Raspberry pp 89-119 | Cite as

Raspberry Fruit Chemistry in Relation to Fruit Quality and Human Nutrition

  • Robert D. HancockEmail author
  • Antonios Petridis
  • Gordon J. McDougall


In recent years raspberry fruit breeding has shifted its focus from traits associated with agronomic performance towards those associated with fruit sensory quality (Jennings et al. 2016) and potential health benefits (Mazzoni et al. 2016). Simultaneously, significant advancements have been made in raspberry genetics and genomics as well as analytical chemistry in soft fruit. These new tools are generating knowledge that has the capacity to significantly accelerate the development of new varieties that meet consumer expectations in terms of sensory experience and health benefits of fruit consumption. Significant research in recent years has identified the environmental, biochemical and genetic controls underlying the accumulation of specific compounds in raspberry fruit. Furthermore, increasing information is becoming available regarding the mechanisms of action of specific phytochemicals in relation to human health outcomes. This information is now providing the underpinning science for the development of new cultivars. In this chapter, we outline current understanding of the biosynthetic pathways associated with the accumulation of significant fruit phytochemicals and describe what is presently known regarding the influence of crop genetics and the growing environment on the accumulation of specific phytochemicals. Finally we outline the latest knowledge regarding how fruit phytochemicals modulate human health outcomes. It is anticipated that the work outlined here will guide molecular breeding targets for future crop improvement.


  1. Aharoni A, Giri AP, Verstappen FWA et al (2004) Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16:3110–3131PubMedPubMedCentralCrossRefGoogle Scholar
  2. Alvarado-Raya HE, Darnell RL, Williamson JG (2007) Root to shoot relations in an annual raspberry (Rubus idaeus L.) production system. HortSci 42:1559–1562Google Scholar
  3. Anttonen MJ, Karjalainen RO (2005) Environmental and genetic variation of phenolic compounds in red raspberry. J Food Compos Anal 18:759–769CrossRefGoogle Scholar
  4. Aprea E, Biasioli F, Gasperi F (2015) Volatile compounds of raspberry fruit: from analytical methods to biological role and sensory impact. Molecules 20:2445–2474PubMedCrossRefGoogle Scholar
  5. Basu A, Rhone M, Lyons TJ (2010) Berries: Emerging impact on cardiovascular health. Nutr Rev 68:168–177PubMedPubMedCentralCrossRefGoogle Scholar
  6. Beekwilder J, Jonker H, Meesters P et al (2005) Antioxidants in raspberry: on-line analysis links antioxidant activity to a diversity of individual metabolites. J Agric Food Chem 55:3313–3320CrossRefGoogle Scholar
  7. Beekwilder J, van der Meer IM, Simic A et al (2008) Metabolism of carotenoids and apocarotenoids during ripening of raspberry fruit. Biofactors 34:57–66PubMedGoogle Scholar
  8. Bhandary B, Lee GH, Marahatta A et al (2012) Water extracts of immature Rubus coreanus regulate lipid metabolism in liver cells. Biol Pharm Bull 35:1907–1913PubMedCrossRefGoogle Scholar
  9. Boath AS, Stewart D, McDougall GJ (2012) Berry components inhibit α-glucosidase in vitro: synergies between acarbose and polyphenols from black currant and rowanberry. Food Chem 135:929–936PubMedCrossRefGoogle Scholar
  10. Bontpart T, Marlin T, Vialet S et al (2016) Two shikimate dehydrogenases, VvSDH3 and VvSDH4, are involved in gallic acid biosynthesis in grapevine. J Exp Bot 67:3537–3550PubMedPubMedCentralCrossRefGoogle Scholar
  11. Borejsza-Wysocki W, Hradzina G (1994) Biosynthesis of p-hydroxyphenylbutan-2-one in raspberry fruits and tissue cultures. Phytochemistry 35:623–628CrossRefGoogle Scholar
  12. Borejsza-Wysocki W, Hrazdina G (1996) Aromatic polyketide synthases. Purification, characterization, and antibody development to benzalacetone synthase from raspberry fruits. Plant Physiol 110:791–799PubMedPubMedCentralCrossRefGoogle Scholar
  13. Borges G, Degeneve A, Mullen W et al (2010) Identification of flavonoid and phenolic antioxidants in black currants, blueberries, raspberries, red currants, and cranberries. J Agric Food Chem 58:3901–3909PubMedCrossRefGoogle Scholar
  14. Bowen-Forbes CS, Zhang YN, Muraleedharan G (2010) Anthocyanin content, antioxidant, anti-inflammatory and anticancer properties of blackberry and raspberry fruits. J Food Compos Anal 23:554–560CrossRefGoogle Scholar
  15. Bradish CM, Perkins-Veazie P, Fernandez GE et al (2012) Comparison of flavonoid composition of red raspberries (Rubus idaeus L.) grown in the Southern United States. J Agric Food Chem 60:5779–5786PubMedCrossRefGoogle Scholar
  16. Brown EM, Gill CIR, McDougall GJ et al (2012) Mechanisms underlying the anti-proliferative effects of berry components in in vitro models of colon cancer. Curr Pharm Biotechnol 13:200–209PubMedCrossRefGoogle Scholar
  17. Brown EM, McDougall GJ, Stewart D et al (2014) Persistence of anticancer activity in berry extracts after simulated gastrointestinal digestion and colonic fermentation. PLoS One 7:e49740CrossRefGoogle Scholar
  18. Burton-Freeman BM, Sandhu AK et al (2016) Red raspberries and their bioactive polyphenols: Cardiometabolic and neuronal health links. Adv Nutr 7:44–65PubMedPubMedCentralCrossRefGoogle Scholar
  19. Bushakra JM, Krieger C, Deng D et al (2013) QTL involved in the modification of cyanidin compounds in black and red raspberry fruit. Theor Appl Genet 126:847–865PubMedCrossRefGoogle Scholar
  20. Bushman BS, Phillips B, Isbell T et al (2004) Chemical composition of caneberry (Rubus spp.) seeds and oils and their antioxidant potential. J Agric Food Chem 52:7982–7987PubMedCrossRefGoogle Scholar
  21. Carvalho E, Fraser PD, Martens S (2013a) Carotenoids and tocopherols in yellow and red raspberries. Food Chem 139:744–752PubMedCrossRefGoogle Scholar
  22. Carvalho E, Franceschi P, Feller A et al (2013b) A targeted metabolomics approach to understand differences in flavonoid biosynthesis in red and yellow raspberries. Plant Physiol Biochem 72:79–86PubMedCrossRefGoogle Scholar
  23. Çekiç Ç, Özgen M (2010) Comparison of antioxidant capacity and phytochemical properties of wild and cultivated red raspberries (Rubus idaeus L.). J Food Compos Anal 23:540–544CrossRefGoogle Scholar
  24. Chen F, Tholl D, Bohlmann J et al (2011) The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J 66:212–229PubMedCrossRefGoogle Scholar
  25. Chen L, Xin X, Yuan Q et al (2014) Phytochemical properties and antioxidant capacities of various colored berries. J Sci Food Agric 94:180–188PubMedCrossRefGoogle Scholar
  26. Chen W, Xu Y, Zhang LX et al (2016a) Blackberry subjected to in vitro gastrointestinal digestion affords protection against ethyl carbamate-induced cytotoxicity. Food Chem 212:620–627PubMedCrossRefGoogle Scholar
  27. Chen W, Su HM, Xu Y et al (2016b) Protective effect of wild raspberry (Rubus hirsutus Thunb.) extract against acrylamide-induced oxidative damage is potentiated after simulated gastrointestinal digestion. Food Chem 196:943–952PubMedCrossRefGoogle Scholar
  28. Cheng Z, White MF (2011) Targeting forkhead box O1 from the concept to metabolic diseases: lessons from mouse models. Antioxid Redox Signal 14:649–661PubMedPubMedCentralCrossRefGoogle Scholar
  29. Chong MF, Macdonald R, Lovegrove JA (2010) Fruit polyphenols and CVD risk: a review of human intervention studies. Br J Nutr 104:S28–S39PubMedCrossRefGoogle Scholar
  30. Claussnitzer M, Skurk T, Hauner H et al (2011) Effect of flavonoids on basal and insulin-stimulated 2-deoxyglucose uptake in adipocytes. Mol Nutr Food Res 55:S26–S34PubMedCrossRefGoogle Scholar
  31. Coates EM, Popa G, Gill CI et al (2007) Colon-available raspberry polyphenols exhibit anti-cancer effects on in vitro models of colon cancer. J Carcinogenesis 18:1–6Google Scholar
  32. Connor AM, McGhie TK, Stephens MJ et al (2005) Variation and heritability estimates of anthocyanins and their relationship to antioxidant activity in a red raspberry factorial mating design. J Am Soc Hortic Sci 130:534–542Google Scholar
  33. de Oliveira PB, Silva MJ, Ferreira RB et al (2007) Dry matter partitioning, carbohydrate composition, protein reserves, and fruiting in ‘Autumn Bliss’ red raspberry vary in response to pruning date and cane density. HortSci 42:77–82Google Scholar
  34. Deighton N, Brennan R, Finn C et al (2000) Antioxidant properties of domesticated and wild Rubus species. J Sci Food Agric 80:1307–1313CrossRefGoogle Scholar
  35. Dincheva I, Badjakov I, Kondakova V et al (2013a) Metabolic profiling of red raspberry (Rubus idaeus) during fruit development and ripening. Int J Agr Sci 3:81–88Google Scholar
  36. Dincheva I, Badjakov I, Kondakova V et al (2013b) Identification of the phenolic components in Bulgarian raspberry cultivars by LC-ESI-MSn. Int J Agr Sci 3:127–138Google Scholar
  37. Dobson P, Graham J, Stewart D et al (2012) Over-seasons analysis of quantitative trait loci affecting phenolic content and antioxidant capacity in raspberry. J Agric Food Chem 60:5360–5366PubMedCrossRefGoogle Scholar
  38. Eid HM, Martineau LC, Saleem A et al (2010) Stimulation of AMP-activated protein kinase and enhancement of basal glucose uptake in muscle cells by quercetin and quercetin glycosides, active principles of the antidiabetic medicinal plant Vaccinium vitis-idaea. Mol Nutr Food Res 54:991–1003PubMedCrossRefGoogle Scholar
  39. Famiani F, Cultrera NGM, Battistelli A et al (2005) Phosphoenol pyruvate carboxykinase and its potential role in the catabolism of organic acids in the flesh of soft fruit during ripening. J Exp Bot 56:2959–2969PubMedCrossRefGoogle Scholar
  40. Feresin RG, Huang JW, Klarich DS et al (2016) Blackberry, raspberry and black raspberry polyphenol extracts attenuate angiotensin II-induced senescence in vascular smooth muscle cells. Food Funct 7:4175–4187PubMedCrossRefPubMedCentralGoogle Scholar
  41. Ferrer J-L, Austin MB, Stewart C et al (2008) Structure and function of enzymes involved in the biosynthesis of phenylpropanoids. Plant Physiol Biochem 46:356–370PubMedCrossRefGoogle Scholar
  42. Fotirić Akšić M, Radović A, Milivojević J et al (2011) Genetic parameters of yield components and pomologic properties in raspberry seedlings. Genetika 43:667–674CrossRefGoogle Scholar
  43. Freeman BL, Stocks JC, Eggett DL et al (2011) Antioxidant and phenolic changes across one harvest season and two storage conditions in primocane raspberries (Rubus idaeus L.) grown in a hot, dry climate. HortSci 46:236–239Google Scholar
  44. Galleano M, Pechanova O, Fraga CG (2010) Hypertension, nitric oxide, oxidants, and dietary plant polyphenols. Curr Pharm Biotechnol 11:837–848PubMedCrossRefGoogle Scholar
  45. Garcia G, Nanni S, Figueira I et al (2012) Bio-accessible (poly)phenol metabolites from raspberry protect neural cells from oxidative stress and attenuate microglia activation. Food Chem 215:274–283CrossRefGoogle Scholar
  46. Gasperotti M, Masuero D, Vrhovsek U et al (2010) Profiling and accurate quantification of Rubus ellagitannins and ellagic acid conjugates using direct UPLC-Q-TOF HDMS and HPLC-DAD analysis. J Agric Food Chem 58:4602–4616PubMedCrossRefGoogle Scholar
  47. Godevac D, Tesević V, Vajs V et al (2009) Antioxidant properties of raspberry seed extracts on micronucleus distribution in peripheral blood lymphocytes. Food Chem Toxicol 47:2853–2859PubMedCrossRefGoogle Scholar
  48. Gonzalez-Sarrias A, Nunez-Sanchez MA, Tomas-Barberan FA et al (2017a) Neuroprotective effects of bioavailable polyphenol-derived metabolites against oxidative stress-induced cytotoxicity in human neuroblastoma SH-SY5Y cells. J Agric Food Chem 65:752–758PubMedCrossRefPubMedCentralGoogle Scholar
  49. Gonzalez-Sarrias A, Nunez-Sanchez MA, Garcia-Villalba R et al (2017b) Antiproliferative activity of the ellagic acid-derived gut microbiota isourolithin A and comparison with its urolithin A isomer: the role of cell metabolism. Eur J Nutr 56:831–841PubMedCrossRefGoogle Scholar
  50. Gorelik S, Lapidot T, Shaham I et al (2005) Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fluid inhibited by dietary polyphenols: health implications. J Agric Food Chem 53:3397–3402PubMedCrossRefGoogle Scholar
  51. Grussu D, Stewart D, McDougall GJ (2011) Berry polyphenols inhibit alpha-amylase in vitro: identifying active components in rowanberry and raspberry. J Agric Food Chem 59:2324–2331PubMedCrossRefGoogle Scholar
  52. Gu L, Kelm MA, Hammerstone JF et al (2003) Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. J Agric Food Chem 51:7513–7521PubMedCrossRefGoogle Scholar
  53. Halliwell B (2007) Biochemistry of oxidative stress. Biochem Soc Trans 35:1147–1150PubMedCrossRefGoogle Scholar
  54. Hampel D, Swatski A, Mosand A et al (2007) Biosynthesis of monoterpenes and norisoprenoids in raspberry fruits (Rubus idaeus L.): the role of cytosolic mevalonate and plastidial methylerythritol phosphate pathway. J Agric Food Chem 55:9296–9304PubMedCrossRefGoogle Scholar
  55. Hancock RD, McDougall GJ, Stewart D (2007) Berry fruit as ‘superfoods’: hope or hype? Biologist 54:73–79Google Scholar
  56. Hanhineva K, Torronen R, Bondia-Pons I et al (2010) Impact of dietary polyphenols on carbohydrate metabolism. Int J Mol Sci 11:1365–1402PubMedPubMedCentralCrossRefGoogle Scholar
  57. He M, Tian H, Luo X et al (2015) Molecular progress in research on fruit astringency. Molecules 20:1434–1451PubMedCrossRefPubMedCentralGoogle Scholar
  58. Hsieh YS, Chu SC, Hsu LS et al (2013) Rubus idaeus L. reverses epithelial-to-mesenchymal transition and suppresses cell invasion and protease activities by targeting ERK1/2 and FAK pathways in human lung cancer cells. Food Chem Toxicol 62:908–918PubMedCrossRefPubMedCentralGoogle Scholar
  59. Hyun TK, Lee S, Kumar D et al (2014) RNA-seq analysis of Rubus idaeus cv. Nova: transcriptome sequencing and de novo assembly for subsequent functional genomics approaches. Plant Cell Rep 33:1617–1628PubMedCrossRefPubMedCentralGoogle Scholar
  60. Im SE, Nam TG, Lee H et al (2013) Anthocyanins in the ripe fruits of Rubus coreanus Miguel and their protective effect on neuronal PC-12 cells. Food Chem 139:604–610PubMedCrossRefPubMedCentralGoogle Scholar
  61. Jennings N, Graham J, Ferguson L et al (2016) New developments in raspberry breeding in Scotland. Acta Hortic 1133:23–28CrossRefGoogle Scholar
  62. Jeong MY, Kim HL, Park J et al (2013) Rubi Fructus (Rubus coreanus) inhibits differentiation to adipocytes in 3T3-L1 cells. Evid Based Complement Alternat Med 2013:475386PubMedPubMedCentralGoogle Scholar
  63. Jeong MY, Kim HL, Park J et al (2015) Rubi Fructus (Rubus coreanus) activates the expression of thermogenic genes in vivo and in vitro. Int J Obes 39:456–464CrossRefGoogle Scholar
  64. Jia H, Liu JW, Ufur HM et al (2011) The antihypertensive effect of ethyl acetate extract from red raspberry fruit in hypertensive rats. Pharmacogn Mag 7:19–24PubMedPubMedCentralCrossRefGoogle Scholar
  65. Jung MS, Lee SJ, Song Y et al (2016) Rubus crataegifolius Bunge regulates adipogenesis through Akt and inhibits high-fat diet-induced obesity in rats. Nutr Metab 13:29CrossRefGoogle Scholar
  66. Kang I, Espin JC, Carr TP et al (2016) Raspberry seed flour attenuates high-sucrose diet-mediated hepatic stress and adipose tissue inflammation. J Nutr Biochem 32:64–72PubMedCrossRefPubMedCentralGoogle Scholar
  67. Kassim A, Poette J, Paterson A et al (2009) Environmental and seasonal influences on red raspberry anthocyanin antioxidant contents and identification of quantitative traits loci (QTL). Mol Nutr Food Res 53:625–634PubMedCrossRefGoogle Scholar
  68. Klee HJ (2010) Improving the flavor of fresh fruits: genomics, biochemistry, and biotechnology. New Phytol 187:44–56PubMedCrossRefPubMedCentralGoogle Scholar
  69. Klesk K, Qian M, Martin RR (2004) Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington. J Agric Food Chem 52:5155–5161PubMedCrossRefGoogle Scholar
  70. Koeduka T, Watanabe B, Suzuki S et al (2011) Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits. Biochem Biophys Res Commun 412:104–108PubMedCrossRefGoogle Scholar
  71. Koli R, Erlund I, Jula A et al (2010) Bioavailability of various polyphenols from a diet containing moderate amounts of berries. J Agric Food Chem 58:3927–3932PubMedCrossRefGoogle Scholar
  72. Krüger E, Dietrich H, Schöpplein E et al (2011) Cultivar, storage conditions and ripening effects on physical and chemical qualities of red raspberry fruit. Postharvest Biol Technol 60:31–37CrossRefGoogle Scholar
  73. Kula M, Majdan M, Glód D et al (2016) Phenolic composition of fruits from different cultivars of red and black raspberries grown in Poland. J Food Compos Anal 52:74–82CrossRefGoogle Scholar
  74. Kumar A, Ellis BE (2001) The phenylalanine ammonia-lyase gene family in raspberry. Structure, expression, and evolution. Plant Physiol 127:230–239PubMedPubMedCentralCrossRefGoogle Scholar
  75. Kumar A, Ellis BE (2003) A family of polyketide synthase genes expressed in ripening Rubus fruits. Phytochemistry 62:513–526PubMedCrossRefGoogle Scholar
  76. Ladiwala AR, Mora-Pale M, Lin JC et al (2011) Polyphenolic glycosides and aglycones utilize opposing pathways to selectively remodel and inactivate toxic oligomers of amyloid beta. Chembiochem 12:1749–1758PubMedPubMedCentralCrossRefGoogle Scholar
  77. Larsen M, Poll L (1990) Odour thresholds of some important aroma compounds in raspberries. Z Lebensm Unters Forsch 191:129–131Google Scholar
  78. Larsen M, Poll L, Callesen O et al (1991) Relations between the content of aroma compounds and the sensory evaluation of 10 raspberry varieties (Rubus idaeus L). Acta Agric Scand 41:447–454CrossRefGoogle Scholar
  79. Lee J (2015) Sorbitol, Rubus fruit, and misconception. Food Chem 166:616–622PubMedCrossRefPubMedCentralGoogle Scholar
  80. Lee SJ, Lee HK (2005) Sanguiin H-6 blocks endothelial cell growth through inhibition of VEGF binding to VEGF receptor. Arch Pharm Res 28:1270–1274PubMedCrossRefPubMedCentralGoogle Scholar
  81. Lee D, Ko H, Kim YJ et al (2016) Inhibition of A2780 human ovarian carcinoma cell proliferation by a Rubus component, sanguiin H-6. J Agric Food Chem 64:801–805PubMedCrossRefGoogle Scholar
  82. Lo Piparo E, Scheib H, Frei N et al (2008) Flavonoids for controlling starch digestion: structural requirements for inhibiting human alpha-amylase. J Med Chem 51:3555–3561PubMedCrossRefGoogle Scholar
  83. Ludwig IA, Mena P, Calani L et al (2015) New insights into the bioavailability of red raspberry anthocyanins and ellagitannins. Free Radic Biol Med 89:758–769PubMedCrossRefGoogle Scholar
  84. Luo T, Miranda-Garcia O, Adamson A et al (2016) Development of obesity is reduced in high-fat fed mice fed whole raspberries, raspberry juice concentrate, and a combination of the raspberry phytochemicals ellagic acid and raspberry ketone. J Berry Res 6:213–223CrossRefGoogle Scholar
  85. Maksimović JJD, Milivojević JM, Poledica MM et al (2013) Profiling antioxidant activity of two primocane fruiting red raspberry cultivars (autumn bliss and polka). J Food Compos Anal 31:173–179CrossRefGoogle Scholar
  86. Malowicki SMM, Martin R, Qian MC (2008) Volatile composition of raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry. J Agric Food Chem 56:4128–4133PubMedCrossRefGoogle Scholar
  87. Manzano S, Williamson G (2010) Polyphenols and phenolic acids from strawberry and apple decrease glucose uptake and transport by human intestinal Caco-2 cells. Mol Nutr Food Res 54:1773–1780PubMedCrossRefGoogle Scholar
  88. Martineau LC, Couture A, Spoor D et al (2006) Anti-diabetic properties of the Canadian lowbush blueberry Vaccinium angustifolium Ait. Phytomed 13:612–623CrossRefGoogle Scholar
  89. Mazur SP, Sønsteby A, Nes A et al (2014a) Effects of post-flowering environmental variation along an altitudinal gradient on chemical composition of ‘Glen Ample’ red raspberry (Rubus idaeus L.). Europ J Hortic Sci 79:267–277Google Scholar
  90. Mazur SP, Sønsteby A, Wold A-B et al (2014b) Post-flowering photoperiod has marked effects on fruit chemical composition in red raspberry (Rubus idaeus). Ann Appl Biol 165:454–465CrossRefGoogle Scholar
  91. Mazur SP, Nes A, Wold A-B et al (2014c) Quality and chemical composition of ten red raspberry (Rubus idaeus L.) genotypes during three harvest seasons. Food Chem 160:233–240PubMedCrossRefGoogle Scholar
  92. Mazzoni L, Perez-Lopez P, Giampieri F et al (2016) The genetic aspects of berries: from field to health. J Sci Food Agric 96:365–371PubMedCrossRefGoogle Scholar
  93. McDougall GJ, Shpiro F, Dobson P et al (2005) Different polyphenolic components of soft fruits inhibit α-amylase and α-glucosidase. J Agric Food Chem 53:2760–2766PubMedCrossRefGoogle Scholar
  94. McDougall GJ, Kulkarni NN, Stewart D (2008a) Current developments on the inhibitory effects of berry polyphenols on digestive enzymes. Biofactors 34:73–80PubMedCrossRefGoogle Scholar
  95. McDougall GJ, Ross HA, Ikeji M et al (2008b) Berry extracts exert different antiproliferative effects against cervical and colon cancer cells grown in vitro. J Agric Food Chem 56:3016–3023PubMedCrossRefGoogle Scholar
  96. McDougall GJ, Kulkarni NN, Stewart D (2009) Berry polyphenols inhibit pancreatic lipase activity in vitro. Food Chem 115:193–199CrossRefGoogle Scholar
  97. McDougall GJ, Conner S, Pereira-Caro G et al (2014) Tracking (poly)phenol components from raspberries in ileal fluid. J Agric Food Chem 62:7631–7641PubMedCrossRefGoogle Scholar
  98. McQuinn RP, Giovannoni JJ, Pogson BJ (2015) More than meets the eye: from carotenoid biosynthesis, to new insights into apocarotenoid signaling. Curr Opin Plant Biol 27:172–179PubMedCrossRefGoogle Scholar
  99. Miller MG, Shukitt-Hale B (2012) Berry fruit enhances beneficial signaling in the brain. J Agric Food Chem 60:5709–5715PubMedCrossRefGoogle Scholar
  100. Mineo S, Noguchi A, Nagakura Y et al (2015) Boysenberry polyphenols suppressed elevation of plasma triglyceride levels in rats. J Nutr Sci Vitaminol 61:306–312PubMedCrossRefGoogle Scholar
  101. Moore PP, Burrows C, Fellman J et al (2002) Genotype x environment variation in raspberry fruit aroma volatiles. Acta Hortic 585:511–516CrossRefGoogle Scholar
  102. Morimoto C, Satoh Y, Hara M et al (2005) Anti-obese action of raspberry ketone. Life Sci 77:194–204PubMedCrossRefGoogle Scholar
  103. Moskowitz HR (1970) Ratio scales of sugar sweetness. Percept Psychophys 7:315–320CrossRefGoogle Scholar
  104. Mullen W, McGinn J, Lean MEJ et al (2002) Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties. J Agric Food Chem 50:5191–5196PubMedCrossRefGoogle Scholar
  105. Niggeweg R, Michael AJ, Martin C (2004) Engineering plants with increased levels of the antioxidant chlorogenic acid. Nat Biotechnol 22:746–754PubMedCrossRefGoogle Scholar
  106. Oh HH, Hwang KT, Shin MK et al (2007) Oils in the seeds of caneberries produced in Korea. J Am Oil Chem Soc 84:549–555CrossRefGoogle Scholar
  107. Oh DR, Kim Y, Choi EJ et al (2016) Antiobesity effects of unripe Rubus coreanus Miquel and its constituents: an in vitro and in vivo characterization of the underlying mechanism. Evid Based Complement Alternat Med 2016:4357656PubMedPubMedCentralCrossRefGoogle Scholar
  108. Oomah BD, Ladet S, Godfrey DV et al (2000) Characteristics of raspberry (Rubus idaeus L.) seed oil. Food Chem 69:187–193CrossRefGoogle Scholar
  109. Panchal SK, Ward L, Brown L (2013) Ellagic acid attenuates high-carbohydrate, high-fat diet-induced metabolic syndrome in rats. Eur J Nutr 52:559–568PubMedCrossRefGoogle Scholar
  110. Park KS (2010) Raspberry ketone increases both lipolysis and fatty acid oxidation in 3T3-L1 adipocytes. Planta Med 76:1654–1658PubMedCrossRefGoogle Scholar
  111. Parry J, Su L, Luther M et al (2005) Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils. J Agric Food Chem 53:566–573PubMedCrossRefGoogle Scholar
  112. Paterson A, Kassim A, McCallum S et al (2013) Environmental and seasonal influences on red raspberry flavor volatiles and identification of quantitative trait loci (QTL) and candidate genes. Theor Appl Genet 126:33–48PubMedCrossRefGoogle Scholar
  113. Payyavula RS, Shakya R, Sengoda VG et al (2015) Synthesis and regulation of chlorogenic acid in potato: rerouting phenylpropanoid flux in HQT-silenced lines. Plant Biotechnol J 13:551–564PubMedCrossRefGoogle Scholar
  114. Prior RL, Wu XL, Gu LW et al (2009) Purified berry anthocyanins but not whole berries normalize lipid parameters in mice fed an obesogenic high fat diet. Mol Nutr Food Res 53:1406–1418PubMedCrossRefGoogle Scholar
  115. Prior RL, Wilkes S, Rogers T et al (2010) Dietary black raspberry anthocyanins do not alter development of obesity in mice fed an obesogenic high-fat diet. J Agric Food Chem 58:3977–3983PubMedCrossRefGoogle Scholar
  116. Prior RL, Wilkes SE, Rogers TR et al (2011) Purified blueberry anthocyanins and blueberry juice alter development of obesity in mice fed an obesogenic high-fat diet. J Agric Food Chem 58:3970–3976CrossRefGoogle Scholar
  117. Radočaj O, Vujasinović V, Dimić E et al (2014) Blackberry (Rubus fruticosus L.) and raspberry (Rubus idaeus L.) seed oils extracted from dried press pomace after longterm frozen storage of berries can be used as functional food ingredients. Eur J Lipid Sci Technol 116:1015–1024CrossRefGoogle Scholar
  118. Rafique MZ, Carvalho E, Stracke R et al (2016) Nonsense mutation inside Anthocyanidin synthase gene controls pigmentation in Yellow Raspberry (Rubus idaeus L.). Front Plant Sci 7:1892PubMedPubMedCentralCrossRefGoogle Scholar
  119. Remberg SV, Sønsteby A, Aaby K et al (2010) Influence of postflowering temperature on fruit size and chemical composition of Glen Ample raspberry (Rubus idaeus L.). J Agric Food Chem 58:9120–9128PubMedCrossRefGoogle Scholar
  120. Roberts DD, Acree TE (1996) Effects of heating and cream addition on fresh raspberry aroma using a retronasal aroma simulator and gas chromatography olfactometry. J Agric Food Chem 44:3919–3925CrossRefGoogle Scholar
  121. Rodrigo R, Miranda A, Vergara L (2011) Modulation of endogenous antioxidant system by wine polyphenols in human disease. Clin Chim Acta 412:410–424PubMedCrossRefGoogle Scholar
  122. Ross HA, McDougall GJ, Stewart D (2007) Antiproliferative activity is predominantly associated with ellagitannins in raspberry extracts. Phytochemistry 68:218–228PubMedCrossRefGoogle Scholar
  123. Rubio A, Rambla JL, Santaella M et al (2008) Cytosolic and plastoglobule-targeted carotenoid cleavage dioxygenases from Crocus sativus are both involved in β-ionone release. J Biol Chem 283:24816–24825PubMedPubMedCentralCrossRefGoogle Scholar
  124. Sakai E, Aoki Y, Yoshimatsu M et al (2016) Sanguiin H-6, a constituent of Rubus parvifolius L., inhibits receptor activator of nuclear factor-κΒ ligand-induced osteoclastogenesis and bone resorption in vitro and prevents tumor necrosis factor-α-induced osteoclast formation in vivo. Phytomed 23:828–837CrossRefGoogle Scholar
  125. Sangiovanni E, Vrhovsek U, Rossoni G et al (2013) Ellagitannins from Rubus berries for the control of gastric inflammation: in vitro and in vivo studies. PLoS One 8:e71762PubMedPubMedCentralCrossRefGoogle Scholar
  126. Savi M, Bocchi L, Mena P et al (2017) In vivo administration of urolithin a and B prevents the occurrence of cardiac dysfunction in streptozotocin-induced diabetic rats. Cardiovas Diabet 16:80CrossRefGoogle Scholar
  127. Scalzo J, Currie A, Stephens J et al (2008) The anthocyanin composition of different Vaccinium, Ribes and Rubus genotypes. Biofactors 34:13–21PubMedCrossRefGoogle Scholar
  128. Scazzocchio B, Vari R, Filesi C et al (2011) Cyanidin-3-O-beta-glucoside and protocatechuic acid exert insulin-like effects by upregulating PPAR-gamma activity in human omental adipocytes. Diabetes 60:2234–2244PubMedPubMedCentralCrossRefGoogle Scholar
  129. Schulenburg K, Feller A, Hoffmann T et al (2016) Formation of β-glucogallin, the precursor of ellagic acid in strawberry and raspberry. J Exp Bot 67:2299–2308PubMedPubMedCentralCrossRefGoogle Scholar
  130. Seeram NP, Adams LS, Zhang YJ et al (2006) Blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry extracts inhibit growth and stimulate apoptosis of human cancer cells in vitro. J Agric Food Chem 54:9329–9339PubMedCrossRefGoogle Scholar
  131. Seymour EM, Tanone II, Urcuyo-Llanes DE et al (2011) Blueberry intake alters skeletal muscle and adipose tissue peroxisome proliferator-activated receptor activity and reduces insulin resistance in obese rats. J Med Food 14:1511–1518PubMedCrossRefGoogle Scholar
  132. Shamaila M, Skura B, Daubeny H et al (1993) Sensory, chemical and gas chromatogtaphic evaluation of five raspberry cultivars. Food Res Int 26:443–449CrossRefGoogle Scholar
  133. Simkin AJ, Underwood BA, Auldridge M et al (2004) Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of β-ionone, a fragrance volatile of petunia flowers. Plant Physiol 136:3504–3514PubMedPubMedCentralCrossRefGoogle Scholar
  134. Spencer JPE (2010) The impact of fruit flavonoids on memory and cognition. Brit J Nutr 104:S40–S47PubMedCrossRefGoogle Scholar
  135. Stavang JA, Freitag S, Foito A et al (2015) Raspberry fruit quality changes during ripening and storage as assessed by colour, sensory evaluation and chamical analyses. Sci Hortic 195:216–225CrossRefGoogle Scholar
  136. Stull AJ, Cash CK, Johnson WD et al (2010) Bioactives in blueberries improve insulin sensitivity in obese, insulin-resistant men and women. J Nutr 140:1764–1768PubMedPubMedCentralCrossRefGoogle Scholar
  137. Sun P, Schuurink RC, Caissard J-C et al (2016) My way: noncanonical biosynthesis pathways for plant volatiles. Trends Plant Sci 21:884–894PubMedCrossRefGoogle Scholar
  138. Sweetlove LJ, Beard KFM, Nunes-Nesi A et al (2010) Not just a circle: flux modes in the plant TCA cycle. Trends Plant Sci 15:462–470PubMedCrossRefGoogle Scholar
  139. Takikawa M, Inoue S, Horio F et al (2010) Dietary anthocyanin-rich bilberry extract ameliorates hyperglycemia and insulin sensitivity via activation of AMP-activated protein kinase in diabetic mice. J Nutr 140:527–533PubMedCrossRefGoogle Scholar
  140. Tavares L, Figueira I, Macedo D et al (2012) Neuroprotective effect of blackberry (Rubus sp.) polyphenols is potentiated after simulated gastrointestinal digestion. Food Chem 131:1443–1452CrossRefGoogle Scholar
  141. Tavares L, Figueira I, McDougall GJ et al (2013) Neuroprotective effects of digested polyphenols from wild blackberry species. Eur J Nutr 52:225–236PubMedCrossRefGoogle Scholar
  142. Tomas-Barberan FA, Gonzalez-Sarrias A, Garcia-Villalba R et al (2017) Urolithins, the rescue of “old” metabolites to understand a “new” concept: Metabotypes as a nexus among phenolic metabolism, microbiota dysbiosis, and host health status. Mol Nutr Food Res 61:1500901CrossRefGoogle Scholar
  143. Tulio AZ, Chang C, Edirisinghe I et al (2012) Berry fruits modulate endothelial cell migration and angiogenesis via phosphoinositide-3 kinase/protein kinase B pathway in vitro in endothelial cells. J Agric Food Chem 60:5803–5812PubMedCrossRefPubMedCentralGoogle Scholar
  144. Villamor RR, Daniels CH, Moore PP et al (2013) Preference mapping of frozen and fresh raspberries. J Food Sci 78:S911–S919PubMedCrossRefPubMedCentralGoogle Scholar
  145. Wang SY, Lin H-S (2000) Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage. J Agric Food Chem 48:140–146PubMedCrossRefPubMedCentralGoogle Scholar
  146. Wang SY, Chen C-T, Wang CY (2009) The influence of light and maturity on fruit quality and flavonoid content of red raspberries. Food Chem 112:676–684CrossRefGoogle Scholar
  147. Whitley AC, Sweet DH, Walle T (2006) Site-specific accumulation of the cancer preventive dietary polyphenol ellagic acid in epithelial cells of the aerodigestive tract. J Pharm Pharmacol 58:1201–1209PubMedCrossRefPubMedCentralGoogle Scholar
  148. Williamson G, Clifford MN (2010) Colonic metabolites of berry polyphenols: the missing link to biological activity? Brit J Nutr 104:S48–S66PubMedCrossRefPubMedCentralGoogle Scholar
  149. Wu X, Beecher GR, Holden JM et al (2004) Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. J Agric Food Chem 52:4026–4037PubMedCrossRefGoogle Scholar
  150. Yang B, Ahotupa M, Määttä P et al (2011) Composition and antioxdative activities of supercritical CO2-extracted oils from seeds and soft parts of northern berries. Food Res Int 44:2009–2017CrossRefGoogle Scholar
  151. Yu O, Jez JM (2008) Nature’s assembly line: biosynthesis of simple phenylpropanoids and polyketides. Plant J 54:750–762PubMedCrossRefGoogle Scholar
  152. Zheng D, Hrazdina G (2008) Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.). Arch Biochem Biophys 470:139–145PubMedCrossRefGoogle Scholar
  153. Zheng D, Schröder G, Schröder J et al (2001) Molecular and biochemical characterization of three aromatic polyketide synthase genes from Rubus idaeus. Plant Mol Biol 46:1–15PubMedCrossRefGoogle Scholar
  154. Zhu Y, Xia M, Yang Y et al (2011) Purified anthocyanin supplementation improves endothelial function via NO-cGMP activation in hyper-cholesterolemic individuals. Clin Chem 57:1524–1533PubMedCrossRefGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2018

Authors and Affiliations

  • Robert D. Hancock
    • 1
    Email author
  • Antonios Petridis
    • 1
  • Gordon J. McDougall
    • 2
  1. 1.Cell & Molecular SciencesThe James Hutton InstituteDundeeUK
  2. 2.Environmental and Biochemical SciencesThe James Hutton InstituteDundeeUK

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