Phellamurin
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
Identifiers
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
C 26 H 30 O 11
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).
Chemical compound
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
^ "Phellamurin" .
^ Fortschritte der Chemie Organischer Naturstoffe . p. 17. ISBN 370918052X .
^ 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 .
^ 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 .
^ 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 .
External links