Abstract
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-l4β,17α-dihydroxy) estrogen. The hydrolytic labile glycosyl moiety is identified as O(β- 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-(α-pentulopyranosyl)-(1 → 4)- O-(α- 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.
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