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Chemotaxonomic Significance of Taxifolin-3-O-arabinopyranoside in Chinese Rhododendron genus

  • Tae Hee Kim (Dr. Oregonin Inc.) ;
  • Hyeon Du Jang (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Ye Ji Kim (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Ye Eun Kwon (Dr. Oregonin Inc.) ;
  • Sun Min Park (Dr. Oregonin Inc.) ;
  • Min Seok Kim (Dr. Oregonin Inc.) ;
  • Chan Ho Lee (Department of Forest Biomaterials Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Sun Eun Choi (Dr. Oregonin Inc.)
  • Received : 2024.03.25
  • Accepted : 2024.04.15
  • Published : 2024.06.30

Abstract

More than half of the global distribution of the Rhododendron genus is found in China, with over 74% being endemic species. However, there is still insufficient data to chemically classify the Rhododendron genus native to China. Therefore, in this study, a chemotaxonomic study was conducted to determine the presence of taxifolin-3-O-arabinopyranoside, a flavonoid compound, in the Rhododendron genus native to China. Forty-three species of Rhododendron native to China-20 from across China, 8 from Beijing, 6 from Yanbian, and 9 from Yunnan-were utilized in the experiment. Through HPLC analysis, the retention time was compared with that of taxifolin-3-O-arabinopyranoside, a standard compound, and quantitative analysis was conducted. As a result, taxifolin-3-O-arabinopyranoside was detected in 22 out of 43 the Chinese Rhododendron species. Afterwards, LC-MS/MS analysis was performed on the 22 species in which taxifolin-3-O-arabinopyranoside was detected to determine whether the molecular weight was consistent with the standard compound. Under negative conditions, it was confirmed that all samples exhibited the same molecular weight as taxifolin-3-O-arabinopyranoside, 435-436 m/z. The same compound was detected in more than half of the Rhododendron species used in the experiment, and taxifolin-3-O-arabinopyranoside was determined to be an indicator compound for Rhododendron species native to China. In addition, the possibility of using the above results as basic data for chemical classification of Chinese Rhododendron genus was confirmed.

Keywords

Acknowledgement

This study was carried out with the support of 'R&D Program for Forest Science Technology (Project No. 2023469A00-2425-EE01, 2019151D10-2323-0301)' provided by Korea Forest Service (Korea Forestry Promotion Institute), and this research was supported by 2023 Regional Industry-linked University Open-Lab Development Support Program through the Commercializations Promotion Agency for R&D Outcomes (COMPA) funded by Ministry of Science and ICT (Research No. 1711202074), and also partially supported by the Starting growth Technological R&D Program (TIPS Program, [RS-2023-00222349]) funded by the Ministry of SMEs and Startups (MSS, Korea) in 2023.

References

  1. Ahn JY, Choi SE, Jeong MS, Park KH, Moon NJ, Joo SS, Lee CS, Choi YW, Li K, Lee MK, Lee MW, Seo SJ. 2010. Effect of taxifolin glycoside on atopic dermatitis-like skin lesions in NC/Nga mice. Phytother Res 24: 1071-1077.
  2. Cao Y, Chu Q, Ye J. 2004. Chromatographic and electrophoretic methods for pharmaceutically active compounds in Rhododendron dauricum. J Chromatogr B Analyt Technol Biomed Life Sci 812: 231-240.
  3. Fu Y, Zhang L, Chen G. 2012. Far infrared-assisted extraction followed by MEKC for the simultaneous determination of flavones and phenolic acids in the leaves of Rhododendron mucronulatum Turcz. J Sep Sci 35: 468-475.
  4. Gui L, Tao YD, Wang WD, Shao Y, Wang QL, Chan XP, Mei LJ. 2020. Chemical constituents of Rhododendron anthopogonoides. Chem Nat Compd 56: 130-133.
  5. Hui Y, Sun ML. 2012. Volatile components of the essential oils from the leaves of Rhododendron dauricum L. by GC-MS. Bull Bot Res 32: 365-368.
  6. Iwata N, Wang N, Yao X, Kitanaka S. 2004. Structures and histamine release inhibitory effects of prenylated orcinol derivatives from Rhododendron dauricum. J Nat Prod 67: 1106-1109.
  7. Kim TH, Kwon YE, Park SM, Kim MS, Jeong YH, Park SY, Bae YS, Cheong EJ, He YC, Gong C, Gao W, Kim HK, Ham YH, Kim JK, Choi SE. 2022. Chemotaxonomic significance of Taxifolin-3-O-arabinopyranoside in Rhododendron species native to Korea. J For Environ Sci 38: 159-173.
  8. Kim YJ, Choi SE, Lee MW, Lee CS. 2008. Taxifolin glycoside inhibits dendritic cell responses stimulated by lipopolysaccharide and lipoteichoic acid. J Pharm Pharmacol 60: 1465-1472.
  9. Liu JY, Guo PJ, Wang XL, Chen HM, Chen LJ, Sang YL, Hao YJ, Lu J. 2022. Study on phytochemical and pharmacological activities of four Rhododendron plants endemic to Northeast China. J Agric Food Res 7: 100255.
  10. Lou XW, Lin QH, Zhang GY, Liu WY, Feng F, Qu W. 2015. Identification and characterization of three new flavonoids from Rhododendron dauricum. Chin J Nat Med 13: 628-633.
  11. Olennikov DN, Tankhaeva LM. 2010. Phenolic compounds from Rhododendron dauricum from the Baikal region. Chem Nat Compd 46: 471-473.
  12. Peng Y, Liu F, Ye J. 2004. Determination of bioactive flavonoids in Rhododendron dauricum L. by capillary electrophoresis with electrochemical detection. Chromatographia 60: 597-602.
  13. Popescu R, Kopp B. 2013. The genus Rhododendron: an ethnopharmacological and toxicological review. J Ethnopharmacol 147: 42-62.
  14. Qiang Y, Zhou B, Gao K. 2011. Chemical constituents of plants from the genus Rhododendron. Chem Biodivers 8: 792-815.
  15. Sun N, Qiu Y, Zhu Y, Liu J, Zhang H, Zhang Q, Zhang M, Zheng G, Zhang C, Yao G. 2019. Rhodomicranosides A-I, analgesic diterpene glucosides with diverse carbon skeletons from Rhododendron micranthum. Phytochemistry 158: 1-12.
  16. Ye C, Jin M, Li R, Sun J, Wang R, Wang J, Li S, Zhou W, Li G. 2020. Phytochemical and chemotaxonomic study on the leaves of Rhododendron dauricum L. Biochem Syst Ecol 90: 104038.
  17. Yu F, Skidmore AK, Wang T, Huang J, Ma K, Groen TA. 2017. Rhododendron diversity patterns and priority conservation areas in China. Divers Distrib 23: 1143-1156.
  18. Zeng K, Ban S, Cao Z, Cao P, Luo X, Wang R, Zhao Z, Xu J. 2021. Phytochemical and chemotaxonomic study on the leaves of Rhododendron amesiae. Biochem Syst Ecol 95: 104232.
  19. Zhang Z, Yan H, Zhu Y, Zhang H, Chai L, Li L, Wang X, Liu Y, Li Y. 2019. New lignans, sesquiterpenes and other constituents from twigs and leaves of Rhododendron micranthum. Fitoterapia 135: 15-21.