Synthetic studies on bioactive natural products related to the chemical control of agricultural ecosystem

农业生态系统化学防治相关生物活性天然产物的综合研究

• 批准号: 13660103
• 负责人: KUWAHARA Shigefumi
• 金额: $ 2.69万
• 依托单位: Tohoku University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2001
• 资助国家: 日本
• 起止时间: 2001 至 2002
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-13660103/
• 关键词: azadirachtin; Eysarcoris parvus; Pseudococcus cryptus; isorobinal; pyricuol; volicitin; phytoalexin; pteridic acid; azadirachtin; antifeedant; Eysarcoris aeneua; isorobinal; volicitin; Pseudococcus cryptus; Hyoscyamus albus; oryzalexin S

Synthetic Studies were conducted on azadirachtin (1, insect antifeedant), (Z)-exo-α-bergamotenal (2, sex pheromone of Eysarcoris parvus), isorobinal (3, novel cyclic monoterpene from the astigmatid mite), volicitin (4, elicitor from the Spodoptera exigua), the sex pheromone of the citriculus mealybug (5), a phytoalexin isolated from Hyoscyamus albus (6), oryzalexin S (7, phytozlexin from the rice plant), tabtoxinine-β-lactam (8, phytotoxin from Pseudomonas tabaci), pyricuol (9, phytotoxin from Magnaporthe grisea), and ptericids A and B (10 and 11, auxin-like plant growth promoter from Streptomyces hygroscopicus). A model compound of 1 containg the bicyclo[2.2.1]heptane ring connected to the B ring was synthesized by using the Beckmann rearrangement of a petacyclic precursor. Synthesis of 2, 3, 4, 5, 9 was accomplished from farnesic acid, perilaldehyde, lactic acid, a-pinene, and 2,3-dimethylpheno1, respectively. Synthetic efforts toward 6, 7, 8, 10, and 11 were now in progress.

印楝素的合成研究（1，昆虫拒食剂），（Z）-exo-α-香柠檬烯醛（2）小眼瓢虫性信息素（3，来自螨类的新环状单萜），volicitin（4）甜菜夜蛾的激发子（elicitor），柑桔粉蚧的性信息素（5），天仙子的植物抗毒素（6），水稻素S（oryzalexin S）（7，来自水稻植物的植物毒素）、烟毒素-β-内酰胺（8，来自烟草假单胞菌的植物毒素）、pyricuol（9，来自稻瘟病菌的植物毒素）和ptericids A和B（10和11，来自吸水链霉菌的生长素样植物生长促进剂）。通过百环前体的Beckmann重排反应，合成了一个含B环和双环[2.2.1]庚烷环的模型化合物1。分别以金合欢酸、紫苏醛、乳酸、α-蒎烯和2，3-二甲基苯酚为原料合成了化合物2，3，4，5，9。现在，对6、7、8、10和11的合成工作正在进行中。

项目成果

T.Liang, S.Kuwahara: "Synthesis of both enantiomers of isorobinal, a novel cyclic monoterpene isolated from the astigmatid mite, Rhyzoglyphus sp."Biosci. Biotechnol. Biochem.. 66. 2501-2503 (2002)

T.Liang，S.Kuwahara：“异红二醛的两种对映体的合成，异红二醛是一种从斑螨 Rhyzoglyphus sp 中分离出来的新型环状单萜。”Biosci。

B.H.Alizadeh, S.Kuwahara, W.S.Leal, H.-C.Men: "Synthesis of the racemate of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhier"Biosci. Biotechnol. Biochem.. 66. 1415-1418 (2002)

B.H.Alizadeh、S.Kuwahara、W.S.Leal、H.-C.Men：“(Z)-exo-α-香柠檬醛的外消旋体的合成，白斑刺虫 Eysarcoris parvus Uhier 的性信息素成分”Biosci。生物化学.. 66. 1415-1418 (2002)

Babak Heidary Alizadeh: "Synthesis of the racemate of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhler"Biosci.ence, Biotechnology, and Biochemistry. 66. 1415-1418 (2002)

Babak Heidary Alizadeh：“(Z)-exo-α-佛手醛的外消旋体的合成，白斑刺虫 Eysarcoris parvus Uhler 的性信息素成分”Biosci.ence、Biotechnology 和 Biochemistry 66. 1415-1418 (2002)。 ）

S.Itoh, S.Kuwahara.M.Hasegawa, O.Kodama: "Synthesis of (17R)-and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm"Biosci. Biotechnol. Biochem.. 66. 2501-2503 (2002)

S.Itoh，S.Kuwahara.M.Hasekawa，O.Kodama：“volicitin（甜菜粘虫口腔分泌物中所含植物挥发物的诱导剂）的（17R）-和（17S）-异构体的合成”Biosci。

B.H.Alizadeh, S.Kuwahara, W.S.Leal, and H-C.Men: "Synthesis of the racemat of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhler"Biosci. Biotechnol. Biochem. 66. 1415-1418 (2002)

B.H.Alizadeh、S.Kuwahara、W.S.Leal 和 H-C.Men：“(Z)-exo-α-佛手醛外消旋体的合成，白斑刺虫 Eysarcoris parvus Uhler 的性信息素成分”Biosci。 . 66. 1415-1418 (2002)