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, Kengo SHIGETOMI Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University Search for other works by this author on: Oxford Academic Shoko OMOTO Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University Search for other works by this author on: Oxford Academic Yasuo KATO Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University Search for other works by this author on: Oxford Academic Makoto UBUKATA Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University Search for other works by this author on: Oxford Academic
Bioscience, Biotechnology, and Biochemistry, Volume 75, Issue 4, 23 April 2011, Pages 718–722, https://doi.org/10.1271/bbb.100845
Published:
23 April 2011
Article history
Received:
30 November 2010
Accepted:
20 January 2011
Published:
23 April 2011
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Kengo SHIGETOMI, Shoko OMOTO, Yasuo KATO, Makoto UBUKATA, Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi, Bioscience, Biotechnology, and Biochemistry, Volume 75, Issue 4, 23 April 2011, Pages 718–722, https://doi.org/10.1271/bbb.100845
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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 via the asymmetric Baylis-Hillman reaction. Tuliposides and tulipalins showed antifungal activities against most of the strains tested at high concentrations (2.5 mm), while Botrytis tulipae 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 Gibberella zeae and inhibitory activity against Fusarium oxysporum f. sp tulipae. These activities were induced at a much lower concentration (0.05 mm) than the antifungal MIC values.
tuliposide, tulipalin, Baylis-Hillman reaction
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© Japan Society for Bioscience, Biotechnology, and Agrochemistry 2011
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