Edge Rewrite
restyle Source code View original
// HTMLRewriter · presentation

This page was redesigned at the edge.

Cloudflare fetched the original article and streamed it through HTMLRewriter to apply an entirely new visual system without rebuilding the source page.

Jump to content

Phellamurin

From Wikipedia, the free encyclopedia
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 X markN
    Key: GRDZTDZJQRPNCN-YIANMRPHSA-N X markN
  • 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).
X markN verify (what is checkYX markN ?)

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]


[edit]

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


References

[edit]
  1. ↑ "Phellamurin".
  2. ↑ Fortschritte der Chemie Organischer Naturstoffe. Springer. 6 December 2012. p. 17. ISBN 978-3709180525.
  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. Bibcode:2005JNAtP..68..115M. 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. Bibcode:1995JCEco..21.1531H. 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.
[edit]
  • Wikimedia Commons logo Media related to Phellamurin at Wikimedia Commons


Retrieved from "https://en.wikipedia.org/w/index.php?title=Phellamurin&oldid=1296404334"