amarogentin
2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-trihydroxy-(1,1'-biphenyl)-2-carboxylate
Identification
| Name | amarogentin |
| 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 Number | 21018-84-8 |
| FDA UNII | 5L82GT5I0W |
| Molecular Formula | C29 H30 O13 |
| Molecular Weight | 586.54770000 |
| Nikkaji Number | J16.196I |
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 Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for amarogentin usage levels up to | not for fragrance use. |
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Potential Uses
Natural Occurrence
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].