Smitilbin

Smitilbin
Names

IUPAC name (2R,3S)-2-(3,5-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
Other names Isoastilbin B
Identifiers
CAS Number	222846-33-5^Y ^[1]
Jmol interactive 3D	Image
PubChem	9889962
SMILES CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=CC(=C4)O)O)O)O)OC[C@H]1C([C@H]([C@H]([C@@H](O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=CC(=C4)O)O)O)O)O
Properties
Chemical formula	C₂₁H₂₂O₁₁
Molar mass	450.39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Smitilbin is a flavanonol, a type of flavonoid. It is a rhamnoside that can be isolated in Smilax glabra^[2] (Chinaroot, sarsaparilla).

Uses

Smitilbin could be used for preventing immunological hepatocyte damage.^[3]

Related compounds

Neosmitilbin

Neosmitilbin is a stereoisomer of smitilbin.

References

↑ Smitilbin on metabolomics.jp
↑ A Flavonol Glycoside from Smilax glabra, Ting Chen, Jian Xin Li, Yu Cai, Qiang Xu, Chinese Chemical Letters, Vol. 13, No 6, 2002, pages 537-538
↑ A new flavanone isolated from rhizoma smilacis glabrae and the structural requirements of its derivatives for preventing immunological hepatocyte damage. Planta Med 65(1):56-9 (1999), T Chen, J Li, J Cao, Q Xu, K Komatsu and T Namba

Flavanonols and their glycosides

3-Hydroxyflavanones:	Ampelopsin (Dihydromyricetin) Aromadedrin (Dihydrokaempferol) Dihydrogossypetin Dihydromorin Fustin (Dihydrofisetin) Garbanzol Taxifolin (Dihydroquercetin)

O-methylated flavanonols	Dihydrokaempferide

dihydroflavonol 3-O-glycosides	Lecontin (+)-fustin glucoside

Glycosides	Astilbin Chrysandroside A Chrysandroside B Engeletin Eucryphin Smitilbin (Isoastilbin B) Xeractinol

Acetylated glycosides	Phellamurin

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