(S)-2-Tryptoline-3-carboxylic acid ethyl ester
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(S)-2-Tryptoline-3-carboxylic acid ethyl ester

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Category
Cyclic Amino Acids
Catalog number
BAT-006635
CAS number
80994-42-9
Molecular Formula
C14H16N2O2
Molecular Weight
244.3
(S)-2-Tryptoline-3-carboxylic acid ethyl ester
Synonyms
H-Tpi-OEt; H-Thnh(3)-OEt; (S)-1,2,3,4-Tetrahydronorharman-3-carboxylic acid ethyl ester
Storage
Store at -20 °C
1. Bioequivalence Demonstration for Ω-3 Acid Ethyl Ester Formulations: Rationale for Modification of Current Guidance
Kevin C Maki, et al. Clin Ther. 2017 Mar;39(3):652-658. doi: 10.1016/j.clinthera.2017.01.019. Epub 2017 Feb 8.
The US Food and Drug Administration (FDA) draft guidance for establishing bioequivalence (BE) of ω-3 acid ethyl esters (containing both eicosapentaenoic acid [EPA] and docosahexaenoic acid [DHA] as ethyl esters), used to treat severe hypertriglyceridemia, recommends the conduct of 2 studies: one with participants in the fasting state and one with participants in the fed state. For the fasting study, the primary measures of BE are baseline-adjusted EPA and DHA levels in total plasma lipids. For the fed study, the primary measures of BE are EPA and DHA ethyl esters in plasma. This guidance differs from that established for icosapent ethyl (EPA ethyl esters) in which the primary measure of BE is baseline-adjusted total EPA in plasma lipids for both the fasting and fed states. The FDA guidance for ω-3 acid ethyl esters is not supported by their physiologic characteristics and triglyceride-lowering mechanisms because EPA and DHA ethyl esters are best characterized as pro-drugs. This article presents an argument for amending the FDA draft guidance for ω-3 acid ethyl esters to use baseline-adjusted EPA and DHA in total plasma lipids as the primary measures of BE for both fasting and fed conditions. This change would harmonize the approaches for demonstration of BE for ω-3 acid ethyl esters and icosapent ethyl (EPA ethyl esters) products for future development programs and is the most physiologically rational approach to BE testing.
2. Increase of medium-chain fatty acid ethyl ester content in mixed H. uvarum/S. cerevisiae fermentation leads to wine fruity aroma enhancement
Kai Hu, Guo-Jie Jin, Wen-Chao Mei, Ting Li, Yong-Sheng Tao Food Chem. 2018 Jan 15;239:495-501. doi: 10.1016/j.foodchem.2017.06.151. Epub 2017 Jun 29.
Medium-chain fatty acid (MCFA) ethyl esters, as yeast secondary metabolites, significantly contribute to the fruity aroma of foods and beverages. To improve the MCFA ethyl ester content of wine, mixed fermentations with Hanseniaspora uvarum Yun268 and Saccharomyces cerevisiae were performed. Final volatiles were analyzed by gas solid phase microextraction-chromatography-mass spectrometry, and aroma characteristics were quantitated by sensory analysis. Results showed that mixed fermentation increased MCFA ethyl ester content by 37% in Cabernet Gernischt wine compared to that obtained by pure fermentation. Partial least-squares regression analysis further revealed that the improved MCFA ethyl esters specifically enhanced the temperate fruity aroma of wine. The enhancement of MCFA ethyl esters was attributed to the increased contents of MCFAs that could be induced by the presence of H. uvarum Yun268 in mixed fermentation. Meanwhile, the timing of yeast inoculations significantly affected the involving biomass of each strain and the dynamics of ethanol accumulation.
3. 7-Hydroxy-2-octenoic acid-ethyl ester mixture as an UV protectant secondary metabolite of an endolichenic fungus isolated from Menegazzia terebrata
Lu Zhao, Jin-Cheol Kim, Jae-Seoun Hur Arch Microbiol. 2022 Jun 16;204(7):395. doi: 10.1007/s00203-022-02997-5.
Enodolichenic fungi (ELF) are considered a promising bio-resource since they produce a variety of novel secondary metabolites with bioactivities. Ultraviolet (UV) radiation in sunlight containing UVA and UVB can cause acute and chronic skin diseases, and the demand for UV protectants in sunscreens has been increasing. Such situations evoke the strong interest of researchers in seeking effective UV protectants from natural products. In this study, we obtained partially purified 7-hydroxy-2-octenoic acid-ethyl ester (7E) from the secondary metabolites of ELF000548, which has UVA absorption activity. The antioxidant properties were performed by in vitro tests. The superoxide anion scavenging activity and inhibition of linoleic acid peroxidation of the 7E mixture were higher than ascorbic acid (ASA) and butyl hydroxyl anisole (BHA). Furthermore, the compound recovered the damage caused by UVB irradiation and inhibited melanin synthesis. Additionally, the 7E mixture exhibited no cytotoxicity toward the mouse melanoma cell lines, B16F1 and B16F10, except for the normal cell line, HaCaT. In general, these results are the first report about bioactivities of 7E, and those demonstrated that this compound might be a UV protectant to go further study.
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