Horticulture, Environment, and Biotechnology : HEB

  • 제59권6호
  • /
  • Pages.909-917
  • /
  • 2018
  • /
  • 2211-3452(pISSN)
  • /
  • 2211-3460(eISSN)
한국원예학회 (Korean Society of Horticultural Science)
권호 표지
DOI QR코드

DOI QR Code

Characterization of quercetin and its glycoside derivatives in Malus germplasm

  • Zhang, Lei (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • Xu, Qipeng (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • You, Yaohua (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • Chen, Weifeng (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • Xiao, Zhengcao (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • Li, Pengmin (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University) ;
  • Ma, Fengwang (State Key Laboratory of Crop Stress Biology for Arid Areas, College of Horticulture, Northwest A&F University)
  • 투고 : 2017.02.24
  • 심사 : 2018.06.01
  • 발행 : 2018.12.31
⟨ 이전 논문 다음 논문 ⟩

초록

Quercetin and its glycoside derivatives were identified and quantified using high-performance liquid chromatograph (HPLC) and liquid chromatograph/mass spectrometer/mass spectrometer (LC/MS/MS) in the leaves, flowers, and fruits of 22 Malus genotypes. In all genotypes, small amounts of quercetin aglycone were present, with water-soluble glycoside forms were the most abundant in different Malus plant tissues, including quercetin-3-galactoside, quercetin-3-rutinoside, quercetin-3-glucoside, quercetin-3-xyloside, quercetin-3-arabinoside, and quercetin-3-rhamnoside. Among these six quercetin glycosides, quercetin-3-galactoside was the common form in Malus plants, except in the leaves and flowers of M. ceracifolia and M. magdeburgensis, and in the fruits of M. micromalus 'Haihong Fruit', where there was a higher concentration of quercetin3-glucoside. Among the different tissues tested, leaves contained the highest concentration of quercetin and its glycosides, while fruits contained the lowest concentrations of these compounds. Among the genotypes we analyzed, no specific genotype consistently contained the highest concentration of quercetin and its glycoside derivatives. M. domestica 'Honeycrisp' had the highest total compound concentration (approximately $1600mg\;kg^{-1}$), whereas M. hupehensis contained the lowest in its fruits. In contrast, the concentration of total quercetin and its glycosides was more than $5000mg\;kg^{-1}$ in the leaves of eight genotypes and greater than $2500mg\;kg^{-1}$ in the flowers of seven species. In general, the concentration of quercetin and its glycoside derivatives depended on the species and tissue type. These results may provide useful information for the evaluation and selection of edible Malus fruits and the materials for quercetin glycoside extraction.

키워드

과제정보

연구 과제 주관 기관 : National Nature Science Foundation of China

참고문헌

  1. Aherne SA, O'Brien NM (2002) Dietary flavonols: chemistry, food content, and metabolism. Nutrition 18:75-81 https://doi.org/10.1016/S0899-9007(01)00695-5
  2. Aron PM, Kennedy JA (2008) Flavan-3-ols: nature, occurrence and biological activity. Mol Nutr Food Res 52:79-104 https://doi.org/10.1002/mnfr.200700137
  3. Ban Y, Kondo S, Ubi BE, Honda C, Bessho H, Moriguchi T (2009) UDP-sugar biosynthetic pathway: contribution to cyaniding 3-galactoside biosynthesis in apple skin. Planta 230:871-881 https://doi.org/10.1007/s00425-009-0993-4
  4. Bi X, Zhang J, Chen C, Zhang D, Li P, Ma F (2014) Anthocyanin contributes more to hydrogen peroxide scavenging than other phenolics in apple peel. Food Chem 152:205-209 https://doi.org/10.1016/j.foodchem.2013.11.088
  5. Bouktaib M, Atmani A, Rolando C (2002) Regio-and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-Dglucuronide. Tetrahedron Lett 43:6263-6266 https://doi.org/10.1016/S0040-4039(02)01264-9
  6. Chen C, Zhang D, Wang Y, Li P, Ma F (2012) Effects of fruit bagging on the contents of phenolic compounds in the peel and flesh of 'Golden Delicious', 'Red Delicious', and 'Royal Gala' apples. Sci Hortic 142:68-73 https://doi.org/10.1016/j.scienta.2012.05.001
  7. Chen C, Li H, Zhang D, Li P, Ma F (2013) The role of anthocyanin in photoprotection and its relationship with the xanthophyll cycle and the antioxidant system in apple peel depends on the light conditions. Physiol Plant 149:354-366
  8. Chinnici F, Bendini A, Gaiani A, Riponi C (2004) Radical scavenging activities of peels and pulps from cv. golden delicious apples as related to their phenolic composition. J Agric Food Chem 52:4684-4689 https://doi.org/10.1021/jf049770a
  9. D'Andrea G (2015) Quercetin: a flavonol with multifaceted therapeutic applications? Fitoter 106:256-271 https://doi.org/10.1016/j.fitote.2015.09.018
  10. Gachon CMM, Langlois-Meurinne M, Saindrenan P (2005) Plant secondary metabolism glycosyltransferases: the emerging functional analysis. Trends Plant Sci 10:542-549 https://doi.org/10.1016/j.tplants.2005.09.007
  11. Heim KE, Tagliaferro AR, Bobilya DJ (2002) Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 13:572-584 https://doi.org/10.1016/S0955-2863(02)00208-5
  12. Hertog MGL, Hollman PCH, Kahn MB (1992) Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 40:2379-2383 https://doi.org/10.1021/jf00024a011
  13. Holderbaum DF, Kon T, Guerra MP (2014) Dynamics of total phenolic content in different apple tissues and genotypes: impacts and relevance for breeding programs. Sci Hortic 168:58-63 https://doi.org/10.1016/j.scienta.2014.01.020
  14. Hollman PCH, de Vries JHM, van Leeuwen SD, Mengelers MJB, Katan MB (1995) Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am J Clin Nutr 62:l276-l282
  15. Jang HL, Yoon KY (2012) Cultivar differences in phenolic contents/biological activities of color-fleshed potatoes and their relationships. Hort. Environ. Biotechnol. 53:175-181 https://doi.org/10.1007/s13580-012-0048-9
  16. Jiang N, Chung SO, Lee J, Ryu D, Lim YP, Park S, Lee C, Song J, Kim K, Park JT, An G (2013) Increase of phenolic compounds in new Chinese cabbage cultivar with red phenotype. Hortic Environ Biotechnol 54:82-88 https://doi.org/10.1007/s13580-013-0136-5
  17. Ju H, Chen SC, Wu K, Kuo H, Hseu Y, Ching H, Wu C (2012) Antioxidant phenolic profile from ethyl acetate fraction of Fructus Ligustri Lucidi with protection against hydrogen peroxide-induced oxidative damage in SH-SY5Y cells. Food Chem Toxicol 50:492-502 https://doi.org/10.1016/j.fct.2011.11.036
  18. Kawabata K, Mukaib R, Ishisakac A (2015) Quercetin and related polyphenols: new insights and implications for their bioactivity and bioavailability. Food Funct 6:1399-1417 https://doi.org/10.1039/C4FO01178C
  19. Khanizadeh S, Tsao R, Rekika D, Yang R, DeEll J (2007) Phenolic composition and antioxidant activity of selected apple genotypes. J Food Agric Environ 5:61-66
  20. Knekt P, Kumpulainen J, Jarvinen R, Rissanen H, Heliovaara M, Reunanen A, Hakulinen T, Aromaa A (2002) Flavonoid intake and risk of chronic diseases. Am J Clin Nutr 76:560-568 https://doi.org/10.1093/ajcn/76.3.560
  21. Koes R, Verweij W, Quattrocchio F (2005) Flavonoids: a colorful model for the regulation and evolution of biochemical pathways. Trends Plant Sci 10:1360-1385
  22. Lee J, Mitchell AE (2012) Pharmacokinetics of quercetin absorption from apples and onions in healthy humans. J Agric Food Chem 60:3874-3881 https://doi.org/10.1021/jf3001857
  23. Li P, Ma F, Cheng L (2013) Primary and secondary metabolism in the sun-exposed peel and the shaded peel of apple fruit. Physiol Plant 148:9-24 https://doi.org/10.1111/j.1399-3054.2012.01692.x
  24. Mattila PH, Hellstrom J, Karhu S, Pihlava JM, Veteläinen M (2016) High variability in flavonoid contents and composition between different North-European currant (Ribes spp.) varieties. Food Chem 204:14-20 https://doi.org/10.1016/j.foodchem.2016.02.056
  25. Montefiori M, Espley RV, Stevenson D, Cooney J, Datson PM, Saiz A, Atkinson RG, Hellens RP, Allan AC (2011) Identification and characterisation of F3GT1 and F3GGT1, two glycosyltransferases responsible for anthocyanin biosynthesis in red-fleshed kiwifruit (Actinidia chinensis ). Plant J 65:106-118 https://doi.org/10.1111/j.1365-313X.2010.04409.x
  26. Parr AJ, Bolwell GP (2000) Phenols in the plant and in man. The potential for possible nutritional enhancement of the diet by modifying the phenols content or profile. J Sci Food Agric 80:985-1012 https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<985::AID-JSFA572>3.0.CO;2-7
  27. Ravichandran R, Rajendran M, Devapiriam D (2014) Antioxidant study of quercetin and their metal complex and determination of stability constant by spectrophotometry method. Food Chem 146:472-478 https://doi.org/10.1016/j.foodchem.2013.09.080
  28. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Bio Med 20:933-956 https://doi.org/10.1016/0891-5849(95)02227-9
  29. Rice-Evans CA, Miller NJ, Paganga G (1997) Antioxidant properties of phenolic compounds. Trends Plant Sci 2:152-159 https://doi.org/10.1016/S1360-1385(97)01018-2
  30. Slimestad R, Fossen T, Vagen IM (2007) Onions: a Source of Unique Dietary Flavonoids. J Agric Food Chem 55:10067-10080 https://doi.org/10.1021/jf0712503
  31. Stanger MC, Steffens CA, Soethe C, Moreira MA, do Amarante CVT (2017) Phenolic content and antioxidant activity during the development of 'Brookfield' and 'Mishima' apples. J Agric Food Chem 65:3453-3459 https://doi.org/10.1021/acs.jafc.6b04695
  32. Stockley C, Teissedre PL, Boban M, Lorenzod CD, Restanid P (2012) Bioavailability of wine-derived phenolic compounds in humans: a review. Food Funct 3:995-1007 https://doi.org/10.1039/c2fo10208k
  33. Sun S, Xin L, Gao H, Wang J, Li P (2014) Response of phenolic compounds in 'Golden Delicious' and 'RedDelicious' apples peel to fruit bagging and subsequent sunlightre-exposure. Sci Hortic 168:161-167 https://doi.org/10.1016/j.scienta.2014.01.031
  34. Treutter D (2001) Biosynthesis of phenolic compounds and its regulation in apple. Plant Growth Regul 34:71-89 https://doi.org/10.1023/A:1013378702940
  35. Trost K, Golc-Wondra A, Prosek M, Milivojevic L (2008) Anthocyanin degradation of blueberry-aronia nectar in glass compared with carton during storage. J Food Sci 73:405-411
  36. Winardiantika V, Lee YH, Park NI, Yeoung YR (2016) Effects of cultivar and harvest time on the contents of antioxidant phytochemicals in strawberry fruits. Hortic Environ Biotechnol 56:732-739
  37. Yamamoto N, Moon JH, Tsushida T, Nagao A, Terao J (1999) Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid peroxidation in human low-density lipoprotein. Arch Biochem Biophys 372:347-354 https://doi.org/10.1006/abbi.1999.1516
  38. Yoo KS, Lee EJ, Patil BS (2010) Quantification of quercetin glycosides in 6 onion cultivars and comparisons of hydrolysis-HPLC and spectrophotometric methods in measuring total quercetin concentrations. J Food Sci 75:160-165 https://doi.org/10.1111/j.1750-3841.2009.01469.x
  39. Yoon J, Kim B, Lee WJ, Lim Y, Chong Y, Ahn J (2012) Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli. Appl Environ Microb 78:4256-4262 https://doi.org/10.1128/AEM.00275-12
  40. Zhang M, Zhang G, You Y, Yang C, Li P, Ma F (2016) Effects of relative air humidity on the phenolic compounds contents and coloration in the 'Fuji' apple (Malus domestica Borkh.) peel. Sci Hortic 201:18-23 https://doi.org/10.1016/j.scienta.2016.01.017
  41. Zhao J (2015) Flavonoid transport mechanisms: how to go, and with whom. Trends Plant Sci 20:1-10 https://doi.org/10.1016/j.tplants.2014.10.009
  42. Zhao J, Liu G, Chang R, Cao K, Shen F, Wu T, Wang Y, Han Z, Zhang X (2015) Diversity of flesh polyphenols and their progressive dilution during fruit expansion in Malus germplasm. Sci Hortic 197:461-469 https://doi.org/10.1016/j.scienta.2015.10.003

피인용 문헌

  1. Analytical Methods for Extraction and Identification of Primary and Secondary Metabolites of Apple (Malus domestica) Fruits: A Review vol.8, pp.7, 2018, https://doi.org/10.3390/separations8070091