功能食品苦味功能因子生理活性及其掩苦技术的研究进展

随着经济发展和生活水平的提高,人们对生活质量和健康的关注度提高,功能食品已成为食品工业21世纪发展的重要方向.本文介绍了功能食品常用的苦味功能因子的化学结构及生理活性,重点从苦味产生的机理概述了功能食品苦味的俺盖技术.     

功能食品苦味功能因子生理活性及其掩苦技术的研究进展

随着经济发展和生活水平的提高,人们对生活质量和健康的关注度提高,功能食品已成为食品工业21世纪发展的重要方向。本文介绍了功能食品常用的苦味功能因子的化学结构及生理活性,重点从苦味产生的机理概述了功能食品苦味的掩盖技术。      

玫瑰花饮料中苦涩味的研究

食用玫瑰花古已有之,用于饮料更是色于外而功于内.为解决玫瑰花饮料的苦涩味问题,对玫瑰花中的苦涩味物质在提取过程中的变化进行了研究,并对一些包埋剂、吸附剂祛除苦味物质的效果以及饮料调配中糖酸用量对饮料风味的影响做了一些探讨.试验结果表明:浸提前增加冷冻工艺可以提高浸提液的可溶性固形物含量;在沸水中浸提3h较好;选用包埋剂...     

Bioresponse-guided decomposition of roast coffee beverage and identification of key bitter taste compounds

Sensory-guided fractionation of a roasted coffee brew by means of sequential solvent extraction, ultrafiltration, and RP-HPLC demonstrated a group of ethyl acetate soluble compounds formed from O-hydroxycinnamoyl quinic acid derivatives upon coffee roasting as the key compounds contributing to the bitter taste of roasted coffee beverages. LC-MS/MS studies, 1D- and 2D-NMR spectroscopy, syntheses, and model roast experiments with 5-O-caffeoyl- and 5-O-feruloylquinic acid led to the unequivocal identification of 3-O-caffeoyl-γ-quinide (2a), 4-O-caffeoyl-γ-quinide (3a), 5-O-caffeoyl-epi-δ-quinide (4a), 4-O-caffeoyl-muco-γ-quinide (5a), 5-O-caffeoyl-muco-γ-quinide (6a), 3-O-feruloyl-γ-quinide (2b), and 4-O-feruloyl-γ-quinide (3b) as intense coffee bitter tastants. Besides these individual bitter compounds, a highly complex and intensely bitter HPLC fraction was isolated from the ethyl acetate extractables of coffee brew. Application of COSY spectroscopy and alkaline hydrolytic degradation gave strong evidence that the bitter taste of that fraction is due to a multiplicity of rather complex quinic acid lactone isomers multiply esterified with p-coumaric acid, caffeic acid, ferulic acid, 3,4-dimethoxycinnamic acid, and quinic acid, respectively. As representatives of this fraction, 3,4-O-dicaffeoyl-γ-quinide (10), 3,5-O-dicaffeoyl-epi-δ-quinide (11), and 4,5-O-dicaffeoyl-muco-γ-quinide (12) have been isolated, purified, and identified as strongly bitter-tasting compounds in roasted coffee. For the first time, bitter taste recognition thresholds were determined for the individual compounds showing that, strongly depending on their chemical structure, the bitter threshold levels ranged between 9.8 and 180 μmol/l (water).     

啤酒中源自酒花α-酸的苦味物质研究进展

提升啤酒风味稳定性是当前啤酒界公认的技术难点与研究热点。贮存过程中啤酒苦味强度的下降、苦感由舒服的苦感向粗糙和后苦的苦感转化,是啤酒风味老化的重要表现。随着分离纯化以及鉴定检测水平的提升,国外同行对可能引起啤酒苦味粗糙与后苦的物质和反应机理进行了系统的研究,取得了突破性的进展。文中对啤酒酿造中源自酒花α酸的苦味物质,尤其是引起啤酒后苦与粗糙的三环和四环异α-酸降解产物的特性及产生机理进行了系统的介绍,旨在提升国内同行对啤酒苦味质量的认知。     

Contribution of linoleic acid to the bitter taste of poppy seeds (Papaver somniferum)

In lipids isolated from poppy seeds which tasted "burning-bitter" the off-taste was associated with the free fatty acids fraction. In this fraction linoleic acid predominates, while oxidized fatty acids were among the minor constituents. The taste threshold of linoleic acid emulsified in water with monolinolein lies in the range of 4.0-6.0 mumol/ml. On the basis of its high concentration and relatively low taste threshold we conclude that free linoleic acid contributes significantly to the "burning-bitter" off-taste in poppy seeds.     

Interaction of denatonium chloride with the bitter taste receptor

Summary The structure — activity relationship study was applied on denatonium chloride and derivatives. It is proposed that this molecule interacts with the bitter receptor by two polar groups: electrophilic by the ammonium nitrogen atom and nucleophilic by oxygen atom of the carbonyl group (distance of 0.32 nm between the two atoms). Previous results and the actual study have revealed two hydrophobic interactions: one corresponding to the benzyldiethylammonium group and another to the 2,6-dimethylphenyl group particularly by the two methyl substituants, in atrans-configuration of the amide bond. This proposed model is applicable to some other bitter compounds.

---

Wechselwirkung des Denatonium-chlorids mit dem Empfänger des Bittergeschmacks

Zusammenfassung Von Denatonium-chlorid und dessen Derivate wurden die Zusammenhänge zwischen Struktur und Aktivität untersucht. Es wird angenommen, daß dieses Molekül mit dem Rezeptor für den Bittergeschmack über die polaren Gruppen in Wechselwirkung tritt. Elektrophil über das Stickstoffatom der Ammoniumgruppe und nucleophil über das Sauerstoffatom der Carbonylgruppe (Abstand zwischen diesen Atomen 0,32 nm). Diese Untersuchung und vorhergehende Ergebnisse haben zwei hydrophobe Wechselwirkungen erkennen lassen: die eine über die Benzyldiethylammoniumgruppe und die andere über die polare 2,6-Dimethylphenylgruppe, insbesondere durch die beiden Methylsubstituenten, bei einer trans-Konfiguration der Amidbindung. Das vorgeschlagene Modell ist auf einige andere bittere Verbindungen anwendbar.

     

烘焙温度对可可豆苦涩味的影响

对不同烘焙温度下的可可豆进行致苦涩味物质分离分析,基于感官评价和相对香味活力值的概念筛选出参与可可豆苦涩味形成的主要组分,并结合热裂解—气质联用技术研究烘焙温度上升时可可豆挥发性物质的变化规律。结果表明:(1)可可豆提取物苦涩味流分共检测出55种挥发性成分,其中醇类7种,酸类5种,酯类9种,醛类8种,酮类6种,烯烃类2种;(2)致苦涩味的关键组分为2-甲基丙醛、2-甲氧基苯酚、2-庚醇、戊醛、2-戊酮、苯甲醛、2,5-二甲基-4-羟基-3(2H)-呋喃酮,修饰组分为3-甲基丁醇、2,3-二甲基-5-乙基吡嗪、2,5-二甲基吡嗪、2,3-二甲基吡嗪、2-甲基丙醇;(3) 130～135℃为降低可可豆苦涩味的最佳烘焙温度。     

降低灵芝保健饮料中苦味的方法

对包埋剂的用量对灵芝饮料苦味的影响进行了试验研究，结果表明加入灵芝抽取液的２－５％的环糊精，能有效地把灵芝的苦味降低到４０％左右，从而获得人们乐于接受的天然保健饮料。     

苦味机理及苦味物质的研究概况

苦味是一种分布广泛、阈值极低的味感,而消费者往往拒食苦味食物,但苦味物质在食品风味和生理调节方面具有重要作用。简要论述了苦味呈味机理、几种苦味物质的功能特性以及苦味抑制剂方面的研究进展。     

Bitterness of cassava: Identification of a new apiosyl glucoside and other compounds that affect its bitter taste

Compounds extracted by methanol from cassava parenchyma and cortex have been separated on a preparative HPLC column and identified by ¹H and ¹³C NMR spectroscopy. A new compound isopropyl-β-D -apiofuranosyl-(1 → 6)-β-D -glucopyranoside (IAG, structure I ) has been found as well as small amounts of phenylalanine and tryptophan. The composition of another HPLC fraction has not been elucidated. The amounts of the identified compounds and of linamarin, lotaustralin, citrate, malate and the various sugars present in cassava have been determined by HPLC methods. The threshold levels of bitterness of aqueous solutions of linamarin, lotaustralin and IAG, have been determined and together with published data on L -phenylalanine and L -tryptophan have allowed our evaluation of their contributions to the bitterness of cassava. Linamarin is the sole contributor in the parenchyma but (with two cultivars out of six studied) IAG contributes more to the bitterness of the cortex than does linamarin. The perception of bitterness of linamarin solutions is confounded in the presence of neutral citrate and malate which have a sour taste. These modify the taste of cassava tubers. There are many compounds that contribute to the taste of cassava tubers, hence it is not surprising that the bitterness of cassava is not always correlated positively with the cyanide potential.     

甜油滋味物质及滋味特征研究

本文以生抽酱油为对照,通过常规指标分析法、十二烷基磺酸钠-聚丙烯酰胺凝胶电泳法（SDS-PAGE）、高效液相色谱法（HPLC）并结合感官评价对甜油的常规指标、蛋白质/多肽分子量分布、氨基酸组成和感官属性特征进行了分析。结果显示:甜油中Na Cl、总糖、还原糖、无盐固形物、总酸含量分别比生抽酱油高约28%、172%、176%、120%、58%,而其氨基酸态氮含量显著低于生抽酱油（约35%）。甜油中高分子量蛋白质/多肽的比例和总含量显著高于生抽酱油。甜油中游离氨基酸以甜味氨基酸（45%）为主,其次为苦味氨基酸和鲜味氨基酸;而生抽酱油以鲜味氨基酸（57%）为主,其次为苦味氨基酸和甜味氨基酸。感官评价结果证实了甜油咸、甜突出,鲜、酸、苦诸味协调。      

黄酒苦味影响因素分析

以苦味值为衡量指标对酒药添加量、酒曲添加量、主发酵温度进行正交试验设计。结果表明对黄酒苦味影响的大小依次为主发酵温度酒曲添加量酒药添加量。按照各因素的最好水平选取出最好的水平组合为主发酵温度均为30℃;酒曲添加量10%,酒药添加量0.8%。在此工艺下生产的黄酒苦味值较低。     

Sweet and bitter taste of oxathiazinone dioxides and benzisothiazolone dioxides

Summary The recognition thresholds for the sweet and bitter tastes of 23 oxathiazinone dioxides were determined and, together with qualitative sensory data from the literature for 26 benzisothiazolone dioxides, discussed in respect of structure-activity relationships. Hydrophobicity and steric parameters are very significant for both the quality and the intensity of the taste, in particular the position of the hydrophobic moiety of a molecule relative to its electrophilic/nucleophilic (e/n) system. The dimensions of molecules from these classes which are allowed for sweet and bitter tastes and the areas, responsible for an intense sweet taste were deduced from the superpositions of the e/n systems. These superpositions were performed with the aid of a computer program for the generation and manipulation of molecules.

---

Süßer und bitterer Geschmack von Oxathiazinondioxiden und Benzisothiazolondioxiden

Zusammenfassung Die Erkennungsschwellenwerte für süßen und bitteren Geschmack von 23 Oxathiazinondioxiden wurden bestimmt und zusammen mit qualitativen Daten der Literatur über den Geschmack von 26 Benzisothiazolondioxiden im Hinblick auf Struktur-Wirkungsbeziehungen diskutiert. Hydrophobität und sterische Parameter sind von großer Bedeutung für Qualität und Intensität des Geschmacks, insbesondere die Stellung des hydrophoben Molekülteils relativ zum elektrophil/nucleophilen (e/n)-System. Durch Superposition der e/n-Systeme konnten die für süßen und bitteren Geschmack erlaubten Abmessungen von Molekülen aus diesen Verbindungsklassen und die für die Süßintensität wichtigen Raumbereiche abgeleitet werden. Die Superpositionen wurden mit Hilfe eines Computerprogramms zur Erzeugung und Manipulation von Molekülen durchgeführt.

---

---

This work was financially supported by the Fonds der Chemischen Industrie     

养殖大黄鱼滋味成分及其呈味贡献的研究

以养殖大黄鱼（Pseudosciaena crocea）为研究对象,通过对其鱼肉游离氨基酸、呈味核苷酸、氧化三甲胺、甘氨酸甜菜碱、有机酸、呈味矿物元素等水溶性呈味化合物的检测,分析其对滋味的贡献。结果表明:养殖大黄鱼的游离氨基酸总量为2463.8mg·kg-1,其中精氨酸对滋味贡献最大;IMP、AMP、GMP、TMAO、甘氨酸甜菜碱对滋味有重要贡献;琥珀酸可能是形成大黄鱼整体滋味的主要物质之一;K+是主要呈味离子;味精当量（EUC）高达13.43g MSG/100g,呈味强度值达447.67,这主要得益于高含量的IMP,是大黄鱼滋味鲜美的主要原因。      

养殖大黄鱼滋味成分及其呈味贡献的研究

以养殖大黄鱼(Pseudosciaena crocea)为研究对象,通过对其鱼肉游离氨基酸、呈味核苷酸、氧化三甲胺、甘氨酸甜菜碱、有机酸、呈味矿物元素等水溶性呈味化合物的检测,分析其对滋味的贡献。结果表明:养殖大黄鱼的游离氨基酸总量为2463.8mg·kg-1,其中精氨酸对滋味贡献最大;IMP、AMP、GMP、TMAO、甘氨酸甜菜碱对滋味有重要贡献;琥珀酸可能是形成大黄鱼整体滋味的主要物质之一;K+是主要呈味离子;味精当量(EUC)高达13.43g MSG/100g,呈味强度值达447.67,这主要得益于高含量的IMP,是大黄鱼滋味鲜美的主要原因。     

Relations between structure and bitter taste of amino acids and peptides. I. Amino acids and related compounds]

About 60 amino acids, amino acid esters, N-acyl amino acids, amines, and other related compounds were tested for bitter taste. The recognition thresholds are in the range from 100 muMol/ml (L-2-amino butyric acid) to 0.8 muMol/ml (benzamide). Essential structural requirements for bitter compounds are a polar (electrophilic) group and a hydrophobic one, which must be arranged in a defined manner. The results are summarized in a model which shows the zones of contact between bitter compound and receptor.     

Identification of bitter compounds in whole wheat bread

Bitterness in whole wheat bread can negatively influence product acceptability and consumption. The overall goal of this project was to identify the main bitter compounds in a commercial whole wheat bread product. Sensory-guided fractionation of the crust (most bitter portion of the bread sample) utilising liquid–liquid extraction, solid-phase extraction, ultra-filtration and 2-D offline RPLC revealed multiple bitter compounds existed. The compounds with the highest bitterness intensities were selected and structurally elucidated based on accurate mass-TOF, MS/MS, 1D and 2D NMR spectroscopy. Eight bitter compounds were identified: Acortatarins A, Acortatarins C, 5-(hydroxymethyl)furfural(HMF), 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP), N-(1-deoxy-d-fructos-1-yl)-l-tryptophan (ARP), Tryptophol (TRO), 2-(2-formyl-5-(hydroxymethyl-1H-pyrrole-1-yl)butanoic acid (PBA) and Tryptophan (TRP). Based on the structures of these compounds, two main mechanisms of bitterness generation in wheat bread were supported, fermentation and Maillard pathways.     

微囊化处理对乳清蛋白酶解物的苦味和吸湿性的改善作用研究

利用麦芽糊精或麦芽糊精/β-环糊精混合物作为壁材,应用喷雾干燥法对WPH进行微囊化处理,改善酶解产物的苦味并提高其稳定性,使其在食品加工中的应用成为可能。结果表明,喷雾干燥法微囊处理可以使乳清蛋白酶解物的苦味值降到原来的1/8,吸湿性显著改善,从60.59%下降至34.41%,使得该产品具有了作为食品原料的潜力。