Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Analysis of polyphenolic metabolites from Artemisia gmelinii Weber ex Stechm. and regional comparison in Korea

  • Park, Mi Hyeon (Natural Medicine Research Center, KRIBB) ;
  • Kim, Doo-Young (Natural Medicine Research Center, KRIBB) ;
  • Jang, Hyun-Jae (Natural Medicine Research Center, KRIBB) ;
  • Jo, Yang Hee (Natural Medicine Research Center, KRIBB) ;
  • Jeong, Jin Tae (Department of Medicinal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Lee, Dae Young (Department of Medicinal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Baek, Nam-In (Graduate School of Biotechnology, Kyung Hee University) ;
  • Ryu, Hyung Won (Natural Medicine Research Center, KRIBB) ;
  • Oh, Sei-Ryang (Natural Medicine Research Center, KRIBB)
  • Received : 2019.11.06
  • Accepted : 2019.11.20
  • Published : 2019.12.31
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Abstract

Artemisia species are widely used as food ingredients and raw material in traditional medicine. However, to date, the secondary metabolites of Artemisia gmelinii Weber ex Stechm. have not been sufficiently investigated. The secondary metabolites of A. gmelinii, which was collected from representative regions in Chungbuk, Gangwon, and Gyeongbuk, were analyzed using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTof MS) combined with an unsupervised principal component analysis (PCA) multivariate analysis. In the loading scatter plot of PCA, significant changes in metabolites were observed between the regions, ten metabolites (3: 5-O-caffeoylquinic acid, 4: 4-O-caffeoylquinic acid, 8: trans-melilotoside, 12: quercetin 3-O-hexoside, 15: 3,4-O-dicaffeoylquinic acid, 17: 3,5-O-dicaffeoylquinic acid, 18: 4,5-O-dicaffeoylquinic acid, 19: syringaldehyde, 20: caffeoylquinic acid derivative, and 23: icariside II) were evaluated as key markers among twenty-five identified metabolites. Interestingly, the contents of the identified marker significantly differed between the three groups. This is the first study to report the presence of marker metabolites and their correlating geographical cultivation in A. gmelinii.

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References

  1. Olennikov DN, Nadezhda K, Chirikova NK, Kashchenko NI, Nikolaev VM, Kim SW, Vennos C (2018) Bioactive phenolics of the aenus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS profile of the siberian species and their inhibitory potential against ${\alpha}$-amylase and ${\alpha}$-glucosidase. Front Pharmacol 9: 756 https://doi.org/10.3389/fphar.2018.00756
  2. Govorko D, Logendra S, Wang Y, Esposito D, Komarnytsky S, Ribnicky D, Poulev A, Wang Z, Cefalu WT, Ilya Raskin I (2017) Polyphenolic compounds from Artemisia dracunculus L. inhibit PEPCK gene expression and gluconeogenesis in an H4IIE hepatoma cell line. Am J Physiol Endocrinol Metab 293: 1503-1510 https://doi.org/10.1152/ajpendo.00420.2007
  3. Yamamoto N, Kanemoto Y, Ueda M, Kawasaki K, Fukuda I, Ashida H (2011) Anti-obesity and anti-diabetic effects of ethanol extract of Artemisia princeps in C57BL/6 mice fed a high-fat diet. Food Funct 2: 45 https://doi.org/10.1039/C0FO00129E
  4. Karabegovic I, Nikolova M, Velickovic D, Sasa Stojicevic S, Vlada Veljkovic V, Lazic M (2011) Comparison of antioxidant and antimicrobial activities of methanolic extracts of the Artemisia sp. recovered by different extraction techniques. Chin J Chem Eng 19(3): 504-511 https://doi.org/10.1016/S1004-9541(11)60013-X
  5. Seo JM, Kang HM, Son KH, Kim JH, Lee CW, Kim HM, Chang SI, Kwon BM (2003) Antitumor activity of flavones isolated from Artemisia argyi. Planta Med 69(3): 218-222 https://doi.org/10.1055/s-2003-38486
  6. Liu KCSC, Yang SL, Roberts MF, Elford BC, Phillipson JD (1992) Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures. Plant Cell Reports 11: 637-640 https://doi.org/10.1007/BF00236389
  7. Arpad K, Zoltan B, Marta MS, Attila R, Viktor H, Judit H, Imre M, Csaba S, Gyorgy MK, Gyorgy TB (2012) Antioxidant activity-guided phytochemical investigation of Artemisia gmelinii Webb. ex Stechm.: Isolation and spectroscopic challenges of 3,5-O-dicaffeoyl (epi?) quinic acid and its ethyl ester. J Pharm Biomed Anal 59: 83-89 https://doi.org/10.1016/j.jpba.2011.10.012
  8. Yuk HJ, Ryu HW, Kim DY, Park MH, Seo WD, Jeong SH, Oh SR (2019) Comparison of flavonoid and policosanol profiles in Korean winter-spinach (Spinacia oleracea L.) cultivated in different regions. Food Chem 279: 202-208 https://doi.org/10.1016/j.foodchem.2018.11.143
  9. Yuk HJ, Oh KY, Kim DY, Song HH, Kim JY, Oh SR, Ryu HW (2017) Metabolomic Profiling, Antioxidant and Anti-inflammatory Activities of Hypericum Species Growing in South Korea. Nat Prod Commun 12(7): 1041-1044
  10. An JH, Yuk HJ, Kim DY, Nho CW, Lee DH, Ryu HW, Oh SR (2018) Evaluation of phytochemicals in Agastache rugosa (Fisch. & C.A.Mey.) Kuntze at different growth stages by UPLC-QTof-MS. Ind Crops Prod 112: 608-616 https://doi.org/10.1016/j.indcrop.2017.12.050
  11. Park MH, Lee SM, Ko SK, Oh KY, Kim JH, Kim H, Kwon MC, Ryoo IJ, Ahn JS, Ryu HW, Oh SR (2018) Analysis of active metabolites of Sophora flavescens for indoleamine 2,3-dioxygenase and monoamine oxidases using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry. Nat Prod commun 13(12): 1649-1653
  12. Song HH, Kim DY, Woo, SY, Lee HK, Oh SR (2013) An approach for simultaneous determination for geographical origins of Korean Panax ginseng by UPLC-QTOF/MS coupled with OPLS-DA models. J Ginseng Res 37(3): 341-348 https://doi.org/10.5142/jgr.2013.37.341
  13. Ryu HW, Song HH, Kim KO, Park YJ, Kim DY, Kim JH, Oh SR (2016) Secondary metabolite profiling and modulation of antioxidants in wild and cultivated Euphorbia supine. Ind Crops Prod 89: 215-224 https://doi.org/10.1016/j.indcrop.2016.05.011
  14. Lee JH, Park MJ, Ryu HW, Yuk HJ, Choi SW, Lee KS, Kim SL, Seo WD (2016) Elucidation of phenolic antioxidants in barley seedlings (Hordeum vulgare L.) by UPLC-PDA-ESI/MS and screening for their contents at different harvest times. J Funct Foods 26: 667-680 https://doi.org/10.1016/j.jff.2016.08.034
  15. Maciejewska U, Bogatek R (2002) Glucose catabolism in leaves of coldtreated winter rape plants. J Plant Physiol 159(4): 397-402 https://doi.org/10.1078/0176-1617-00636
  16. Schulz E, Tohge T, Zuther E, Fernie AR, Hincha DK (2016) Flavonoids are determinants of freezing tolerance and cold acclimation in Arabidopsis thaliana. Scientific Reports 6: 34027 https://doi.org/10.1038/srep34027
  17. Barbehenn RV, Constabel CP (2011) Tannins in plant-herbivore interactions. Phytochem 72(13): 1551-1565 https://doi.org/10.1016/j.phytochem.2011.01.040
  18. Khanbabaee K, van Ree T (2001) Tannins: classification and definition. Nat Prod Rep 18: 641-649 https://doi.org/10.1039/b101061l
  19. Scoparo CT, Souza LM, Dartora N, Sassaki GL, Gorin PA, Iacomini M (2012) Analysis of Camellia sinensis green and black teas via ultra high performance liquid chromatography assisted by liquid-liquid partition and two-dimensional liquid chromatography (size exclusion$\times$reversed phase). J Chromatogr A 1222: 29-37 https://doi.org/10.1016/j.chroma.2011.11.038
  20. Gouveia SC, Castilho PC (2013) Artemisia annua L.: Essential oil and acetone extract composition and antioxidant capacity. Ind Crops Prod 45: 170-181 https://doi.org/10.1016/j.indcrop.2012.12.022
  21. Amorim MR, Rinaldo D, Amaral FP, Vilegas W, Magentad MAG, Vieira GM, Santos LD (2014) HPLC-DAD based method for the quantification of flavonoids in the hydroethanolic extract of Tonina fluviatilis Aubl. (Eriocaulaceae) and their radical scavenging activity. Quim Nova 37(7): 1122-1127
  22. Mammela P (2001) Phenolics in selected european hardwood species by liquid chromatography-electrospray ionisation mass spectrometry. Analyst 126: 1535-1538 https://doi.org/10.1039/b104584a
  23. Sanz M, Simon BF, Cadahi E, Esteruelas E, Munoz AM, Teresa Hernandez T, Estrella I, Pinto E (2012) LC-DAD/ESI-MS/MS study of phenolic compounds in ash (Fraxinus excelsior L. and F. americana L.) heartwood. Effect of toasting intensity at cooperage. J Mass Spectrom 47: 905-918 https://doi.org/10.1002/jms.3040
  24. Jianpeng DOU, Zhiqiang LIU, Shuying LIU (2006) Structure identification of a prenylflavonol glycoside from Epimedium koreanum by electrospray ionization tandem mass spectrometry. Anal Sci 22: 449-452 https://doi.org/10.2116/analsci.22.449
  25. Meng Xue M, Hang Shi H, Jiao Zhang J, Qing-Quan Liu QQ, Jun Guan J, Zhang JY, Qun Ma Q (2016) Stability and degradation of caffeoylquinic acids under different storage conditions studied by highperformance liquid chromatography with photo diode array detection and high-performance liquid chromatography with electrospray ionization collision-induced dissociation tandem mass spectrometry. Molecules 21: 948 https://doi.org/10.3390/molecules21070948
  26. Zeng WZ, Quesheng, Zhang QY, Liang H (2014) Two new oplopane sesquiterpenes from Artemisia gmelinii Web. ex Stechm. Chin Chem Lett 25: 1153-1156 https://doi.org/10.1016/j.cclet.2014.05.040
  27. Hvattum E, Ekeberg D (2003) Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. J Mass Spectrom 38: 43-49 https://doi.org/10.1002/jms.398

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