Oroxindin

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Oroxindin
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Names
IUPAC name
5-Hydroxy-8-methoxy-4-oxoflav-2-en-7-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[(5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic acid
Other names
Wogonin-7-O-β-D-glucuronide
Identifiers
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3D model (JSmol)
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  • InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1 checkY
    Key: LNOHXHDWGCMVCO-NTKSAMNMSA-N checkY
  • COc1c(cc(c2c1oc(cc2=O)c3ccccc3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O
Properties
C22H20O11
Molar mass 460.388 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Oroxindin is a flavone, a type of phenolic chemical compound. It is a wogonoside, more accurately a wogonin glucuronide isolated from Oroxylum indicum (Bignoniaceae),[1] Bacopa monnieri (Plantaginaceae), and Holmskioldia sanguinea (Chinese hat plant, Verbenaceae).[2]

Formation

A glucuronosyltransferase anzyme converts wogonin to its glucuronide by adding a sugar acid to one of the phenolic hydroxy group, with uridine diphosphate (UDP) as byproduct:[3]

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References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Ramachandran Nair, A. G.; Joshi, B. S. (1979). "Oroxindin—A new flavone glucuronide from Oroxylum indicum Vent". Proceedings / Indian Academy of Sciences. 88 (5): 323–327. doi:10.1007/BF02844710.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Chaudhuri, P. K.; Srivastava, Rashmi; Kumar, Sunil; Kumar, Sushil (2004). "Phytotoxic and antimicrobial constituents of Bacopa monnieri and Holmskioldia sanguinea". Phytotherapy Research. 18 (2): 114–117. doi:10.1002/ptr.1278.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela (2023). "Flavones: Structure, Properties, Sources and Food Applications". Handbook of Food Bioactive Ingredients. pp. 111–158. doi:10.1007/978-3-031-28109-9_4. ISBN 978-3-031-28108-2.

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