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(Synonyms: 环丙嘧啶醇) 目录号 : GC48874 复制 一键复制产品信息

Ancymidol是一种具有生物活性的嘧啶类植物生长调节剂。

Ancymidol Chemical Structure

Cas No.:12771-68-5

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Description

Ancymidol is a biologically active pyrimidine-class plant growth regulator. Ancymidol can block the abnormal elongation of plant cells by inhibiting the oxidation of gibberellin biosynthetic intermediates, while also suppressing plant growth by interfering with cellulose biosynthesis. Ancymidol can be used in related research in plant pathology and mycology[1-4].

In vitro, maize suspension-cultured cells were treated with Ancymidol (12.5μM–2mM) for 8 days. Ancymidol significantly inhibited cell growth and induced a globular cell shape, while reducing cellulose deposition in the cell wall and promoting xylan synthesis as a compensatory response[5]. Phaseolus vulgaris seedlings and Gibberella fujikuroi cultures were treated with Ancymidol (10–100μg/ml). Ancymidol significantly inhibited the endogenous gibberellin biosynthesis and the gibberellin-like activity in the extracts; Phaseolus vulgaris seedlings cultured in the dark were treated with Ancymidol (10μg/ml) for 0 to 4 days. Ancymidol significantly induced or enhanced the production of compounds that inhibited the leaf sheath elongation of Oryza sativa[6].

References:
[1] Coolbaugh RC, Hirano SS, West CA. Studies on the Specificity and Site of Action of alpha-Cyclopropyl-alpha-[p-methoxyphenyl]-5-pyrimidine Methyl Alcohol (Ancymidol), a Plant Growth Regulator. Plant Physiol. 1978 Oct;62(4):571-6.
[2] Chen J, Ziv M. The effect of ancymidol on hyperhydricity, regeneration, starch and antioxidant enzymatic activities in liquid-cultured Narcissus. Plant Cell Rep. 2001 Jan;20(1):22-27.
[3] Feng XR, Wolyn DJ. Development of haploid asparagus embryos from liquid cultures of anther-derived calli is enhanced by ancymidol. Plant Cell Rep. 1993 Mar;12(5):281-5.
[4] Li B, Wolyn DJ. The effects of ancymidol, abscisic acid, uniconazole and paclobutrazol on somatic embryogenesis of asparagus. Plant Cell Rep. 1995 May;14(8):529-33.
[5] Hernández-Altamirano JM, Largo-Gosens A, Martínez-Rubio R, et al. Effect of ancymidol on cell wall metabolism in growing maize cells. Planta. 2018 Apr;247(4):987-999.
[6] Shive JB, Sisler HD. Effects of Ancymidol (a Growth Retardant) and Triarimol (a Fungicide) on the Growth, Sterols, and Gibberellins of Phaseolus vulgaris (L.). Plant Physiol. 1976 Apr;57(4):640-4.

Ancymidol是一种具有生物活性的嘧啶类植物生长调节剂。Ancymidol可通过抑制赤霉素(gibberellin)生物合成中间体的氧化来阻断植物细胞的异常伸长,同时通过干扰纤维素的生物合成以抑制植物生长。Ancymidol可用于植物病理学与真菌学的相关研究[1-4]

在体外,Ancymidol(12.5μM–2mM)处理玉米悬浮培养细胞8天。Ancymidol显著抑制细胞生长并诱导球状细胞形态,同时降低细胞壁中纤维素的沉积并促进木聚糖合成作为补偿[5]。Ancymidol(10–100μg/ml)处理Phaseolus vulgaris幼苗及Gibberella fujikuroi培养物。Ancymidol显著抑制了内源赤霉素的生物合成及提取物中的赤霉素样活性;Ancymidol(10μg/ml)处理暗培养的Phaseolus vulgaris 0至4天。Ancymidol显著诱导或增强了导致Oryza sativa叶鞘伸长受抑的化合物的产生[6]

实验参考方法

Cell experiment [1]:

Cell lines

Maize (Zea mays L. Black Mexican sweet corn) suspension-cultured cells

Preparation Method

Maize cells were maintained in Murashige and Skoog (MS) medium supplemented with 10μM 2,4-D and 20g/L sucrose (pH=5.6), at 25°C under photoperiodic conditions (16:8 light/dark cycle; 41μmol/m²/s) with rotary shaking (110rpm), and routinely subcultured fortnightly. Ancymidol (dissolved in ethanol) was applied at varying concentrations immediately after subculturing. In reversal experiments, 500μM Ancymidol-treated cultures were supplemented with 100μM GA₃.

Reaction Conditions

12.5μM to 2mM; 8 days

Applications

Ancymidol concentrations ≤500μM progressively reduced cell growth and induced a globular cell shape without affecting cell viability; the I₅₀ value for the inhibitory effect on fresh weight gain was 658μM, and this growth inhibition was reversed by supplementation with 100μM GA₃. Ancymidol impaired cellulose accumulation in cell walls, as 500μM Ancymidol caused reduction in cellulose content and reduced the incorporation of [¹⁴C]glucose into α-cellulose, which was not reversed by the simultaneous application of GA₃. Ancymidol increased the incorporation of [³H]arabinose into a hemicellulose-enriched (4M KOH) fraction and up-regulated ZmIRX9 and ZmIRX10L gene expression, indicating an enhancement in arabinoxylan biosynthesis as a compensatory response to cellulose reduction.

References:
[1] Hernández-Altamirano JM, Largo-Gosens A, Martínez-Rubio R, et al. Effect of ancymidol on cell wall metabolism in growing maize cells. Planta. 2018 Apr;247(4):987-999.

化学性质

Cas No. 12771-68-5 SDF
别名 环丙嘧啶醇
Canonical SMILES OC(C1=CC=C(C=C1)OC)(C2CC2)C3=CN=CN=C3
分子式 C15H16N2O2 分子量 256.3
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml,Ethanol: 1 mg/ml 储存条件 -20°C
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1 mM 3.9017 mL 19.5084 mL 39.0168 mL
5 mM 780.3 μL 3.9017 mL 7.8034 mL
10 mM 390.2 μL 1.9508 mL 3.9017 mL
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