Phellamurin

Phellamurin
Names
IUPAC name
(2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Other names
Fellavine
8-Prenyldihydrokaempferol 7-glucoside
Epimedoside C
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH C016043
Properties
C26H30O11
Molar mass 518.52 g·mol−1
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

Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin,[1] and may be seen as the 7-O-glucoside of noricaritin.[2] Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible.

It can be found in Commiphora africana[3] and in Phellodendron amurense.[4]


6"′-O-acetyl phellamurin is found in the leaves of Phellodendron japonicum.[5]


References

  1. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/Phellamurin
  2. ↑ page 17 "Fortschritte der Chemie Organischer Naturstoffe" ISBN 370918052X
  3. ↑ A Dihydroflavonol Glucoside from Commiphora africana that Mediates DNA Strand Scission, Ji Ma, Shannon H. Jones, and Sidney M. Hecht, 2005
  4. ↑ A flavonoid glucoside, phellamurin, regulates differential oviposition on a rutaceous plant, Phellodendron amurense, by two sympatric swallowtail butterflies, Papilio protenor and P. xuthus: The front line of a coevolutionary arms race? Keiichi Honda and Nanao Hayashi, 1995
  5. ↑ Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity, Chih-Yang Chiu, Chia-Ying Li, Chao-Chen Chiu, Masatake Niwa, Susumu Kitanaka, Amooru Gangaiah Damu, E-Jian Lee and Tian-Shung Wu, 2005
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