Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Nakano, Sei-ichi; Todoroki, Yasushi; Hirai, Nobuhiro; Ohigashi, Hajime

doi:10.1271/bbb.59.1699

Cited by 21 publications

(13 citation statements)

References 12 publications

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“…对比脱落酸与脱落酸类似物的结构, 我们可以发现脱落酸的结构改造集中在以下几个方面: (1) C-1 的羧基可以是醇、醛或者酯; (2)侧链中的 C(4)-C(5)反式双键被碳碳叁键代替; (3)侧链中的 C-2 上的氢被氟原子取代 [8] , 侧链被苯环 [9] 、五元杂环代替 [10] 或者侧链中 C-2, C-3 和 C-6 的烯丙基结构被三元环代替 [11] ; (4)增加六元和 C-7'烯丙基结构被环丙烷代替, 或者 C-5', C-6'和 C-8' 被环丙烷结构代替 [12] ; (5)降低六元环的饱和度: C-5', C-6'单键被碳碳双键代替, 同时 C-6'上脱掉一个甲基或者 C-2', C-3'和 C-7'烯丙基结构被苯环代替 [7] ; (6) C-7'甲基氟化为 CHF 2 [13] ; (7) C-8', C-9'上的氢原子被甲氧基 [4] 、烷基 [14] 、烯基、炔基 [6] 、氟原子 [5] 和氘原子取代 [15] ; (8) C-1'…”

Section: 基脱落酸(4)、8'-乙炔基脱落酸(5)unclassified

“…之前的研究都是通过改变侧链的结构设计合成脱落酸类似物, 并没有对侧链位置变化进行研究. 我们将脱落酸的侧链位置与 4'-羰基互换, 通过炔基锂在空间位阻影响下的选择性加成 [18] 等关键步骤合成了侧链位置异构的异脱落酸(11)和 2',3'-二氢异脱落酸(12)、异炔酸 (13)和异脱落酸内酯 (14). 经手性制备色谱实现混旋异脱落酸 11 的分离, 得到了(＋)-11 和(-)-11(图 2).…”

Section: 基脱落酸(4)、8'-乙炔基脱落酸(5)unclassified

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Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

Han¹,

Wan²,

Yang³

et al. 2014

Chin. J. Org. Chem.

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Section: 基脱落酸(4)、8'-乙炔基脱落酸(5)unclassified

Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

Han¹,

Wan²,

Yang³

et al. 2014

Chin. J. Org. Chem.

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“…11 4, 1997 are strong ABA agonists, suggesting that modifying the geminal dimethyl groups in some instances does not hinder recognition of the molecule as ABA-like. Similarly, alkyl substitutions at the 7', 8', and 9' positions revealed that high hormonal activity was generally maintained for molecules with the same absolute stereochemistry as (+)-ABA (Nakano et al, 1995). In the course of these studies Nakano et al (1995) showed that an analog with a methyl group added to the 8'-C atom, (+)-8'-methyl ABA (Fig.…”

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confidence: 94%

“…Similarly, alkyl substitutions at the 7', 8', and 9' positions revealed that high hormonal activity was generally maintained for molecules with the same absolute stereochemistry as (+)-ABA (Nakano et al, 1995). In the course of these studies Nakano et al (1995) showed that an analog with a methyl group added to the 8'-C atom, (+)-8'-methyl ABA (Fig. I), was nearly as active as (+)-ABA in blocking GA,-stimulated a-amylase activity, and was more active than (+)-ABA in inhibiting germination of lettuce seed, stomatal opening of spiderwort, and elongation of rice seedling leaves.…”

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confidence: 96%

“…This would suggest that there might be some latitude in altering the substrate binding site (8' C) without affecting the part of the molecule that is critica1 for receptor binding (7' C). ABA analogs bearing a methoxy or alkyl group on either the 8'-or 9'-C atom (Todoroki et al, 1994;Nakano et al, 1995) or fluorines on the 8'-C atom (Kim et al, 1995;Todoroki et al, et al Plant Physiol. Vol.…”

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8[prime]-Methylene Abscisic Acid (An Effective and Persistent Analog of Abscisic Acid)

et al. 1997

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l h e alteration in the ABA structure causes the analog to be metabolized more slowly than ABA, resulting in longer-lasting and more effective biological activity relative to ABA.The plant hormone (+)-ABA ( Fig. 1) regulates diverse aspects of plant growth, including development and germination of seeds, transpiration, and adaptive responses to environmental stresses (Zeevaart and Creelman, 1988;Davies and Jones, 1991). Considerable progress has been made in the identification of ABA-responsive genes, mutant characterization, and signaling (Bray, 1993;Chandler and Robertson, 1994;Giraudat et al., 1994). However, examination of the mechanisms of ABA action, identification of receptor proteins, and cellular localization of the hormone have been restricted by the rapid turnover of ABA in plants. Similarly, agricultura1 uses of applied ABA have been limited by its rapid metabolism in plants. Thus, the aim of the current research was to develop potent biologically stable ABA analogs that can be used to prolong ABA-like effects in plants for agricultural and basic research applications.Biologically stable analogs of other plant hormones, especially of the auxins, have proven to be useful tools for This is National Research Council of Canada paper no. 40712.

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Soil effects on the plant growth inhibitory activity of S-abscisic acid

Muñoz-Muñoz,

López-Cabeza,

Gámiz

et al. 2024

Biol Fertil Soils

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The use of natural plant growth regulators (PGRs) as ecofriendly agrochemicals is gaining much attention, but the fate of these compounds once they enter the soil environment is poorly understood. In this work, we compared the plant growth inhibitory activity of the phytohormone S-abscisic acid (S-ABA) in the presence of three soils with that observed in soilless (Petri dish) conditions and related the differences in activity to the sorption and dissipation processes of the phytohormone in the soils. In Petri dishes, S-ABA inhibited the germination of Eruca sativa, Allium porrum, Lactuca sativa, and Hordeum vulgare with mean inhibitory concentration values (IC50) in the range of 0.5–8.2 mg/L. Eruca sativa was selected for subsequent studies based on its high sensitivity to S-ABA (IC50 = 0.5 mg/L). The inhibition of germination of E. sativa by S-ABA was fully reversible at a low phytohormone concentration (5 mg/L) and partially reversible at a higher phytohormone concentration (60 mg/L). S-ABA also inhibited the growth of pre-germinated seedlings of E. sativa, albeit at higher concentrations than those at which it inhibited germination. The three soils used in the study weakened the inhibitory activity of S-ABA by soil factors in the range of 0.008–0.380. As S-ABA displayed low or even negative sorption in the soils tested, the decrease in the activity of S-ABA was attributed to its biodegradation in the soils, rather than to a decrease in its bioavailability due to sorption. Despite the reduction in the activity of S-ABA observed in the presence of the soils, the phytohormone still expressed its activity at quite low soil concentrations (0.3–20 mg/kg), showing higher activity in soils where the compound degraded more slowly.

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Synthesis and Biological Activity of 7′-, 8′-, and 9′-Alkyl Analogues of Abscisic Acid

Cited by 21 publications

References 12 publications

Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

8[prime]-Methylene Abscisic Acid (An Effective and Persistent Analog of Abscisic Acid)

Soil effects on the plant growth inhibitory activity of S-abscisic acid

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