title: A novel synthetic fluoro-containing jasmonate derivative acts as a chemical inducing signal for plant secondary metabolism.
abstract: A novel fluoro-containing jasmonate derivative was chemically synthesized and evaluated as a potential elicitor with respect to the induction of plant defense responses and the biosynthesis of plant secondary metabolites. A bioactive taxuyunnanine C (Tc)-producing cell line of Taxus chinensis was taken as a model plant cell system. The presence of novel synthesized pentafluoropropyl jasmonate (PFPJA) induced two early and important events in plant defense responses, including an oxidative burst and activation of L-phenylalanine ammonia lyase. In addition, PFPJA was found to significantly increase Tc accumulation, without any inhibition of cell growth. Moreover, Tc accumulation was increased more in the presence of PFPJA compared with methyl jasmonate (MJA) and previously reported trifluoroethyl jasmonate (TFEJA). For example, addition of 100 muM PFPJA on day 7 led to a high Tc content (38.2 +/- 0.3 mg/g) at day 21, while the Tc content was 29.3 +/- 0.3 mg/g and 34.9 +/- 0.9 mg/g with the addition of 100 microM MJA and TFEJA, respectively. Quantitative structure-activity analysis of fluoro-containing jasmonates suggests that the increase in the fluoro-groups introduced into the carboxyl side-chain of MJA resulted in a higher stimulatory activity for Tc biosynthesis, which corresponds well with the markedly increased lipophilicity after fluorine introduction. These results indicate that newly synthesized fluoro-containing PFPJA can act as a powerful chemical inducing signal for secondary metabolism in plant cell cultures.
authors.affiliation: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200237, China.
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: Qian
authors.forename: Zhen-Jiang
authors.initials: ZJ
authors.lastname: Zhao
authors.forename: Yufang
authors.initials: Y
authors.lastname: Xu
authors.forename: Xuhong
authors.initials: X
authors.lastname: Qian
authors.forename: Jian-Jiang
authors.initials: JJ
authors.lastname: Zhong
mesh_terms: D002478:Cells, Cultured; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000494:pharmacology*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000494:pharmacology*; D008956:Models, Chemical; D015394:Molecular Structure; D054883:Oxylipins; D015398:Signal Transduction; D043823:Taxoids / Q000378:metabolism; D020946:Taxus / Q000187:drug effects* / Q000378:metabolism*; D013997:Time Factors; D005466:Fluorocarbons
chemical_list: D003517:Cyclopentanes; D006845:Hydrocarbons, Fluorinated; D054883:Oxylipins; D043823:Taxoids; C497006:pentafluoropropyl jasmonate; D005466:Fluorocarbons; C494600:taxuyunnanine C