<i>Podophyllum</i>‐ Lignane: Struktur und Absolutkonfiguration von Podorhizol‐β‐<scp>D</scp>‐glucosid ( = Lignan F). 19. Mitt. über mitosehemmende Naturstoffe [1]

Abstract

Abstract Podorhizol‐β‐ D ‐glucoside ( 1 ) ( = lignan F), C 28 H 34 O 13 , a new lignan from the roots and rhizomes of Podophyllum species, represents one of the rare glucosides which are cleaved by acids as well as by bases. Acid hydrolysis furnished the intact aglycone podorhizol ( 3 ) and in addition two cyclisation products characterized as desoxy‐podophyllotoxin ( 10 ) and (−)‐isodesoxypodophyllotoxin ( 11 ), respectively. Base catalysed fission of the glucoside 1 yielded D ‐glucose and anhydropodorhizol ( 9 ). Podorhizol was smoothly oxidized to the corresponding ketone podorhizone ( 5 ), which upon treatment with NaOCH 3 underwent cleavage into methyl 3,4,5‐trimethoxy‐benzoate ( 8 ) and the benzylbutyrolactone derivative 7 . These findings combined with spectroscopical evidence revealed the structure of podorhizol as a 2,3‐dibenzylbutyrolactone derivative.