Gibberellin A4
(Synonyms: 赤霉素A4) 目录号 : GC47401
A plant hormone with plant signaling and growth stimulatory activities
Cas No.:468-44-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Gibberellin A4 is a plant hormone originally isolated from G. fujikuroi that has plant signaling and growth stimulatory activities.1 Gibberellin A4 is found in the micropylar endothelium cells of Arabidopsis maternal seed tissue and triggers suspensor programmed cell death (PCD) in the embryo.2 It increases hypocotyl, but not radicle, growth of cucumber seedlings when used at concentrations ranging from 6-100 µM.3 Gibberellin A4 also increases flowering in apple trees when applied post-flowering in the previous year.4
1.Takahashi, N., Seta, Y., Kitamura, H., et al.A new gibberellin, gibberellin A4Bull. Agri. Chem. Soc. Japan21(6)396-398(1957) 2.Shi, C., Luo, P., Du, Y.-T., et al.Maternal control of suspensor programmed cell death via gibberellin signalingNat. Commun.10(1)3484(2019) 3.Halevy, A.H., and Cathey, H.M.Effects of structure and concentration of gibberellins on the growth of cucumber seedlingsBot. Gaz.122(1)63-67(1960) 4.Looney, N.E., Pharis, R.P., and Noma, M.Promotion of flowering in apple trees with gibberellin A4 and C-3 epi-gibberellin A4Planta165(2)292-294(1985)
| Cas No. | 468-44-0 | SDF | |
| 别名 | 赤霉素A4 | ||
| Canonical SMILES | OC([C@H]1[C@@]2([H])[C@]3(OC([C@@]2([C@H](CC3)O)C)=O)[C@@]4([H])[C@]15C[C@H](C(C5)=C)CC4)=O | ||
| 分子式 | C19H24O5 | 分子量 | 332.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0084 mL | 15.0421 mL | 30.0842 mL |
| 5 mM | 0.6017 mL | 3.0084 mL | 6.0168 mL |
| 10 mM | 0.3008 mL | 1.5042 mL | 3.0084 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Gibberellin A4 monohydrate
Acta Crystallogr Sect E Struct Rep Online 2007 Dec 6;64(Pt 1):o30.PMID:21200864DOI:10.1107/S160053680706062X.
The title compond, C(19)H(24)O(5)·H(2)O, has two Gibberellin A4 mol-ecules and two water mol-ecules in the asymmetric unit. The A and B rings have chair conformations, whereas the C and D rings have envelope conformations; the two rings which contain the lactone and carbonyl bridge adopt chair and envelope conformations. The crystal structure is established by O-H⋯O hydrogen bonds and supported by C-H⋯O hydrogen bonds.
A Study on the Anti-NF-κB, Anti- Candida, and Antioxidant Activities of Two Natural Plant Hormones: Gibberellin A4 and A7
Pharmaceutics 2022 Jun 25;14(7):1347.PMID:35890244DOI:10.3390/pharmaceutics14071347.
Introduction: Gibberellins (GA) are terpenoids that serve as important plant hormones by acting as growth and response modulators against injuries and parasitism. In this study, we investigated the in vitro anti-NF-κB, anti-Candida, and antioxidant activity of Gibberellin A4 (GA4) and A7 (GA7) compounds, and further determined their toxicity in vivo. Methods: GA4 and GA7 in vitro toxicity was determined by MTT method, and nontoxic concentrations were then tested to evaluate the GA4 and GA7 anti-NF-κB activity in LPS-activated RAW-luc macrophage cell culture (luminescence assay). GA4 in silico anti-NF-κB activity was evaluated by molecular docking with the software "AutoDock Vina", "MGLTools", "Pymol", and "LigPlot+", based on data obtained from "The Uniprot database", "Protein Data Bank", and "PubChem database". The GA4 and GA7 in vitro anti-Candida effects against Candida albicans (MYA 2876) were determined (MIC and MFC). GA7 was also evaluated regarding the viability of C. albicans preformed biofilm (microplate assay). In vitro antioxidant activity of GA4 and GA7 was evaluated against peroxyl radicals, superoxide anions, hypochlorous acid, and reactive nitrogen species. GA4 and GA7 in vivo toxicity was determined on the invertebrate Galleria mellonella larvae model. Results: Our data show that GA4 at 30 µM is nontoxic and capable of reducing 32% of the NF-κB activation on RAW-luc macrophages in vitro. In vitro results were confirmed via molecular docking assay (in silico), since GA4 presented binding affinity to NF-κB p65 and p50 subunits. GA7 did not present anti-NF-κB effects, but exhibited anti-Candida activity with low MIC (94 mM) and MFC (188 mM) values. GA7 also presented antibiofilm properties at 940 mM concentration. GA4 did not present anti-Candida effects. Moreover, GA4 and GA7 showed antioxidant activity against peroxyl radicals, but did not show scavenging activity against the other tested radicals. Both compounds did not affect the survival of G. mellonella larvae, even at extremely high doses (10 g/Kg). Conclusion: Our study provides preclinical evidence indicating that GA4 and GA7 have a favorable low toxicity profile. The study also points to GA4 and GA7 interference with the NF-κB via, anti-Candida activity, and a peroxyl radical scavenger, which we argue are relevant biological effects.
Enhanced production of Gibberellin A4 (GA4) by a mutant of Gibberella fujikuroi in wheat gluten medium
J Ind Microbiol Biotechnol 2010 Mar;37(3):297-306.PMID:19967447DOI:10.1007/s10295-009-0673-1.
Mutants of Gibberella fujikuroi with different colony characteristics, morphology and pigmentation were generated by exposure to UV radiation. A mutant, Mor-189, was selected based on its short filament length, relatively high gibberellin A(4) (GA(4)) and gibberellin A(3) (GA(3)) production, as well as its lack of pigmentation. Production of GA(4) by Mor-189 was studied using different inorganic and organic nitrogen sources, carbon sources and by maintaining the pH of the fermentation medium using calcium carbonate. Analysis of GA(4) and GA(3) was done by reversed-phase high-performance liquid chromatography and LC-MS. The mutants of G. fujikuroi produced more GA(4) when the pH of the medium was maintained above 5. During shake flask studies, the mutant Mor-189 produced 210 mg l(-1) GA(4) in media containing wheat gluten as the nitrogen source and glucose as the carbon source. Fed-batch fermentation in a 14 l agitated fermenter was performed to evaluate the applicability of the mutant Mor-189 for the production of GA(4). In 7-day fed-batch fermentation, 600 mg l(-1) GA(4) were obtained in the culture filtrate. The concentration of GA(4) and GA(3) combined was 713 mg l(-1), of which GA(4) accounted for 84% of the total gibberellin. These values are substantially higher than those published previously. The present study indicated that, along with maintenance of pH and controlled glucose feeding, the use of wheat gluten as the sole nitrogen source considerably enhances GA(4) production by the mutant Mor-189.
Enzymatic and structural characterization of hydrolysis of Gibberellin A4 glucosyl ester by a rice β-D-glucosidase
Arch Biochem Biophys 2013 Sep 1;537(1):39-48.PMID:23811195DOI:10.1016/j.abb.2013.06.005.
In order to identify a rice gibberellin ester β-D-glucosidase, Gibberellin A4 β-D-glucosyl ester (GA4-GE) was synthesized and used to screen rice β-glucosidases. Os3BGlu6 was found to have the highest hydrolysis activity to GA4-GE among five recombinantly expressed rice glycoside hydrolase family GH1 enzymes from different phylogenic clusters. The kinetic parameters of Os3BGlu6 and its mutants E178Q, E178A, E394D, E394Q and M251N for hydrolysis of p-nitrophenyl β-D-glucopyranoside (pNPGlc) and GA4-GE confirmed the roles of the catalytic acid/base and nucleophile for hydrolysis of both substrates and suggested M251 contributes to binding hydrophobic aglycones. The activities of the Os3BGlu6 E178Q and E178A acid/base mutants were rescued by azide, which they transglucosylate to produce β-D-glucopyranosyl azide, in a pH-dependent manner, while acetate also rescued Os3BGlu6 E178A at low pH. High concentrations of sodium azide (200-400 mM) inhibited Os3BGlu6 E178Q but not Os3BGlu6 E178A. The structures of Os3BGlu6 E178Q crystallized with either GA4-GE or pNPGlc had a native α-D-glucosyl moiety covalently linked to the catalytic nucleophile, E394, which showed the hydrogen bonding to the 2-hydroxyl in the covalent intermediate. These data suggest that a GH1 β-glucosidase uses the same retaining catalytic mechanism to hydrolyze 1-O-acyl glucose ester and glucoside.
Interconversion of Gibberellin A4 to gibberellins A 1 and A 34 by dwarf rice, cultivar Tan-ginbozu
Planta 1973 Dec;109(4):357-61.PMID:24474212DOI:10.1007/BF00387104.
Interconversion of GA4 to GA1 and GA34 occurred within 24 h of application of 1,2-[(3)H]-GA4 to seedlings of dwarf rice, cv. Tan-ginbozu. Identification was made by direct comparison of the trimethylsilyl ether derivatives of the methyl esters of Silica-gel partition-column fractions on gas-liquid radiochromatography with derivatized GA1 and GA34 standards on three columns: 2% QF-1, 2% SE-30, and 1% XE-60. GA2, an artifact of the purification and chromatography system, may also be formed by the plant. The conversions from GA4 to GA1 and GA34 are single hydroxylations. At least two unidentified radioactive products were also formed by the plant. Interconversions were in the order of 0.3 to 0.8% of applied [(3)H]-GA4.