Theograndin I

Theograndin I is a sulfated flavone glucuronide found in Cupuaçu (Theobroma grandiflorum).[1] It is a glucuronide of isoscutellarein (8-Hydroxyapigenin).

Theograndin I
Chemical structure of theograndin I.
Names
IUPAC name
4′,5,7-Trihydroxyflavon-8-yl 3-O-sulfo-β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3R,4S,5R,6S)-6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-8-yl]oxy}-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1
    Key: RUJCBFMBNQPWBK-DLSLMLROSA-N
  • InChI=1/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1
    Key: RUJCBFMBNQPWBK-DLSLMLROBZ
  • C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)C(=O)O)O)OS(=O)(=O)O)O)O
Properties
C21H18O15S
Molar mass 542.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Yang, H; Protiva, P; Cui, B; Ma, C; Baggett, S; Hequet, V; Mori, S; Weinstein, IB; Kennelly, EJ (2003). "New bioactive polyphenols from Theobroma grandiflorum ("cupuaçu")". Journal of Natural Products. 66 (11): 1501–4. doi:10.1021/np034002j. PMID 14640528.


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