Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지
DOI QR코드

DOI QR Code

Development and Validation of Quantitative Analysis Method for Phenanthrenes in Peels of the Dioscorea Genus

  • Kim, Hunseong (School of Food Science and Biotechnology, College of Agriculture and Life Sciences, Kyungpook National University) ;
  • Cao, Thao Quyen (Coastal Agriculture Research Institute, Kyungpook National University) ;
  • Yeo, Chae-eun (Department of Integrative Biotechnology, Kyungpook National University) ;
  • Shin, Seung Ho (Department of Food and Nutrition, Institute of Agriculture and Life Science, Gyeongsang National University) ;
  • Kim, Hiyoung (Department of Biomedical Science and Engineering, Konkuk University) ;
  • Hong, Dong-Hyuck (School of Bio-Industrial Machinery Engineering, Kyungpook National University) ;
  • Hahn, Dongyup (School of Food Science and Biotechnology, College of Agriculture and Life Sciences, Kyungpook National University)
  • Received : 2022.06.18
  • Accepted : 2022.07.18
  • Published : 2022.08.28
Download PDF
⟨ Previous Next ⟩

Abstract

Phenanthrenes are bioactive phenolic compounds found in genus Dioscorea, in which they are distributed more in peel than in flesh. Recent studies on phenanthrenes from Dioscorea sp. peels have revealed the potential for valuable biomaterials. Herein, an analytical method using high-performance liquid chromatography (HPLC) for quantitation of bioactive phenanthrenes was developed and validated. The calibration curves were obtained using the phenanthrenes (1-3) previously isolated from Dioscorea batatas concentrations in the range of 0.625-20.00 ㎍/ml with a satisfactory coefficient of determination (R2) of 0.999. The limit of detection (LOD) and the limit of quantification (LOQ) values of the isolated phenanthrenes ranged from 0.78-0.89 and 2.38-2.71 ㎍/ml, respectively. The intraday and interday precision ranged from 0.25-7.58%. The recoveries of the isolated phenanthrenes were from 95 to 100% at concentrations of 1.25, 2.5, and 5.0 ㎍/ml. Additionally, phenanthrenes (1-3) were found in all investigated peel extracts. Hence, the developed method was encouraging for the quantitative analysis of phenanthrenes in genus Dioscorea.

Keywords

Acknowledgement

This work was supported by the Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, and Forestry (IPET) through the Useful Agricultural Life Resources Industry Technology Development Program, funded by the Ministry of Agriculture, Food and Rural Affairs (MAFRA) (Grant No. 121049-2), Korea Basic Science Institute (National Research Facilities and Equipment Center) grant funded by the Ministry of Education (2021R1A6C101A416), and a project to train professional personnel in biological materials by the Ministry of Environment.

References

  1. Toth B, Hohmann J, Vasas A. 2018. Phenanthrenes: a promising group of plant secondary metabolites. J. Nat. Prod. 81: 661-678. https://doi.org/10.1021/acs.jnatprod.7b00619
  2. Cao TQ, Kim JA, Woo MH, Min BS. 2021. SARS-CoV-2 main protease inhibition by compounds isolated from Luffa cylindrica using molecular docking. Bioorg. Med. Chem. Lett. 40: 127972. https://doi.org/10.1016/j.bmcl.2021.127972
  3. Kovacs A, Vasas A, Hohmann J. 2008. Natural phenanthrenes and their biological activity. Phytochemistry 69: 1084-1110. https://doi.org/10.1016/j.phytochem.2007.12.005
  4. Kim M, Gu MJ, Lee JG, Chin J, Bae JS, Hahn D. 2019. Quantitative analysis of bioactive phenanthrenes in Dioscorea batatas Decne peel, a discarded biomass from postharvest processing. Antioxidants 8: 541. https://doi.org/10.3390/antiox8110541
  5. Ngan NTT, Hoang NH, Hien NT, Lan NN, Lien NTK, Quang TH, et al. 2020. Cytotoxic phenanthrenes and phenolic constituents from the tubers of Dioscorea persimilis. Phytochem. Lett. 40: 139-143. https://doi.org/10.1016/j.phytol.2020.10.005
  6. Bus C, Kusz N, Kincses A, Szemeredi N, Spengler G, Bakacsy L, et al. 2020. Antiproliferative phenanthrenes from Juncus tenuis: Isolation and diversity-oriented semisynthetic modification. Molecules 25: 5983. https://doi.org/10.3390/molecules25245983
  7. 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. https://doi.org/10.1186/s13765-019-0436-2
  8. Matsuda H, Morikawa T, Xie H, Yoshikawa M. 2004. Antiallergic phenanthrenes and stilbenes from the tubers of Gymnadenia conopsea. Planta Med. 70: 847-855. https://doi.org/10.1055/s-2004-827234
  9. Adomeniene A, Venskutonis PR. 2022. Dioscorea spp.: Comprehensive review of antioxidant properties and their relation to phytochemicals and health benefits. Molecules 27: 2530. https://doi.org/10.3390/molecules27082530
  10. Chi VV. 2012. Dictionary of medicinal plants in Vietnam. Vietnamese Publisher of Medicine 1: 654-655.
  11. Zhu F. 2015. Isolation, composition, structure, properties, modifications, and uses of yam starch. Compr. Rev. Food Sci. Food Saf. 14: 357-386. https://doi.org/10.1111/1541-4337.12134
  12. Salehi B, Sener B, Kilic M, Sharifi-Rad J, Naz R, Yousaf Z, et al. 2019. Dioscorea plants: A genus rich in vital nutra-pharmaceuticals - A review. Iran J. Pharm. Res. 18: 68-89.
  13. Chaniad P, Wattanapiromsakul C, Pianwanit S, Tewtrakul S. 2016. Anti-HIV-1 integrase compounds from Dioscorea bulbifera and molecular docking study. Pharm. Biol. 54: 1077-1085. https://doi.org/10.3109/13880209.2015.1103272
  14. Woo KW, Kwon OW, Kim SY, Choi SZ, Son MW, Kim KH, et al. 2014. Phenolic derivatives from the rhizomes of Dioscorea nipponica and their anti-neuroinflammatory and neuroprotective activities. J. Ethnopharmacol. 155: 1164-1170. https://doi.org/10.1016/j.jep.2014.06.043
  15. Boudjada A, Touil A, Bensouici C, Bendif H, Rhouati S. 2019. Phenanthrene and dihydrophenanthrene derivatives from Dioscorea communis with anticholinesterase, and antioxidant activities. Nat. Prod. Res. 33: 3278-3282. https://doi.org/10.1080/14786419.2018.1468328
  16. Du D, Zhang R, Xing Z, Liang Y, Li S, Jin T, et al. 2016. 9,10-Dihydrophenanthrene derivatives and one 1,4-anthraquinone firstly isolated from Dioscorea zingiberensis C.H. Wright and their biological activities. Fitoterapia 109: 20-24. https://doi.org/10.1016/j.fitote.2015.11.022
  17. 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. https://doi.org/10.1016/j.jep.2021.114633
  18. Lee W, Jeong SY, Gu MJ, Lim JS, Park EK, Baek MC, et al. 2019. Inhibitory effects of compounds isolated from Dioscorea batatas Decne peel on particulate matter-induced pulmonary injury in mice. J. Toxicol. Environ. Health A 82: 727-740. https://doi.org/10.1080/15287394.2019.1646174
  19. Yoon KD, Yang MH, Nam SI, Park JH, Kim YC, Kim J. 2007. Phenanthrene derivatives, 3,5-dimethoxyphenanthrene-2,7-diol and batatasin-I, as non-polar standard marker compounds for Dioscorea rhizome. Nat. Prod. Sci. 13: 378-383.
  20. ICH. 1995. International council for harmonisation of technical requirements for pharmaceuticals for human use (ICH), Validation of analytical procedures: Text and methodology Q2 (R1). Available online: https://www.ema.europa.eu/en/documents/scientificguideline/ich-q-2-r1-validation-analytical-procedures-text-methodology-step-5_en.pdf.
  21. Choi SI, Han X, Lee SJ, Men X, Oh G, Lee DS, et al. 2022. Validation of an analytical method for the determination of thiabendazole in various food matrices. Separations 9: 135. https://doi.org/10.3390/separations9060135
  22. Karnes HT, March C. 1993. Precision, accuracy, and data acceptance criteria in biopharmaceutical analysis. Pharm. Res. 10: 1420-1426. https://doi.org/10.1023/A:1018958805795
  23. AOAC. 2016. Appendix F: Guidelines for standard method performance requirements. AOAC Official methods of analysis. Available online: http://www.eoma.aoac.org/app_f.pdf.
  24. Dutta B. 2015. Food and medicinal values of certain species of Dioscorea with special reference to Assam. J. Pharmacogn. Phytochem. 3: 15-18.
  25. Trimanto, Hapsari L. 2015. Diversity and utilization of Dioscorea spp. tuber as alternative food source in Nganjuk Regency, East Java. Agrivita. 37: 97-107.
  26. 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
  27. 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
  28. Sautour M, Mitaine-Offer AC, Lacaille-Dubois MA. 2007. The Dioscorea genus: a review of bioactive steroid saponins. J. Nat. Med. 61: 91-101. https://doi.org/10.1007/s11418-006-0126-3
  29. Liao YH, Tseng CY, Chen W. 2006. Structural characterization of dioscorin, the major tuber protein of yams, by near infrared Raman spectroscopy. J. Phys. Conf. Ser. 28: 119-122. https://doi.org/10.1088/1742-6596/28/1/025
  30. Obidiegwu JE, Lyons JB, Chilaka CA. 2020. The Dioscorea genus (Yam) - An appraisal of nutritional and therapeutic potentials. Foods 9: 1034. https://doi.org/10.3390/foods9081034
  31. Li X, Zhao C, Jing S, Sun J, Li X, Man S, et al. 2017. Novel phenanthrene and isocoumarin from the rhizomes of Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting (Dioscoreaceae). Bioorg. Med. Chem. Lett. 27: 3595-3601. https://doi.org/10.1016/j.bmcl.2017.03.095
  32. 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