DOI QR코드

DOI QR Code

Isolation and Identification of Two Flavonoids from Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) Fruit Peel

추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 2종의 Flavonoids의 단리·동정

  • Lee, Sang Won (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lee, Yu Geon (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Cho, Jeong-Yong (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Kim, Young Chool (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lee, Sang-Hyun (Asian Pear Research Institute, Chonnam National University) ;
  • Kim, Wol-Soo (Asian Pear Research Institute, Chonnam National University) ;
  • Moon, Jae-Hak (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University)
  • 이상원 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이유건 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 조정용 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 김영출 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이상현 (전남대학교 동양배연구소) ;
  • 김월수 (전남대학교 동양배연구소) ;
  • 문제학 (전남대학교 식품공학과 및 기능성식품연구센터)
  • Received : 2014.12.19
  • Accepted : 2015.01.20
  • Published : 2015.04.30

Abstract

The methanol extract of Asian pear (Pyrus pyrifolia N. cv. Chuhwangbae) fruit peel was purified using solvent fractionation, Sephadex LH-20 column chromatography, and octadecylsilane high performance liquid chromatography. Based on the electrospray ionization mass spectrometry and nuclear magnetic resonance data, the two isolated compounds were identified as quercetin 3-O-${\beta}$-D-glucopyranoside (1) and 3,5,6,7,8,3',4'-heptahydroxyflavan [(-)-dulcisflavan, 2]. Compounds 1 and 2 were isolated and identified for the first time from Asian pears and pears, respectively.

본 연구에서는 국산배의 기능학적 우수성 증명을 위해 국산배로부터 생리활성 화합물을 밝히고자 하였다. 이에 배 과피 MeOH 추출물을 용매분획하여 얻은 EtOAc-산성획분을 대상으로 Sephadex LH-20 column chromatography와 ODS-HPLC를 이용하여 순차적으로 정제를 행하여 2종의 화합물을 단리하였다. 단리된 화합물 1과 2는 MS 및 NMR 분석을 통하여 각각 quercetin 3-O-${\beta}$-Dglucopyranoside(화합물 1)와 3,5,6,7,8,3',4'-heptahydroxyflavan [(-)-dulcisflavan, 화합물 2)]으로 동정되었다. 단리된 화합물 1은 동양배로부터, 그리고 화합물 2는 배로부터 처음 동정된 화합물이다. 본 연구결과가 국산배의 기능학적 우수성 증명을 위한 기초자료로 활용되길 기대한다.

Keywords

References

  1. Iwashina T. The structure and distribution of the flavonoids in plants. J. Plant Res. 113: 287-299 (2000) https://doi.org/10.1007/PL00013940
  2. Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry 55: 481-504 (2000) https://doi.org/10.1016/S0031-9422(00)00235-1
  3. Mattila P, Hellstrom J. Phenolic acids in potatoes, vegetables, and some of their products. J. Food Compos. Anal. 20: 152-160 (2007) https://doi.org/10.1016/j.jfca.2006.05.007
  4. Crozier A, Lean MEJ, McDonald MS, Black C. Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce and celery. J. Agr. Food Chem. 45: 590-595 (1997) https://doi.org/10.1021/jf960339y
  5. Kubola J, Siriamornpun S, Meeso N. Phytochemicals, vitamin C and sugar content of Thai wild fruits. Food Chem. 126: 972-981 (2011) https://doi.org/10.1016/j.foodchem.2010.11.104
  6. Martin A, Prior R, Shukitt-Hale B, Cao G, Joseph JA. Effect of fruits, vegetables, or vitamin E-rich diet on vitamins E and C distribution in peripheral and brain tissues: implications for brain function. J. Gerontol. A-Biol. 55: B144-B151 (2000) https://doi.org/10.1093/gerona/55.3.B144
  7. Kamada C, da Silva EL, Ohnishi-Kameyama M, Moon JH, Terao J. Attenuation of lipid peroxidation and hyperlipidemia by quercetin glucoside in the aorta of high cholesterol-fed rabbit. Free Radical Res. 39: 185-194 (2005) https://doi.org/10.1080/10715760400019638
  8. Wang X, Zhao X, Gu L, Lv C, He B, Liu Z, Hou P, Bi K, Chen X. Simultaneous determination of five free and total flavonoids in rat plasma by ultra HPLC-MS/MS and its application to a comparative pharmacokinetic study in normal and hyperlipidemic rats. J. Chromatogr. B 953-954: 1-10 (2014) https://doi.org/10.1016/j.jchromb.2014.01.042
  9. Yokozawa T, Kim HY, Cho EJ, Choi JS, Chung HY. Antioxidant effects of isorhamnetin 3,7-di-O-${\beta}$-D-glucopyranoside isolated from mustard leaf (Brassica juncea) in rats with streptozotocininduced diabetes. J. Agr. Food Chem. 50: 5490-5495 (2002) https://doi.org/10.1021/jf0202133
  10. Siriwardhana N, Kalupahana NS, Cekanova M, LeMieux M, Greer B, Moustaid-Moussa N. Modulation of adipose tissue inflammation by bioactive food compounds. J. Nutr. Biochem. 24: 613-623 (2013) https://doi.org/10.1016/j.jnutbio.2012.12.013
  11. Lu Y, Foo LY. Constitution of some chemical components of apple seed. Food Chem. 61: 29-33 (1998) https://doi.org/10.1016/S0308-8146(97)00123-4
  12. Pacifico S, D'brosca B, Scognamiglio M, Gallicchio M, Potenza N, Piccolella S, Russo A, Monaco P, Fiorentino A. Metabolic profiling of strawberry grape (Vitis $\times$ labruscana cv. 'sabella' components by nuclear magnetic resonance (NMR) and evaluation of their antioxidant and antiproliferative properties. J. Agr. Food Chem. 59: 7679-7687 (2011) https://doi.org/10.1021/jf200926t
  13. Bocco A, Cuvelier ME, Richard H, Berset C. Antioxidant activity and phenolic composition of citrus peel and seed extracts. J. Agr. Food Chem. 46: 2123-2129 (1998) https://doi.org/10.1021/jf9709562
  14. Choi HJ, Park JH, Han HS, Son JH, Son GM, Bae JH, Choi C. Effect of polyphenol compound from Korean pear (Pyrus pyrifolia Nakai) on lipid metabolism. J. Korean Soc. Food Sci. Nutr. 33: 299-304 (2004) https://doi.org/10.3746/jkfn.2004.33.2.299
  15. Cui T, Nakamura K, Ma L, Li JZ, Kayahara H. Analyses of arbutin and chlorogenic acid, the major phenolic constituents in Oriental pear. J. Agr. Food Chem. 53: 3882-3887 (2005) https://doi.org/10.1021/jf047878k
  16. Lin LZ, Harnly JM. Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.). J. Agr. Food Chem. 56: 9094-9101 (2008) https://doi.org/10.1021/jf8013487
  17. Amiot MJ, Tacchini M, Aubert SY, Oleszek W. Influence of cultivar, maturity stage, and storage conditions on phenolic composition and enzymic browning of pear fruits. J. Agr. Food Chem. 43: 1132-1137 (1995) https://doi.org/10.1021/jf00053a004
  18. Oleszek W, Amiot MJ, Aubert SY. Identification of some phenolics in pear fruit. J. Agr. Food Chem. 42: 1261-1265 (1994) https://doi.org/10.1021/jf00042a002
  19. Lee KH, Cho JY, Lee HJ, Ma YK, Kwon J, Park SH, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Hydroxycinnamoylmalic acids and their methyl esters from pear (Pyrus pyrifolia Nakai) fruit peel. J. Agr. Food Chem. 59: 10124-10128 (2011) https://doi.org/10.1021/jf2022868
  20. Lee KH, Cho JY, Lee HJ, Park KY, Ma YK, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Isolation and identification of phenolic compounds from an asian pear (Pyrus pyrifolia Nakai) fruit peel. Food Sci. Biotechnol. 20: 1539-1545 (2011) https://doi.org/10.1007/s10068-011-0213-4
  21. Lee YG, Cho JY, Kim CM, Lee SH, Kim WS, Jeon TI, Park KH, Moon JH. Coumaroyl quinic acid derivatives and flavonoids from immature pear (Pyrus pyrifolia Nakai) fruit. Food Sci. Biotechnol. 22: 803-810 (2013) https://doi.org/10.1007/s10068-013-0148-z
  22. Cho JY, Kim CM, Lee HJ, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma. J. Agr. Food Chem. 61: 4563-4569 (2013) https://doi.org/10.1021/jf400524b
  23. Cho JY, Lee YG, Lee SH, Kim WS, Park KH, Moon JH. An ether and three ester derivatives of phenylpropanoid from pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit and their radicalscavenging activity. Food Sci. Biotechnol. 23: 253-259 (2014) https://doi.org/10.1007/s10068-014-0035-2
  24. Lee YG, Cho JY, Lee HJ, Lee YH, Lee SH, Han TH, Kim WS, Park KH, Moon JH. Isolation and identification of a sterol and three glucosides from the peel of pear (Pyrus pyrifolia Nakai cv. Chuhwangbae). Korean J. Food Sci. Technol. 45: 557-564 (2013) https://doi.org/10.9721/KJFST.2013.45.5.557
  25. Lee YG, Cho JY, Kim CM, Jeong HY, Lee DI, Kim SR, Lee SH, Kim WS, Park KH, Moon JH. Isolation and identification of 3 low-molecular compounds from pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit peel. Korean J. Food Sci. Technol. 45: 174-179 (2013) https://doi.org/10.9721/KJFST.2013.45.2.174
  26. Huang LJ, Gao WY, Li X, Zhao WS, Huang LQ, Liu CX. Evaluation of the in vivo anti-inflammatory effects of extracts from Pyrus bretschneideri Rehd. J. Agr. Food Chem. 58: 8983-8987 (2010) https://doi.org/10.1021/jf101390q
  27. Li X, Zhang J, Gao W, Wang H. Study on chemical composition, anti-inflammatory and anti-microbial activities of extracts from Chinese pear fruit (Pyrus bretschneideri Rehd.). Food Chem. Toxicol. 50: 3673-3679 (2012) https://doi.org/10.1016/j.fct.2012.07.019
  28. Li X, Wang T, Zhou B, Gao W, Cao J, Huang L. Chemical composition and antioxidant and anti-inflammatory potential of peels and flesh from 10 different pear varieties (Pyrus spp.). Food Chem. 152: 531-538 (2014) https://doi.org/10.1016/j.foodchem.2013.12.010
  29. Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Bioch. 58: 1780-1783 (1994) https://doi.org/10.1271/bbb.58.1780
  30. Kim JY, Cho JY, Ma YK, Park KY, Lee SH, Ham KS, Lee HJ, Park KH, Moon JH. Dicaffeoylquinic acid derivatives and flavonoid glucosides from glasswort (Salicornia herbacea L.) and their antioxidative activity. Food Chem. 125: 55-62 (2011) https://doi.org/10.1016/j.foodchem.2010.08.035
  31. Deachathai S, Mahabusarakam W, Phongpaichit S, Taylor WC. Phenolic compounds from the fruit of Garcinia dulcis. Phytochemistry 66: 2368-2375 (2005) https://doi.org/10.1016/j.phytochem.2005.06.025
  32. Miyake Y, Fukumoto S, Okada M, Sakaida K, Nakamura Y, Osawa T. Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. J. Agr. Food Chem. 53: 22-27 (2005) https://doi.org/10.1021/jf048743h
  33. Glasser G, Graefe EU, Struck F, Veit M, Gebhardt R. Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine 9: 33-40 (2002) https://doi.org/10.1078/0944-7113-00080
  34. Vallejo F, Tomas-Barberan FA, Ferreres F. Characterisation of flavonols in broccoli (Brassica oleracea L. var. italica) by liquid chromatography-UV diode-array detection-electrospray ionisation mass spectrometry. J. Chromatogr. A 1054: 181-193 (2004) https://doi.org/10.1016/j.chroma.2004.05.045
  35. Miura S, Watanabe J, Sano M, Tomita T, Osawa T, Hara Y, Tomita I. Effects of various natural antioxidants on the Cu2+-mediated oxidative modification of low-density lipoprotein. Biol. Pharm. Bull. 18: 1-4 (1995) https://doi.org/10.1248/bpb.18.1
  36. Yamamoto N, Moon JH, Tsushida T, Nagao A, Terao J. 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 (1999) https://doi.org/10.1006/abbi.1999.1516
  37. Zheng SY, Li Y, Jiang D, Zhao J, Ge JF. Anticancer effect and apoptosis induction by quercetin in the human lung cancer cell line A-549. Mol. Med. Rep. 5: 822-826 (2012)
  38. Moon JH, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-${\beta}$-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radical Bio. Med. 30: 1274-1285 (2001) https://doi.org/10.1016/S0891-5849(01)00522-6
  39. Moon JH, Nakata R, Oshima S, Inakuma T, Terao J. Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women. Am. J. Physiol. 279: R461-R467 (2000)
  40. Yokoyama A, Sakakibara H, Crozier A, Kawai Y, Matsui A, Terao J, Kumazawa S, Shimoi K. Quercetin metabolites and protection against peroxynitrite-induced oxidative hepatic injury in rats. Free Radical Res. 43: 913-921 (2009) https://doi.org/10.1080/10715760903137010
  41. Tai BH, Trung TN, Nhiem NX, Ha DT, Men CV, Duong VB, Luong HV, Song SB, Bae K, Kim YH. A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels of Wisteria floribunda. J. Asian Nat. Prod. Res. 13: 1061-1068 (2011) https://doi.org/10.1080/10286020.2011.603306