A facile test system based on the accumulation of benzo[c]phenanthridine alkaloids in Eschscholzia californica cell suspension culture (an indicator of defense gene activation) has been used to analyze a series of synthetic compounds for elicitor-like activity. Of the 200 jasmonic acid and coronatine analogs tested with this system, representative results obtained with 49 of them are presented here. The following can be summarized concerning structure-activity relationships: there is a large degree of plasticity allowed at the C-3 of jasmonic acid in the activation of defense genes. The carbonyl moiety is not strictly required, but exocyclic double bond character appears necessary. The pentenyl side chain at C-2 cannot tolerate bulky groups at the terminal carbon and still be biologically active. Substitutions to the C-1' position are tolerated if they can potentially undergo beta-oxidation. Either an alkanoic acid or methyl ester is required at C-1, or a side chain that can be shortened by beta-oxidation or by peptidase hydrolysis. Coronatine and various derivatives thereof are not as effective as jasmonic acid, and derivatives in inducing benzo[c]phenanthridine alkaloid accumulation. Jasmonic acid rather than the octadecanoic precursors is therefore considered to be a likely signal transducer of defense gene activation in planta.

译文

基于苯并 [c] 菲吡啶生物碱在加利福尼亚Eschscholzia细胞悬浮培养物 (防御基因激活的指标) 中的积累的简便测试系统已用于分析一系列具有激发子样活性的合成化合物。在用该系统测试的200茉莉酸和冠冕素类似物中,用其中的49个获得的代表性结果在这里给出。关于结构-活性关系,可以总结以下内容: 在防御基因的激活中,茉莉酸的C-3允许有很大程度的可塑性。羰基部分不是严格要求的,但是环外双键特征似乎是必需的。在C-2处的戊烯基侧链不能耐受末端碳处的大体积基团并且仍然具有生物活性。如果它们可能经历 β-氧化,则对C-1位置的取代是可以容忍的。C-1需要链烷酸或甲酯,或者可以通过 β-氧化或肽酶水解缩短的侧链。Coronatine及其各种衍生物在诱导苯并 [c] 菲吡啶生物碱积累方面不如茉莉酸有效。因此,茉莉酸而不是十八碳前体被认为是植物中防御基因激活的可能信号转导子。

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