Valoneic acid dilactone

Valoneic acid dilactone
Chemical structure of valoneic acid dilactone
Names
Preferred IUPAC name
3,4,5-Trihydroxy-2-[(3,7,8-trihydroxy-5,10-dioxo-5,10-dihydro[1]benzopyrano[5,4,3-cde][1]benzopyran-2-yl)oxy]benzoate
Other names
Valoneic acid bislactone
Valoneic acid bilactone
Identifiers
CAS Number
  • 60202-70-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8327382 ☒N
PubChem CID
  • 10151874
UNII
  • UH5C3DT5LR checkY
CompTox Dashboard (EPA)
  • DTXSID60436184 Edit this at Wikidata
InChI
  • InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29) ☒N
    Key: BPAOAXAAABIQKR-UHFFFAOYSA-N ☒N
  • InChI=1/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)
    Key: BPAOAXAAABIQKR-UHFFFAOYAM
  • Oc1cc5c(=O)oc3c(O)c(Oc4c(C(=O)O)cc(O)c(O)c4O)cc2c3c5c(c1O)oc2=O
Properties
Chemical formula
 C21H10O13
Molar mass 470.28 g/mol
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 ?)
Infobox references
Chemical compound

Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laevifolia[1] and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).[2]

It shows an inhibitory effect on 5α-reductase,[1] an enzyme involved in steroids metabolism and prostate cancer.

References

  1. ^ a b 5A-Reductase inhibitory tannin-related compounds isolated from Shorea laevifolia. Yoshio Hirano, Ryuichiro Kondo and Kokki Sakai, Journal of wood science, Volume 49, Number 4, pp.339-343,doi:10.1007/s10086-002-0481-y
  2. ^ Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainenb, Lasse Lindroosa, Juhani Kangasd and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83, doi:10.1016/S0021-9673(00)00624-5

External links

  • Valoneic acid dilactone at Phenol-Explorer.eu
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Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
  • Elaeocarpusin
  • Helioscopin B
  • Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other


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