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Polymerization of Proanthocyanidins Catalyzed by Polyphenol Oxidase from Lotus Seedpod

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Polymerization of Proanthocyanidins Catalyzed by Polyphenol Oxidase from Lotus Seedpod Eur Food Res Technol (2014) 238:727–739 DOI 10.1007/s00217-013-2114-7 ORIGINAL PAPER Polymerization of proanthocyanidins catalyzed by polyphenol oxidase from lotus seedpod Xiao-ru Liu · Ru-peng Xie · Ya-wei Fan · Jiang-ning Hu · Ting Luo · Hong-yan Li · Ze-yuan Deng Received: 28 March 2013 / Revised: 9 October 2013 / Accepted: 14 October 2013 / Published online: 7 January 2014 © Springer-Verlag Berlin Heidelberg 2014 Abstract This study aimed to investigate the profiles MWS Model wine system change in proanthocyanidins (PAs) catalyzed by polyphenol CD Circular dichroism spectroscopy oxidase (PPO) from lotus seedpod in a model wine system FT-IR Fourier transform infrared spectroscopy (MWS). Results showed that PAs from lotus seedpod con- SDS-PAGE Sodium dodecyl sulfate–polyacrylamide gel sisted of dimer (74.00 %) and trimer (22.75 %). PPO could electrophoresis tolerate ethanol concentrations below 20 % (v/v). The opti- TPC Total other phenolic compounds (excluding mum temperature of PPO activity was 80 °C, and the optimal proanthocyanidins) pH was 9.0. Its molecular weight was approximately 31 kDa, and its secondary structures were α-helix (59.0 %), β-sheet (4.3 %), turns (14.1 %), and random coils (22.6 %). In the Introduction MWS, the trimers gradually increased from 22.55 % at 0 h (control) to 100 % at 10 h incubation, while the dimers Lotus (Nelumbo nucifera, Gaertn) is a perennial aquatic herb decreased from 74.33 % (control) to 0 % at 10 h incubation. with creeping rhizome throughout the world. All parts of lotus Moreover, the composition of the precipitate formed at dif- can be used for culinary and medicinal purposes. Its seedpod is ferent incubation time points was approximately 16.54 % of usually discarded after harvest of lotus seeds. In recent years, monomers, 21.03 % of dimers, and 62.43 % of trimers at 2 h polyphenols, especially proanthocyanidins (PAs) in lotus incubation with PPO. The results from this study have pro- seedpod, have been found to exhibit many health benefits such vided in vitro evidence for a possible application of PPO in as anti-cancer, anti-oxidation, anti-myocardial ischemia, and red wine aging. anti-radiative effects [1–4]. Furthermore, their activities against melanoma, cognitive dysfunction, and Alzheimer’s Keywords Proanthocyanidin · Polyphenol oxidase · disease have also been reported recently [5–7]. Lotus seedpod · Polymerization Polyphenols are considered as crucial components in terms of the sensory characteristics and nutritional benefits Abbreviations of red wine. Polyphenols in red wine can usually be clas- PPO Polyphenol oxidase sified into two types: compounds of low molecular weight PAs Proanthocyanidins such as phenolic acids, stilbenes, flavanols, flavonols and anthocyanins and compounds of high molecular weight such as PAs [8]. All these compounds are released from the Xiao-ru Liu and Ru-peng Xie have contributed equally to this work; they are co-first authors. grape seeds and skins into the wine during fermentation and maceration. The crucial factors affecting the phenolic X. Liu · R. Xie · Y. Fan · J. Hu · T. Luo · H. Li · Z. Deng (&) profiles of wines are the making process itself and the State Key Laboratory of Food Science and Technology, reactions during aging [9, 10]. Profiles analyses revealed Institute for Advanced Study, Nanchang University, that the polymerization of low molecular weight phe- NO. 235, Nanjing East Road, 330047 Nanchang, Jiangxi, People’s Republic of China nols progressively occurred throughout the wine-making e-mail: [email protected] process [11–15]. However, the red wine aging is a time- 123 728 Eur Food Res Technol (2014) 238:727–739 consuming and inefficient process by some conventional Germany). All other reagents used in this study were of techniques. Enzyme-assisted autolysis is a common analytical grade. method to ameliorate the problem. β-glucanase and pec- tinase were reported to accelerate the release of Preparation and characterization of PAs from lotus anthocyanins and saccharides before or during the fer- seedpod mentation[9, 16]. But these methods could not shorten the aging time for that red wine aging is mostly reflected in PAs preparation phenolic compounds polymerization and color stabiliza- tion. However, to our knowledge, little related research has The powder (100 g) of lotus seedpods was first extracted by been carried on so far. 200 ml of 70 % acetone (v/v) containing 1 g/L of Polyphenol oxidase (PPO) may be a highly efficient cata- L-ascorbic acid to avoid oxidation for 12 h. The filtrate was lyst of phenolic polymerization. It is known that PPO exists in vacuum-dried to 50 ml at 45 °C. Then, 100 ml of trichlo- numerous plants and seems always harmful in food industry romethane, 100 ml of diethyl ether and 100 ml of ethyl because of its contribution to enzymatic browning in vegeta- acetate were successively added to remove the lipids, bles and fruits. The catalytic process is composed of two steps: flavonoids and chlorophylls, respectively. The aqueous first, the monophenols changed into O-diphenols by hydrox- layer was vacuum-dried to remove the remnant organic ylation, and then, the O-diphenols are oxidized and solvent and freeze-dried to powder, and 0.5 g of powder accumulated into O-quinones [17–19]. The excess presence was dissolved in 10 ml of H O for following purification. and activity of the PPO are undesirable when exposed to 2 AB-8 resin column (Φ 1.5 cm 9 35 cm) was used for oxygen in red wine. PPO may cause browning in wines under preliminary purification, with 200 ml of water and 200 ml aerobic condition; however, under anoxic condition, trans- of 50 % ethanol (v/v) as eluents, respectively. The ethanol formation from phenols to O-quinones might be the first step eluent was collected and vacuum-dried to 10 ml and further of polymerization in red wine. The formed quinones will react purified by Sephadex LH-20 column (Φ 3.2 cm 9 40 cm). with other phenols with an electron-rich ring. When the Then, 400 ml of water, 600 ml of 25 % methanol (v/v), reaction occurs, a new bond is formed between the two phe- 200 ml of 50 % methanol (v/v) and 300 ml of 70 % acetone nolic compounds resulting in the generation of a PA [20, 21]. (v/v) were successively added to elute the column. The Based on these studies, we think about whether this system acetone and methanol eluents were collected, concentrated could be used to improve the quality of young red wine. and freeze-dried to powder as described above. The objectives of the present study were mainly to examine the characteristics of the PAs and PPO extracted from lotus seedpod, respectively. The changes in profiles of Determination of PAs by HPLC–QTOF–MS total phenolic acids and PAs catalyzed by the PPO in a model wine system were investigated. The results from this The PAs powder (0.1 mg) was dissolved in methanol study might provide not only a valuable way to utilize the (1 ml), and concentration of PAs was determined by an lotus seedpod, but also may put forward a new efficient Agilent 1200 N HPLC system (Agilent Technologies, PPO-assisted method for red wine aging. Shanghai, China) using an ODS C18 column (250 9 4.6 mm, 5 μm) at 25 °C with a flow rate of 0.5 ml/ min and injection volume of 10 μl. Mobile phases consisted Materials and methods of 0.5 % formic acid in water (A) and acetonitrile (B). The diode array detector (DAD) monitored at 278 nm, and Plant materials and chemical reagents linear gradient was carried out in 50 min under the fol- lowing conditions: 0–20 min, A 3.0–8.0 %; 20–40 min, A Lotus seedpods were obtained from Guangchang County, 8.0–13.0 %; 40–41 min, A 13.0–3.0 %; 41–50 min A Jiangxi Province, China. The undamaged ripe lotus seed- 3.0 %. The HPLC system was coupled to a hybrid quad- pods without seeds were stored at 2 °C within 12 h after rupole time-of-flight (QTOF) mass spectrometer (ABSciex, harvest to minimize oxidation and microbial contamina- USA). The MS was performed in negative ionization mode, tion. The lotus seedpods were divided into two groups. One and data of full scans were collected between a m/z range group was dried to constant weight. The other was stored at of 50–1,300. Mass parameters were as follows: ion spray −20 °C for PPO extraction. Each group was in triplicate. voltage, −4,200 V; declustering potential, −60 V; focusing The chromatographic polyphenolic reference standards potential, −190 V; declustering potential 2, −15 V; ion of HPLC grade, including ferulic acid, chlorogenic acid, release delay, 6 V; ion release width, 5 V; temperature, caffeic acid, vanillic acid, trans-cinnamic acid and quer- 400 °C with curtain gas (N2), 50 a.u. (arbitrary units); cetin, were purchased from Sigma Company (Steinheim, auxiliary gas, 50 a.u. and nebulizer gas (N2), 50 a.u. IDA 123 Eur Food Res Technol (2014) 238:727–739 729 was performed using the criteria: ions that exceeded 5 A Jasco MOS-450 spectropolarimeter circular dichroism counts, ion tolerance 50 mDa, collision energy fixed at (CD) chromatograph was used to determine the secondary −30 V, dynamic background substract activated. Quantifi- structure of PPO. Sample solution (1 ‰, m/v) was prepared cation was measured by the area of each peak through the in PBS (0.1 M, pH 6.8) and filtered by 0.02 μm membrane HPLC diagram using (+)-catechin as external standard via prior to CD measurements with the working parameters: calibration curve method. 0.1 cm of optical distance, 2 mdeg/cm of sensibility and 0.01 mdeg of distinguish ability.
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