Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots

Access this Article

Search this Article

Author(s)

Abstract

The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3, 4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalco-hol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyra-nosylvanillylalcohol was obtained as the main product. In the case of 3, 4-dimethoxybenzaldehyde, 3, 4, 5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.

Journal

  • Chemical & pharmaceutical bulletin

    Chemical & pharmaceutical bulletin 53(4), 361-365, 2005-04-01

    The Pharmaceutical Society of Japan

References:  14

Cited by:  2

Codes

  • NII Article ID (NAID)
    10016652873
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092363
  • NDL Article ID
    7292008
  • NDL Source Classification
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-D167
  • Data Source
    CJP  CJPref  NDL  NII-ELS  J-STAGE 
Page Top