Phellamurin

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.

Phellamurin
Names
IUPAC name
(2R,3R)-7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
Systematic IUPAC name
(2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Fellavine
8-Prenyldihydrokaempferol 7-glucoside
Epimedoside C
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH C016043
UNII
  • InChI=1S/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1 ☒N
    Key: GRDZTDZJQRPNCN-YIANMRPHSA-N ☒N
  • InChI=1/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1
    Key: GRDZTDZJQRPNCN-YIANMRPHBT
  • CC(=CCC1=C(C=C(C2=C1O[C@@H]([C@H](C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C
Properties
C26H30O11
Molar mass 518.515 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

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. "Phellamurin".
  2. Fortschritte der Chemie Organischer Naturstoffe. p. 17. ISBN 370918052X.
  3. Ma, Ji; Jones, Shannon H.; Hecht, Sidney M. (2005). "A Dihydroflavonol Glucoside from Commiphora a fricana that Mediates DNA Strand Scission". Journal of Natural Products. 68 (1): 115–117. doi:10.1021/np0400510. PMID 15679332.
  4. Honda, Keiichi; Hayashi, Nanao (1995). "A flavonoid glucoside, phellamurin, regulates differential oviposition on a rutaceous plant,Phellodendron amurense, by two sympatric swallowtail butterflies,Papilio protenor andP. Xuthus: The front line of a coevolutionary arms race?". Journal of Chemical Ecology. 21 (10): 1531–1539. doi:10.1007/BF02035150. PMID 24233681. S2CID 8258780.
  5. Chiu, C. Y.; Li, C. Y.; Chiu, C. C.; Niwa, M.; Kitanaka, S.; Damu, A. G.; Lee, E. J.; Wu, T. S. (2005). "Constituents of leaves of Phellodendron japonicum MAXIM. And their antioxidant activity". Chemical & Pharmaceutical Bulletin. 53 (9): 1118–1121. doi:10.1248/cpb.53.1118. PMID 16141579.
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