Saponarin

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Saponarin
Chemical structure of saponarin
IUPAC name

5-hydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Other names

Isovitexin-7-O-glucoside
Saponaretin-7-O-glucoside

Identifiers
CAS number 20310-89-8
PubChem 4636593
Jmol-3D images Image 1
Properties
Molecular formula C27H30O15
Molar mass 594.52 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Saponarin is a flavone glucoside. It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower. This coloration has been shown to be an example of copigmentation, a result of the presence of malvin (an anthocyanin) and saponarin in the ratio 1:9. Under the alkaline conditions (pH 7.9) found in the sap of the epidermal cells, this combination produced a blue-green pigmentation; the pH of the colorless inner floral tissue was found to be lower, at pH 5.6. Experiments showed that saponarin produced a strong yellow colouring in slightly alkaline conditions, resulting in the greenish tone of the flower.[1] It is also found in passion flowers (Passiflora sp.).

References

  1. ↑ Greenish blue flower colour of Strongylodon macrobotrys. Kosaku Takeda, Aki Fujii, Yohko Senda and Tsukasa Iwashina, Biochemical Systematics and Ecology, Volume 38, Issue 4, August 2010, Pages 630–633, doi:10.1016/j.bse.2010.07.014
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
  • 6-Hydroxyluteolin
  • Hypolaetin (8-Hydroxyluteolin)
  • Tricetin (5,7,3',4',5'-Pentahydroxyflavone)
O-methylated flavones
  • Acacetin (Apigenin 4'-methyl ether)
  • Artocarpetin (Norartocarpetin 7-methyl ether)
  • Chrysoeriol (Luteolin 3'-methyl ether)
  • Cirsilineol (4',5-Dihydroxy-3',6,7-trimethoxyflavone)
  • Cirsiliol (3',4',5-trihydoxy-6,7-dimethoxyflavone)
  • Cirsimaritin (Scutellarein 6,7-dimethyl ether)
  • Diosmetin (Luteolin 4'-methyl ether)
  • Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone)
  • Genkwanin (Apigenin 7-methyl ether)
  • Nepetin (Luteolin 6-methyl ether)
  • Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone)
  • Oroxylin A (Baicalein 6-methyl ether)
  • Pratol (7-Hydroxy-4-methoxyflavone)
  • Salvigenin (5-Hydroxy-6,7,4'-trimethoxyflavone)
  • Sinensetin (3',4',5,6,7-Pentamethoxyflavone)
  • Tangeritin (4',5,6,7,8-Pentamethoxyflavone)
  • Techtochrysin (Chrysin 7-methyl ether)
  • Tricin (Tricetin 3',5'-dimethyl ether)
  • Wogonin (Norwogonin 8-methyl ether)
  • Zapotin (2,6,5,6-tetramethoxyflavone)
Glycosides
of apigenin
  • Apiin (Apigenin-7-O-apioglucoside)
  • Apigetrin (Apigenin 7-O-glucoside)
  • Isovitexin (Apigenin 6-C-glucoside)
  • Rhoifolin (Apigenin 7-O-neohesperidoside)
  • Saponarin (Isovitexin-7-O-glucoside)
  • Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside)
  • Vicenin-2 (Apigenin 6,8-di-C-glucoside)
  • Vitexin (Apigenin-8-C-glucoside)
of baicalein
  • Baicalin (Baicalein 7-O-glucuronide)
  • Tetuin (Baicalein 6-O-glucoside)
of hypolaetin
  • Hypolaetin 8-glucoside
  • Hypolaetin 8-glucuronide
of luteolin
  • Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
  • Nepitrin (Nepetin 7-O-glucoside)
  • Oroxindin (Wogonin 7-O-glucuronide)
  • Scutellarin (Scutellarein 7-O-glucuronide)
Acetylated
  • Artocarpetin A (prenylated artocarpetin)
  • Artoindonesianin P (prenylated)
Sulfated glycosides
Theograndin I (sulfated glucuronide of isoscutellarein) and II
Polymers
Drugs
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