Synthesis of Brassinosteroids of Varying Acyl Side Chains and Evaluation of Their Brassinolide-like Activity

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概要

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• Brassinosteroids containing various side chain moieties were synthesized and their activity was determined as the reciprocal logarithm of the ED50 (50% effective dose per plant in moles) in the rice lamina inclination assay using synergist indole-3-acetic acid (IAA). The introduction of a hydroxyl group in the α-position to the carbonyl group of the ester structure significantly enhanced the activity. 2α,3α-Dihydroxy-17β-[(2R,3S)-2-hydroxy-3-methylpentanoyl]oxy-B-homo-7-oxa-5α-androstan-6-one showed the highest activity, for which the pED50 was determined to be 10.5 under synergistic conditions with IAA. Under identical conditions, the pED50 values of brassinolide and castasterone were determined to be 13.6 and 12.3 respectively. With respect to the α-carbon of the acyl moiety, the R-form was 10 times more potent than the corresponding S-form. Substituting the terminal structure (Et) of the side chain to that of the most potent compound, brassinolide (i-Pr), did not increase the activity.

• 社団法人 日本農芸化学会の論文
• 2004-05-23

著者

• NAKAGAWA Yoshiaki

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• MIYAGAWA Hisashi

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• Miyagawa Hisashi

  Plant Functions And Their Control Crest Japan Science And Technology Agency

• Miyagawa Hisashi

  Department Of Agricultural Chemistry Kyoto University

• Miyagawa Hisashi

  Div. Of Applied Life Sciences Graduate School Of Agriculture Kyoto Univ.

• Hisashi Miyagawa

  Division Of Applied Life Sciences Graduate School Of Agriculture Kyoto University

• OTSUKI Junko

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• UESUSUKI Shinya

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• WATANABE Bunta

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• YAMAMOTO Shuji

  Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

• Watanabe Bunta

  Division Of Applied Life Sciences Graduate School Of Agriculture Kyoto University

• Nakagawa Yoshiaki

  Div. Of Applied Life Sciences Graduate School Of Agriculture Kyoto Univ.

• Nakagawa Yoshiaki

  Division Of Applied Life Sciences Graduate School Of Agriculture Kyoto University

• Otsuki Junko

  Division Of Applied Life Sciences Graduate School Of Agriculture Kyoto University

• Uesusuki Shinya

  Division Of Applied Life Sciences Graduate School Of Agriculture Kyoto University

• Miyagawa Hisashi

  Division Of Applied Life Science Graduate School Of Agriculture Kyoto University

• Yamamoto Shuji

  Division Of Anesthesia Obihiro Kosei Hospital

• Miyagawa Hisashi

  Kyoto Univ. Kyoto Jpn

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