Contribution of amylose-procyanidin complexes to slower starch digestion of red-colored rice prepared by cooking with adzuki bean

References

• Amarowicz R, Pegg RB. 2006. Content of proanthocyanidins in selected plant extract as determined via n-butanol/HCl hydrolysis and a colorimetric assay or by HPLC − a short report. Pol J Food Nutr Sci. 56:319–322.
   Google Scholar
• Amarowicz R, Estrella I, Hernández T, Troszyńska A. 2008. Antioxidant activity of extract of adzuki bean and its fractions. J Food Lipids. 15(1):119–136.
   Google Scholar
• Ariga T, Asao Y. 1981. Isolation, identification and organoleptic astringency of dimeric proanthocyanidins occurring in adzuki bean. Agr Biol Chem. 45:2709–2712.
   Web of Science ®Google Scholar
• Barros F, Awika J, Rooney LW. 2014. Effect of molecular weight profile of sorghum proanthocyanidins on resistant starch formation. J Sci Food Agric. 94(6):1212–1217.
   PubMed Web of Science ®Google Scholar
• Barros F, Awika JM, Rooney LW. 2012. Interaction of tannins and other sorghum phenolic compounds with starch and effects on in vitro starch digestibility. J Agric Food Chem. 60(46):11609–11617.
   PubMed Web of Science ®Google Scholar
• Bidzińska E. 2015. Thermally generated radicals as indicators of the starch modification studied by EPR spectroscopy: a review. Carbohyd Polym. 124:139–149.
   PubMed Web of Science ®Google Scholar
• Bordenave N, Hamaker BR, Ferruzzi MG. 2014. Nature and consequences of non-covalent interactions between flavonoids and macronutrients in foods. Food Funct. 5(1):18–34.
   PubMed Web of Science ®Google Scholar
• Chao C, Cai J, Yu J, Copeland L, Wang S, Wang S. 2018. Toward a better understanding of starch-monoglyceride-protein interactions. J Agric Food Chem. 66(50):13253–13259.
   PubMed Web of Science ®Google Scholar
• Choy YY, Waterhouse AL. 2014. Proanthocyanidin metabolism, a mini review. Nutr Aging. 2(2–3):111–116.
   Google Scholar
• Chung HJ, Liu Q, Lee L, Wei D. 2011. Relationship between the structure, physicochemical properties and in vitro digestibility of rice starches with different amylose contents. Food Hydrocolloid. 25(5):968–975.
   Web of Science ®Google Scholar
• Cires MJ, Wong X, Carrasco-Pozo C, Gotteland M. 2017. The gastrointestinal tract as a key target organ for the health-promoting effects of dietary proanthocyanidins. Front Nutr. 3:57.
   PubMed Web of Science ®Google Scholar
• Cohen R, Orlova Y, Kovalev M, Ungar Y, Shimoni E. 2008. Structural and functional properties of amylose complexes with genistein. J Agric Food Chem. 56(11):4212–4218.
   PubMed Web of Science ®Google Scholar
• Crowe TC, Seligman SA, Copeland L. 2000. Inhibition of enzymatic digestion of amylose by free fatty acids in vitro contributes to resistant starch formation. J Nutr. 130(8):2006–2008.
   PubMed Web of Science ®Google Scholar
• de Freitas VA, Glories Y, Bourgeois G, Vitry C. 1998. Characterisation of oligomeric and polymeric procyanidins from grape seeds by liquid secondary ion mass spectrometry. Phytochemistry. 49(5):1435–1441.
   Web of Science ®Google Scholar
• De Taeye C, Kankolongo Cibaka ML, Jerkovic V, Collin S. 2014. Degradation of (−)-epicatechin and procyanidin B2 in aqueous and lipidic model systems. First evidence of “chemical” flavan-3-ol oligomers in processed cocoa. J Agric Food Chem. 62(36):9002–9016.
   PubMed Web of Science ®Google Scholar
• Guzar I, Ragaee S, Seetharaman K. 2012. Mechanism of hydrolysis of native and cooked starches from different botanical sources in the presence of tea extracts. J Food Sci. 77(11):C1192–C1196.
   PubMed Web of Science ®Google Scholar
• Han K-H, Kitano-Okada T, Seo J-M, Kim S-J, Sasaki K, Shimada K-i, Fukushima M. 2015. Characterisation of anthocyanins and proanthocyanidins of adzuki bean extracts and their antioxidant activity. J Funct Food. 14:692–701.
   Web of Science ®Google Scholar
• Hanashiro I, Ohta K, Takeda C, Mizukami H, Takeda Y. 2004. Leaching of amylose and amylopectin during cooking of rice grains and their effect on adhesiveness of cooked rice. J Appl Glycosci. 51(4):349–354.
   Google Scholar
• Hirota S, Takahama U. 2014. Reactions of apple fruit polyphenols with nitrite under conditions of the gastric lumen: generation of nitric oxide and formation of nitroso catechins. Food Sci Technol Res. 20(2):439–447.
   Web of Science ®Google Scholar
• Hirota S, Takahama U. 2015. Reactions of polyphenols in masticated apple fruit with nitrite under stomach simulating conditions: formation of nitroso compounds and thiocyanate conjugates. Food Res Int. 75:20–26.
   PubMed Web of Science ®Google Scholar
• Hirota S, Takahama U. 2017. Inhibition of pancreatin-induced digestion of cooked rice starch by adzuki (Vigana angularis) bean flavonoids and the possibility of a decrease in the Inhibitory effects in the stomach. J Agric Food Chem. 65(10):2172–2179.
   PubMed Web of Science ®Google Scholar
• Hirota S, Takahama U. 2018. Suppression of pancreatin-induced digestion of starch in starch granules by starch/fatty acid and starch/flavonoid complexes in retrograding rice flour. Foods. 7(8):128.
   Web of Science ®Google Scholar
• Hofmann T, Glabasnia A, Schwarz B, Wisman K N, Gangwer K A, Hagerman A E. 2006. Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-Penta-O-galloyl-D-glucopyranose, castalagin, and grandinin. J Agric Food Chem. 54(25):9503–9509.
   PubMed Web of Science ®Google Scholar
• Kawakami K, Aketa S, Nakanami M, Iizuka S, Hirayama M. 2010. Major water-soluble polyphenols, proanthocyanidins, in leaves of persimmon (Diospyros kaki) and their α-amylase inhibitory activity. Biosci Biotechnol Biochem. 74(7):1380–1385.
   PubMed Web of Science ®Google Scholar
• Kwasniewska-Karolak I, Nebesny E, Rosicka-Kaczmarek J. 2008. Characterization of amylose-lipid complexes derived from different wheat varieties and their susceptibility to enzymatic hydrolysis. Food Sci Technol Int. 14:29–37.
   Web of Science ®Google Scholar
• Łabanowska M, Kurdziel M, Filek M, Walas S, Tobiasz A, Wesełucha-Birczyńska A. 2014. The influence of the starch component on thermal radical generation in flours. Carbohyd Polym. 101:846–856.
   PubMed Web of Science ®Google Scholar
• Magallanes-Cruz PA, Flores-Silva PC, Bello-Perez LA. 2017. Starch structure influences its digestibility: A review. J Food Sci. 82:2016–2023.
   PubMed Web of Science ®Google Scholar
• Ohta H, Aibara S, Yamashita H, Sekiyama F, Morita Y. 1990. Post-harvest drying of fresh rice grain and its effects on deterioration of lipid during storage. Agr Biol Chem. 54:1157–1164.
   Web of Science ®Google Scholar
• Ozdal T, Capanoglu E, Altay F. 2013. A review on protein-phenolic interactions and associated changes. Food Res Int. 51(2):954–970.
   Web of Science ®Google Scholar
• Porter LJ, Hrstich LN, Chan BG. 1985. The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry. 25(1):223–230.
   Web of Science ®Google Scholar
• Poupard P, Sanoner P, Baron A, Renard C, Guyot S. 2011. Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry. J Mass Spectrom. 46(11):1186–1197.
   PubMed Web of Science ®Google Scholar
• Ravindranatha P, Pasham D, Balaji U, Cardenas J, Gu J, Toden S, Goel A. 2018. Mechanistic insights into anticancer properties of oligomeric proanthocyanidins from grape seeds in colorectal cancer. Carcinogenesis. 39:767–777.
   PubMed Web of Science ®Google Scholar
• Renard CM, Watrelot AA, Le Bourvellec C. 2017. Interactions between polyphenols and polysaccharides: mechanisms and consequences in food processing and digestion. Trends Food Sci Tech. 60:43–51.
   Web of Science ®Google Scholar
• Sun L, Gidley MJ, Warren FJ. 2018. Tea polyphenols enhance binding of porcine pancreatic α-amylase with starch granules but reduce catalytic activity. Food Chem. 258:164–173.
   PubMed Web of Science ®Google Scholar
• Sutcliffe TC, Winter AN, Punessen NC, Linseman DA. 2017. Procyanidin B2 protects neurons from oxidative, nitrosative, and excitotoxic stress. Antioxidants. 6(4):77.
   Web of Science ®Google Scholar
• Takahama U, Hirota S, Morina F. 2020. Procyanidins in rice cooked with adzuki bean and their contribution to the reduction of nitrite to nitric oxide (NO) in artificial gastric juice. Int J Food Sci Nutr. 71(1):63–73.
   PubMed Web of Science ®Google Scholar
• Takahama U, Hirota S, Yanase E. 2019. Slow starch digestion in the rice cooked with adzuki bean: contribution of procyanidins and the oxidation products. Food Res Int. 119:187–195.
   PubMed Web of Science ®Google Scholar
• Takahama U, Hirota S. 2013. Effects of starch on nitrous acid-induced oxidation of kaempferol and inhibition of α-amylase-catalysed digestion of starch by kaempferol under conditions simulating the stomach and the intestine. Food Chem. 141(1):313–319.
   PubMed Web of Science ®Google Scholar
• Takahama U, Hirota S. 2017. Possible reactions of dietary phenolic compounds with salivary nitrite and thiocyanate in the stomach. Antioxidants. 65:pii: E53.
   Google Scholar
• Takahama U, Yamauchi R, Hirota S. 2013. Interactions of starch with a cyanidin-catechin pigment (vignacyanidin) isolated from Vigna angularis bean. Food Chem. 141(3):2600–2605.
   PubMed Web of Science ®Google Scholar
• Takahama U, Yamauchi R, Hirota S. 2016. Antioxidative flavonoids in adzuki-meshi (rice boiled with adzuki bean) react with nitrite under simulated stomach conditions. J Funct Food. 26:657–666.
   Web of Science ®Google Scholar
• Tamura M, Ogawa Y. 2012. Visualization of the coated layer at the surface of rice grain cooked with varying amounts of cooking water. J Cereal Sci. 56(2):404–409.
   Web of Science ®Google Scholar
• US Department of Agriculture Nutrient Data Laboratory (USDA). 2004. USDA database for the proanthocyanidin content of selected foods. US Department of Agriculture. [accessed 2020 Jan 20]. http://www.nal.usda.gov/fnic/foodcomp.
   Google Scholar
• Wang H, Liu T, Song L, Huang D. 2012. Profiles and α-amylase inhibition activity of proanthocyanidins in unripe manikara zapota (Chiku). J Agri Food Chem. 60:3089–3104.
   Web of Science ®Google Scholar
• Wang S, Li C, Copeland L, Niu Q, Wang S. 2015. Starch retrogradation: a comprehensive review. Compr Rev Food Sci F. 14(5):568–585.
   Google Scholar
• Wang S, Zheng M, Yu J, Wang S, Copeland L. 2017. Insights into the formation and structures of starch–protein–lipid complexes. J Agric Food Chem. 65(9):1960–1966.
   PubMed Web of Science ®Google Scholar
• Wu Y, Lin Q, Chen Z, Xiao H. 2011. The interaction between tea polyphenols and rice starch during gelatinization. Food Sci Technol Int. 17(6):569–577.
   PubMed Web of Science ®Google Scholar
• Xie F, Poller E, Halley PJ, Avérous L. 2014. Advanced nano-biochomposites based on starch. In: Ranawat K, Merillon JM, editors. Polysaccharides. Cham: Springer. p. 1–75.
   Google Scholar
• Yang L, Sun YH, Liu Y, Mao Q, You LX, Hou JM, Ashraf MA. 2016. Effects of leached amylose and amylopectin in rice cooking liquid on texture and structure of cooked rice. Braz Arch Biol Techn. 59:e16160504.
   Web of Science ®Google Scholar