DOI QR코드

DOI QR Code

Quantification of Allantoin in Yams (Dioscorea sp.) Using a 1H NMR Spectroscopic Method

  • Thao Quyen Cao (Institute of Agricultural Science and Technology, Kyungpook National University) ;
  • Dongyup Hahn (Institute of Agricultural Science and Technology, Kyungpook National University)
  • 투고 : 2023.01.04
  • 심사 : 2023.01.30
  • 발행 : 2023.05.28

초록

Allantoin is an abundant component of yams and has been known as a skin protectant due to its pharmacological activities. In previous methods for allantoin determination using high-performance liquid chromatography (HPLC), the separation was unsatisfactory. We herein developed a 1H quantitative nuclear magnetic resonance (qNMR) method for quantification of allantoin in the flesh and peel of yams. The method was carried out based on the relative ratio of signals integration of allantoin to a certain amount of the internal standard dimethyl sulfone (DMSO2) and validated in terms of specificity, linearity (range 62.5-2000 ㎍/ml), sensitivity (limit of detection (LOD) and quantification (LOQ) 4.63 and 14.03 ㎍/ml, respectively), precision (RSD% 0.02-0.26), and recovery (86.35-92.11%). The method was then applied for the evaluation of allantoin in flesh and peel extracts of four different yams cultivated in Korea.

키워드

과제정보

This work was technically supported by Korea Basic Science Institute (National research Facilities and Equipment center) grant funded by the Ministry of Education (2021R1A6C101A416).

참고문헌

  1. Bharti SK, Roy R. 2012. Quantitative 1H NMR spectroscopy. Trends Anal. Chem. 35: 5-26.  https://doi.org/10.1016/j.trac.2012.02.007
  2. Truzzi E, Marchetti L, Benvenuti S, Righi V, Rossi MC, Gallo V, et al. 2021. A novel qNMR application for the quantification of vegetable oils used as adulterants in essential oils. Molecules 26: 5439. 
  3. Cao R, Liu X, Liu Y, Zhai X, Cao T, Wang A, et al. 2021. Applications of nuclear magnetic resonance spectroscopy to the evaluation of complex food constituents. Food Chem. 342: 128258. 
  4. Malz F, Jancke H. 2005. Validation of quantitative NMR. J. Pharm. Biomed. Anal. 38: 813-823.  https://doi.org/10.1016/j.jpba.2005.01.043
  5. Pauli GF, Chen SN, Simmler C, Lankin DC, Godecke T, Jaki BU, et al. 2014. Importance of purity evaluation and the potential of quantitative 1H NMR as a purity assay. J. Med. Chem. 57: 9220-9231.  https://doi.org/10.1021/jm500734a
  6. Kemprai P, Mahanta BP, Bora PK, Das DJ, Boruah JLH, Saikia SP, et al. 2020. A 1H NMR spectroscopic method for the quantification of propenylbenzenes in the essential oils: Evaluation of key odorants, antioxidants and post-harvest drying techniques for Piper betle L. Food Chem. 331: 127278. 
  7. Cheilari A, Sturm S, Intelmann D, Seger C, Stuppner H. 2016. Head-to-head comparison of ultra-high-performance liquid chromatography with diode array detection versus quantitative nuclear magnetic resonance for the quantitative analysis of the silymarin complex in Silybum marianum fruit extracts. J. Agric. Food Chem. 64: 1618-1626.  https://doi.org/10.1021/acs.jafc.5b05494
  8. Zhang L, Liu Y, Chen G. 2004. Simultaneous determination of allantoin, choline and L-arginine in Rhizoma Dioscoreae by capillary electrophoresis. J. Chromatogr. A 1043: 317-321.  https://doi.org/10.1016/j.chroma.2004.06.003
  9. Chen XB, Matuszewski W, Kowalczyk J. 1996. Determination of allantoin in biological, cosmetic, and pharmaceutical samples. J. AOAC Int. 79: 628-635.  https://doi.org/10.1093/jaoac/79.3.628
  10. Ahn YJ, Park SJ, Woo H, Lee HE, Kim HJ, Kwon G, et al. 2014. Effects of allantoin on cognitive function and hippocampal neurogenesis. Food Chem. Toxicol. 64: 210-216.  https://doi.org/10.1016/j.fct.2013.11.033
  11. Manca ml, Matricardi P, Cencetti C, Peris JE, Melis V, Carbone C, et al. 2016. Combination of argan oil and phospholipids for the development of an effective liposome-like formulation able to improve skin hydration and allantoin dermal delivery. Int. J. Pharm. 505: 204-211.  https://doi.org/10.1016/j.ijpharm.2016.04.008
  12. Lee MY, Lee NH, Jung D, Lee JA, Seo CS, Lee H, et al. 2010. Protective effects of allantoin against ovalbumin (OVA)-induced lung inflammation in a murine model of asthma. Int. Immunopharmacol. 10: 474-480.  https://doi.org/10.1016/j.intimp.2010.01.008
  13. Ma J, Meng X, Liu Y, Yin C, Zhang T, Wang P, et al. 2020. Effects of a rhizome aqueous extract of Dioscorea batatas and its bioactive compound, allantoin in high fat diet and streptozotocin-induced diabetic mice and the regulation of liver, pancreas and skeletal muscle dysfunction. J. Ethnopharmacol. 259: 112926. 
  14. Go HK, Rahman MM, Kim GB, Na CS, Song CH, Kim JS, et al. 2015. Antidiabetic effects of yam (Dioscorea batatas) and its active constituent, allantoin, in a rat model of streptozotocin-induced diabetes. Nutrients 7: 8532-8544.  https://doi.org/10.3390/nu7105411
  15. Chen MF, Tsai JT, Chen LJ, Wu TP, Yang JJ, Yin LT, et al. 2014. Antihypertensive action of allantoin in animals. Biomed Res. Int. 2014: 690135. 
  16. Fu YC, Ferng LHA, Huang PY. 2006. Quantitative analysis of allantoin and allantoic acid in yam tuber, mucilage, skin and bulbil of the Dioscorea species. Food Chem. 94: 541-549.  https://doi.org/10.1016/j.foodchem.2004.12.006
  17. Yamamoto R, Seki M, Ouchi K, Koyano SI, Nakazawa S, Nagatani Y, et al. 1998. A rapid determination of allantoin by high-performance liquid chromatography using tris(hydroxymethyl)aminomethane-HCl buffer as a mobile phase. J. Pharm. Soc. Jpn. 118: 310-316.  https://doi.org/10.1248/yakushi1947.118.8_310
  18. Ninomiya A, Murata Y, Tada M, Shimoishi Y. 2003. Quantitative analysis of allantoin in fresh tubers of Dioscorea opposita 'Tsukuneimo'. J. Japan Soc. Hort. Sci. 72: 321-323.  https://doi.org/10.2503/jjshs.72.321
  19. Lee M, Kim JM, Kim H, Hahn D. 2021. Quantitative analysis of allantoin in Dioscorea japonica peel using an amino bonded-phase HPLC column. J. Food Hyg. Saf. 36: 347-352.  https://doi.org/10.13103/JFHS.2021.36.4.347
  20. ICH. 2006. ICH Harmonised Tripartite Guideline Validation of Analytical Procedures: Text and Methodology Q2(R1). Geneva, Switzerland: https://www.ich.org/page/quality-guidelines. 
  21. Lanza IR, Zhang S, Ward LE, Karakelides H, Raftery D, Nair KS. 2010. Quantitative metabolomics by 1H-NMR and LC-MS/MS confirms altered metabolic pathways in diabetes. PLoS One 5: e10538. 
  22. Raletsena MV, Mdlalose S, Bodede OS, Assress HA, Woldesemayat AA, Modise DM. 2022. 1H-NMR and LC-MS based metabolomics analysis of potato (Solanum tuberosum L.) cultivars irrigated with fly ash treated acid mine drainage. Molecules 27: 1187. 
  23. Beltran A, Suarez M, Rodriguez MA, Vinaixa M, Samino S, Arola L, et al. 2012. Assessment of compatibility between extraction methods for NMR and LC/MS-based metabolomics. Anal. Chem. 84: 5838-5844.  https://doi.org/10.1021/ac3005567
  24. Nishinami S, Hirano A, Arakawa T, Shiraki K. 2018. Effects of allantoin and dimethyl sulfoxide on the thermal aggregation of lysozyme. Int. J. Biol. Macromol. 119: 180-185.  https://doi.org/10.1016/j.ijbiomac.2018.07.043
  25. Kim H, Cao TQ, Yeo CE, Shin SH, Kim H, Hong DH, et al. 2022. Development and validation of quantitative analysis method for phenanthrenes in peels of the Dioscorea genus. J. Microbiol. Biotechnol. 32: 976-981.  https://doi.org/10.4014/jmb.2206.06037
  26. Jegal J, Park NJ, Bong SK, Jegal H, Kim SN, Yang MH. 2017. Dioscorea quinqueloba ameliorates oxazolone- and 2,4-dinitrocholorobenzene-induced atopic dermatitis symptoms in murine models. Nutrients 9: 1324-1336.  https://doi.org/10.3390/nu9121324
  27. Kim JH, Lee SM, Lee DC. 2018. Immunopotentiating effect of protein extract from Dioscorea quinqueloba in stressed mice. Korean J. Food Nutr. 31: 252-257. 
  28. Sato K, Fujita S, Iemitsu M. 2017. Dioscorea esculenta-induced increase in muscle sex steroid hormones is associated with enhanced insulin sensitivity in a type 2 diabetes rat model. FASEB J. 31: 793-801.  https://doi.org/10.1096/fj.201600874R
  29. Liu YH, Lin YS, Liu DZ, Han CH, Chen CT, Fan M, et al. 2009. Effects of different types of yams (Dioscorea alata) products on the blood pressure of spontaneously hypertensive rats. Biosci. Biotechnol. Biochem. 73: 1371-1376.  https://doi.org/10.1271/bbb.90022
  30. Lim JS, Hahn D, Gu MJ, Oh J, Lee JS, Kim JS. 2019. Anti-inflammatory and antioxidant effects of 2,7-dihydroxy-4,6-dimethoxy phenanthrene isolated from Dioscorea batatas Decne. Appl. Biol. Chem. 62: 29. 
  31. Lim JS, Oh J, Yun HS, Lee JS, Hahn D, Kim JS. 2022. Anti-neuroinflammatory activity of 6,7-dihydroxy-2,4-dimethoxy phenanthrene isolated from Dioscorea batatas Decne partly through suppressing the p38 MAPK/NF-κB pathway in BV2 microglial cells. J. Ethnopharmacol. 282: 114633. 
  32. Byeon S, Oh J, Lim JS, Lee JS, Kim JS. 2018. Protective effects of Dioscorea batatas flesh and peel extracts against ethanol-induced gastric ulcer in mice. Nutrients 10: 1680. 
  33. Kim KM, Kang MK, Kim JS, Kim GC, Choi SY. 2015. Physicochemical composition and antioxidant activities of Korean Dioscorea species. J. East Asian Soc. Dietary Life 25: 880-886. https://doi.org/10.17495/easdl.2015.10.25.5.880