Mabry, T. J. (Tom J.)Roux, Stanley J.1828601452008-08-282008-08-282006http://hdl.handle.net/2152/3514My chemistry studies of the genus Silphium involved the flavonoids and phenolic acids among eleven species. In the course of these investigations, five new flavonol triglycosides were isolated and characterized: isorhamnetin 3-O-α-L-rhamnosyl (1'''→6'')- O-β-D-galactopyranoside 7-O-β-L-apiofuranoside (1A), quercetin 3-O-α-L-rhamnosyl (1'''→6'')-O-β-D-galactopyranoside 7-O-β-L-apiofuranoside (2A), quercetin 3-O-β-Lgalactosyl (1'''→6'')-O-β-D-rhamnopyranoside 7-O-α-L-apiofuranoside (3A), kaempferol 3-O-β-D-apiofuranoside 7-O-α-L-rhamnosyl (1''''→6''')-O-β-D-galactopyranoside (4A) and kaempferol 3-O-β-D-apiofuranoside 7-O-α-L-rhamnosyl (1''''→6''')-O-β-D (2'''-O-E- caffeoylgalactopyranoside) (5A). Many other known mono and diglycosidic flavonoids were also isolated and identified. The structures of all these compounds were established by chemical methods and spectral analyses using 1 H NMR, 13C NMR, HMQC, HMBC, ROESY, TOCSY and LC/MS techniques. The distribution of the flavonoids and phenolic acids in all eleven members were compared with Dr. Jennifer Clevinger’s DNA-based revision of the genus. In addition to the detailed chemical investigations, I present my evaluations of the chemosystematic and medicinal value of the compounds I characterized; moreover, the new flavonoids are now being made available for medicinal and pharmaceutical studies.electronicengCopyright © is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.Silphium (Genus)FlavonoidsPhenolic acidsMateria medica, VegetableThesis