title: Novel chemically synthesized hydroxyl-containing jasmonates as powerful inducing signals for plant secondary metabolism.
abstract: Novel hydroxyl-containing jasmonate derivatives were chemically synthesized and evaluated by bioassay as potential elicitors for stimulating the biosynthesis of plant secondary metabolites. A suspension culture of Taxus chinensis, which produces a bioactive taxoid, taxuyunnanine C (Tc), was taken as a model plant cell system. Experiments on the timing of addition of jasmonates and dose response indicated that day 7 and 100 microM was the optimal elicitation time and concentration, respectively, for both cell growth and Tc accumulation. Tc accumulation was increased more in the presence of novel hydroxyl-containing jasmonates compared to that with methyljasmonate (MJA) addition. For example, addition of 100 microM 2,3-dihydroxypropyl jasmonate on day 7 led to a very high Tc content of 47.2 +/- 0.5 mg/g (at day 21), whereas the Tc content was 29.2 +/- 0.6 mg/g (on the same day) with addition of 100 microM MJA. Quantitative structure-activity analysis of various jasmonates suggests that the optimal lipophilicity and the number of hydroxyl groups may be two important factors affecting their elicitation activity. In addition, the jasmonate elicitors were found to induce plant defense responses, including oxidative burst and activation of L-phenylalanine ammonia lyase (PAL). Interestingly, a higher level of H(2)O(2) production and PAL activity was detected with elicitation by the synthesized jasmonates compared with that by MJA, which corresponded well to the superior stimulating activity in the former. This work indicates that the newly synthesized hydroxyl-containing jasmonates can act as powerful inducing signals for secondary metabolite biosynthesis in plant cell cultures.
authors.affiliation: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 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: D000085:Acetates / Q000378:metabolism; D002460:Cell Line; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006861:Hydrogen Peroxide / Q000378:metabolism; D015394:Molecular Structure; D054883:Oxylipins; D010650:Phenylalanine Ammonia-Lyase / Q000378:metabolism; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D043823:Taxoids / Q000378:metabolism / Q000494:pharmacology; D020946:Taxus / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism*
chemical_list: C494599:2,3-dihydroxypropyl jasmonate; C494597:2-hydroxyethoxyethyl jasmonate; D000085:Acetates; D003517:Cyclopentanes; D004952:Esters; D005960:Glucosides; D054883:Oxylipins; D010937:Plant Growth Regulators; D043823:Taxoids; C494598:glucosyl jasmonate; C494600:taxuyunnanine C; C011006:jasmonic acid; C072239:methyl jasmonate; D006861:Hydrogen Peroxide; D010650:Phenylalanine Ammonia-Lyase