Unusual immuno-modulatory triterpene-caffeates in the skins of russeted varieties of apples and pears

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 11, 2013, Pages 2773-2779

  Andre, Christelle M ^a,d   Larsen, Lesley ^b,d   Burgess, Elaine J ^b,d   Jensen, Dwayne J ^a,d   Cooney, Janine M ^a,d   Evers, Danièle ^c   Zhang, Jingli ^a   Perry, Nigel B ^b,d   Laing, William A ^a,d  

^a THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED   (New Zealand)

^b UNIVERSITY OF OTAGO   (New Zealand)

^c LUXEMBOURG INSTITUTE OF SCIENCE AND TECHNOLOGY   (Luxembourg)

^d Nutrigenomics New Zealand   (New Zealand)

Author keywords

apple; betulinic acid; betulinic acid 3 O caffeate; inflammation; NF B; pear; russet; TNF ; triterpene

Indexed keywords

APPLE; BETULINIC ACID; BETULINIC ACID-3- O -CAFFEATE; INFLAMMATION; PEAR; RUSSET; TRITERPENES;

TISSUE;

FRUITS;

ANTIINFLAMMATORY AGENT; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PLANT EXTRACT; TRITERPENE;

ADULT; ARTICLE; CELL LINE; CHEMISTRY; DRUG EFFECT; FRUIT; HUMAN; IMMUNOLOGY; MACROPHAGE; MALUS; MIDDLE AGED; PYRUS;

ADULT; ANTI-INFLAMMATORY AGENTS; CAFFEIC ACIDS; CELL LINE; FRUIT; HUMANS; MACROPHAGES; MALUS; MIDDLE AGED; NF-KAPPA B; PLANT EXTRACTS; PYRUS; TRITERPENES;

BACTERIA (MICROORGANISMS); MALUS X DOMESTICA; PYRUS;

EID: 84875438138     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf305190e     Document Type: Article

References (37)

1. FAOSTAT 2009, http://faostat.fao.org; last accessed on 10/01/2012.
2. Hyson, D. A. A comprehensive review of apples and apple components and their relationship to human health Adv. Nutr. 2011, 2, 408-420
3. Andre, C. M.; Greenwood, J.; Walker, E.; Rassam, M.; Sullivan, M.; Evers, D.; Perry, N.; Laing, W. Anti-inflammatory procyanidins and triterpenes in 109 apple varieties J. Agric. Food Chem. 2012, 60, 10546-10554
4. Petronelli, A.; Pannitteri, G.; Testa, U. Triterpenoids as new promising anticancer drugs Anti-Cancer Drugs 2009, 20, 880-892
5. Shanmugam, M. K.; Nguyen, A. H.; Kumar, A. P.; Tan, B. K. H.; Sethi, G. Targeted inhibition of tumor proliferation, survival, and metastasis by pentacyclic triterpenoids: Potential role in prevention and therapy of cancer Cancer Lett. 2012, 320, 158-170
6. Salvador, J. A. R.; Moreira, V. M.; Goncalves, B. M. F.; Leal, A. S.; Jing, Y. Ursane-type pentacyclic triterpenoids as useful platforms to discover anticancer drugs Nat. Prod. Rep. 2012, 29, 1463-1479
7. He, X.; Liu, R. H. Triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for apple's anticancer activity J. Agric. Food Chem. 2007, 55, 4366-4370
8. Brendolise, C.; Yauk, Y.-K.; Eberhard, E. D.; Wang, M.; Chagne, D.; Andre, C.; Greenwood, D. R.; Beuning, L. L. An unusual plant triterpene synthase with predominant α-amyrin-producing activity identified by characterizing oxidosqualene cyclases from Malus × domestica FEBS J. 2011, 278, 2485-2499
9. Jager, S.; Trojan, H.; Kopp, T.; Laszczyk, M. N.; Armin, S. Pentacyclic triterpene distribution in various plants-Rich sources for a new group of multi-potent plant extracts Molecules 2009, 14, 2016-2031
10. Kunst, L.; Samuels, A. L. Biosynthesis and secretion of plant cuticular wax Prog. Lipid Res. 2003, 42, 51-80
11. Belding, R. D.; Blankenship, S. M.; Young, E.; Leidy, R. B. Composition and variability of epicuticular waxes in apple cultivars J. Am. Soc. Hortic. Sci. 1998, 123, 348-356
12. Gershenzon, J.; Dudareva, N. The function of terpene natural products in the natural world Nat. Chem. Biol. 2007, 3, 408-414
13. Veraverbeke, E. A.; Lammertyn, J.; Saevels, S.; Nicolaï, B. M. Changes in chemical wax composition of three different apple (Malus domestica Borkh.) cultivars during storage Postharvest Biol. Technol. 2001, 23, 197-208
14. Sironval, C.; Clijsters, H. Sur la nature de la rugosite chez la pomme Cox's Orange Bull. Soc. R. Bot. Belg. 1963, 95, 34-45
15. Gildemacher, P. R.; Heijne, B.; Houbraken, J.; Vromans, T.; Hoekstra, E. S.; Boekhout, T. Can phyllosphere yeasts explain the effect of scab fungicides on russeting of Elstar apples? Eur. J. Plant Pathol. 2004, 110, 929-937
16. Tanachatchairatana, T.; Bremner, J. B.; Chokchaisiri, R.; Suksamrarn, A. Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids Chem. Pharm. Bull. 2008, 56, 194-198
17. Pan, H.; Lundgren, L. N.; Andersson, R. Triterpene caffeates from bark of Betula pubescens Phytochemistry 1994, 37, 795-799
18. Otsuka, H.; Fujioka, S.; Komiya, T.; Goto, M.; Hiramatsu, Y.; Fujimura, H. Studies on anti-inflammatory agents. V. A new anti-inflammatory constituent of Pyracantha crenulata Roem Chem. Pharm. Bull. (Tokyo) 1981, 29, 3099-3104
19. Chen, B.; Duan, H.; Takaishi, Y. Triterpene caffeoyl esters and diterpenes from Celastrus stephanotifolius Phytochemistry 1999, 51, 683-687
20. Kim, K. H.; Choi, S. U.; Lee, K. R. Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana Bioorg. Med. Chem. Lett. 2010, 20, 1944-1947
21. Tsuchiya, S.; Kobayashi, Y.; Goto, Y.; Okumura, H.; Nakae, S.; Konno, T.; Tada, K. Induction of maturation in cultured human monocytic leukemia cells by a phorbol diester Cancer Res. 1982, 42, 1530-1536
22. O'Brien, J.; Wilson, I.; Orton, T.; Pognan, F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity Eur. J. Biochem. 2000, 267, 5421-5426
23. Krasutsky, P. A. Birch bark research and development Nat. Prod. Rep. 2006, 23, 919-942
24. Rao, Y. K.; Fang, S.-H.; Tzeng, Y.-M. Antiinflammatory activities of flavonoids and a triterpene caffeate isolated from Bauhinia variegata Phytother. Res. 2008, 22, 957-962
25. Jeong, W.; Hong, S. S.; Kim, N.; Yang, Y. T.; Shin, Y. S.; Lee, C.; Hwang, B. Y.; Lee, D. Bioactive triterpenoids from Callistemon lanceolatus Arch. Pharm. Res. 2009, 32, 845-849
26. Ma, C.-Y.; Musoke, S. F.; Tan, G. T.; Sydara, K.; Bouamanivong, S.; Southavong, B.; Soejarto, D. D.; Fong, H. H. S.; Zhang, H.-J. Study of antimalarial activity of chemical constituents from Diospyros quaesita Chem. Biodiversity 2008, 5, 2442-2448
27. Pan, M.-H.; Chen, C.-M.; Lee, S.-W.; Chen, Z.-T. Cytotoxic triterpenoids from the root bark of Helicteres angustifolia Chem. Biodiversity 2008, 5, 565-574
28. Gou, J.-Y.; Yu, X.-H.; Liu, C.-J. A hydroxycinnamoyltransferase responsible for synthesizing suberin aromatics in Arabidopsis Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 18855-18860
29. Viatour, P.; Merville, M.-P.; Bours, V.; Chariot, A. Phosphorylation of NF-κB and IκB proteins: implications in cancer and inflammation Trends Biochem. Sci. 2005, 30, 43-52
30. Marquez Martin, A.; de la Puerta Vazquez, R.; Fernandez-Arche, A.; Ruiz-Gutierrez, V. Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages Free Radical Res. 2006, 40, 295-302
31. Kim, J. A.; Son, J. H.; Yang, S. Y.; Song, S. B.; Song, G. Y.; Kim, Y. H. A new lupane-type triterpene from the seeds of Panax ginseng with its inhibition of NF-kappaB Arch. Pharm. Res. 2012, 35, 647-651
32. Bedir, E.; Pugh, N.; Calis, I.; Pasco, D. S.; Khan, I. A. Immunostimulatory effects of cycloartane-type triterpene glycosides from astragalus species Biol. Pharm. Bull. 2000, 23, 834-837
33. Watanabe, K.; Shuto, T.; Sato, M.; Onuki, K.; Mizunoe, S.; Suzuki, S.; Sato, T.; Koga, T.; Suico, M. A.; Kai, H.; Ikeda, T. Lucidenic acids-rich extract from antlered form of Ganoderma lucidum enhances TNFalpha induction in THP-1 monocytic cells possibly via its modulation of MAP kinases p38 and JNK Biochem. Biophys. Res. Commun. 2011, 408, 18-24
34. Zdzisinska, B.; Rzeski, W.; Paduch, R.; Szuster-Ciesielska, A.; Kaczor, J.; Wejksza, K.; Kandefer-Szerszen, M. Differential effect of betulin and betulinic acid on cytokine production in human whole blood cell cultures Pol. J. Pharmacol. 2003, 55, 235-238
35. Tsytsykova, A. V.; Falvo, J. V.; Schmidt-Supprian, M.; Courtois, G.; Thanos, D.; Goldfeld, A. E. Post-induction, stimulus-specific regulation of tumor necrosis factor mRNA expression J. Biol. Chem. 2007, 282, 11629-11638
36. Ikeda, Y.; Murakami, A.; Ohigashi, H. Ursolic acid: An anti- and pro-inflammatory triterpenoid Mol. Nutr. Food Res. 2008, 52, 26-42
37. Fang, N.; Yu, S.; Badger, T. M. Characterization of triterpene alcohol and sterol ferulates in rice bran using LC-MS/MS J. Agric. Food Chem. 2003, 51, 3260-3267