The flavonoids and phenolic acids of the genus Silphium and their chemosystematic value.
The current review outlines the distribution of flavonoids and phenolic acids in eleven species of Silphium (Asteraceae). The chemosystematic significance of these findings is discussed and compared with DNA and morphological-based assignments for eleven species. Special attention is given to the five flavonol triglycosides that were previously isolated and characterized from Silphium species: isorhamnetin 3-O-alpha-L-rhamnosyl (1""-->6")-O-beta-D-galactopyranoside 7-O-beta-L-apiofuranoside (1), quercetin 3-O-alpha-L-rhamnosyl (1"'-->6")-O-beta-D-galactopyranoside 7-O-beta-L-apiofuranoside (2), quercetin 3-O-beta-L-galactosyl (1"'-->6")-O-beta-D-rhamnopyranoside 7-O-alpha-L-apiofuranoside (3), kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl (1""-6"')-O-beta-D-galactopyranoside (4) and kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl (1""-->6"')-O-beta-D (2"'-O-E-caffeoylgalactopyranoside) (5). In addition, several other known mono and diglycosidic flavonoids, along with 18 phenolic acids, were also identified and the structures of all of the compounds were established by LC/MS and NMR spectral investigations.
School of Biological Sciences, Molecular Cell and Developmental Biology, The University of Texas at Austin, Austin, TX 78712, USA.
Jeffrey D
JD
Williams
Małgorzata
M
Wojcińska
Lalita M
LM
Calabria
Klaus
K
Linse
Jennifer A
JA
Clevinger
Tom J
TJ
Mabry
D019659:Asteraceae / Q000737:chemistry* / Q000145:classification; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids / Q000032:analysis* / Q000302:isolation & purification; D062385:Hydroxybenzoates / Q000032:analysis* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010802:Phylogeny; D013045:Species Specificity
D005419:Flavonoids; D062385:Hydroxybenzoates; C017616:phenolic acid