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Saponarin

From Wikipedia, the free encyclopedia
Saponarin
Chemical structure of saponarin
Names
IUPAC name
5-Hydroxy-6-(β-D-glucopyranosyl)-7-(β-D-glucopyranosyloxy)flavone
Systematic IUPAC name
5-Hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Isovitexin-7-O-glucoside
Saponaretin-7-O-glucoside
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(40-15)18-14(41-27-25(38)23(36)20(33)16(8-29)42-27)6-13-17(21(18)34)11(31)5-12(39-13)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
    Key: HGUVPEBGCAVWID-KETMJRJWSA-N
  • InChI=1/C27H30O15/c28-7-15-19(32)22(35)24(37)26(40-15)18-14(41-27-25(38)23(36)20(33)16(8-29)42-27)6-13-17(21(18)34)11(31)5-12(39-13)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
    Key: HGUVPEBGCAVWID-KETMJRJWBK
  • c1cc(ccc1c2cc(=O)c3c(o2)cc(c(c3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
Properties
C27H30O15
Molar mass594.52 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Saponarin is aflavoneglucoside. It is found inSaponaria officinalis and inStrongylodon macrobotrys where it imparts the characteristicjade color to the flower. This coloration has been shown to be an example ofcopigmentation, a result of the presence ofmalvin (ananthocyanin) and saponarin in the ratio 1:9. Under thealkaline conditions (pH 7.9) found in thesap of theepidermal 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

[edit]
  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
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs
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