Smitilbin

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

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
3D model (JSmol)
ChemSpider
  • InChI=1S/C23H26O9/c1-9-4-10(2)16-15(5-9)31-21(12-6-13(24)8-14(25)7-12)22(18(16)27)32-23-20(29)19(28)17(26)11(3)30-23/h4-8,11,17,19-26,28-29H,1-3H3/t11-,17-,19+,20+,21+,22+,23-/m0/s1 ☒N
    Key: XIFOLBFVNYGHBL-SZGUTPPVSA-N ☒N
  • Cc1cc(c2c(c1)O[C@@H]([C@@H](C2=O)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)c4cc(cc(c4)O)O)C
Properties
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).
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Infobox references

Uses

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

Neosmitilbin

Neosmitilbin is a stereoisomer of smitilbin.


References
  1. Smitilbin on metabolomics.jp
  2. 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
  3. 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
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