amarogentin

2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-trihydroxy-(1,1'-biphenyl)-2-carboxylate

CAS: 21018-84-8 C29 H30 O13 MW: 586.54770000 bitter

Identification

Nameamarogentin
IUPAC[(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
CAS Number21018-84-8
FDA UNII5L82GT5I0W
Molecular FormulaC29 H30 O13
Molecular Weight586.54770000
Nikkaji NumberJ16.196I

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 928.00 to 292.00 °C. @ 760.00 mm Hg (est)
Flash Point 584.00 °F. TCC ( 306.67 °C. )
logP (o/w) 2.503 (est)
Soluble in water, 99.5 mg/L @ 25 °C (est)

Organoleptic Properties

Taste Description very bitter

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for amarogentin usage levels up tonot for fragrance use.

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Potential Uses

None Found

Natural Occurrence

gentiana spp. root gentian indian gentian PMC swertia spp.

Synonyms

[(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5- ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester 2-(4aS-(4aalpha,5beta,6alpha))-3,3',5- trihydroxy-(1,1'-biphenyl)-2-carboxylate PubMed: Amelioration of oxidative and inflammatory changes by Swertia chirayita leaves in experimental arthritis. PubMed: Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. PubMed: Amarogentin ameliorates diabetic disorders in animal models. PubMed: Amarogentin Induces Apoptosis of Liver Cancer Cells via Upregulation of p53 and Downregulation of Human Telomerase Reverse Transcriptase in Mice. PubMed: [Chemical constituents of Swertia patens]. PubMed: Chemotaxonomic Studies of Nine Gentianaceae Species from Western China Based on Liquid Chromatography Tandem Mass Spectrometry and Fourier Transform Infrared Spectroscopy. PubMed: Chromatographic Evaluation and Characterization of Components of Gentian Root Extract Used as Food Additives. PubMed: Phytochemical investigation of crude methanol extracts of different species of Swertia from Nepal. PubMed: Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. PubMed: Receptor Polymorphism and Genomic Structure Interact to Shape Bitter Taste Perception. PubMed: Chinese medicine amygdalin and β-glucosidase combined with antibody enzymatic prodrug system as a feasible antitumor therapy. PubMed: Amarogentin regulates self renewal pathways to restrict liver carcinogenesis in experimental mouse model. PubMed: Contents of therapeutic metabolites in Swertia chirayita correlate with the expression profiles of multiple genes in corresponding biosynthesis pathways. PubMed: LC-ESI/MS determination of xanthone and secoiridoid glycosides from in vitro regenerated and in vivo Swertia chirayita. PubMed: Detection of intermediates through high-resolution mass spectrometry for constructing biosynthetic pathways for major chemical constituents in a medicinally important herb, Swertia chirayita. PubMed: Expression and functional activity of the bitter taste receptors TAS2R1 and TAS2R38 in human keratinocytes. PubMed: Comparative HPLC/ESI-MS and HPLC/DAD study of different populations of cultivated, wild and commercial Gentiana lutea L. PubMed: Amarogentin, a secoiridoid glycoside, abrogates platelet activation through PLC γ 2-PKC and MAPK pathways. PubMed: The bitter barricading of prostaglandin biosynthesis pathway: understanding the molecular mechanism of selective cyclooxygenase-2 inhibition by amarogentin, a secoiridoid glycoside from Swertia chirayita. PubMed: Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats. PubMed: Inhibition of vascular smooth muscle cell proliferation by Gentiana lutea root extracts. PubMed: Prevention of liver carcinogenesis by amarogentin through modulation of G1/S cell cycle check point and induction of apoptosis. PubMed: Inhibition of aldose reductase by Gentiana lutea extracts. PubMed: Phenolic-linked biochemical rationale for the anti-diabetic properties of Swertia chirayita (Roxb. ex Flem.) Karst. PubMed: Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts. PubMed: Activity-guided isolation of antioxidant xanthones from Swertia chirayita (Roxb.) H. Karsten (Gentianaceae). PubMed: The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin. PubMed: Protocol for in vitro regeneration and marker glycoside assessment in Swertia chirata Buch-Ham. PubMed: Assessment of systemic interaction between Swertia chirata extract and its Bioactive constituents in rabbits. PubMed: Determination of gentisin, isogentisin, and amarogentin in Gentiana lutea L. by capillary electrophoresis. PubMed: Simultaneous estimation of mangiferin and four secoiridoid glycosides in rat plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study of herbal preparation. PubMed: Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS. PubMed: Liquid chromatography/tandem mass spectrometric study and analysis of xanthone and secoiridoid glycoside composition of Swertia chirata, a potent antidiabetic. PubMed: Amarogentin can reduce hyperproliferation by downregulation of Cox-II and upregulation of apoptosis in mouse skin carcinogenesis model. PubMed: Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae). PubMed: A sensitive and selective LC-MS-MS method for simultaneous determination of picroside-I and kutkoside (active principles of herbal preparation picroliv) using solid phase extraction in rabbit plasma: application to pharmacokinetic study. PubMed: Evaluation of the anticarcinogenic activity of Swertia chirata Buch.Ham, an Indian medicinal plant, on DMBA-induced mouse skin carcinogenesis model. PubMed: Production of amarogentin in root cultures of Swertia chirata. PubMed: Synthesis of 3,3',5-trihydroxybiphenyl-2-carboxylic acid, a component of the bitterest natural product amarogentin and its coenzyme A and N-acetyl cysteamine thiol esters. PubMed: Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms. PubMed: Secoiridoids and xanthones from Gentianella nitida. PubMed: Secoiridoid glucosides from Swertia mileensis. PubMed: Amarogentin, a naturally occurring secoiridoid glycoside and a newly recognized inhibitor of topoisomerase I from Leishmania donovani. PubMed: [Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug "long dan" by high performance liquid chromatography]. PubMed: Desorption/Chemical ionization mass spectrometry of bitter glycosides from gentiana1. PubMed: [High-performance liquid-liquid chromatography in beverage analysis].