Korean Journal of Food Science and Technology (한국식품과학회지)

Korean Society of Food Science and Technology (한국식품과학회)
권호 표지
DOI QR코드

DOI QR Code

Isolation and Identification of a Sterol and Three Glucosides from the Peel of Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae)

추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 1종의 Sterol과 3종의 배당체 화합물의 단리 · 동정

  • 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) ;
  • Lee, Hyun Joo (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lee, Yong Hyun (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lee, Sang-Hyun (Korea Pear Research Organization Chonnam National University) ;
  • Han, Tae-Ho (Department of Horiticulture, Chonnam National University) ;
  • Kim, Wol-Soo (Korea Pear Research Organization Chonnam National University) ;
  • Park, Keun-Hyung (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Moon, Jae-Hak (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University)
  • 이유건 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 조정용 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이현주 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이용현 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이상현 (전남대학교 배수출연구사업단) ;
  • 한태호 (전남대학교 원예학과) ;
  • 김월수 (전남대학교 배수출연구사업단) ;
  • 박근형 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 문제학 (전남대학교 식품공학과 및 기능성식품연구센터)
  • Received : 2013.05.01
  • Accepted : 2013.08.13
  • Published : 2013.10.31
Download PDF
⟨ Previous Next ⟩

Abstract

We isolated and identified antioxidants from acidic and neutral ethyl acetate fractions of the peel of pear (Pyrus pyrifolia N. cv. Chuhwangbae). We isolated 4 compounds from the methanol extract, by using 3 different types of column chromatography (Sephadex LH-20, silica gel, and octadecylsilane) and preparative HPLC. We identified the isolated compounds as (S)-(+)-2-cis-abscisic acid O-${\beta}$-D-glucopyranosyl ester (compound 1), 1-[4-O-${\beta}$-D-glucopyranosyl]phenyl ethanone (picroside, compound 2), ${\beta}$-sitosterol (compound 3), and ${\beta}$-sitosteryl 3-O-${\beta}$-D-glucopyranoside (compound 4) by nuclear magnetic resonance analysis. We are the first to report the identification of compounds 1, 2, and 4 from pear.

본 연구에서는 배의 유용성 증명을 위한 일환으로 배의 화학성분을 분자수준에서 밝히고자 하였다. 이에 배 과피 MeOH 추출물을 용매분획하여 얻은 EtOAc-산성 분획과 EtOAc-중성분획을 대상으로 Sephadex LH-20, silica gel, 그리고 ODS colmn chromatography와 HPLC를 이용하여 정제 및 단리하였다. 그 결과, EtOAc-산성 분획과 EtOAc-중성 분획으로부터 각각 2종씩의 화합물을 단리하였다. 단리된 화합물 1-4는 $^1H$- 및 $^{13}C$-NMR 분석을 통하여 각각 (S)-(+)-2-cis-abscisic acid O-${\beta}$-D-glucopyranosyl ester (화합물 1), 1-[4-O-${\beta}$-D-glucopyranosyl]phenyl ethanone (piceoside, 화합물 2), ${\beta}$-sitosterol (화합물 3), 그리고 ${\beta}$-sitosteryl 3-O-${\beta}$-D-glucopyranoside (화합물 4)로 동정되었다. 단리된 3종의 배당체 화합물(화합물 1, 2, 4)들은 본 연구에 의해 배로부터 처음 동정되었으며, 화합물 3은 추황배로부터 처음 동정되었다. 본 연구결과가 배 함유 성분연구는 물론 배의 기능성 해명 연구에도 추후 중요한 기초자료로 활용되길 기대한다.

Keywords

References

  1. Saruwatari A, Okamura S, Nakajima Y, Narukawa Y, Takeda T, Tamura H. Pomegranate juice inhibits sulfoconjugation in Caco-2 human colon carcinoma cells. J. Med. Food 11: 623-628 (2008) https://doi.org/10.1089/jmf.2007.0050
  2. Bonarska-Kujawa D, Sarapuk J, Bielecki K, Oszmianski J, Kleszczynska H. Antioxidant activity of extracts from apple, chokeberry and strawberry. Pol. J. Food Nutr. Sci. 62: 229-234 (2012)
  3. Bagchi D, Bagch M, Stohs SJ, Das DK, Ray SD, Kuszynski CA, Joshi SS, Pruess HG. Free radical and grape seed proanthocyanidin extract: importance in human health and disease prevention. Toxicol. 143: 187-197 (2000)
  4. Giugliano D. Dietary antioxidants for cardiovascular prevention. Nutr. Metab. Cardiovas. 10: 38-44 (2000)
  5. Amiot M, Tacchini M, Aubert S, Nicolas J. Phenolic composition and browning susceptibility of various apple cultivars at maturity. J. Food Sci. 57: 958-962 (1992) https://doi.org/10.1111/j.1365-2621.1992.tb14333.x
  6. Ham AJ, Liebler DC. Antioxidant reactions of vitamin E in the perfused rat liver: product distribution and effect of dietary vitamin E supplementation. Arch. Biochem. Biophys. 339: 157-164 (1997) https://doi.org/10.1006/abbi.1996.9856
  7. Martin A, Frei B. Both intracellular and extracellular vitamin C inhibit atherogenic modification of LDL by human vascular endothelial cells. Arterioscl. Throm. Vas. 17: 1583-1590 (1997) https://doi.org/10.1161/01.ATV.17.8.1583
  8. Shiba Y, Kinoshita T, Chuman H, Taketani Y, Takeda E, Kato Y, Naito M, Kawabata K, Ishisaka A, Terao J, Kawai Y. Flavonoids as substrates and inhibitors of myeloperoxidase: molecular actions of aglycone and metabolites. Chem. Res. Toxicol. 21: 1600-1609 (2008) https://doi.org/10.1021/tx8000835
  9. Iacopini P, Baldi M, Storchi P, Sebastiani L. Catechin, epicatechin, quercetin, rutin and resveratrol in red grape: Content, in vitro antioxidant activity and interactions. J. Food Comp. Anal. 21: 589-598 (2008) https://doi.org/10.1016/j.jfca.2008.03.011
  10. Karaman S, Tutem E, Baskan KS, Apak R. Comparison of total antioxidant capacity and phenolic composition of some apple juices with combined HPLC-CUPRAC assay. Food Chem. 120: 1201-1209 (2010) https://doi.org/10.1016/j.foodchem.2009.11.065
  11. Mulvihill EE, Huff MW. Citrus flavonoids and the prevention of atherosclerosis. Cardiovasc. Hematol. Disord. Drug Targets 12: 84-91 (2012) https://doi.org/10.2174/1871529X11202020084
  12. 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
  13. Huang LJ, Gao WY, Li X, Zhao WS. 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
  14. 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
  15. 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
  16. 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
  17. 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. 15: 4563-4569 (2013)
  18. 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
  19. 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
  20. Kato-Noguchi H, Tanaka Y, Murakami T, Yamamura S, Fujihara S. Isolation and identification of an allelopathic substance from peel of Citrus junos. Phytochem. 61: 849-853 (2002) https://doi.org/10.1016/S0031-9422(02)00382-5
  21. Kobayashi Y, Nabeta K, Matsuura H. Chemical inhibitors of viviparous germination in the fruit of watermelon. Plant Cell Physiol. 51: 1594-1598 (2010) https://doi.org/10.1093/pcp/pcq103
  22. Wang, M, Kikuzaki H, Lin CC, Kahyaoglu A, Huang MT, Nakatani N, Ho CT. Acetophenone glycosides form Thyme (Thymus vulgaris L.) J. Agr. Food Chem. 47: 1911-1914 (1999) https://doi.org/10.1021/jf981282d
  23. Lee SH, Kim KS, Shim SH, Park YM, Kim BK. Constituents from the non-polar fraction of Artemisia apiacea. Arch. Pharm. Res. 26: 902-905 (2003) https://doi.org/10.1007/BF02980197
  24. Wang Y, Lai D, Zhang Y, Kang A, Cao Y, Sun W. Study of steroidal saponins in Dioscorea zingiberensis C.H. Wright. J. Nat. Prod. 2: 123-132 (2009)
  25. Saito S, Hirai N, Matsumoto C, Ohigashi H, Ohta D, Sakata K, Mizutani M. Arabidopsis CYP707As encode (+)-abscisic acid 8-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid. Plant Physiol. 134: 1439-1449 (2004) https://doi.org/10.1104/pp.103.037614
  26. Tanabe K, Tani H, Nakajima H, Mori M, Sakuno E. Biologically active gibberellins and abscisic acid in fruit of two late-maturing Japanese pear cultivars with contrasting fruit size. J. Am. Soc. Hort. Sci. 132: 452-458 (2007)
  27. Silva TMS, Santos FPS, Evangelista-Todrigues A, Silva EMS, Silva GS, Novais JS, Santos FAR, Camara CA. Phenolic compounds, melissopalynological, physicochemical analysis and antioxidant activity of jandaira (Melipona subnitida) honey. J. Food Comp. Anal. 29: 10-18 (2013) https://doi.org/10.1016/j.jfca.2012.08.010
  28. Wang H, Sun Y, Ye WC, Xiong F, Wu JJ, Yang CH, Zhao SX. Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora. Chem. Pharm. Bull. 52: 615-617 (2004) https://doi.org/10.1248/cpb.52.615
  29. Li X, Liu Z, Zhang XF, Wang LJ, Zheng YN, Yuan CC, Sun GZ. Isolation and characterization of phenolic compounds from the leaves of Salix matsudana. Molecules 13: 1530-1537 (2008) https://doi.org/10.3390/molecules13081530
  30. Hashem FA, Saleh MM. Antimicrobial components of some cruciferae plants (Diplotaxis harra Forsk. and Erucaria microcarpa Boiss.). Phytother. Res. 13: 329-332 (1999) https://doi.org/10.1002/(SICI)1099-1573(199906)13:4<329::AID-PTR458>3.0.CO;2-U
  31. Mo J, Wu B. A phytochemical and chemotaxomic study on Viburnum lancifolium. Biochem. Syst. Ecol. 39: 857-860 (2011) https://doi.org/10.1016/j.bse.2011.04.007
  32. Tamokou JDD, Kuiate JR, Tene M, Kenla Nwemeguela TJ, Tane P. The antimicrobial activities of extract and compounds isolated from Brillantaisia lamium. Iran. J. Med. Sci. 36: 24-31 (2011)
  33. Yang ZG, Matsuzaki K, Takamatsu S, Kitanaka S. Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells. Molecules 16: 6010-6022 (2011) https://doi.org/10.3390/molecules16076010
  34. Park MH, Chung IM, Ahmad A, Kim BH, Hwang SJ. Growth inhibition of unicellular and colonial Microsistis strains (Cyanophyceae) by compounds isolated from rice (Oryza sativa) hulls. Aqua. Bot. 90: 309-314 (2009) https://doi.org/10.1016/j.aquabot.2008.11.007
  35. Chung IM, Hahn SJ, Ahmad A. Confirmation of potential herbicidal agents in hulls of rice, Oryza sativa. J. Chem. Ecol. 31: 1339-1352 (2005) https://doi.org/10.1007/s10886-005-5290-5
  36. Zubair M, Anwar F, Ashraf M, Uddin MK. Characterization of high-value bioactives in some selected varieties of Pakistani rice (Oryza sativa L.). Int. J. Mol. Sci. 13: 4608-4622 (2012) https://doi.org/10.3390/ijms13044608
  37. Arisawa M, Hatashita T, Numata Y, Tanaka M, Sasaki T. Cytotoxic principles from Chrysosplenium flagelliferum. Int. J. Pharm. 35: 141-143 (1997) https://doi.org/10.1076/phbi.35.2.141.13285
  38. Chidrawar VR, Patel KN, Bothra SB, Shiromwar SS, Koli AR, Kalyankar GG. Anti-obesity effect of Stellaria media methanolic extract in the murine model of cafeteria diet induced obesity. Int. J. Nutr. Pharm. Neur. Dis. 2: 121-131 (2013)

Cited by

  1. Effect of Extraction Solvent on the Physiological Properties of Korean Pear Peel (Pyrus pyrifolia cv. Niitaka) vol.47, pp.2, 2015, https://doi.org/10.9721/KJFST.2015.47.2.254
  2. Isolation and Identification of Two Flavonoids from Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) Fruit Peel vol.47, pp.2, 2015, https://doi.org/10.9721/KJFST.2015.47.2.170
  3. Isolation of five proanthocyanidins from pear (Pyrus pyrifolia Nakai) fruit peels 2017, https://doi.org/10.1007/s10068-017-0157-4