5'-Methoxyhydnocarpin

5'-Methoxyhydnocarpin (5′-MHC) is a chemical compound that has been isolated from Berberis[1] and Hydnocarpus wightianus.[2]

5'-Methoxyhydnocarpin
Names
IUPAC name
(5′′R,6′′R)-5,7-Dihydroxy-6′′-(4-hydroxy-3-methoxyphenyl)-5′′-(hydroxymethyl)-5′-methoxy-5′′,6′′-dihydro[1,4]dioxino[2′′,3′′:3′,4′]flavone
Systematic IUPAC name
5,7-Dihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-8-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-1-benzopyran-4-one
Other names
5′-MHC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C26H22O10/c1-32-19-5-12(3-4-15(19)29)25-23(11-27)36-26-21(33-2)6-13(7-22(26)35-25)18-10-17(31)24-16(30)8-14(28)9-20(24)34-18/h3-10,23,25,27-30H,11H2,1-2H3/t23-,25-/m1/s1
    Key: NIOAGUZTTGFPGK-ILBGXUMGSA-N
  • InChI=1/C26H22O10/c1-32-19-5-12(3-4-15(19)29)25-23(11-27)36-26-21(33-2)6-13(7-22(26)35-25)18-10-17(31)24-16(30)8-14(28)9-20(24)34-18/h3-10,23,25,27-30H,11H2,1-2H3/t23-,25-/m1/s1
    Key: NIOAGUZTTGFPGK-ILBGXUMGBF
  • COC1=CC(=CC2=C1O[C@@H]([C@H](O2)C3=CC(=C(C=C3)O)OC)CO)C4=CC(=O)C5=C(C=C(C=C5O4)O)O
Properties
C26H22O10
Molar mass 494.452 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5′-MHC potentiates the antimicrobial effect of berberine in vitro.[1]

References
  1. Stermitz, F. R.; Lorenz, P; Tawara, J. N.; Zenewicz, L. A.; Lewis, K. (February 15, 2000). "Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5'-methoxyhydnocarpin, a multidrug pump inhibitor". Proceedings of the National Academy of Sciences. National Academy of Sciences. 97 (4): 1433–1437. Bibcode:2000PNAS...97.1433S. doi:10.1073/pnas.030540597. ISSN 1091-6490. PMC 26451. PMID 10677479.
  2. Williams, Cheryll (2013). Medicinal Plants in Australia Volume 4: An Antipodean Apothecary. Rosenberg Publishing. p. 171. ISBN 978-1-925078-08-4.


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