds

HMJGBP_2019_v47n4_498_t0002.png 이미지

References

  1. Ahn, B.T., Oh, K.J., Park, S.K., Chung, S.G., Cho, E.H. Kim, J.G., Ro J.S., Lee, K.S. 1996. Phenolic compounds from leaves of Spiraea salicifolia. Korean Journal of Pharmacognosy 27(3): 178-183.
  2. Aviram, M. 2000. Review of human studies on oxidative damage and antioxidant protection related to cardiovascular diseases. Free Radical Research 33: 85-97.
  3. Choi, Y.Y., Sohn, H.S., Shin, H.T. 2010. Clinical benefit of delf-Monitoring of blood glucose in non-insulin treated patients with type 2 diabetes : A systematic review and meta-analysis. Korean Journal of Clinical Pharmacy 20(3): 189-192.
  4. Denizot, F., Lang, R. 1986. Rapid colorimetric assay for cell growth and survival: modification of the tetrazolium dye procedure giving improved sensitivity and reliability. Journal of Immunological Methods 89: 271-277. https://doi.org/10.1016/0022-1759(86)90368-6
  5. Eizirik, D.L., Mandrup-Poulsen T. 2001. A choice of death-the signal-transduction of immune-mediated ${\beta}$-cell apoptosis. Diabetologia 44: 2115-2133. https://doi.org/10.1007/s001250100021
  6. Erben, B., Benjamin, H.S.L. 2000. Pycnogenol inhibits generation of inflammatory mediators in macrophage. Nutrition Research 20: 249-259. https://doi.org/10.1016/S0271-5317(99)00157-8
  7. Evans, J.L., Goldfine, I.D., Maddux, B.A., Grodsky, G.M. 2002. Oxidative stress and stress-activated signaling pathways: a unifying hypothesis of type 2 diabetes. Endocrine Reviews 23(5): 599-622. https://doi.org/10.1210/er.2001-0039
  8. Fabio, V., Kobuchi, H., Lester, P. 1998. Procyanidins extracted from Pinus maritima (Pycnogenol${(R)}$) : Scavengers of free radical species and modulators of nitrogen monoxide metabolism in activated murine RAW 264.7 macrophages. Free Radical Biology and Medicine 24: 1120-1129. https://doi.org/10.1016/S0891-5849(97)00430-9
  9. Foo, L., Karchesy, J.J. 1989. Procyanidin dimers and trimers from Douglas fir inner bark. Phytochemistry 28(6): 1743-1747. https://doi.org/10.1016/S0031-9422(00)97836-1
  10. Ham, Y.H., Bae, Y.S. 1995, Flavonoids extractives of Populus albaglandulosa. Journal of the Korean Wood Science and Technology 23(2): 94-99
  11. Harborne, J.B., Mabry, T.J. 1982. The flavonoid: advances in research, Chapman and Hall Ltd.
  12. Heo, S.J., Hwang, J.Y., Choi, J.I., Han, J.S., Kim, H.J., Jeon, Y.J. 2009. Diphlorethohydroxycarmalol isolated from Ishige okamurae, a brown algae, a potent alpha-glucosidase and alpha-amylase inhibitor, alleviates postprandial hyperglycemia in diabetic mice. European Journal of Pharmacology 615(1-3): 252-256. https://doi.org/10.1016/j.ejphar.2009.05.017
  13. Ho, G.T.T., Kase, E.T., Wangensteen, H3., Barsett, H. 2017. Effect of phenolic compounds from elderflowers on glucose- and fatty acid uptake in human myotubes and HepG2-cells. Molecules 22(1): 1-15. https://doi.org/10.3390/molecules22010001
  14. Jeong, M.J., Yang, J.Y., Choi, W.S., Kim, J.W., Kim, S.J., Park, M.J. 2017. Chemical Compositions and Antioxidant Activities of Essential Oil Extracted from Neolitsea aciculata (Blume) Koidz Leaves. Journal of the Korean Wood Science and Technology 45(1): 96-106. https://doi.org/10.5658/WOOD.2017.45.1.96
  15. Jung, J.Y., Yang, J.K., Lee, W.H. 2017. Antioxidant and Safety Test of Natural Extract of Quercus mongolica. Journal of the Korean Wood Science and Technology 45(1): 116-125. https://doi.org/10.5658/WOOD.2017.45.1.116
  16. Kim, B.H., Son, S.M. 2006. Mechanism of developing diabetic vascular complication by oxidative stress. journal of the Korean Endocrine Society 21(6): 448-459. https://doi.org/10.3803/jkes.2006.21.6.448
  17. Kim, I.H., Ko, Y.J., Choi, I.D., Kim, Y.G., Ryu, C.H., Shin, K.H. 2012. Antioxidative activities of pine needles and quality characteristics of Korean wheat noodle with pine needle powder. Journal of Agriculture & Life Science 46(5): 127-136.
  18. Kim, J.W., Im, S.B., Jeong, H.R., Jung, Y.S., Lee, I.I., Kim, K.J., Park, S.K., Kim, D.O. 2018. Neuroprotective effects of korean red pine (Pinus densiflora) bark extract and its phenolics. Journal of Microbiology and Biotechnology 28(5): 679-687. https://doi.org/10.4014/jmb.1801.01053
  19. Kim, S.H., Lee, S.Y., Cho, S.M., Hong, C.Y., Park, S.Y., Park, M.J., Choi, I.G. 2017. Antioxidant activities of cryptomeria japonica leaves extracts by extraction methods. Journal of the Korean Wood Science and Technology 45(5): 495-510. https://doi.org/10.5658/WOOD.2017.45.5.495
  20. Kim, T.W. 1996. Korean Tree. Kyohak. 28-36.
  21. Lee, Y.J., Han, O.T., Choi, H.S., Lee, B.Y., Chung. H.J., Lee, O.H. 2013. Antioxidant and antiadipogenic effects of PineXol. Korean Journal of Food Science and Technology 45(1): 97-103. https://doi.org/10.9721/KJFST.2013.45.1.97
  22. Liu, X., Wei, J., Tan, F., Zhou, S., Wurthwein, G., Rohdewald, P. 2004. Antidiabetic effec of pycnogenol ${(R)}$ french maritime pine bark extract in patients with diabetes type II. Life Sciences 75: 2505-2513. https://doi.org/10.1016/j.lfs.2003.10.043
  23. Miriam, C., Nils, W., Jonas, J.C., Anne, J., Sigurd, L. and Decio, L.E. 2005. Mechanisms of pancreatic ${\beta}$-cell death in type 1 and type 2 diabetes: many differences, few similarities. Diabetes 54: 97-107. https://doi.org/10.2337/diabetes.54.suppl_2.S97
  24. Novo, E., Parola, M. 2008. Redox mechanisms in hepatic chronic wound healing and fibrogenesis. Fibrogenesis Tissue Repair 1: 1-58. https://doi.org/10.1186/1755-1536-1-1
  25. Shinn, S.H., Min, H.J., Bae, Y.S. 2019. Phenolic compounds from japanese anise (Illicium anisatum L.) leaves. Journal of Korean Wood Science and Technology 47(1): 1-7. https://doi.org/10.5658/WOOD.2019.47.1.1
  26. Standl, E., Schnell, O. 2012. Alpha-glucosidase inhibitors cardiovascular considerations and trial evaluation. Diabetes and Vascular Disease Research 9(3): 163-169. https://doi.org/10.1177/1479164112441524