Novel, unnatural benzo-1,2,3-thiadiazole-7-carboxylate elicitors of taxoid biosynthesis.
In order to establish the chemical biological technology for production of valuable secondary metabolites, a novel family of unnatural elicitors derived from the plant activator benzo-1,2,3-thiadiazole-7-carboxylic acid were designed and synthesized. New synthetic elicitors that showed powerful eliciting activities upon taxoid biosynthesis by Taxus chinensis suspension cells were obtained. For example, benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoxyl)ethyl ester was more effective and resulted in nearly 40% increase in taxuyunnanine C content and production in comparison with methyl jasmonate, which was previously reported as the most powerful chemical elicitor for taxoid biosynthesis. The novel class of elicitors was found to induce plant defense responses, including promotion of H(2)O(2) levels originating from oxidative burst and activation of phenylalanine ammonia lyase. Interestingly the plant defense responses induced corresponded well to the superior stimulating activity in T. chinensis cell cultures. The work indicates that the newly synthesized benzothiadiazoles can act as a new family of elicitors for taxoid biosynthesis in plant cells.
Xu
Yufang
Y
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, P.O. Box 544, 130 Meilong Road, Shanghai 200237, China.
Zhao
Zhengjiang
Z
Qian
Xuhong
X
Qian
Zhigang
Z
Tian
Wenhong
W
Zhong
Jianjiang
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000378:metabolism; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D018929:Cell Culture Techniques; D010650:Phenylalanine Ammonia-Lyase / Q000378:metabolism; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000494:pharmacology; D043823:Taxoids / Q000138:chemical synthesis* / Q000378:metabolism; D020946:Taxus / Q000187:drug effects / Q000378:metabolism*; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D010937:Plant Growth Regulators; D043823:Taxoids; D013830:Thiadiazoles; D010650:Phenylalanine Ammonia-Lyase