Structure-activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica Jacq.
Structure-activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica Jacq.
复制标题
DOI：
10.1007/s004250050506
复制
发表时间：
1999-01-01
期刊：
影响因子：
4.3
通讯作者：
Weiler, EW
中科院分区：
文献类型：
--
作者：
Blechert, S;Bockelmann, C;Weiler, EW
Bryonia dioica 卷须卷曲测定为茉莉酸提供了快速、灵敏和选择性的生物测定。使用该测定法，分析了大量茉莉酸和冠菌素类似物的生物活性。在一项系统研究中，比较了茉莉酸的 C-3 类似物、C-2 类似物、C-1 同系物和类似物、C-1(1') 类似物，以及氨基酸和冠发酸部分均发生改变的冠发素类似物。结果表明，至少有两个结构上不重叠的生物活性中心，一个以茉莉酸结构为中心，仅允许较小的 C-1(1') 修饰，第二个中心以 12-氧代植物二烯酸结构为中心，具有不同的活性结构要求，因此允许完全不同的结构修饰。茉莉酸的 C18 基团 [12-氧代植物二烯酸和 3-氧代-2(2'(Z)-戊烯基)-环戊烷-1-辛酸]，冠菌素是其结构模拟物，当外部施用时，它是更有效的卷须卷曲诱导剂。机械刺激的卷须中茉莉酸和3-氧代-2(2'(Z)戊烯基)-环戊烷-1-辛酸的水平仍然非常低，并且没有发生可检测到的变化，而12-氧代植物二烯酸的水平先前已被证明在卷曲反应的开始和进展期间发生剧烈且短暂的变化。因此，12-氧代植物二烯酸，而不是茉莉酸或3-ore-2(2'(Z)-戊烯基)-环戊烷-1-辛酸，必须被视为B，二烯机械转导中的内源信号转导器。
The Bryonia dioica tendril-coiling assay provides a rapid, sensitive and selective bioassay for jasmonates. Using this assay, a large number of jasmonate and coronatine analogs were analyzed for their biological activities. In a systematic study, C-3 analogs, C-2 analogs, C-1 homologs and -analogs, C-1(1') analogs of jasmonic acid, as well as analogs of coronatine altered in both the amino acid and the coronafacic acid moiety, were compared. The results demonstrated at least two structurally non-overlapping centers of biological activity, one centered around the structure of jasmonic acid allowing only minor C-1(1') modifications and a second center around the structure of 12-oxophytodienoic acid and having different structural requirements for activity, thus allowing quite different structural modifications. The C18-group of the jasmonates [12-oxophytodienoic acid and 3-oxo-2(2'(Z)-pentenyl)-cyclopentane-1-octanoic acid], for which coronatine is a structural mimic, was the much more potent inducer of tendril coiling, when applied externally. The levels of jasmonic acid and 3-oxo-2(2'(Z)pentenyl)-cyclopentane-1-octanoic acid in mechanically stimulated tendrils remained very low and did not change detectably, while the level of 12-oxophytodienoic acid had earlier been shown to change drastically and transiently during the onset and progression of the coiling reaction. Thus, 12-oxophytodienoic acid, rather than jasmonic acid or 3-ore-2(2'(Z)-pentenyl)-cyclopentane-1-octanoic acid, has to be considered as an endogenous signal transducer in B, dioica mechanotransduction.