Carolinoside: a phytosteroidal glycoside from Solanum carolinense.
The glycoside of a new class of phytosteroids has been isolated from Solanum carolinense. The steroidal aglycone (carolinone) is alkylated at C-3 and is identified as C-[(2,4,5-trideoxy-3-keto-4,5-dehydro)-pentulopyranosyl]-(5----3)- (13,14- seco-14 beta,17 alpha-dihydroxy) estrogen. The hydrolytic labile glycosyl moiety is identified as O-(beta-D-glucopyranosyl) (1----1)-[L-(2,6-dideoxy-3-C-methyl)- arabinopyranose]. The linkage of this disaccharide in the steroidal glycoside (carolinoside) is shown to be O-(alpha-pentulopyranosyl)- (1----4)-O-(beta-L-arabinopyranosyl)-(1----1)-D-glucopyranose. Carolinoside occurs at concentrations of 10(-7)-10(-6) M in leaf tissue and was shown to be the host plant specific feeding induction factor for Manduca sexta.
Department of Chemistry, North Carolina State University, Raleigh 27695.
J D
JD
Thacker
J
J
Bordner
C
C
Bumgardner
D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification*; D010944:Plants / Q000032:analysis*
D006027:Glycosides; D010840:Phytosterols