Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

The effects of (+)-8',8',8'-trifluoroabscisic acid (trifluoro-ABA) on alpha-amylase expression were studied in rice embryoless half-seeds, scutella, and suspension-cultured cells derived from the embryo, and the effects of the analog on sugar accumulation were also studied in scutella and suspension-cultured cells. Treatment with (+)-trifluoro-ABA strongly inhibited the gibberellic acid-inducible expression of alpha-amylase I-1 encoded by RAmy1A in the aleurone layers of embryoless half-seeds at the levels of transcription, protein synthesis, and enzyme activity. It was also found that (+)-trifluoro-ABA stimulated (i) the uptake of glucose from the incubation medium and (ii) the synthesis of sucrose in scutellar tissues and suspension-cultured cells of rice. The biological activity of (+)-trifluoro-ABA was found to be more potent and persistent than that of natural ABA. We further examined the effects of trifluoro-ABA on the expression of alpha-amylase I-1 in scutellar tissues and suspension-cultured cells. It was found that (+)-trifluoro-ABA did not inhibit the formation of alpha-amylase I-1 in the absence of external glucose. However, glucose and (+)-trifluoro-ABA cooperatively suppressed the formation of alpha-amylase I-1. Judging from these results, we conclude that the regulatory mechanism for the expression of alpha-amylase I-1 in the scutellar epithelium is distinguishable from that operating in the aleurone layer.

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“…Nipponkai) (Todoroki et al 1997). We thus believe that the high potency of (+)-tri¯uoro-ABA results from its low turnover rate.…”

Section: Discussionmentioning

confidence: 93%

Effects of (+)-8′,8′,8′-trifluoroabscisic acid on a-amylase expression and sugar accumulation in rice cells

Kashem

Hori

Itoh

et al. 1998

Planta

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“…Modifying C-8 and C-9 with small functional groups has negligible effects on the binding to ABA receptors, but these modifications impact the persistence of these analogs [62]. For example, 8 ,8 ,8 -trideuterato ABA is long-lasting in plants [65,66]. Because the C-D bond is stronger than C-H, the deuterated methyl group at C-8' is more tolerant than the methyl group to oxidation.…”

Section: Analogs Resistance To Aba 8 -Hydroxylasementioning

confidence: 99%

Persistence of Abscisic Acid Analogs in Plants: Chemical Control of Plant Growth and Physiology

Nguyen

Yan

Nambara

2023

Genes

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Abscisic acid (ABA) is a plant hormone that regulates numerous plant processes, including plant growth, development, and stress physiology. ABA plays an important role in enhancing plant stress tolerance. This involves the ABA-mediated control of gene expression to increase antioxidant activities for scavenging reactive oxygen species (ROS). ABA is a fragile molecule that is rapidly isomerized by ultraviolet (UV) light and catabolized in plants. This makes it challenging to apply as a plant growth substance. ABA analogs are synthetic derivatives of ABA that alter ABA’s functions to modulate plant growth and stress physiology. Modifying functional group(s) in ABA analogs alters the potency, selectivity to receptors, and mode of action (i.e., either agonists or antagonists). Despite current advances in developing ABA analogs with high affinity to ABA receptors, it remains under investigation for its persistence in plants. The persistence of ABA analogs depends on their tolerance to catabolic and xenobiotic enzymes and light. Accumulated studies have demonstrated that the persistence of ABA analogs impacts the potency of its effect in plants. Thus, evaluating the persistence of these chemicals is a possible scheme for a better prediction of their functionality and potency in plants. Moreover, optimizing chemical administration protocols and biochemical characterization is also critical in validating the function of chemicals. Lastly, the development of chemical and genetic controls is required to acquire the stress tolerance of plants for multiple different uses.

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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

Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

Han¹,

Wan²,

Yang³

et al. 2014

Chin. J. Org. Chem.

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Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

Cited by 12 publications

References 11 publications

Effects of (+)-8′,8′,8′-trifluoroabscisic acid on a-amylase expression and sugar accumulation in rice cells

Effects of (+)-8′,8′,8′-trifluoroabscisic acid on a-amylase expression and sugar accumulation in rice cells

Persistence of Abscisic Acid Analogs in Plants: Chemical Control of Plant Growth and Physiology

Synthesis and Plant Growth Regulating Activities ofiso-Abscisic Acid

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