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Podophyllum ‐ Lignane: Struktur und Absolutkonfiguration von Podorhizol‐β‐ D ‐glucosid ( = Lignan F) . 19. Mitt. über mitosehemmende Naturstoffe [1]
Author(s) -
Kuhn M.,
Von Wartbung A.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500614
Subject(s) - chemistry , lignan , podophyllum , podophyllotoxin , glucoside , stereochemistry , aglycone , derivative (finance) , hydrolysis , berberidaceae , acid hydrolysis , glycoside , organic chemistry , botany , medicine , alternative medicine , pathology , financial economics , economics , biology
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.