Hydroxycinnamoylmalic acids and their methyl esters from pear (Pyrus pyrifolia Nakai) fruit peel

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 18, 2011, Pages 10124-10128

  Lee, Ki Hoon ^a   Cho, Jeong Yong ^a   Lee, Hyoung Jae ^a   Ma, Young Kyu ^a   Kwon, Joseph ^b   Park, Seong Hwa ^b   Lee, Sang Hyun ^a   Cho, Jeong An ^a   Kim, Wol Soo ^a   Park, Keun Hyung ^a   Moon, Jae Hak ^a  

^a Chonnam National University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

caffeoyl malate; coumaroyl malate; hydroxycinnamoylmalic acid methyl ester; pear fruit; Pyrus pyrifolia Nakai

Indexed keywords

CAFFEOYL MALATE; COUMAROYL MALATE; HYDROXYCINNAMOYLMALIC ACID METHYL ESTER; PEAR FRUIT; PYRUS PYRIFOLIA NAKAI;

CHEMICAL COMPOUNDS; ESTERIFICATION; FRUITS;

ESTERS;

CAFFEIC ACID DERIVATIVE; CAFFEOYLMALIC ACID; COUMARIC ACID; ESTER; MALIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FRUIT; ISOLATION AND PURIFICATION; PYRUS;

CAFFEIC ACIDS; COUMARIC ACIDS; ESTERS; FRUIT; MALATES; MOLECULAR STRUCTURE; PYRUS;

PYRUS; PYRUS PYRIFOLIA;

EID: 80053112409     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2022868     Document Type: Article

References (38)

1. Choi, H. J.; Park, J. H.; Han, H. S.; Son, J. H.; Son, G. M.; Bae, J. H.; Choi, J. Effect of polyphenol compound from Korean pear (Pyrus pyrifolia Nakai) on lipid metabolism J. Korean Soc. Food Sci. Nutr. 2004, 33, 299-304
2. Cui, T.; Nakamura, K.; Ma, L.; Li, J. Z.; Kayahara, H. Analyses of arbutin and chlorogenic acid, the major phenolic constituents in Oriental pears J. Agric. Food Chem. 2005, 53, 3882-3887 (Pubitemid 40936738)
3. Hamauze, Y.; Forest, F.; Hiramatsu, K.; Sugimoto, M. Effect of pear (Pyrus communis L.) procyanidins on gastric lesions induced by HCl/ethanol in rats Food Chem. 2007, 100, 255-263
4. Huang, L. J.; Gao, W. Y.; Li, X.; Zhap, W. S.; Huang, L. Q.; Liu, C. X. Evaluation of the in vivo anti-inflammatory effects of extracts from Pyrus bretschneideri Rehd J. Agric. Food Chem. 2010, 58, 8983-8987
5. Salta, J.; Martins, A.; Santos, R. S.; Neng, N. R.; Nogueira, J. M. F.; Justino, J.; Rauter, A. P. Phenolic composition and antioxidant activity of Rocha pear and other pear cultivars-A comparative study J. Funct. Foods 2010, 2, 153-157
6. Leontowicz, M.; Gorinstein, S.; Leontowicz, H.; Krzaeminski, R.; Lojek, A.; Katrich, E.; Ciz, M.; Martin-Belloso, O.; Soliva-Fortuny, R.; Haruenkit, R.; Trakhtenberg, S. Apple and pear peel and pulp and their influence on plasma lipids and antioxidant potentials in rats fed cholesterol-containing diets J. Agric. Food Chem. 2003, 51, 5780-5785
7. Chen, J. L.; Wang, Z. F.; We, J. H.; Wang, Q.; Hu, X. S. Chemical compositional characterization of eight pear cultivars grown in China Food Chem. 2007, 104, 268-275 (Pubitemid 46578274)
8. Colaric, M.; Stampar, F.; Solar, A.; Hudina, M. Influence of branch bending on sugar, organic acid and phenolic content in fruits of "Williams" pears (Pyrus communis L.) J. Sci. Food Agric. 2006, 86, 2463-2467 (Pubitemid 44690171)
9. Galvis-Sánchez, A. C.; Gil-Izquierdo, A.; Gil, M. I. Comparative study of six pear cultivars in terms of their phenolic and vitamin C contents and antioxidant capacity J. Sci. Food Agric. 2003, 83, 995-1003 (Pubitemid 36941029)
10. Ramadan, M. F.; Morsel, J. T. Recovered lipids from prickly pear [ Opuntia ficus-indica (L.) Mill] peel: a good source of polyunsaturated fatty acids, natural antioxidant vitamins and sterols Food Chem. 2003, 83, 447-456 (Pubitemid 37108708)
11. Wang, J.; Xu, J. Z.; Chen, H. J.; Zhang, H. J.; Li, S. L. The determination of volatile matters and amino acids content in the fruit of Ya pear Food Technol. 2002, 9, 71-73
12. Ferreira, D.; Guyot, S.; Marnet, N.; Delgadill, I.; Renard, C. M.; Coimbra, M. A. Composition of phenolic compounds in a Portuguese pear (Pyrus communis L. var. S. Bartolomeu) and changes after sun-drying J. Agric. Food. Chem. 2002, 50, 4537-4544 (Pubitemid 34823978)
13. Tanrioven, D; Eksi, A. Phenolic compounds in pear juice from different cultivars Food Chem. 2005, 93, 89-93 (Pubitemid 40603418)
14. Schieber, A.; Keller, P.; Carle, R. Determination of phenolic acids and flavonoids of apple and pear by high-performance liquid chromatography J. Chromatogr., A 2001, 910, 265-273 (Pubitemid 32126294)
15. Oleszek, W.; Amiot, M. J.; Aubert, S. Y. Identification of some phenolics in pear fruit J. Agric. Food Chem. 1994, 42, 1261-1265
16. Es-Safi, N. E.; Guyot, S.; Ducrot, P. H. NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity J. Agric. Food Chem. 2006, 54, 6969-6977 (Pubitemid 44554909)
17. Amiot, M. J.; Tacchini, M.; Auber, S. Y. Influence of cultivar, maturity stage, and storage conditions on phenolic composition and enzymatic browing of pear fruits J. Agric. Food Chem. 1995, 43, 1132-1137
18. Thavarajah, P.; Nicholas, H. L. Adulteration of apple with pear juice: Emphasis on major carbohydrates, proline, and arbutin J. Agric. Food Chem. 2006, 54, 4861-4867 (Pubitemid 44133739)
19. Branca, M. S.; Paula, B. A. Phenolic profile in the evaluation of commercial quince jellies authenticity Food Chem. 2000, 71, 281-285
20. Lin, L. Z.; Harnly, J. M. Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.) J. Agric. Food Chem. 2008, 56, 9094-9101
21. Liang, Y. S.; Kim, H. K.; Lefever, A. W. M.; Erkelens, C.; Choi, Y. H.; Verpoorte, R. Indentification of phenylpropanoids in methyl jasmonate treated Brassica rapa leaves using two-dementsional nuclear magnetic resonance spectroscopy J. Chromatogr., A 2006, 1112, 148-155
22. Lee, M. K.; Jeon, H. Y.; Lee, K. Y.; Kim, S. H.; Ma, C. J.; Sung, S. H.; Lee, H. S.; Park, M. J.; Kim, Y. C. Inhibitory constituents of Euscaphis japonica on lipolysaccharide-induced nitric oxide production in BV2 microglia Planta Med. 2007, 73, 782-786
23. Liang, Y. S.; Choi, Y. H.; Kim, H. K.; Linthorst, H. J. M.; Verpoorte, R. Metabolomic analysis of methyl jasmonate treated Brassica rapa leaves by 2-dementsional NMR spectroscopy Phytochemistry 2006, 672, 2503-2511 (Pubitemid 44602131)
24. Liu, Y. J.; Lotero, E.; Goodwin, J. G. Effect of carbon chain length on esterification of carboxylic acids with methanol using acid catalysis J. Catal. 2006, 243, 221-228 (Pubitemid 44415829)
25. Sullivan, M. L. A novel red clover hydroxycinnamoyl transferase has enzymatic activities consistent with a role in phaselic acid biosynthesis Plant Physiol. 2009, 150, 1866-1879
26. Jones, B. A.; Hatfield, R. D.; Muck, R. E. Screening legume forages for soluble phenols, polyphenol oxidase and extract browning J. Sci. Food Agric. 1995, 67, 109-112
27. Winters, A. L.; Minchin, F. R.; Michaelson-Yeates, T. P. T.; Lee, M. R. F.; Morris, P. Latent and active polyphenol oxidase (PPO) in red clover (Trifolium pretense) and use of a low PPO mutant to study the role of PPO in proteolysis reduction J. Agric. Food Chem. 2008, 56, 2817-2824 (Pubitemid 351685230)
28. Moon, J. H.; Terao, J. Antioxidantactivity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein J. Agric. Food Chem. 1998, 46, 5062-5065 (Pubitemid 128488258)
29. Chao, P. C.; Hsu, C. C.; Yin, M. C. Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in carfia tissue of diabetic mice Nutr. Metab. 2009, 33, 1-8
30. Cárdenas, M.; Marder, M.; Blank, V. C.; Roguin, L. R. Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines Bioorg. Med. Chem. 2006, 14, 2966-2971
31. Li, P. G.; Xu, J. W.; Ikeda, K.; Kobayakawa, A.; Kayano, Y.; Mitani, T.; Ikami, T.; Yamori, Y. Caffeic acid inhibits vascular smooth muscle cell proliferation induced by angiotensin II in stroke-prone spontaneously hypertensive rats Hypertens. Res. 2005, 28, 369-377 (Pubitemid 40895060)
32. Abdel-Farid, I. B.; Kim, H. K.; Choi, Y. H.; Verpoorte, R. Metabolic characterization of Brassica rapa leaves by NMR spectroscopy J. Agric. Food Chem. 2007, 55, 7936-7943 (Pubitemid 47522210)
33. Tazaki, H.; Ito, M.; Miyoshi, M.; Kawabata, J.; Fukushi, E.; Fujita, T.; Motouri, M.; Furuki, T.; Nabeta, K. Subulatin, an antioxidic caffeic acid derivative isolated from the in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophyllla, and Scapania parvitexta Biosci., Biotechnol., Biochem. 2002, 66, 255-261 (Pubitemid 39251044)
34. Jahangir, M.; Kim, H. K.; Choi, Y. H.; Verpoorte, R. Metabolomic response of Brassica rapa submitted to pre-harvest bacterial contamination Food Chem. 2008, 107, 362-368 (Pubitemid 47633868)
35. Simoh, S.; Quintana, N.; Kim, H. K.; Choi, Y. H.; Verpoorte, R. Metabolic changes in Agrobacterium tumefaciens -infected Brassica rapa J. Plant Physiol. 2009, 166, 1005-1014
36. Abdel-Farid, I. B.; Jahangir, M.; van den Hondel, C. A. M. J. J.; Kim, H. K.; Choi, Y. H.; Verpoorte, R. Fungal infection-induced metabolites in Brassica rapa Plant Sci. 2009, 176, 608-615
37. Hendrawati, O.; Yao, Q.; Kim, H. K.; Linthorst, H. J. M.; Erkelens, C.; Lefeber, A. W. M.; Choi, Y. H.; Verpoorte, R. Metabolic differentiation of Arabidopsis treated with methyl jasmonate using nuclear magnetic resonance spectroscopy Plant Sci. 2006, 170, 1118-1124
38. Housti, F.; Andary, C.; Gargadennec, A.; Amssa, M. Effects of wounding and salicylic acid on hydroxycinnamoylmalic acids in Thunbergia alata Plant Physiol. Biochem. 2002, 40, 761-769 (Pubitemid 35224874)