Alpinumisoflavone

Alpinumisoflavone is a pyranoisoflavone, a type of isoflavone. It can be found in the bark of Rinorea welwitschii.[1] It can also be found in the molluscicide plant Millettia thonningii and is thought to be an antischistosomal agent[2] since it has been shown to kill the snails which transmit the schistosomiasis and also the larvae of the parasite itself.[3]

Alpinumisoflavone
Chemical structure of alpinumisoflavone
Names
IUPAC name
4′,5-Dihydroxy-6′′,6′′-dimethyl-6′′H-pyrano[3′′,2′′:6,7]isoflavone
Systematic IUPAC name
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:5,4-b′]dipyran-4-one
Other names
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethylpyrano[3,2-g]chromen-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H16O5/c1-20(2)8-7-13-15(25-20)9-16-17(18(13)22)19(23)14(10-24-16)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3 checkY
    Key: RQAMSFTXEFSBPK-UHFFFAOYSA-N checkY
  • InChI=1/C20H16O5/c1-20(2)8-7-13-15(25-20)9-16-17(18(13)22)19(23)14(10-24-16)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3
    Key: RQAMSFTXEFSBPK-UHFFFAOYAG
  • CC1(C=CC2=C(O1)C=C3C(=C2O)C(=O)C(=CO3)C4=CC=C(C=C4)O)C
  • O=C2/C(c1ccc(O)cc1)=C\Oc4c2c(O)c3\C=C/C(Oc3c4)(C)C
Properties
C20H16O5
Molar mass 336.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Pyranoisoflavones from Rinorea welwitschii. M. Stewart, B. Bartholomew, F. Currie, D. K. Abbiw, Z. Latif, S. D. Sarker and R. J. Nash, Fitoterapia, Volume 71, Issue 5, 1 September 2000, Pages 595-597, doi:10.1016/S0367-326X(00)00210-0
  2. The plant molluscicide Millettia thonningii (Leguminosae) as a topical antischistosomal agent. S. Perrett, P. J. Whitfield, L. Sanderson and A. Bartlett, Journal of Ethnopharmacology, Volume 47, Issue 1, 23 June 1995, Pages 49-54
  3. Aqueous degradation of isoflavonoids in an extract of Millettia thonningii (Leguminosae) which is larvicidal towards schistosomes. Perrett S. and Whitfield P. J., PTR. Phytotherapy, 1995, vol. 9, no6, pp. 401-404


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