Amarogentin

Source: Wikipedia, the free encyclopedia.
Amarogentin
Chemical structure of amarogentin
Chemical structure of amarogentin
Chemical structure of amarogentin
Chemical structure of amarogentin
Names
IUPAC name
(4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside 2-(3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate)
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{[(4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.166.688 Edit this at Wikidata
UNII
  • InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1 checkY
    Key: DBOVHQOUSDWAPQ-WTONXPSSSA-N checkY
  • InChI=1/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
    Key: DBOVHQOUSDWAPQ-WTONXPSSBG
  • O=C/1OCC[C@@H]5C\1=C\O[C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4OC(=O)c3c(c2cccc(O)c2)cc(O)cc3O)CO)[C@@H]5\C=C
Properties
C29H30O13
Molar mass 586.546 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Amarogentin is a chemical compound found in gentian (

Swertia chirata.[1]

Amarogentin and gentiopicrin, the bitter glycosides from gentian root

Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are

bitter natural compounds known[2] and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor TAS2R50.[3] The biphenylcarboxylic acid moiety is biosynthesized by a polyketide-type pathway, with three units of acetyl-CoA and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid.[4]

It also shows an

inhibitor of topoisomerase I.[6]

See also

References

  1. S2CID 21149742
    .
  2. ^ Heilpflanzen:Gentiana lutea Archived 2009-09-02 at the Wayback Machine (German)
  3. PMID 19817411
    .
  4. doi:10.1002/1099-0690(200104)2001:8<1459::AID-EJOC1459>3.0.CO;2-0
    .
  5. PMID 10590280
    .
  6. PMID 8984149
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Amarogentin&oldid=1197835713"