Relationship between Bitterness of Peptides and their Chemical Structures

Matoba, Teruyoshi; Hata, Toshiyuki

doi:10.1080/00021369.1972.10860410

Cited by 117 publications

(85 citation statements)

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“…This suggests that amino and carboxy groups may contribute to the weakening of the bitterness of phenylalanine; that is, its bitterness is intensified when those groups are blocked by the formation of peptide bonds. Matoba and Hata [84] synthesized various peptides and derivatives of peptides and amino acids to systematically investigate their structure-bitterness relationships. Glycyl peptides containing amino acids with hydrophobic side chains, such as Gly-Leu, ValGly, and Gly-Phe-Gly, were all bitter.…”

Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

“…The bitterness of hydrophobic amino acids intensified when they were introduced into peptide chains, and was stronger when both amino and carboxy groups were blocked than when only one side was blocked. Furthermore, the role of amino and carboxyl groups in the bitterness of peptides was investigated using acetylated and esterified amino acids as a simple peptide model [84]. Hydrophobic amino acids were bitterer when amino and/or carboxyl groups were blocked by acetylation and esterification, and acetyl amino acid methyl esters such as Ac-Leu-OMe were bitterer than acetyl amino acids and methyl esters with only one group blocked.…”

Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

“…1). To further explain the mechanism responsible for the intensity of bitterness, Tamura et al [84] proposed that the receptor recognizes the hydrophobicity of the peptide, and that the intensity of the bitterness is determined at a hydrophobicity recognition zone located on the wall of a pocket of the receptor when the BU and SU are located at the bottom of the receptor. Bitter peptides are composed of fewer than eight amino acids, and the bitterness of the peptides increases as the number of amino acids increases.…”

Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

See 2 more Smart Citations

Bitter peptides and bitter taste receptors

Maehashi

Huang

2009

Cell. Mol. Life Sci.

160

118

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Bitter peptides are a structurally diverse group of oligopeptides often generated in fermented, aged, and hydrolyzed food products that make them unfavorable for consumption. Humans perceive bitterness by a repertoire of 25 human bitter receptors, termed T2Rs. Knowledge of the structural features of bitter receptors and of the factors that stimulate bitter receptors will aid in understanding the mechanism responsible for bitter taste perception. This article reviews the current knowledge regarding structural features of bitter peptides and bitter taste receptors.

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Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

Section: Structure-bitterness Relationships In Peptidesmentioning

confidence: 99%

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Bitter peptides and bitter taste receptors

Maehashi

Huang

2009

Cell. Mol. Life Sci.

160

118

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“…The increase in the bitterness of hydrolysates has been associated with the release of peptides containing hydrophobic residues [50], which in turn would interact with the taste buds to give a bitter taste [51][52][53]. However, extensive hydrolysis breaks these peptides into smaller units, decreasing the undesirable bitter taste.…”

Section: Effect Of Hydrolysis On Flavourmentioning

confidence: 99%

Antioxidative Properties of Fish Protein Hydrolysates

Raghavan

Kristinsson

Þorkelsson

et al. 2010

Handbook of Seafood Quality, Safety and Health Applications

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Seafoods including fish are an important source of protein in the human diet, providing nearly 20% of the animal protein consumed by the world population [1]. Fish contains all the essential amino acids required for human growth and nutrition and hence constitutes an excellent source of nutritive and digestible protein [2]. Over the last several decades, an increasing demand and consumption of seafood products has lead to over-exploitation of world fish stocks. In addition to over-exploitation, large amounts of protein rich by-products are discarded without any attempt to recover them. If one merely looks at the processing by-products from filleting, these raw materials may contain as much as 10 to 20% of fish protein and in many cases are not utilized for human or animal consumption. Possibly, more than 60% of fish tissue remaining after processing (species dependent) is considered as a processing waste and not used for human food.In recent years, strict environmental regulations have been imposed, which no longer allow fish processors to discard their offal, resulting in high cost of refining the material before it is discarded or directing it into low-grade fish meal or plant fertilizers [3]. Dwindling fish stocks and under-utilization of aquatic by-products has provoked a strong and urgent need to develop alternative methods for better utilization of fish and seafood by-products. However, in order to be accepted by the industry, these processes have to be economically feasible compared to discarding the by-products or using them for feed or fertilizer [4,5]. A number of methods to better utilize raw materials of aquatic origin have been proposed, one of them being enzymatic hydrolysis to produce what is collectively called fish protein hydrolysate (FPH).The use of enzymes for predigesting food proteins has been used for centuries for tenderizing meat and for making products such as tempeh, tofu, fish sauce, and fermented herring. By applying enzyme technology to recover and modify fish proteins present in the by-products of fish processing, it is possible to produce a broad spectrum of protein ingredients with a wide range of food and nutraceutical applications [4,6]. This approach could make better use of by-products and at the same time be employed for under-utilized fish species, increasing the margin of profit for the fishing industry and creating a more environmentally friendly industry. Significant work on recovery of fish proteins was conducted in the 1960s Handbook of Seafood Q uality, Safety and Health ApplicationsEdited by Cesarettin Alasalvar, Fereidoon Shahidi, Kazuo Miyashita and Udaya Wanasundara

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“…Intense bitterness is also associated with peptides having at least two hydrophobic amino acids at the C-terminal [21]. In addition, peptide bitterness may increase with the number of Leu, Phe, and Tyr residues [9,12,17].…”

Section: Introductionmentioning

confidence: 97%

Debittering effect of Actinomucor elegans peptidases on soybean protein hydrolysates

Zuoyi

Yang

et al. 2007

J Ind Microbiol Biotechnol

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Effects of the enzymes in Actinomucor elegans extract and the enzyme Alcalase 2.4L on debittering the soybean protein hydrolysates were investigated. When the protein was treated only with the latter, a strong bitterness formed; but it decreased if the protein was treated with both the enzymes. The more the enzymes were used, weaker was the bitterness tasted. SDS-PAGE profile and ESI-MS spectrum of the hydrolysates evidenced that the Alcalase could convert the protein into peptides rapidly, while the enzymes in the A. elegans extract were able to further degrade some peptides which were difficult or unable to be hydrolyzed by the Alcalase. Further systematic analysis of the peptidases showed that the Alcalase exhibited a significant endopeptidase activity towards NBZ-Phe-pNA substrate (p < 0.01), whereas many exopeptidases in the A. elegans extract had the carboxypeptidase activity towards N-CBZ-Ile-Leu (p < 0.01). It is concluded that those exopeptidases presented in the A. elegans extract can benefit by decreasing the bitterness of the soybean protein hydroysate. They are also capable of being used with the Alcalase in a single-step enzymatic reaction to prepare the bitterless protein hydrolysate, which may be an efficient application for food industry.

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Relationship between Bitterness of Peptides and their Chemical Structures

Cited by 117 publications

References 0 publications

Bitter peptides and bitter taste receptors

Bitter peptides and bitter taste receptors

Antioxidative Properties of Fish Protein Hydrolysates

Debittering effect of Actinomucor elegans peptidases on soybean protein hydrolysates

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