Simultaneous Determination of Isoegomaketone and Perillaketone in Perilla frutescens (L.) Britton Leaves by HPLC-DAD

HPLC-DAD를 이용한 차조기 잎의 Isoegomaketone 및 Perillaketone의 동시분석법 확립

  • Received : 2015.12.15
  • Accepted : 2016.03.10
  • Published : 2016.03.31

Abstract

This study developed an HPLC analysis method for the determination of isoegomaketone (IK) and perillaketone (PK) in Perilla frutescens (L.) Britton leaves. P. frutescens ethanol extract was optimized through an HPLC analysis using a C18 column ($250{\times}4.6mml$, D, $S-5{\mu}m$, 12 nm) with gradient elution of water and acetonitrile as the mobile phase at a flow rate of 1 mL/min and a UV detection wavelength of 254 nm. The results of this method showed linearity in the calibration curve at a coefficient of correlation ($R^2$) of IK 0.9995, PK 0.9998. The limits of detection (LOD) for IK and PK were $0.234{\mu}g/mL$ and $0.952{\mu}g/mL$. The limits of quantification (LOQ) for IK and PK were $0.017{\mu}g/mL$ and $0.043{\mu}g/mL$. The inter-day precision RSDs of IK and PK in the P. frutescens were 1.25 to 2.69% and 0.36 to 1.10%, respectively, and the intra-day precision RSDs of IK and PK were 0.96 to 2.51% and 0.90 to 1.93%, respectively. The accuracies of IK and PK were 96.31 to 97.92% and 101.26 to 105.14%. In conclusion, this method was applied successfully to the detection of IK and PK in P. frutescens.

Keywords

References

  1. Jun, H. I., Kim, B. T., Song, G. S. and Kim, Y. S. (2014) Structural characterization of phenolic antioxidants from purple perilla (Perilla frutescens var. acuta) leaves. Food Chem. 148: 367-372. https://doi.org/10.1016/j.foodchem.2013.10.028
  2. Peng, Y., Ye, J. and Kong, J. (2005) Determination of phenolic compounds in Perilla frutescens L. by capillary electrophoresis with electrochemical detection. Food Chem. 53: 8141-8147. https://doi.org/10.1021/jf051360e
  3. Ahn, H. (2006) Available components of chajogi (Perilla sikokiana) at different harvest periods. Korea J. Food Preserv. 13: 8141-8147.
  4. Kim, J. M., Kim, D. J., Kim, T. H., Kim, H. S. and Choe, M. (2010) Anti-oxidative and anti-inflammatory effect of water extract from Perilla semen in RBL-2H3 cells. Korean J. Nutr. 43: 367-373. https://doi.org/10.4163/kjn.2010.43.4.367
  5. Yang, S. Y., Kang, J. H. and Lee, K. W. (2013) Protective effect of functional perilla frutescens hot-water extract against tert-butyl hydroperoxide-induces liver oxidative damage in rats. J. Fd. Hyg. Safety 28: 146-151. https://doi.org/10.13103/JFHS.2013.28.2.146
  6. Lee, J. H., Park, K. H., Lee, M. H., Kim, H. T., Seo, W. D., Kim, J. Y., Baek, I. Y., Jang, D. S. and Ha, T. J. (2013) Identification, chracterisation, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (perilla frutescens) cultivars. Food Chem. 136: 843-852. https://doi.org/10.1016/j.foodchem.2012.08.057
  7. Zhou, X. J., Yan, L. L., Yin, P. P., Shi, L. L., Zhang, J. H., Liu, Y. J. and Ma, C. (2014) Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed perilla frutescens var. arguta seed flour. Food Chem. 164: 150-157. https://doi.org/10.1016/j.foodchem.2014.05.062
  8. Jin, C. H., Lee, H. J., Park, Y. D., Choi, D. S., Kim, D. S., Kang, S. Y., Seo, K. I. and Jeong, I. Y. (2010) Isoegomaketone inhibits lipopolysaccharide-Induced nitric oxide Production in RAW 264.7 macrophages through the heme oxygenase-1 induction and inhibition of the interferon-${\beta}$-STAT-1 pathway. J. Agric. Food Chem. 58: 860-867. https://doi.org/10.1021/jf9033333
  9. Park, Y. D., Jin, C. H., Choi, D. S., Byun, M. Y. and Jeong, I. Y. (2011) Biological evaluation of isoegomaketone isolated from Perilla frutescens and its synthetic derivatives as antiinflammatory agents. Arch. Pharm. Res. 34: 1277-1282. https://doi.org/10.1007/s12272-011-0806-8
  10. Kwon, S. J., Lee, J. H., Moon, K. D., Jeong, I. Y., Ahn, D. U., Lee, M. K. and Seo, K. I. (2014) Induction of apoptosis by isoegomaketone from perilla frutescens L. in B16 melanoma cells is mediated through ROS generation and mitochondrialdependent, -independent pathway. Food Chem. Toxicol. 65: 97-104. https://doi.org/10.1016/j.fct.2013.12.031
  11. Cho, B. O., Jin, C. H., Park, Y. D., Ryu, H. W., Byun, M. W., Seo, K. I. and Jeong, I. Y. (2011) Isoegomaketone induces apoptosis through caspase-dependent and caspase-independent pathways in human DLD1 cells. Biosci. Biotechnol. Biochem. 75: 1306-1311. https://doi.org/10.1271/bbb.110088
  12. Lee, J. H., Cho, H. D., Jeong, I. Y., Lee, M. K., Seo, M. W. and Seo, K. I. (2014) Sensitization of tumor necrosis factorrelated apoptosis- inducing ligand (TRAIL)-resistant primary prostate cancer cell by isoegomaketone from perilla frutescens. J. Nat. Prod. 77: 2438-2443. https://doi.org/10.1021/np500452e
  13. Park, S. Y., Kim, J. E., Choi, C. Y., Lee, D. W., Kim, K. M., Yoon, G., Yoon, I. S., Moon, H. S. and Cho, S. S. (2015) Analytical validation of rosmarinic acid in water extract of Perilla frutescens Britton var. acuta Kudo as functional health ingredient. J. Korean Soc. Food Sci. Nutr. 44: 85-88. https://doi.org/10.3746/jkfn.2015.44.1.085
  14. Park, Y. D., Lee, Y. M., Kang, M. A., Lee, H. J., Jin, C. H., Choi, D. S., Kim, D. S., Kang, S. Y., Kim, W. G. and Jeong, I. Y. (2010) Phytochemical profiles and in vitro anti-inflammatory properties of Perilla frutescens cv. Choolyoupjaso mutants induced by mutagenesis with ${\gamma}$-ray. Food Sci. Biotechol. 19: 305-311. https://doi.org/10.1007/s10068-010-0044-8
  15. Bassoli, A., Borgonovo, G., Caimi, S., Scaglioni, L., Morini, G., Moriello, A. S., Marzo, V. D. and Petrocellis, L. D. (2009) Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens. Bioorg. Med. Chem. 17: 1636-1639. https://doi.org/10.1016/j.bmc.2008.12.057
  16. Lee, B. H., Jin, Y. M., Weon, J. B., Yang, H. J., Yun, B. R. and Ma, C. J (2012) Simultaneous determination of three compounds in ejung tang by HPLC-DAD and LC-ESI-MS. Kor. J. Pharmacogn. 43: 10-15.
  17. Avula. B., Wnag, Y. H., Wang, M., Smillie, T. J. and Khan, I. K. (2012) Simultaneous determination of sesquiterpenes and pyrrolizidine alkaloids from the rhizomes of Petasites hybridus (L.) G.M. et Sch. and dietary supplements using UPLC-UV and HPLC-TOF-MS methods. J.Pharmaceut. Biomed. 70: 53-63. https://doi.org/10.1016/j.jpba.2012.05.021