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http://dx.doi.org/10.9721/KJFST.2013.45.5.557

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

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)
Publication Information
Korean Journal of Food Science and Technology / v.45, no.5, 2013 , pp. 557-564 More about this Journal
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.
Keywords
abscisic acid glucoside; antioxidant; ${\beta}$-sitosterol; ${\beta}$-sitosteryl glucoside; picroside;
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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)   DOI   ScienceOn
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)   DOI
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI   ScienceOn
11 Mulvihill EE, Huff MW. Citrus flavonoids and the prevention of atherosclerosis. Cardiovasc. Hematol. Disord. Drug Targets 12: 84-91 (2012)   DOI
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI
16 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)   DOI   ScienceOn
17 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)   DOI
18 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)
19 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)   DOI
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)   DOI   ScienceOn
21 Kobayashi Y, Nabeta K, Matsuura H. Chemical inhibitors of viviparous germination in the fruit of watermelon. Plant Cell Physiol. 51: 1594-1598 (2010)   DOI   ScienceOn
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)   DOI   ScienceOn
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)   DOI   ScienceOn
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 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)   DOI   ScienceOn
26 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)   DOI   ScienceOn
27 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)
28 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)   DOI   ScienceOn
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)   DOI   ScienceOn
30 Hashem FA, Saleh MM. Antimicrobial components of some cruciferae plants (Diplotaxis harra Forsk. and Erucaria microcarpa Boiss.). Phytother. Res. 13: 329-332 (1999)   DOI   ScienceOn
31 Mo J, Wu B. A phytochemical and chemotaxomic study on Viburnum lancifolium. Biochem. Syst. Ecol. 39: 857-860 (2011)   DOI   ScienceOn
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)   DOI
34 Arisawa M, Hatashita T, Numata Y, Tanaka M, Sasaki T. Cytotoxic principles from Chrysosplenium flagelliferum. Int. J. Pharm. 35: 141-143 (1997)   DOI   ScienceOn
35 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)   DOI   ScienceOn
36 Chung IM, Hahn SJ, Ahmad A. Confirmation of potential herbicidal agents in hulls of rice, Oryza sativa. J. Chem. Ecol. 31: 1339-1352 (2005)   DOI
37 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)   DOI
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)