H-Glu-Tyr-OH
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H-Glu-Tyr-OH

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Category
Others
Catalog number
BAT-015576
CAS number
3422-39-7
Molecular Formula
C14H18N2O6
Molecular Weight
310.30
H-Glu-Tyr-OH
IUPAC Name
4-amino-5-[[1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-5-oxopentanoic acid
Synonyms
alpha-glutamyltyrosine; alpha-L-Glutamyl-L-tyrosine
Appearance
White Powder
Purity
>99%
Density
1.414 g/cm3
Sequence
H-DL-Glu-DL-Tyr-OH
InChI
InChI=1S/C14H18N2O6/c15-10(5-6-12(18)19)13(20)16-11(14(21)22)7-8-1-3-9(17)4-2-8/h1-4,10-11,17H,5-7,15H2,(H,16,20)(H,18,19)(H,21,22)
InChI Key
YSWHPLCDIMUKFE-UHFFFAOYSA-N
Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)NC(=O)C(CCC(=O)O)N)O
1. Characterization of volatile organic compounds with anti-atherosclerosis effects in Allium macrostemon Bge. and Allium chinense G. Don by head space solid phase microextraction coupled with gas chromatography tandem mass spectrometry
Zifei Qin, Shuyi Duan, Yuan Li, Xinqiang Li, Han Xing, Zhihong Yao, Xiaojian Zhang, Xinsheng Yao, Jing Yang Front Nutr. 2023 Feb 1;10:996675. doi: 10.3389/fnut.2023.996675. eCollection 2023.
Introduction: Allium macrostemon Bge. (AMB) and Allium chinense G. Don (ACGD) are both edible Allium vegetables and named officinal Xiebai (or Allii Macrostemonis Bulbus) in East Asia. Their medicinal qualities involve in lipid lowering and anti-atherosclerosis effects. And steroidal saponins, nitrogenous compounds and sulfur compounds are like the beneficial components responsible for medicinal functions. Sulfur compounds are the recognized main components both in the volatile oils of AMB and ACGD. Besides, few researches were reported about their holistic chemical profiles of volatile organic compounds (VOCs) and pharmacodynamic effects. Methods: In this study, we first investigated the lipid-lowering and anti-atherosclerotic effects of volatile oils derived from AMB and ACGD in ApoE -/- mice with high fat and high cholesterol diets. Results: The results showed the volatile oils of AMB and ACGD both could markedly reduce serum levels of TG, TC, and LDL-C (p < 0.05), and had no alterations of HDL-C, ALT, and AST levels (p > 0.05). Pathological results displayed they both could obviously improve the morphology of cardiomyocytes and the degree of myocardial fibrosis in model mice. Meanwhile, oil red O staining results also proved they could apparently decrease the lesion areas of plaques in the aortic intima (p < 0.05). Furthermore, head space solid phase microextraction coupled with gas chromatography tandem mass spectrometry combined with metabolomics analysis was performed to characterize the VOCs profiles of AMB and ACGD, and screen their differential VOCs. A total of 121 and 115 VOCs were identified or tentatively characterized in the volatile oils of AMB and ACGD, respectively. Relative-quantification results also confirmed sulfur compounds, aldehydes, and heterocyclic compounds accounted for about 85.6% in AMB bulbs, while approximately 86.6% in ACGD bulbs were attributed to sulfur compounds, ketones, and heterocyclic compounds. Multivariate statistical analysis showed 62 differentially expressed VOCs were observed between AMB and ACGD, of which 17 sulfur compounds were found to be closely associated with the garlic flavor and efficacy. Discussion: Taken together, this study was the first analysis of holistic chemical profiles and anti-atherosclerosis effects of AMB and ACGD volatile oils, and would benefit the understanding of effective components in AMB and ACGD.
2. Antioxidant activity of organic sulfides from fresh Allium macrostemon Bunge and their protective effects against oxidative stress in Caenorhabditis elegans
Zhong-Qin Wu, Ke Li, Jin-Kui Ma, Qing Huang, Xing Tian, Zong-Jun Li J Food Biochem. 2020 Nov;44(11):e13447. doi: 10.1111/jfbc.13447. Epub 2020 Sep 10.
Long-stamen chive (Allium macrostemon Bunge; AMB), which is prevalent in the Wuling Mountain area of China, is a characteristic food of the nation. In the study, we evaluated the as-yet-unknown nutritional value and antioxidant activity of fresh AMB. The free amino acid content, volatile components, and free radical-scavenging capacity of isolated organic sulfides were analyzed to evaluate the qualitative and physiological properties of fresh AMB. The plant was found to be rich in free essential amino acids and contain multiple flavor-imparting amino acids. The organic sulfides showed an apparent free radical-scavenging activity in vitro. Furthermore, these sulfides alleviated oxidative stress in Caenorhabditis elegans. Notably, the organic sulfides isolated from AMB enhanced the activities of superoxide dismutase, catalase, and glutathione peroxidase; improved motility; and extended the lifespan in oxidative stress-affected nematodes. In conclusion, our study indicates that AMB is a nutritious vegetable with potential to be developed as a functional food. PRACTICAL APPLICATIONS: Long-stamen chive is a wild edible vegetable belonging to the genus Allium (A. macrostemon Bunge; AMB). However, its quality and physiological properties have not been comprehensively investigated. Herein, we analyzed the free amino acid content, composition of volatile compounds, and potential antioxidative properties of AMB. Our results indicated that AMB is rich in essential amino acids, making it a highly nutritious food. Further analysis indicated that AMB contains a high proportion of organic sulfides, which have been previously been shown to have antioxidative properties. Together, our findings indicate that AMB contains important bioactive components and can be developed as a functional food or health supplement. Furthermore, our findings will enhance public awareness regarding this wild resource and provide new directions for the research and development of natural products derived from it.
3. Rapid and sensitive ultrasonic-assisted derivatisation microextraction (UDME) technique for bitter taste-free amino acids (FAA) study by HPLC-FLD
Guang Chen, Jun Li, Zhiwei Sun, Shijuan Zhang, Guoliang Li, Cuihua Song, Yourui Suo, Jinmao You Food Chem. 2014 Jan 15;143:97-105. doi: 10.1016/j.foodchem.2013.07.099. Epub 2013 Jul 27.
Amino acids, as the main contributors to taste, are usually found in relatively high levels in bitter foods. In this work, we focused on seeking a rapid, sensitive and simple method to determine FAA for large batches of micro-samples and to explore the relationship between FAA and bitterness. Overall condition optimisation indicated that the new UDME technique offered higher derivatisation yields and extraction efficiencies than traditional methods. Only 35min was needed in the whole operation process. Very low LLOQ (Lower limit of quantification: 0.21-5.43nmol/L) for FAA in twelve bitter foods was obtained, with which BTT (bitter taste thresholds) and CABT (content of FAA at BTT level) were newly determined. The ratio of CABT to BTT increased with decreasing of BTT. This work provided powerful potential for the high-throughput trace analysis of micro-sample and also a methodology to study the relationship between the chemical constituents and the taste.
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