Synthesis and bioactivity of 2',3'-benzoabscisic acid analogs.
2',3'-Benzoabscisic acid 4a is significantly more active than (±)-ABA and can be potentially used as a plant growth regulator for agriculture. In this study, six 4a analogs were designed and synthesized. Bioassay showed that 4a displayed greater activity than (±)-ABA and the six analogs produced less inhibition than 4a itself. Specially, some analogs displayed markedly different activities to different physiological and biochemical process, which were largely different from ABA and 4a. Compared to (±)-ABA, 4b and 4c were more effective germination inhibitors for lettuce, but less effective inhibitors for rice elongation. Five-membered analog 5 was higher or slightly weaker in inhibiting Arabidopsis seed germination and rice elongation, respectively, but at least 10 times less effective than (±)-ABA in lettuce seed germination. Dual acid 6 and alkyne acid 20 nearly produced no inhibitory activity for Arabidopsis seed germination, but displayed excellent activity in inhibiting rice seedling growth. The preference of the analogs to different physiology process indicated that they might provide a strategy to develop novel ABA agonists or antagonist and be used as probe to investigate the function of different ABA receptors.
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China; College of Agricultural, Shihezi University, Shihezi 832000, China.
Xiaoqiang
X
Han
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China.
Chuan
C
Wan
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China.
Xiuyun
X
Li
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China.
Hong
H
Li
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China.
Dongyan
D
Yang
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China.
Shijie
S
Du
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China. Electronic address: xiaoyumei@cau.edu.cn.
Yumei
Y
Xiao
Department of Applied Chemistry, China Agricultural University, Beijing 100193,China. Electronic address: qinzhaohai@263.net.
Zhaohai
Z
Qin
D000040:Abscisic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D017360:Arabidopsis / Q000187:drug effects / Q000254:growth & development; D001681:Biological Assay; D018525:Germination / Q000187:drug effects; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D012275:Oryza / Q000187:drug effects / Q000254:growth & development; D012639:Seeds / Q000187:drug effects / Q000254:growth & development
D009281:Naphthalenes; D000040:Abscisic Acid
Abscisic acid; Benzoabscisic acid analogs; Bioassay; Plant hormone; Synthesis