Theograndin I

Theograndin I
Names

IUPAC name (2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy-3,5-dihydroxy-4-sulfooxyoxane-2-carboxylic acid
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	9332093
PubChem	11156985
InChI 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
SMILES 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
Chemical formula	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

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

References

↑ 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.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	6-Hydroxyflavone

Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone

Trihydroxyflavones	Apigenin Baicalein Norwogonin

Tetrahydroxyflavones	Isoscutellarein Luteolin Norartocarpetin Scutellarein

Pentahydroxyflavones	6-Hydroxyluteolin Hypolaetin Tricetin

O-methylated flavones	Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeritin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin

of baicalein	Baicalin Tetuin

of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide

of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide

Giraldiin A and B
Nepitrin
Oroxindin
Scutellarin

Acetylated

Artocarpetin A
Artoindonesianin P

Sulfated glycosides

Theograndin I and II

Polymers

Amentoflavone

Drugs

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