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

• SHIGETOMI Kengo

  Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University

• OMOTO Shoko

  Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University

• KATO Yasuo

  Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University

• UBUKATA Makoto

  Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University

抄録

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.

収録刊行物

• Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ

  Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ 75 (4), 718-722, 2011

  公益社団法人 日本農芸化学会

キーワード

• tuliposide
• tulipalin
• Baylis-Hillman reaction

詳細情報

• CRID: 1390282681453641600
• NII論文ID: 10028271584
• NII書誌ID: AA10824164
• DOI: 10.1271/bbb.100845
• ISSN: 13476947
• ISSN: 09168451
• NDL書誌ID: 11071052
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I11071052
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.100845
• 本文言語コード: en
• データソース種別:
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• 抄録ライセンスフラグ: 使用不可