Sterubin

Last updated
Sterubin
Sterubin.png
Names
IUPAC name
(2S)-3′,4′,5-Trihydroxy-7-methoxyflavan-4-one
Systematic IUPAC name
(2S)-2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names
7-Methoxy-3′,4′,5-trihydroxyflavanone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Yes check.svgY
    Key: DSAJORLEPQBKDA-AWEZNQCLSA-N Yes check.svgY
  • InChI=1/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
    Key: DSAJORLEPQBKDA-AWEZNQCLBS
  • O=C2c3c(O[C@H](c1ccc(O)c(O)c1)C2)cc(OC)cc3O
Properties
C16H14O6
Molar mass 302.28 g/mol
Density 1.458 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sterubin (7-methoxy-3',4',5-trihydroxyflavanone) is a bitter-masking flavanone extracted from Yerba Santa ( Eriodictyon californicum ) a plant growing in America. [1]

Sterubin is one of the four flavanones identified by Symrise in this plant which elicit taste-modifying properties. The others are homoeriodictyol, its sodium salt, and eriodictyol. [2]

Recent research has demonstrated some neuroprotective properties of Sterubin in vitro, but more research is needed before it can be considered a true drug candidate. [3] [4] [5]

References

  1. ↑ Patricia Kaminski and Richard Katz. Yerba Santa Eriodictyon californicum. Flower Essence Society.
  2. ↑ Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ (July 2005). "Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae)". J. Agric. Food Chem. 53 (15): 6061–6. doi:10.1021/jf0505170. PMID   16028996.
  3. ↑ Wolfgang Fischer; Antonio Currais; Zhibin Liang; Antonio Pinto; Pamela Maher (February 2019). "Old age-associated phenotypic screening for Alzheimer's disease drug candidates identifies sterubin as a potent neuroprotective compound from Yerba santa". Redox Biology. 21 101089. doi:10.1016/j.redox.2018.101089. PMC   6309122 . PMID   30594901.
  4. ↑ Zhibin Liang; Pamela Maher (November 2022). "Structural Requirements for the Neuroprotective and Anti-Inflammatory Activities of the Flavanone Sterubin". Antioxidants. 11 (11): 2197. doi: 10.3390/antiox11112197 . PMC   9686938 . PMID   36358569.
  5. ↑ Batya Swift Yasgur. . (Paywalled) Medscape. February 2019.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.