Production of oligomeric procyanidins by mild steam explosion treatment of grape seeds

Abstract

Background

Sixty five percent of procyanidins in grape seeds is polymeric procyanidins (PPC), and they could not be assimilated directly by human. To enhance procyanidin assimilation, steam explosion treatment (SE) was used to facilitate the preparation of oligomeric procyanidins (OPC) from grape seeds.

Results

The results indicate that SE treatment made grape seeds loose and porous, and decreased the mean degree of polymerization (mDP) of procyanidins. The procyanidins content and total phenolic content (TPC) were decreased with the increase of SE severity, while the amount of catechin (CA), epicatechin (EC) and epicatechin-3-O-gallate (ECG) were increased, resulting in significant increase of antioxidant activity.

Conclusions

Although SE treatment could depolymerize PPC and produce CA/EC/ECG with high yield, it caused the yield loss of total procyanidins. SE treatment is a potential effective method to prepare procyanidins with low degree of polymerization and high antioxidant activity. However, it still needs to study further how to balance the yield of total procyanidins and catechin monomers (CA/EC/ECG).

Keywords

Polymeric procyanidins / Oligomeric procyanidins / Steam explosion / Depolymerization / Antioxidant activities

References

[1] Alvira P, Tomás-Pejó E, Ballesteros M, Negro MJ. Pretreatment technologies for an efficient bioethanol production process based on enzymatic hydrolysis: a review. Bioresource Technol, 2010, 101(13): 4851-4861.

[2] Bordiga M, Travaglia F, Locatelli M, Coïsson JD, Arlorio M. Characterisation ofpolymeric skin and seed proanthocyanidins during ripening in six Vitis vinifera L. cv. Food Chem, 2011, 127(1): 180-187.

[3] Çam M, Hışıl Y. Pressurised water extraction of polyphenols from pomegranate peels. Food Chem, 2010, 123(3): 878-885.

[4] Carvalheiro F, Duarte LC, Gírio FM. Hemicellulose biorefineries: a review on biomass pretreatments. J Sci Ind Res India, 2008, 67(11): 849-864.

[5] Chen G, Chen H. Extraction and deglycosylation of flavonoids from sumac fruits using steam explosion. Food Chem, 2011, 126(4): 1934-1938.

[6] Chen W, Fu C, QinY HD. One-pot depolymerizative extraction of proanthocyanidins from mangosteen pericarps. Food Chem, 2009, 114(3): 874-880.

[7] Choy YY, Jaggers GK, Oteiza PI, Waterhouse AL. Bioavailability of intact proanthocyanidins in the rat colon after ingestion of grape seed extract. J Agr Food Chem, 2013, 61(1): 121-127.

[8] Conde E, Cara C, Moure A, Ruiz E, Castro E, Domínguez H. Antioxidant activity of the phenolic compounds released by hydrothermal treatments of olive tree pruning. Food Chem, 2009, 114(3): 806-812.

[9] Furuuchi R, Yokoyama T, Watanabe Y, Hirayama M. Identification and quantification of short oligomeric proanthocyanidins and other polyphenols in boysenberry seeds and juice. J Agr Food Chem, 2011, 59(8): 3738-3746.

[10] Gong L, Huang L, Zhang Y. Effect of steam explosion treatment on barley bran phenolic compounds and antioxidant capacity. J Agr Food Chem, 2012, 60(29): 7177-7184.

[11] Gu L, Kelm M, Hammerstone JF, Beecher G, Cunningham D, Vannozzi S, Prior RL. Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC−MS fluorescent detection method. J Agr Food Chem, 2002, 50(17): 4852-4860.

[12] Gu L, Kelm MA, Hammerstone JF, Beecher G, Holden J, Haytowitz D, Prior RL. Concentrations of proanthocyanidins in common foods and estimations of normal consumption. J Nutr, 2004, 134(3): 613-617.

[13] Hayasaka Y, Waters EJ, Cheynier V, Herderich MJ, Vidal S. Characterization of proanthocyanidins in grape seeds using electrospray mass spectrometry. Rapid Commun Mass Sp, 2003, 17(1): 9-16.

[14] Hellström JK, Mattila PH. HPLC determination of extractable and unextractable proanthocyanidins in plant materials. J Agr Food Chem, 2008, 56(17): 7617-7624.

[15] Hümmer W, Schreier P. Analysis of proanthocyanidins. Mol Nutr Food Res, 2010, 52: 1381-1398.

[16] Ito C, Oki T, Yoshida T, Nanba F, Yamada K, Toda T. Characterisation of proanthocyanidins from black soybeans: Isolation and characterisation of proanthocyanidin oligomers from black soybean seed coats. Food Chem, 2013, 141(3): 2507-2512.

[17] Jacquet N, Maniet G, Vanderghem C, Delvigne F, Richel A. Application of steam explosion as pretreatment on lignocellulosic material: a review. Ind Eng Chem Res, 2015, 54(10): 2593-2598.

[18] Li L, Zhang S, Cui Y, Li Y, Luo L, Zhou P, Sun B. Preparative separation of cacao bean procyanidins by high-speed counter-current chromatography. J Chromatog B, 2016, 1036: 10-19.

[19] Li Z, Zeng J, Tong Z, Qi Y, Gu L. Hydrogenolytic depolymerization of procyanidin polymers from hi-tannin sorghum bran. Food Chem, 2015, 188: 337-342.

[20] Lin Q, Cao Q, Huo Q. Study on Degradation process of procyanidins. Asian J Chem, 2014, 26(19): 6665-6668.

[21] Liu H, Zou T, Gao JM, Gu L. Depolymerization of cranberry procyanidins using (+)-catechin, (−)-epicatechin, and (−)-epigallocatechin gallate as chain breakers. Food Chem, 2013, 141(1): 488-494.

[22] Luo L, Cui Y, Zhang S, Li L, Li Y, Zhou P, Sun B. Preparative separation of grape skin polyphenols by high-speed counter-current chromatography. Food Chem, 2016, 212: 712-721.

[23] Luo L, Cui Y, Cheng J, Fang B, Wei Z, Sun B. An approach for degradation of grape seed and skin proanthocyanidin polymers into oligomers by sulphurous acid. Food Chem, 2018, 256: 203-211.

[24] Matthews S, Mila I, Scalbert A, Pollet B, Lapierre C, Catherine LM, Donnelly DM. Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J Agr Food Chem, 1997, 45(4): 1195-1201.

[25] Meeran SM, Katiyar SK. Grape seed proanthocyanidins promote apoptosis in human epidermoid carcinoma A431 cells through alterations in Cdki-Cdk-cyclin cascade, and caspase – 3 activation via loss of mitochondrial membrane potential. Exp Dermatol, 2007, 16(5): 405-415.

[26] Monagas M, Quintanilla-López JE, Gómez-Cordovés C, Bartolomé B, Lebrón-Aguilar R. MALDI-TOF MS analysis of plant proanthocyanidins. J Pharmaceut Biomed, 2010, 51(2): 358-372.

[27] Oldoni TLC, Melo PS, Massarioli AP, Moreno IAM, Bezerra RMN, Rosalen PL, Silva GVJD, Nascimento AM, Alencar SM. Bioassay-guided isolation of proanthocyanidins with antioxidant activity from peanut (Arachis hypogaea) skin by combination of chromatography techniques. Food Chem, 2016, 192: 306-312.

[28] Ou K, Gu L. Absorption and metabolism of proanthocyanidins. J Funct Foods, 2014, 7: 43-53.

[29] Porter LJ. Harborne JB. Flavans and proanthocyanidins. The flavonoids advances in research since 1980, 1988, London and New York: Chapman and Hall, 21-62.

[30] Prieur C, Rigaud J, Cheynier V, Moutounet M. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry, 1994, 36(3): 781-784.

[31] Qin L, Chen H. Enhancement of flavonoids extraction from fig leaf using steam explosion. Ind Crop Prod, 2015, 69: 1-6.

[32] Serrano A, Fermoso FG, Alonso-Fariñas B, Rodríguez-Gutierrez G, Fernandez-Bolaños J, Borja R. Phenols recovery after steam explosion of Olive Mill Solid Waste and its influence on a subsequent biomethanization process. Bioresource Technol, 2017, 243: 169-178.

[33] Silvan JM, Gutiérrez-Docio A, Moreno-Fernandez S, Alarcón-Cavero T, Prodanov M, Martinez-Rodriguez AJ. Procyanidin-rich extract from grape seeds as a putative tool against helicobacter pylori. Foods, 2020, 9(10): 1370.

[34] Souquet JM, Cheynier V, Brossaud F, Moutounet M. Polymeric proanthocyanidins from grape skins. Phytochemistry, 1996, 43(2): 509-512.

[35] Spranger I, Sun B, Mateus AM, Freitas VD, Ricardo-da-Silva JM. Chemical characterization and antioxidant activities of oligomeric and polymeric procyanidin fractions from grape seeds. Food Chem, 2008, 108(2): 519-532.

[36] Sun B, Neves AC, Fernandes TA, Fernandes AL, Mateus N, De Freitas V, Leandro C, Spranger MI. Evolution of phenolic composition of red wine during vinification and storage and its contribution to wine sensory properties and antioxidant activity. J Agr Food Chem, 2011, 59(12): 6550-6557.

[37] Unusan N. Proanthocyanidins in grape seeds: An updated review of their health benefits and potential uses in the food industry. J Funct Foods, 2020, 67: 103861.

[38] Vivas N, Nonier MF, De Gaulejac NV, Absalon C, Bertrand A, Mirabel M. Differentiation of proanthocyanidin tannins from seeds, skins and stems of grapes (Vitis vinifera) and heartwood of Quebracho (Schinopsis balansae) by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and thioacidolysis/liquid chromatography/electrospray ionization mass spectrometry. Anal Chim Acta, 2004, 513(1): 247-256.

[39] Wang S, Ouyang X, Wang W, Yuan Q, Yan A. Comparison of ultrasound-assisted Fenton reaction and dilute acid-catalysed steam explosion pretreatment of corncobs: cellulose characteristics and enzymatic saccharification. RSC Adv, 2016, 6(80): 76848-76854.

[40] White BL, Howard LR, Prior RL. Release of bound procyanidins from cranberry pomace by alkaline hydrolysis. J Agr Food Chem, 2010, 58(13): 7572-7579.

[41] Wojtasz-Mucha J, Hasani M, Theliander H. Hydrothermal pretreatment of wood by mild steam explosion and hot water extraction. Bioresource Technol, 2017, 241: 120-126.

[42] Wu Z, Zhu X, Guo H, Jiang Y, Gu X. A kinetic study of lignin pyrolysis over base catalyst during steam exploded depolymerization. Catal Today, 2019, 327: 226-234.

[43] Xia Q, Wang L, Xu C, Mei J, Li Y. Effects of germination and high hydrostatic pressure processing on mineral elements, amino acids and antioxidants in vitro bioaccessibility, as well as starch digestibility in brown rice (Oryza sativa L.). Food Chem, 2017, 214: 533-542.

[44] Xu C, Yagiz Y, Borejsza-Wysocki W, Lu J, Gu L, Ramírez-Rodrigues MM, Marshall MR. Enzyme release of phenolics from muscadine grape (Vitis rotundifolia Michx.) skins and seeds. Food Chem, 2014, 157: 20-29.

[45] Zhang HJ, Fan XG, Qiu XL, Zhang QX, Wang WY, Li SX, Yuan QP. A novel cleaning process for industrial production of xylose in pilot scale from corncob by using screw-steam-explosive extruder. Bioproc Biosyst Eng, 2014, 37(12): 2425-2436.

[46] Zhang S, Cui Y, Li L, Li Y, Zhou P, Luo L, Sun B. Preparative HSCCC isolation of phloroglucinolysis products from grape seed polymeric proanthocyanidins as new powerful antioxidants. Food Chem, 2015, 188: 422-429.

[47] Zhang Y, Zhao W, Yang R. Steam flash explosion assisted dissolution of keratin from feathers. ACS Sustain Chem Eng, 2015, 3(9): 2036-2042.

Funding

National Key Research and Development Program of China(No. 2016YFD0400601)

National Natural Science Foundation of China(No. 21606014)