Fruit cuticular waxes as a source of biologically active triterpenoids

Phytochemistry Reviews

Volumn 11, Issue 2-3, 2012, Pages 263-284

  Szakiel, Anna ^a   Pączkowski, Cezary ^a   Pensec, Flora ^b   Bertsch, Christophe ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

Cuticular waxes; Fruit peel; Health benefits; Triterpenoids

Indexed keywords

2ALPHA HYDROXYURSOLIC ACID; 3BETA TRANS CINNAMOYLOXY 2ALPHA HYDROXYURS 12 EN 28 OIC ACID; 3BETA TRANS PARA COUMAROYLOXY 2ALPHA HYDROXYURS 12 EN 28 OIC ACID; ALPHA AMYRIN; BETA AMYRIN; BETA SITOSTEROL 6' LINOLENOYL 3 O BETA DEXTRO GLUCOPYRANOSIDE; BETULIC ACID; DELTA AMYRIN; ERYTHRODIOL; HERBACEOUS AGENT; LUPEOL; MASLINIC ACID; OLEANOLIC ACID; OLEANOLIC ALDEHYDE; OLIVE OIL; PARA COUMARYLOXY ESTER; PLANT MEDICINAL PRODUCT; SITOGLUSIDE; SITOSTEROL; TARAXASTEROL; TERPENOID; TORMENTIC ACID; TRITERPENOID; UNCLASSIFIED DRUG; URSOLIC ACID; UVAOL;

ANTIDIABETIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ANTIVIRAL ACTIVITY; APPLE; AUBERGINE; BIOCHEMICAL COMPOSITION; BLUEBERRY; CHRONIC OBSTRUCTIVE LUNG DISEASE; CLEMENTINE; CLONORCHIS SINENSIS; COLON CANCER; CONCENTRATION RESPONSE; COUNTER CURRENT CHROMATOGRAPHY; CRANBERRY; DIARRHEA; DRUG STRUCTURE; FRUIT (STRUCTURE); FRUIT CUTICULAR WAX; GRAPE; GRAPEFRUIT; HEART DISEASE; HEPATITIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYPERLIPIDEMIA; LEMON; LINGONBERRY; LIVER DISEASE; LUNG CANCER; MALARIA; MALUS; MALUS PUMILA; MANDARIN; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; OLIVE TREE; PHYTOCHEMISTRY; PLANT TISSUE; PRIORITY JOURNAL; PYRUS; PYRUS BRETCHNEIDERI; REVIEW; SOLVENT EXTRACTION; STOMACH PAIN; SWEET CHERRY; TOMATO; VACCINIUM; VACCINIUM ANGUSTIFOLIUM; VACCINIUM ASHEI; VACCINIUM MYRTILLUS;

LYCOPERSICON ESCULENTUM; MALUS X DOMESTICA; VITACEAE;

EID: 84876413596     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-012-9241-9     Document Type: Review

References (137)

1. Akihisa T, Ogihara J, Kato J et al (2001) Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36:507-512
2. Ali K, Maltese F, Choi YH et al (2010) Metabolic constituents of grapevine and grape-derived products. Phytochem Rev 9:357-378
3. Amico V, Napoli EM, Renda A et al (2004) Constituents of grape pomace from the Sicilian cultivar 'Nerello Mascalese'. Food Chem 88:599-607
4. Ángel Siles López J, Li Q, Thompson IP (2010) Biorefinery of waste orange peel. Crit Rev Biotechnol 30:63-69
5. Antonisamy P, Duraipandiyan V, Ignacimuthu S (2011) Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models. J Pharm Pharmacol 63:1070-1077
6. Aramon G, Saucier C, Tijou S et al (2003) Estimation of triterpenes in wines, spirits, and oak heartwoods by LC-MS. LCGC North Am 21:910-918
7. Awad AB, Fink CS (2000) Phytosterols as anticancer dietary components: evidence and mechanism of action. J Nutr 130:2127-2130
8. Bauer S, Schulte E, Thier H-P (2004a) Composition of the surface wax from tomatoes. I. Identification of the components by GC/MS. Eur Food Res Technol 219:223-228
9. Bauer S, Schulte E, Thier H-P (2004b) Composition of the surface wax from tomatoes. II. Quantification of the components at the ripe red stage and during ripening. Eur Food Res Technol 219:487-491
10. Bauer S, Schulte E, Thier H-P (2005) Composition of the surface waxes from bell pepper and eggplant. Eur Food Res Technol 220:5-10
11. Beindorff C, Cain FW, Pierce JH et al (2001) Blends of ursolic acid/oleanolic acid. US Patent 09/863,439, 24 May 2001
12. Belding RD, Blankenship SM, Young E et al (1998) Composition and variability of epicuticular waxes in apple cultivars. J Am Soc Hortic Sci 123:348-356
13. Belding RD, Sutton TB, Blankenship SM (2000) Relationship between apple fruit epicuticular wax and growth of Pelaster fructicola and Leptodontidium elatius, two fungi that cause sooty bloth disease. Plant Dis 84:767-772
14. Bianchi G, Murelli C, Vlahov G (1992) Surface waxes from olive fruits. Phytochemistry 31:3503-3506
15. Bianchi G, Pozzi N, Vlahov G (1994) Pentacyclic triterpene acids in olives. Phytochemistry 37:205-207
16. Bishayee A, Ahmed S, Brankov N et al (2011) Triterpenoids as potential agents for the prevention and therapy of breast cancer. Front Biosci 1(16):980-996
17. Bringe K, Schumacher CFA, Schmitz-Eiberger M (2006) Ontogenic variation in chemical and physical characteristics of adaxial apple leaf surfaces. Phytochemistry 67:161-170
18. Buschhaus C, Jetter R (2011) Composition differences between epicuticular and intracuticular wax substructures: how do plants seal their epidermal surfaces? J Exp Bot 62:841-853
19. Casado CG, Heredia A (1999) Structure and dynamics of reconstituted cuticular waxes of grape berry cuticle (Vitis vinifera L.). J Exp Bot 50:175-182
20. Casado CG, Heredia A (2001) Ultrastructure of the cuticle during growth of the grape berry (Vitis vinifera). Physiol Plant 111:220-224
21. Cefarelli G, D'Abrosca B, Fiorentino A et al (2006) Free-radical- scavenging and antioxidant activities of secondary metabolites from reddened cv. Annurca apple fruits. J Agric Food Chem 54:803-809
22. Chen M, Zhong Z, Tan W et al (2011) Recent advances in nano particle formulation of oleanolic acid. Chin Med 6:20. doi: 10.1186/1749-8546-6-20
23. Ching J, Lin HS, Tan CH et al (2011) Quantification of α- and β-amyrin in rat plasma by gas chromatography-mass spectrometry: application to preclinic pharmacokinetic study. J Mass Spectrom 46:457-464
24. Comménil P, Brunet L, Audran JC (1997) The development of the grape berry cuticle in relation to susceptibility to bunch rot disease. J Exp Bot 48:1599-1607
25. Croteau R, Fagerson IS (1971) The chemical composition of the cuticular wax of cranberry. Phytochemistry 10:3239-3245
26. Dagna L, Gasparini G, Icardi ML et al (1982) Study of some components of the unsaponifiable fraction in the skin of grapes. Am J Enol Vitic 33:201-206
27. De Pablos LM, dos Santos MFB, Montero E (2010) Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. Parasitol Res 107:601-604
28. Djilas S, Čanadanovič-Brunet J, Četkovič G (2009) By-products of fruit processing as a source of phytochemicals. Chem Ind Chem Eng Quat 15:191-202
29. Dzubak P, Hajduch M, Vydra D et al (2006) Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat Prod Rep 23:394-411
30. Ellgardt K (2006) Triterpenes in apple cuticle of organically and IP cultivated apples. Bachelor project in the Dannish-Swedish Horticulture Programme, ISSN 1652-1579, Dept of Crop Science, Sveriges Lantbruksuniversitet, Alnarp
31. Emmanuel E, Levy AA (2002) Tomato mutants as tools for functional genomics. Curr Opinion Plant Biol 5:112-117
32. Fernández-Bolaños J, Rodríguez G, Rodríguez R et al (2006) Extraction of interesting organic compounds from olive oil waste. Grasas Aceites 57:95-106
33. Fernández-Mar MI, Mateos R, Garcia-Parrilla MC et al (2011) Bioactive compounds in wine: resveratrol, hydroxytyrosol and melatonin: a review. Food Chem 130:797-813
34. Fernández-Navarro M, Peragón J, Esteban FJ et al (2006) Maslinic acid as a feed additive to stimulate growth and hepatic protein-turnover rates in rainbow trout (Onchorhynchus mykiss). Comp Biochem Physiol Part C 144:130-140
35. Frankel EN, Kannel J, German JB et al (1993) Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 341:454-457
36. Freeman B, Albigo LG, Biggs RH (1979) Ultrastructure and chemistry of cuticular waxes of developing Citrus leaves and fruits. J Amer Soc Hortic Sci 104:801-808
37. Frighetto RTS, Welendorf RM, Nigro EN et al (2008) Isolation of ursolic acid from apple peels by high speed counter-current chromatography. Food Chem 106:767-771
38. Gallo MBC, Sarachine MJ (2009) Biological activities of lupeol. Int J Biomed Pharm Sci 3(Special Issue 1):44-66
39. Ganbold M, Barker J, Ren M et al (2010) Cytotoxicity and bioavailability studies on a decoction of Oldenlandia diffusa and its fractions separated by HPLC. J Ethnopharm 131:396-403
40. García A, Brenes M, Dobaranges MC et al (2008) Enrichment of pomace oil in triterpenic acids during storage of "Alpeorujo" olive paste. Eur J Lipid Sci Technol 110:1136-1141
41. Glinsky J, Branly K (2001) Pentacyclic triterpenes. US Patent 09/207406, 16 October 2001
42. Guinda A, Rada M, Delgado T et al (2010) Pentacyclic triterpenoids from olive fruit and leaf. J Agric Food Chem 58:9685-9691
43. He X, Liu RH (2006) Cranberry phytochemicals: isolation, structure elucidation, and their antiproliferative and antioxidant activities. J Agric Food Chem 54:7069-7074
44. He X, Liu RH (2007) Triterpenoids isolated from apple peel have potent antiproliferative activity and may be partially responsible for apple's anticancer activity. J Agric Food Chem 55:4366-4370
45. Hill RA, Connolly JD (2011) Triterpenoids. Nat Prod Rep 28:1087-1117
46. Hooper L, Cassidy A (2006) A review of the health care potential of bioactive compounds. J Sci Food Agric 86:1805-1823
47. Iriti M, Faoro F (2009) Bioactivity of grape chemicals for human health. Nat Prod Commun 4:611-634
48. Jäger S, Trojan H, Kopp T et al (2009) Pentacyclic triterpene distribution in various plants - rich sources for a new group of multi-potent plant extracts. Molecules 14:2016-2031
49. Jeong DW, Kim YH, Kim HH et al (2007) Dose-linear pharmacokinetics of oleanolic acid after intravenous and oral administration in rats. Biopharm Drug Dispos 28:51-57
50. Jetter R, Schäffer S (2001) Chemical composition of the Prunus laurocerasus leaf surface. Dynamic changes of the epicuticular wax film during leaf development. Plant Physiol 126:1725-1737
51. Jetter R, Schäffer S, Riederer M (2000) Leaf cuticular waxes are arranged in chemically and mechanically distinct layers: evidence from Prunus laurocerasus L. Plant, Cell Environ 23:619-628
52. Juan ME, Planas JM (2010) Effects of pentacyclic triterpenes from olives on colon cancer. In: Watson RR, Preedy VR (eds) Bioactive food and extracts. CRC Press, Boka Raton, pp 403-413
53. Juan ME, Wenzel U, Ruiz-Gutierrez V et al (2006) Olive fruit extracts inhibit proliferation and induce apoptosis in HT-29 colon cancer cells. J Nutr 136:2553-2557
54. Juan ME, Planas JM, Ruiz-Gutierrez V et al (2008) Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. Brit J Nutr 100:36-43
55. Kondo M, MacKinnon SL, Craft CC et al (2011) Ursolic acid and its esters: occurrence in cranberries and other Vaccinium fruit and effects on matrix metalloproteinase activity in DU145 prostate tumor cells. J Sci Food Agric 91:789-796
56. Kosma DK, Parsons EP, Isaacson T (2010) Fruit cuticle lipid composition during development in tomato ripening mutants. Physiol Plant 139:107-117
57. Kuo RY, Quian K, Morris-Natschke SL et al (2009) Plant-derived triterpenes and analogues as antitumor and anti-HIV agents. Nat Prod Rep 26:1321-1344
58. Laszczyk MN (2009) Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med 75:1549-1560
59. Le Fur Y, Hory C, Bard MH et al (1994) Evolution of phytosterols in Chardonnay grape berry skins during last stages of ripening. Vitis 33:127-131
60. Leide J, Hildebrandt U, Reussing K et al (2007) The developmental pattern of tomato fruit wax accumulation and its impact on cuticular transpiration barrier properties: effects of a deficiency in a β-ketoacyl-coenzyme A synthase (LeCER6). Plant Physiol 144:1667-1679
61. Leide J, Hildebrandt U, Vogg G et al (2011) The positional sterile (ps) mutation affects cuticular transpiration and wax biosynthesis of tomato fruits. J Plant Physiol 168:871-877
62. Leifert WR, Abeywardena MY (2008) Cardioprotective actions of grape polyphenols. Nutr Res 28:729-737
63. Liu RH (2003) Health benefits of fruits and vegetables are from additive and synergistic combination of phytochemicals. Am J Clin Nutr 78:517S-520S
64. Liu J (2005) Oleanolic acid and ursolic acid: research perspectives. J Ethnopharm 100:92-94
65. Liu T, Ma L, Zhao J et al (2007) Protective effects of triterpenoids from Vitis vinifera L. on immunological liver injury in vitro. J Xinjiang Med Univers 30:1222-1225
66. Liu T, Zhao J, Li H et al (2010) Evaluation on anti-hepatitis viral activity of Vitis vinifera L. Molecules 15:7415-7421
67. Liu J, Sun H, Shang J et al (2011) Effect of olive pomace extracts on hyperlipidaemia. Nat Prod Res 25:1190-1194
68. Ma CM, Cai SQ, Cui JR et al (2005) The cytotoxic activity of ursolic acid derivatives. Eur J Med Chem 40:582-589
69. Marchal A, Waffo-Teguo P, Genin E, Merillon JM, Dubourdieu D (2011) Identification of new natural sweet compounds in wine using centrifugal partition chromatography-gustatometry and Fourier transform mass spectrometry. Anal Chem 83:9629-9637
70. Martín R, Ibeas E, Carvalho-Tavares J et al (2009) Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. PLoS ONE 4:e5975. doi: 10.1371/journal.pone.0005975
71. Martín R, Carvalho-Tavares J, Hernández M et al (2010) Beneficial effects of oleanolic acid in an experimental model of multiple sclerosis: a potential therapeutic role. Biochem Pharmacol 79:198-208
72. McGhie TK, Hudault S, Lunken RCM, Christeller JT (2012) Apple peels, from seven cultivars, have lipase-inhibitory activity and contain numerous ursenoic acids as identified by LC-ESI-QTOF-HRMS. J Agric Food Chem 60:482-491
73. Melo C, Carvalho KMMB, de Sousa Neves JC et al (2010) α, β-Amyrin, a natural triterpenoid ameliorates l-arginine-induced acute pancreatitis in rats. World J Gastroenterol 14:4272-4280
74. Mintz-Oron S, Mandel T, Rogachev I et al (2008) Gene expression and metabolism in tomato fruit surface tissues. Plant Physiol 147:823-851
75. Moneriz C, Mestres J, Bautista JM et al (2011) Multi-targeted activity of maslinic acid as an antimalarial natural compound. FEBS J 16:2951-2961
76. Moyer RA, Hummer KE, Finn CE et al (2002) Anthocyanins, phenolics and antioxidant capacity in diverse small fruits: Vaccinium, Rubus and Ribes. J Agric Food Chem 50:519-525
77. Müller C, Riederer M (2005) Plant surface properties in chemical ecology. J Chem Ecol 31:2621-2651
78. Murphy BT, MacKinnon SL, Yan X et al (2003) Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon). J Agric Food Chem 51:3541-3545
79. Neto CC (2007) Cranberry and blueberry: evidence for protective effects against cancer and vascular diseases. Mol Nutr Food Res 51:652-664
80. Neto CC (2011) Ursolic acid and other pentacyclic triterpenoids: anticancer activities and occurrence in berries. In: Stoner GD, Seeram NP (eds) Berries and cancer prevention. Springer, LLC, pp 41-49
81. Niaounakis M, Halvadakis CP (2006) Olive processing waste management: literature review and patent survey. Elsevier Ltd, London
82. Norby HE, McDonald RE (1994) Friedelin, the major component of grapefruit epicuticular wax. J Agric Food Chem 42:708-713
83. Norby HE, McDonald RE (1995) Variations in chilling injury and epicuticular wax composition of white grapefruit with canopy position and fruit development during the season. J Agric Food Chem 43:1828-1833
84. Ono M, Koto M, Komatsu H et al (2004) Cytotoxic triterpenes and sterol from the fruit of rabbiteye blueberry (Vaccinium ashei). Food Sci Technol Res 10:56-59
85. Orbán N, Kozák IO, Drávucz M et al (2009) LC-MS method development to evaluate major triterpenes in skins and cuticular waxes of grape berries. Int J Food Sci Tech 44:869-873
86. Ortega RM (2006) Importance of functional foods in the Mediterranean diet. Public Health Nutr 9:1136-1140
87. Owen RW, Haubner R, Wurtele G et al (2004) Olives and olive oil in cancer prevention. Eur J Cancer Prev 13:319-326
88. Patočka J (2003) Biologically active pentacyclic triterpenes and their current medicine signification. J Appl Biomed 1:7-12
89. Pereira SI, Freire CSR, Neto CP et al (2005) Chemical composition of the epicuticular wax from the fruits of Eucalyptus globulus. Phytochem Anal 16:364-369
90. Pérez-Camino MC, Cert A (1999) Quantitative determination of hydroxyl pentacyclic triterpene acids in vegetable oils. J Agric Food Chem 47:1558-1562
91. Peschel S, Franke R, Schreiber L et al (2007) Composition of the cuticle of developing sweet cherry fruit. Phytochemistry 68:1017-1025
92. Petronelli A, Pannitteri G, Testa U (2009) Triterpenoids as new promising anticancer drugs. Anticancer Drugs 20:880-892
93. Piironen V, Lindsay DG, Miettinen TA et al (2000) Plant sterols: biosynthesis, biological function and their importance to human nutrition. J Sci Food Agric 80:939-966
94. Rada M, Ruiz-Gutiérrez V, Guinda A (2011) Determination of triterpenic acid in human serum by high-performance liquid chromatography: triterpenoid interaction with serum protein. J Agric Food Chem 59:2308-2313
95. Radler F (1965a) The surface waxes of the sultana vine (Vitis vinifera cv. Thompson seedless). Aust J Chem 18:1045-1056
96. Radler F (1965b) The main constituents of the surface waxes of varieties and species of genus VITIS. Am J Enol Vitic 16:159-167
97. Radler F, Horn DHS (1965) The composition of grape cuticle wax. Aust J Chem 18:1059-1069
98. Rezanka T, Siristova L, Sigler K (2009) Sterols and triterpenoids with antiviral activity. Anti Infect Agents Med Chem 8:193-210
99. Rivero-Cruz JF, Zhu M, Kinghorn AD et al (2008) Antimicrobial constituents of Thompson seedless raisins (Vitis vinifera) against selected oral pathogens. Phyt Lett 1:151-154
100. Rodriguez-Rodriguez R, Perona JS, Herrera MD, Ruiz-Gutierrez V (2006) Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats. J Agric Food Chem 54:2096-2102
101. Romero C, García A, Medina E (2010) Triterpenic acids in table olives. Food Chem 118:670-674
102. Rudell DR, Mattheis JP, Hertog MLATM (2009) Metabolomic change precedes apple superficial scald symptoms. J Agric Food Chem 57:8459-8466
103. Sala JM (2000) Content, chemical composition and morphology of epicuticular wax of Fortune mandarin fruits in relation to peel pitting. J Sci Food Agric 80:1887-1894
104. Sala JM, Lafuente T, Cuñat P (1992) Content and chemical composition of epicuticular wax of 'Navelina' oranges and 'Satsuma' mandarins as related to rindstaining of fruit. J Sci Food Agric 59:489-495
105. Shishodia S, Majumdar S, Banerjee S, Aggarwal BB (2003) Ursolic acid inhibits nuclear factor-κB activation induced by carcinogenic agents through suppression of IκBα kinase and p65 phosphorylation: correlation with down-regulation of cyclooxygenase 2, matrix metalloproteinase 9, and cyclin D1. Cancer Res 63:4375-4383
106. Soldi C, Pizzolatti MG, Luiz AP et al (2008) Synthetic derivatives of the α- and β-amyrin triterpenes and their antinociceptive properties. Bioorg Med Chem 16:3377-3386
107. Sorokina IV, Tolstikova TG, Zhukova NA et al (2004) Betulonic acid and derivatives, a new group of agents reducing side effects of cytostatics. Doklady Biol Sci 399:434-437
108. Sporn MB, Liby KT, Yore MM et al (2011) New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J Nat Prod 74:537-545
109. Stiti N, Hartmann MA (2012) Nonsterol triterpenoids as major constituents of Olea europaea. J Lipids. doi: 10.1155/2012/476595
110. Stiti N, Triki S, Hartmann MA (2007) Formation of triterpenoids throughout Olea europaea fruit ontogeny. Lipids 42:55-67
111. Sun H, Fang WS, Wang WZ et al (2006) Structure-activity relationship of oleanane- and ursane-type triterpenoids. Bot Studies 47:339-368
112. Szakiel A, Mroczek A (2007) Distribution of triterpene acids and their derivatives in organs of cowberry (Vaccinium vitis-idaea L.) plant. Acta Biochim Polon 54:733-740
113. Szakiel A, Chołuj A, Pa̧czkowski C (2007) Comparison of the content of triterpene acids in edible berries of three wild Vaccinium species occurring in Poland. Acta Biochim Polon 54(Suppl.4):77
114. Szakiel A, Pa̧czkowski C, Koivuniemi H, Huttunen S (2012) Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland. J Agric Food Chem 60:4994-5002
115. Thoppil RJ, Bishayee A (2011) Terpenoids as potential chemopreventive and therapeutic agents in liver cancer. World J Hepatol 27:228-249
116. Vasilevsky SF, Gavdi AI, Sorokina IV et al (2011) Rapid access to new bioconjugates of betulonic acid via click chemistry. Bioorg Med Chem Lett 21:62-65
117. Verardo G, Pagani E, Geatti P et al (2003) A thorough study of the surface wax of apple fruits. Anal Bioanal Chem 376:659-667
118. Villasenor IM, Angelada J, Canlas AP et al (2002) Bioactivity studies on β-sitosterol and its glucoside. Phytother Res 16:417-421
119. Vioque E, Maza MP (1963) On triterpenic acids from olive and olive pomace oils. Grasas Aceites 14:9-11
120. Vislocky LM, Fernandez ML (2010) Biomedical effects of grape products. Nutr Rev 68:656-670
121. Vogg G, Fischer S, Leide J et al (2004) Tomato fruit cuticular waxes and their effects on transpiration barrier properties: functional characterization of a mutant deficient in a very-long-chain fatty acid β-ketoacyl-CoA synthase. J Exp Bot 55:1401-1410
122. Wang Z, Guhling O, Yao R et al (2011) Two oxidosqualene cyclases responsible for biosynthesis of tomato fruit cuticular triterpenoids. Plant Physiol 155:540-552
123. Willet WC (1994) Diet and health: what should we eat? Science 264:532-537
124. Wolfe KL, Liu RH (2003) Apple peels as a value-added food ingredient. J Agric Food Chem 51:1676-1683
125. Wolfe KL, Wu XZ, Liu RH (2003) Antioxidant activity of apple peels. J Agric Food Chem 51:609-614
126. Wolska KI, Grudniak AM, Fiecek B et al (2010) Antibacterial activity of oleanolic and ursolic acids and their derivatives. Cent Eur J Biol 5:543-553
127. World Health Statistics Annual (1989) World Health Organization, Geneva, ISBN 13: 9789240678903
128. Wu CD (2009) Grape products and oral health. J Nutr 39:S1818-S1823
129. Yadav M, Jain S, Bhardavi A et al (2009) Biological and medicinal properties of grapes and their bioactive constituents: an update. J Med Food 12:473-484
130. Yadav VR, Prasad S, Sung B et al (2010) Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins 2:2428-2466
131. Yamaguchi H, Noshita T, Kidachi Y et al (2008) Isolation of ursolic acid from apple peels and its specific efficacy as a potent antitumor agent. J Health Sci 54:654-660
132. Yamamura H, Naito R (1983) The surface wax of several grapes in Japan. J Jap Soc Hortic Sci 52:266-272
133. Yeats TH, Buda GJ, Wang Z et al (2012) The fruit cuticles of wild tomato species exhibit architectural and chemical diversity, providing a new model for studying the evolution of cuticle function. Plant J 69:655-666
134. Yeung MF, Che CT (2009) Literature review on pharmaceutical activities of oleanolic acid. Nat Proda Med 2:291-298
135. Yin Y, Bi Y, Chen S et al (2011) Chemical composition and antifungal activity of cuticular wax isolated from Asian pear fruit (cv. Pingguoli). Sci Hortic 129:577-582
136. Yogeeswari P, Sriram D (2005) Betulinic acid and its derivatives: a review on their biological properties. Curr Med Chem 12:657-666
137. Zhang Y, Jayaprakasam B, Seeram NP (2004) Insulin secretion and cyclooxygenase enzyme inhibition by Cabernet Sauvignon grape skin compounds. J Agric Food Chem 52:228-233