Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi

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Abstract

The structure-activity relationship was investigated to evaluate the antifungal activities of tuliposides and tulipalins against tulip pathogenic fungi. 6-Tuliposide B was effectively synthesized <I>via</I> the asymmetric Baylis-Hillman reaction. Tuliposides and tulipalins showed antifungal activities against most of the strains tested at high concentrations (2.5 m<small>M</small>), while <I>Botrytis tulipae</I> was resistant to tuliposides. Tulipalin formation was involved in the antifungal activity, tulipalin A showed higher inhibitory activity than 6-tuliposide B and tulipalin B. Both the tuliposides and tulipalins showed pigment-inducing activity against <I>Gibberella zeae</I> and inhibitory activity against <I>Fusarium oxysporum</I> f. sp <I>tulipae</I>. These activities were induced at a much lower concentration (0.05 m<small>M</small>) than the antifungal MIC values.

Journal

  • Agricultural and Biological Chemistry  

    Agricultural and Biological Chemistry 75(4), 718-722, 2011-04-23 

    Japan Society for Bioscience, Biotechnology, and Agrochemistry

References:  21

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Codes

  • NII Article ID (NAID)
    10028271584
  • NII NACSIS-CAT ID (NCID)
    AA10824164
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    09168451
  • NDL Article ID
    11071052
  • NDL Source Classification
    ZR7(科学技術--農林水産--農産) // ZR2(科学技術--生物学--生化学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-G223
  • Data Source
    CJP  NDL  J-STAGE 
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