花色苷与蛋白质相互作用的研究进展

花色苷作为一种功能活性物质备受关注,但因稳定性差、生物利用率低限制了其应用。蛋白质作为人体必需的三大营养素之一,具有较好的生物相容性和生物可降解性,常用于食品加工中,但其功能性质有待改善。食品组分中的蛋白质与花色苷通常是共存的成分,很容易发生相互作用,作用方式包括非共价和共价作用,其中非共价作用方式最为普遍,包括氢键、疏水相互作用、静电相互作用、范德华力。本文总结了花色苷-蛋白质相互作用的研究进展,包括蛋白质对花色苷稳定性和生物利用率的影响、花色苷对蛋白质功能性质的影响,以及复合物功能产品的应用现状,以期为花色苷与蛋白质在食品深加工中的应用提供理论参考。     

Cancer cell antiproliferation activity and metabolism of black carrot anthocyanins

The antiproliferation activity of a black carrot anthocyanin-rich extract (BC-ARE) on human cancer cells (HT-29 colorectal adenocarcinoma and HL-60 promyelocytic leukaemia) and metabolism of its characteristic anthocyanins (acylated and nonacylated forms) in humans were investigated. Cancer cells were exposed for 24 h to 0.0–2.0 mg/mL of BC-ARE. Anthocyanin-rich extract inhibited proliferation of both types of cancer cells in a dose-dependent manner. After ingestion of a black carrot concentrate, three acylated and two nonacylated anthocyanins were excreted in the volunteers (n = 4) urine (0.048% of the administered dose). The anthocyanins were characterized by HPLC-DAD-ESI-MS/MS. Urine recovery of nonacylated anthocyanins was 8-fold higher than that of acylated anthocyanins.Industrial relevanceNatural pigments have achieved commercial significance as food colorants due to the fact that consumers perceive them as safe additives. At present extracts rich in acylated anthocyanins, which are known for their outstanding stability, serve as a major source of natural food colours for the food colorant industry with purple sweetpotato, red cabbage and black carrot being the major sources. Beside aesthetic values, anthocyanins possess enhanced physiological activity due to their potent antioxidant properties and enhance the health-promoting qualities of foods. Our findings on cancer cell antiproliferation activity of an anthocyanin-rich black carrot extract as well as information about the bioavailability of black carrot anthocyanins could lead to an increased application of these natural food colorants by the food industry.     

利用超微粉碎提高花色苷生物可接受率

探讨超微粉碎对不同食物来源花色苷体外模拟消化生物可接受率的影响。选择蓝莓、紫甘蓝、紫番薯和黑米分别作为浆果、蔬菜、薯类和谷物的代表性食物,充分干燥后进行分级粉碎,得到粗粉和超微粉,测定粉体粒径分布和营养成分;经过模拟胃肠消化后利用高相液相色谱法检测消化液花色苷峰面积,计算得到花色苷生物可接受率。与粗粉相比,超微粉粒径分布更加均匀,平均粒径<25μm,主要营养成分含量没有明显差异,而花色苷含量检测值显著升高;超微粉碎能够将花色苷生物可接受率提高23.78%~87.72%,差异均具有统计学意义(p<0.05)。超微粉碎可以解除细胞壁和纤维素等食物基质对花色苷释放的阻碍作用,提高不同食物来源的花色苷生物可接受率。     

Encapsulation of mangosteen pericarp anthocyanin-rich extract by spray drying

Mangosteen pericarp anthocyanin-rich extract (MPA) was encapsulated by maltodextrin dextrose equivalent 20 (MD20) combined with gum arabic (GA), inulin (IN) or pectin (PEC) using spray drying. The highest encapsulation efficiency and anthocyanin content exhibited MD20:PEC and MD20:IN combinations. The MPA-encapsulated powders had a crystalline-mixed amorphous structure. Scanning electron microscopy (SEM) analysis showed smooth, round, fine particles. Fourier transform infrared spectroscopy (FTIR) analysis confirmed entrapment of anthocyanins by carrier agents. Thermogravimetric analysis (TGA) revealed a high thermal stability of encapsulated powders at temperatures <200°C and found that encapsulation reduced thermal degradation of anthocyanins. Incorporation of MPA-encapsulated powders into natural yoghurt produced shelf-stable naturally coloured product but slightly suppressed the multiplication of Lactobacillus bulgaricus. Encapsulation of anthocyanin-rich mangosteen pericarp extract using spray drying presents a viable opportunity for food technologists to utilise this source in the development of functional food products.     

花色苷基于分子辅色机制的稳态化制备与应用技术研究进展

源于天然植物的花色苷是集着色、增香和保健作用于一体的新一代功能性食品配料,但在食品加工过程中易受多种外界因素的影响而发生水解或去糖基开环反应,导致产品褪色、风味品质劣变及生物活性丧失。而研究发现在自然生化条件下,植物花色苷通过其内部的多种化学成分(多酚、生物碱、核苷酸和金属离子等)的分子辅色作用而维持稳定性,从而实现花色苷食品的色泽、风味和营养的稳态化。目前通过模拟植物花色苷的分子辅色作用也成为研究功能性色素的重要内容之一。本文在分析花色苷分子辅色作用机制基础上,重点综述了近年来的天然植物花色苷基于分子辅色技术的稳态化制备工艺及相关应用技术取得的最新进展,为植物花色苷食品的稳态化加工技术研究提供依据和参考。     

Dietary anthocyanin-rich plants: biochemical basis and recent progress in health benefits studies

Anthocyanins are one type of flavonoid phytopigment. Although the role of anthocyanins as a functional food factor remains relatively less established than that of other flavonoids, progress in this area has been made at the molecular level in recent years. This review discusses the potential health benefits of plant-derived anthocyanin-rich foods, with a focus on the role of anthocyanins in obesity control, diabetes control, cardiovascular disease prevention, and improvement of visual and brain functions, areas that have attracted much attention. Such health benefits are not necessarily derived from the antioxidant effect of anthocyanins, but in fact are produced by currently unestablished chemical properties beyond the antioxidant capacity of the molecules. However, a better understanding of the physiological functionality of anthocyanins remains to be elucidated. It is desirable, therefore, to clarify the molecular type and composition of the anthocyanins that confer specific health benefits and to conduct further investigation into the underlying molecular mechanisms. The pharmacological actions of anthocyanins could not be fully established without knowledge on the effects of treatment of anthocyanins alone, the effects of non-anthocyanin components, and the possible interactions between anthocyanin and non-anthocyanin species.     

Acylated anthocyanins: A review on their bioavailability and effects on postprandial carbohydrate metabolism and inflammation

Anthocyanins, the natural red and purple colorants of berries, fruits, vegetables, and tubers, improve carbohydrate metabolism and decrease the risk factors of metabolic disorders, but their industrial use is limited by their chemical instability. Acylation of the glycosyl moieties of anthocyanins, however, changes the chemical properties of anthocyanins and provides enhanced stability. Thus, acylated anthocyanins are more usable as natural colorants and bioactive components of innovative functional foods. Acylated anthocyanins are common in pigmented vegetables and tubers, the consumption of which has the potential to increase the intake of health-promoting anthocyanins as part of the daily diet. For the first time, this review presents the current findings on bioavailability, absorption, metabolism, and health effects of acylated anthocyanins with comparison to more extensively investigated nonacylated anthocyanins. The structural differences between nonacylated and acylated anthocyanins lead to enhanced color stability, altered absorption, bioavailability, in vivo stability, and colonic degradation. The impact of phenolic metabolites and their potential health effects regardless of the low bioavailability of the parent anthocyanins as such is discussed. Here, purple-fleshed potatoes are presented as a globally available, eco-friendly model food rich in acylated anthocyanins, which further highlights the industrial possibilities and nutritional relevance of acylated anthocyanins. This work supports the academic community and industry in food research and development by reviewing the current literature and highlighting gaps of knowledge.     

The influence of milk with different compositions on the bioavailability of blackberry polyphenols in model sports nutrition beverages

This study aimed to determine whether the fat and protein content in dairy-fruit blends prepared using full-fat, semi-skimmed, skimmed or high-protein milk in combination with freeze-dried blackberry puree influenced the bioaccessibility and bioavailability of blackberry polyphenols and organic acids. Samples were subjected to in vitro digestion, after which bioavailability was analysed with a Caco-2 cell model. The addition of puree to milk resulted in the formation of protein aggregates, which partially protected anthocyanins during digestion. Milk fat may have increased the bioaccessibility of anthocyanins while reducing permeability through the Caco-2 cells, leading to a lower bioavailability in tested samples.     

Anthocyanin stability studies in Tibouchina semidecandra L.

The effects of pH, storage period, temperature, light and dark conditions on the stability of anthocyanins extracted from Tibouchina semidecandra flowers of different developmental stages was evaluated. Fully formed but unopened flower bud had the highest amount of total anthocyanin extracted from fresh petals. The anthocyanin contents for all flower developmental stages were stable at pH 0.5–3.0 but the colour of the extracts faded at higher pH values. Degradation percentages of total anthocyanins in the extracts kept at 25 °C were 7–20% lower than that maintained at 31 °C. Extracts stored in darkness at 25 °C maintained their purple colour for 26 days while light exposure reduced it to an average of 10 days. The study shows that suitable storage condition for coloured anthocyanin pigments in extracted form is in acidic conditions in the dark. This implies the potential usage of coloured anthocyanins as natural food colourants and shelf life indicator for acidic foods.     

Interactions between phytochemicals from fruits and vegetables: Effects on bioactivities and bioavailability

The combinations of two or more phytochemicals bring about changes in the ultimate biological effects and/or the bioavailability of each component. A number of mixtures of pure bioactive compounds or phytochemical-containing plant extracts provide synergy with regard to antioxidant status, anti-inflammation, anti-cancer and chemoprevention of several oxidative stress and metabolic disorders in vitro. The biological activities of food phytochemicals depend upon their bioaccessibility and bioavailability which can be affected by the presence of other food components including other bioactive constituents. The interactions between phytochemicals during intestinal absorption could result in changes in the bioavailability of the compounds, which in turn affects the intensity of their bioactivities. This paper provides an overview of combined biological effects of phytochemical mixtures derived from fruits and vegetables with a focus on anti-oxidative, anti-inflammatory and anti-carcinogenic activities. The bioavailability impairment or enhancement caused by the co-consumption of dietary phytochemicals is also discussed. Finally, research gaps for future studies on phytochemical interactions are identified.     

Influence of β-carotene-rich vegetables on the bioaccessibility of zinc and iron from food grains

Widespread deficiencies of iron and zinc, commonly found in populations dependent on plant foods, necessitate food-based strategies to maximise their bioavailability from plant foods. In this study, β-carotene-rich vegetables were evaluated for their effects on the bioaccessibility of iron and zinc from cereals and pulses by employing a simulated gastrointestinal digestion procedure involving equilibrium dialysis. Addition of carrot or amaranth (2.5 g and 5 g per 10 g of grain) significantly enhanced the bioaccessibility of iron and zinc from the food grains, the percent increase being 13.8–86.2 in the case of carrot and 11–193% in the case of amaranth. Pure β-carotene added at an equivalent level also enhanced the bioaccessibility of iron (19.6–102% increase) and zinc (16.5–118.0% increase) from the cereals examined. This is the first report on the beneficial influence of β-carotene on iron and zinc bioaccessibilities.     

Health Benefits of Anthocyanins and Their Encapsulation for Potential Use in Food Systems: A Review

Anthocyanins are one of the six subgroups of large and widespread group of plant constituents known as flavonoids. These are responsible for the bright and attractive orange, red, purple, and blue colors of most fruits, vegetables, flowers and some cereal grains. More than 600 structurally distinct anthocyanins have been identified in nature. Earlier, anthocyanins were only known for their coloring properties but now interest in anthocyanin pigments has intensified because of their possible health benefits as dietary antioxidants, which help to prevent neuronal diseases, cardiovascular illnesses, cancer, diabetes, inflammation, and many such others diseases. Ability of anthocyanins to counter oxidants makes them atherosclerosis fighters. Therefore, anthocyanin-rich foods may help to boost overall health by offering an array of nutrients. However, the incorporation of anthocyanins into food and medical products is a challenging task due to their low stability toward environmental conditions during processing and storage. Encapsulation seems to be an efficient way to introduce such compounds into these products. Encapsulating agents act as a protector coat against ambient adverse conditions such as light, humidity, and oxygen. Encapsulated bioactive compounds are easier to handle and offer improved stability. The main objective of this review is to explore health benefits of anthocyanins and their extraction, characterization, encapsulation, and delivery.     

ANTHOCYANINS AS FOOD COLORANTS —A REVIEW

A number of factors affecting anthocyanin stability and color are discussed in this review. The anthocyanins are probably the most spectacular of plant pigments since they are responsible for most of the red, purple and blue pigmentation of flowers, fruits and vegetables. However, because of their highly reactive nature, anthocyanins readily degrade, or react with other constituents in the media, to form colorless or brown colored compounds. The presence of an ox-onium ion adjacent to carbon 2 makes the anthocyanins particularly susceptible to nucleophilic attack by such compounds as sulfur dioxide, ascorbic acid, hydrogen peroxide and even water. Loss of anthocyanin pigmentation also occurs in the presence of oxygen and various enzymes, and as a result of high temperature processing. A certain degree of pigment stabilization may be conferred by acylation with various organic acids, copigmentation, self-association and/or metal chelation. In addition, pH has a marked effect on anthocyanin stability, and on the color of media containing these pigments. A number of anthocyanin-rich sources have been investigated for their potential as commercial pigment extracts. Although their application is primarily limited to acidic media, continued research on the chemistry of anthocyanins may lead to application and stabilization of these pigments in a wider variety of food products.     

仿生研究食品中铝的体内迁移分配及其生物利用率评价

目的重新界定食品铝进入人体后的形态(水溶态和单层脂质体亲和态),分别考察食品铝(粉条和千层饼)在胃肠中的溶出率及其迁入体循环系统的比率(生物利用率)。方法以"仿生胃肠消化、仿脂质体生物膜亲合吸附"为模型,对食品中铝在人体内的迁移分配进行了体外仿生消化研究。结果被测食品中铝在胃肠溶液中的溶出率为31.0%～42.5%,单层脂质体亲和态占比为69.4%～76.8%。结论食品铝在人体中具有与食品基质和体内环境相适应的生物可给性和生物利用率,不能以食品中铝的总量测定简单代替。因此,对于铝的每周耐受摄入量的确定应在同时考虑人体消化系统溶出率和食品铝的生物有效性的基础上制定。     

Barriers impairing mineral bioaccessibility and bioavailability in plant-based foods and the perspectives for food processing

Abstract

Plant-based foods gain more importance since they play a key role in sustainable, low-meat and healthy diets. In developing countries, these food products, especially legumes and cereals, are important staple foods. Nevertheless, the question arises on how efficient they are to deliver minerals and if it is useful to encourage their consumption to reduce the prevalence of mineral deficiencies? This review paper focuses on the discrepancy between the mineral content and the amount of minerals that can be released and absorbed from plant-based foods during human digestion which can be attributed to several inherent factors such as the presence of mineral antinutrients (phytic acid, polyphenols and dietary fiber) and physical barriers (surrounding macronutrients and cell wall). Further, this review paper summarizes the effects of different processing techniques (milling, soaking, dehulling, fermentation, germination and thermal processing) on mineral bioaccessibility and bioavailability of plant-based foods. The positive impact of these techniques mostly relies on the fact that antinutrients levels are reduced due to removal of fractions rich in antinutrients and/or due to their leaching into the processing liquid. Although processing can have a positive effect, it also can induce leaching out of minerals and a reduced mineral bioaccessibility and bioavailability.     

Natural Pigments: Stabilization Methods of Anthocyanins for Food Applications

The production of natural food pigments continues to grow worldwide. The global market is expected to grow at a compound annual growth rate of 6.22%, by revenue, over the period 2015 to 2019. Pigments such as anthocyanins, carotenoids, betalains, and chlorophylls have been used to color foods. However, there are challenges related to color losses during food processing, storage, and commercialization due to a low stability of natural pigments compared to synthetic colorants. This review summarizes the most recent studies and patents aimed at enhancing anthocyanin stability in food systems. The stabilizing methods include additions of copigment compounds, such as polymers, phenolic compounds, and metals. In addition, the exclusion of O₂ during processing and storage, hard‐panned candy coating methods for blue, green, and brown colors, and various encapsulation techniques were considered. Combining strategies and evaluating new materials capable of stabilizing anthocyanins will enhance their potential for use as value‐added natural food pigments.     

Combination of freeze drying and molecular inclusion techniques improves the bioaccessibility of microencapsulated anthocyanins from black rice (Oryza sativa L.) and lavender (Lavandula angustifolia L.) essential oils in a model food system

Black rice and lavender are promising sources of bioactives, in terms of anthocyanins and essential oils. Their bioaccessibility were improved by microencapsulation, followed by mixing in order to benefit both from colour and flavour, along with radical scavenging and biological properties. The mixed powder showed a satisfactory anthocyanins of 2.55 mg g⁻¹ DW, leading to a radical scavenging activity of 65.14 mmol g⁻¹ DW. The powder displayed an inhibitory effect against α-glucosidase (~49%) and α-amylase (39%), respectively, with a controlled release in intestinal environment. To further examine the functional properties, the powder was added to a food model system. During storage, a release in anthocyanins and flavonoids were found, leading to an increase in radical scavenging activity. The sensorial analysis showed that supplemented biscuits were appreciated for colour and lavender aroma. The obtained results were promising in tailoring the health benefits of secondary metabolites, underutilised in human’s nutrition due to their low stability and bioavailability.     

An eco-friendly pressure liquid extraction method to recover anthocyanins from broken black bean hulls

This study aimed to recover the anthocyanin-rich extract from broken black bean hulls by pressurized liquid extraction (PLE) and to study their chemical stability, inhibition capacity toward carbohydrate-enzymes and application in gelatin. A Box-Behnken design (BBD) coupled to response surface methodology (RSM) was applied in order to maximize the anthocyanin extraction conditions. Optimum PLE conditions obtained were ethanol:citric acid solution 0.1 mol L⁻¹ (30:70, v/v), a flow rate of 4 mL min⁻¹_, and 60 °C. Delphinidin-3-glucoside was the main anthocyanin quantified. The PLE crude and purified anthocyanin-rich extracts inhibited α-amylase (IC₅₀: 0.52 and 2.85 mg mL⁻¹) and α-glucosidase (0.03 and 0.15 mg mL⁻¹) enzymes, respectively. The PLE anthocyanin-rich extracts showed higher stability in low temperatures and in the absence of light. Besides, the application in gelatin provided a natural color and supplementation with antioxidant compounds. Overall, anthocyanin-rich extract obtained from black bean by-product using an eco-friendly PLE method shows potential as natural colorant and supplement.Industrial relevancePLE method is an emerging technique that performs fast and efficient extractions under high temperature and pressure conditions. The association of green technologies with green solvents makes PLE an eco-friendly technology. This article provides information about the extraction of anthocyanin-rich extracts from the broken black bean hulls by green PLE process under optimized conditions. The process allowed to obtain antioxidant-rich extracts with high application potential in food, supplements, and pharmaceutical industries.     

In vitro absorption and antiproliferative activities of monomeric and polymeric anthocyanin fractions from açai fruit (Euterpe oleracea Mart.)

Anthocyanins are among the most important and widely consumed natural pigments in foods, and have attracted increased attention as natural food colourants and potent bioactive agents. However, anthocyanins are generally unstable and may undergo chemical changes that include oxidative and polymerisation reactions during processing and storage. The role of anthocyanin polymerisation reactions on in vitro intestinal absorption and anti-cancer properties has not been assessed. This study investigated the chemical composition, antioxidant properties, antiproliferative activity, and in vitro absorption of monomeric and polymeric anthocyanin fractions from açai fruit (Euterpe oleracea Mart.). Cyanidin-3-rutinoside (58.5 ± 4.6%) and cyanidin-3-glucoside (41.5 ± 1.1%) were the predominant compounds found in monomeric fractions, while a mixture of anthocyanin adducts were found in polymeric fractions and characterised using HPLC–ESI-MSⁿ analyses. Monomeric fractions (0.5–100 μg cyanidin-3-glucoside equivalents/ml) inhibited HT-29 colon cancer cell proliferation by up to 95.2% while polymeric anthocyanin fractions (0.5–100 μg cyanidin-3-glucoside equivalents/ml) induced up to 92.3% inhibition. In vitro absorption trials using Caco-2 intestinal cell monolayers demonstrated that cyanidin-3-glucoside and cyanidin-3-rutinoside were similarly transported from the apical to the basolateral side of the cell monolayers (0.5–4.9% efficiency), while no polymeric anthocyanins were transported following incubation for up to 2 h. The addition of polymeric anthocyanin fractions also decreased monomeric anthocyanin transport by up to 40.3 ± 2.8%. Results from this study provide novel information regarding the relative size, absorption, and bioactive properties of anthocyanin monomers and polymer adducts.     

Determination of color, pigment, and phenolic stability in yogurt systems colored with nonacylated anthocyanins from Berberis boliviana L. as compared to other natural/synthetic colorants

ABSTRACT:  Anthocyanins are of interest to the food industry because of their antioxidant power, attractive color, and stability in high acid foods. Powder from the Peruvian berry Berberis boliviana Lechler, rich in nonacylated anthocyanins (7% to 8% dry weight), was incorporated into yogurt samples containing 3 different fat levels. Color (CIE L , a , b , chroma, and hue angle), pigment (monomeric anthocyanin and polymeric color), and total phenolics were monitored over 8 wk of storage and compared to yogurt treatments containing purple carrot acylated anthocyanins, red beet betalaines, or FD&C Red nr 40. Anthocyanin profiles were analyzed by HPLC coupled to photodiode array and mass detectors. Color of yogurt containing B. boliviana anthocyanins at 20 mg cyanidin-3-glucoside (cy-3-glu) equivalents/100 g yogurt ( L *= 65, chroma = 14, and hue angle = 335°) was similar to commercial blueberry yogurt ( L *= 65, chroma = 10.5, and hue angle = 341°). High color, pigment, and phenolic stability were observed in yogurts colored with B. boliviana , independent of the fat matrix. Acylated anthocyanins from purple carrot extracts exhibited increased stability with higher fat content. Anthocyanin degradation followed 1st-order kinetics. Pigment half-lives were 125 and 104 d for nonacylated anthocyanins at 10 and 20 mg cy-3-glu equivalents/100 g yogurt and 550.2, 232.6, and 128.9 d for acylated anthocyanins at 20 mg of cy-3-glu equivalents/100 g of 4%, 2%, and 0% fat yogurt. Addition of B. boliviana whole berry powder to yogurt matrices produced an attractive, stable anthocyanin-rich product, eliminating the need for industrial colorant extraction.