Synthesis and Plant Growth Regulating Activities of<i>iso</i>-Abscisic Acid

Han, Xiaoqiang; Wan, Chuan; Yang, Dongyan; Du, Shijie; Yuan, Xiaoyong; Xiao, Yumei; Qin, Zhaohai

doi:10.6023/cjoc201402034

Cited by 7 publications

(5 citation statements)

References 10 publications

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“…These results reveal that steric hindrance at C6′ might affect the different physiological processes of ABA. Interestingly, divinyl dienoic ABA analogue ( 16 ), iso -ABA ( 17 ,) and 8′-demethyl ABA ( 18 ) show activities nearly at the same order of magnitude as ABA, which means that one of the methyl groups at C6′ is not essential for biological activity. It has also been reported that the 6′-monomethyl substituted substrate can be recognized by the enzyme …”

Section: Introductionmentioning

confidence: 99%

“…It has also been reported that the 6′-monomethyl substituted substrate can be recognized by the enzyme. 51 Inspired by tetralone abscisic acid analogue (19) 52 and iso-ABA (17), 49 we previously reported a highly effective ABA-like plant growth regulator iso-PhABA (20). 53 In order to examine the importance of the ring methyls and the influence of steric hindrance on its activity, in this work, four PhABA analogues, dimethyl PhABA (21), demethyl-iso-PhABA (22), demethyl-PhABA (23), and 11′-methoxy-iso-PhABA (24) were designed and synthesized (Figure 1B).…”

Section: ■ Introductionmentioning

confidence: 99%

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Role of the Ring Methyl Groups in 2′,3′-Benzoabscisic Acid Analogues

Wan¹,

Hong²,

Zhang³

et al. 2019

J. Agric. Food Chem.

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Five analogues of iso-PhABA (20) developed earlier by our research group were designed and synthesized. The bioassay results show that the number and position of methyl groups along with the substitution of hydrogen atoms of the methyl group have a great influence on the activity. Compared with iso-PhABA, the inhibitory activity of diMe-PhABA (21) on seed germination and rice seedling growth decreased slightly; however, it significantly reduced the capability of inhibiting wheat embryo germination. Both 3′-deMe-iso-PhABA ( 22) and 2′-deMe-PhABA (23) exhibited weak inhibitory activities, and 11′methoxy iso-PhABA (24a/24b) was much more efficient than its isomer 24c/24d in all bioassays. These results reveal the preservation of quaternary carbon at the 2′ or 3′ position is necessary to maintain its ABA-like biological activity, and demethylation at the 3′ position has a more significant effect. The selectivity of these compounds to different physiological processes makes them available as selective probes for different ABA receptors.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Role of the Ring Methyl Groups in 2′,3′-Benzoabscisic Acid Analogues

Wan¹,

Hong²,

Zhang³

et al. 2019

J. Agric. Food Chem.

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“…A successful case of 8′-hydroxylation resistant analog was 2′,3′-benzoabscisic acid 2 [ 24 , 25 ] ( Figure 1 ), which had excellent bioactivity and relatively efficient synthetic route. Inspired by this compound and iso -ABA 3 [ 26 ], in our previous works, we had developed 2′,3′- iso -Benzoabscisic acid ( iso -PhABA) 4a [ 27 ], which is an excellent and easier preparation ABA analog. The deeply investigations of bioactivity and agonist-receptor interactions for 4a suggested that it is a state-of-art ABA-like regulator and a selective ABA agonist, i.e., PYL10 has the highest inhibitory effect on the phosphatase activity of HAB1 in the presence of (+)- iso -PhABA.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of 2′,3′-iso-Aryl-abscisic Acid Analogs

et al. 2017

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2′,3′-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, including the substitution of phenyl ring and replacing the ring with heterocycles. Thus, 16 novel analogs of iso-PhABA were synthesized and screened with three bioassays, Arabidopsis and lettuce seed germination and rice seedling elongation. Some of them, i.e., 2′,3′-iso-pyridoabscisic acid (iso-PyABA) and 2′,3′-iso-franoabscisic acid (iso-FrABA), displayed good bioactivities that closed to iso-PhABA and natural (+)-ABA. Some others, for instance, substituted-iso-PhABA, exhibited certain selectivity to different physiological process when compared to iso-PhABA or (+)-ABA. These analogs not only provided new candidates of ABA-like synthetic plant growth regulators (PGRs) for practical application, but also new potential selective agonist/antagonist for probing the specific function of ABA receptors.

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“…Considering cis-CpABA 3 is a mixture of two couples of cis-cyclopropyl enantiomers 36,37,38 , it is necessary to acquire the optically pure isomers and to evaluate their bioactivity. As part of our continuous efforts on developing novel ABA analogs and evaluating their bioactivity 39,40,41 . Herein, we report our results concerning the synthesis of cis-cyclopropyl ABA analogs 2S,3S-2,3-cyclopropanated abscisic acid (3a) and 2R,3R-2,3-cyclopropanated abscisic acid (3b).…”

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confidence: 99%