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C3 unit addition reaction accompanied by formation of C-C bond in phytotoxin biosynthesis of phytopathogen.

C3 unit addition reaction accompanied by formation of C-C bond in phytotoxin biosynthesis of phytopathogen.
植物病原体的植物毒素生物合成中伴随C-C键形成的C3单元加成反应。
批准号:
09660118
负责人:
NAKAJIMA Hiromitsu
金额:
$2.11万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
1997
资助国家:
日本
项目状态:
已结题
起止时间:
1997 至 1998

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中文摘要
翻译
Sorokinianin是由引起小麦和其它草的斑点病或根腐病的病原体的Bipolaris sorokiniana的菌株(OB-25-l)产生的植物毒素。推测该毒素由一个长蠕孢酚型倍半萜和一个C_3部分组成。为了阐明其生物合成来源,我们进行了三个实验:[1,2-^<13>C_2]乙酸钠补料实验; C_3单元前体的候选物与菌株OB-25-1的主要代谢产物prehelminthosporol一起的置换培养实验;以及[2,3-^<13>C_2]琥珀酸补料实验。这些实验的结果表明,sorokinianin合成从prehelminthosporol的反应,包括添加的TCA循环,脱羧和内酯化的成员。为了确定C_3单元的直接前体,我们<18>用过氧化氢酶和H_2_O从富马酸制备L-[羟基-^ O]苹果酸<18>,并进行了L-[羟基-^<18>O]苹果酸的补料实验。实验结果表明,C_3单元的直接前体不是苹果酸/丁二酸,而是富马酸/丁二酸。
英文摘要
Sorokinianin is a phytotoxin produced by a strain (OB-25-l) of Bipolaris sorokiniana, a pathogen causing spot blotch or foot and root rot diseases of wheat and other grasses. This toxin is assumed to be composed of a helminthosporol-type sesquiterpene and a C_3 portion. To clarify the biosynthetic origin we conducted three experiments : a [1,2-^<13>C_2] sodium acetate feeding experiment ; a replacement culture experiment with the candidates for the C_3 unit precursor, together with prehelminthosporol, the major metabolite of the strain OB-25-1 ; and a [2,3-^<13>C_2] succinic acid feeding experiment. The results of these experiments suggested that sorokinianin was synthesized from prehelminthosporol by reactions that include the addition of a member of the TCA cycle, decarboxylation and lactonization. To determine the direct C_3 unit precursor we prepared L-[hydroxy-^<18>O] malic acid from fumaric acid by fumarase and H_2_<18>O and conducted a L-[hydroxy-^<18>O] malic acid feeding experiment. The results of the experiment indicated that the direct C_3 unit precursor was not malic acid/oxalacetic acid but fumaric acid/succinic acid.
期刊论文(0)
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会议论文
H.Nakajima: "Cochliospicin A:a new metabolite related to spiciferinone,a phytotoxin of the fungus Cochliobolus spicifer" Journal of Natural Products. 60. 414-416 (1997)
H.Nakajima:“Cochliospicin A:一种与 spiciferinone 相关的新代谢物,一种真菌 Cochliobolus spicifer 的植物毒素”《天然产物杂志》。
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通讯作者:
中島廣光 (分担執筆): "植物病害の化学" 市原耿民・上野民夫編 学会出版センター, 290 (1997)
中岛宏光(撰稿人):《植物病害化学》,市原小民和上野民夫编辑,学会出版中心,290(1997)
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H.Nakajima: "Cochliospicin A : a new metabolite related to spiciferinoe, a phytotoxin of the fungus Cochliobolus spicifer" J.Nat.Prod.60. 414-416 (1997)
H.Nakajima:“Cochliospicin A:一种与 spiciferinoe 相关的新代谢物,spiciferinoe 是真菌 Cochliobolus spicifer 的植物毒素”J.Nat.Prod.60。
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14
    Biosynthesis of phytotoxins in phytopathogenic fungi
    • 批准号:
      13660108
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.24万
    • 财政年份:
      2001
    • 负责人:
      NAKAJIMA Hiromitsu
    • 依托单位:
    C3 unit addition reaction accompanied by formation of C-C bond in phytotoxin biosynthesis of phytopathogen.
    • 批准号:
      11660111
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.05万
    • 财政年份:
      1999
    • 负责人:
      NAKAJIMA Hiromitsu
    • 依托单位:
    Study on biosynthesis of the phytotoxins produced by the phytopathogens, with the aim for plant protection.
    • 批准号:
      07660138
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $0.26万
    • 财政年份:
      1995
    • 负责人:
      NAKAJIMA Hiromitsu
    • 依托单位:
    海外基金