Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Application of Caffeic Acid Methoxy Polyethylene Glycol Ester

카페산 메톡시 폴리에틸렌글리콜 에스테르의 합성 및 응용

  • Lee, Hyun-Gi (Department of Engineering Chemistry, College of Engineering Chungbuk National University Chemistry) ;
  • Jeong, Noh-Hee (Department of Engineering Chemistry, College of Engineering Chungbuk National University Chemistry)
  • 이현기 (충북대학교 공과대학 공업화학과) ;
  • 정노희 (충북대학교 공과대학 공업화학과)
  • Received : 2011.04.24
  • Accepted : 2011.09.17
  • Published : 2011.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Caffeic acid is a kind of phytochemicals occurred in coffee, which is worked as a carcinogenesis restrainer and antioxidants on the human body. In this study, as one type of caffeic acid derivatives, methoxypolyethylene glycol caffeate(MPC) was synthesized by the esterification between caffeic acid and methoxypolyethylene glycol with N,N'-dicyclohexyl carbodiimide, 4-dimethylamino pyridine. The synthesized product was confirmed by using FT-IR and $^1H$-NMR, thin-layer chromatography. And these compound was investigated as antioxidant, Tyrosinase hindrance and skin moisturizers. In the free radical scavenging study, antioxidant effect of MPC was averagely high than the red ginseng extract that be used as a natural antioxidants. The result of Tyrosinase anti-activity test was better than embryo bud of rice extract at low concentration. At the iNOS anti-activity tested by using Raw 264.7 cell, and confirmed anti-inflammatory function. For the MPC handled with sodium lauryl sulfate, was tested for the skin moisture content and skin moisture loss.

Keywords

References

  1. 신물질탐색연구회(1996), 신물질탐색, 서울, 자유아카데미
  2. J. S. Jang, Y. H. Lee, J. H. Hong, K. T. Lee, "Oxidation stability of fish oil containing commercially available antioxidants.", J. Food Preserv, 13, 66 (2006).
  3. J. Cabral, P. Haake, "Asocorbic acid. 2. Structural Determination and Synthesis of 2-and 3-Acyl Derivatives of 5,6-O-Isopropylidene-L-ascorbic acid.", J. Org. Chem, 53, 5742 (1988). https://doi.org/10.1021/jo00259a025
  4. O. H. Jhee, C. B. Yang, "Antioxidative activity of extract from Bangah herb.", J. Food Sci. Technol, 28, 1157 (1996).
  5. L. Johanna, C. J. Lurn, "Interindividual Differences in Phytochemical Metabolism and Disposition.", Semin Cancer Biol., 17, 347 (2007). https://doi.org/10.1016/j.semcancer.2007.05.003
  6. M. J. Jang, H. E. Kim, S. M. Son, M. J. Kim, E. W. SEO, Y. H Kim, J. S. Kim, "Over-expression of NSAID activated gene-1 by caffeic acid phenethyl ester.", J. Life Sci, 19, 1787 (2009). https://doi.org/10.5352/JLS.2009.19.12.1787
  7. A. Widjaja, T. H. Yeh, Y. H. Ju, "Enzymatic sysnthesis of caffeic acid phenethyl ester.", J. The Chinese Institute of Chemical Engineers, 39, 413 (2008). https://doi.org/10.1016/j.jcice.2008.05.003
  8. T. Y. Kim, "Antioxidant and cosmetic.", Korean dermatological association, 60, 99 (2008).
  9. H. J. Kim, T. H. Kim, K. C. Kang, H. B. Pyo and N. H. Jeong, "Microencapsulation of rosmarinic acid using polycaprolactone and various surfactants.", J. Cosm. Scie., 32, 185, (2010). https://doi.org/10.1111/j.1468-2494.2010.00526.x
  10. K. C. Kang, C. I. Lee, H. B. Pyo, and N. H. Jeong, "Preparation and characterization of SLNs(W/O/W Type) contained lipoic acid PEG ester by variation lipid." J. Industrial. chem., 15, 529, (2009). https://doi.org/10.1016/j.jiec.2009.02.004
  11. H. S. Song, T. W. Park, U. D. Sohn, Y. K. Shin, B. C. Choi, C. J. Kim and S. S. Sim, "The Effect of Caffeic acid on Wound Healing in Skin-incised Mice.", J. Physiol Pharmacol, 12, 343 (2008). https://doi.org/10.4196/kjpp.2008.12.6.343
  12. J. H. Park, J. S. Kim, A. Y. J대ng and J. D. Lee, "Phytochemical Study on the vitis thunbergii var. sinuata.", J. Plant Res, 9, 55 (1996). https://doi.org/10.1046/j.1365-313X.1996.09010055.x
  13. K. Natarajan, S. Singh, T. R. Burke, Jr. D. grunberger and B. B. Aggarwal, "Caffeic acid phenetyl ester is a potent and spectific inhibitor of activation of nuclear transciption factor NF-${\kappa}B$.", Proc. Natl. Acad. Sci. 93, 9090 (1996). https://doi.org/10.1073/pnas.93.17.9090
  14. D. K. Choi, J. O. Han, Y. N. Lee, J. Y. Choi, S. Y. Han, S. C. Hong, H. C. Jeon, Y. M. Kim and Y. J. Jung, "Caffeic acid phenethyl ester is a potent inhibitor of HIF prolyl hydroxylas : structural analsis and pharmacological implication.", J. Nutritional Biochemistry, 21, 809 (2010). https://doi.org/10.1016/j.jnutbio.2009.06.002
  15. J. mata, D. Varade, P. Bahadur, "Aggregation behavior of quaternary salt based cationic surfactants.", Thermochimica Acta, 428, 147 (2005). https://doi.org/10.1016/j.tca.2004.11.009
  16. F. Borrelli, I. Posadas, R. Capasso, G. Aviello, V. Ascione, F. Capasso, "Effect of caffeic acid phenethyl ester on gastric acid secretion in vitro.", J. Pharmacology, 521, 136 (2005).
  17. Y. J. Lee, P. H. Liao, W. K. Chen, C. C. Yang, "Preferential cytotoxicity of caffeic acid phenethyl ester analogues on ral cancer cells.", J. Cancer Letters, 153, 51 (2000). https://doi.org/10.1016/S0304-3835(00)00389-X
  18. K. J. Shin, N. H. Jeon,." Characterization of Natural Antiseptic System Utilized Propolis and Herb Essential Oil .", J. of Korean Oil Chemist's Soc., 24, 99, (2007).
  19. I. Y. Yoon, H. J. Park, K. S. Kwack and N. H. Jeong, "Synthesis of Silver Nanoparticles by Microemulsion.", J. of Korean Oil Chemist's Soc., 20, 118, (2003).
  20. N. H. Jeong, Y. J. Moon, H. W. Lee and K. D. Nam, "The Evaluation for Stabilization and Application of Microemulsion Containing Isoflavone."J. of Korean Oil Chemist's Soc., 19, 167, (2002).