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Gibberellin A4

Cat No.:V41414 Purity: ≥98%
Gibberellin A4 is a natural compound extracted from Sphaceloma manihoticola.
Gibberellin A4
Gibberellin A4 Chemical Structure CAS No.: 468-44-0
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Gibberellin A4 is a natural compound extracted from Sphaceloma manihoticola. Gibberellin A4 is the causative agent of cassava hyperelongation disease.
Gibberellin A4 is a bioactive plant hormone of the gibberellin class, originally isolated from the fungus Gibberella fujikuroi. It has a molecular weight of 332.39 g/mol, a formula of C19H24O5, and a CAS number of 468-44-0. Beyond its established role in plant physiology, where it promotes flowering and growth, Gibberellin A4 has garnered interest in biomedical research due to its demonstrated anti-inflammatory and antioxidant activities. It is a valuable tool for studying inflammatory pathways and is applicable in research focused on periodontal diseases.
Biological Activity I Assay Protocols (From Reference)
Targets
Gibberellin A4 primarily targets gibberellin receptors in plants. In the context of biomedical research, its key molecular target of interest is the transcription factor NF-κB, where it exhibits anti-NF-κB activity. By modulating this pathway, Gibberellin A4 can reduce inflammation, as demonstrated by its ability to decrease LPS-induced NF-κB activation in RAW 264.7 macrophages.
ln Vitro
In vitro, Gibberellin A4 demonstrates significant anti-NF-κB and antioxidant activities. It has been shown to reduce LPS-induced NF-κB activation in RAW 264.7 macrophages, highlighting its potential as an anti-inflammatory agent. These activities make it a useful compound for investigating inflammatory pathways in cell-based systems, where it can modulate key signaling cascades involved in the immune response.
ln Vivo
In vivo, Gibberellin A4 is primarily recognized for its potent plant growth-regulating effects, promoting flowering and other developmental processes. While its anti-inflammatory and antioxidant properties have been characterized in vitro, specific in vivo efficacy data in animal models of disease are not detailed in the available sources. Its documented anti-NF-κB activity suggests potential for in vivo applications in inflammation research.
Enzyme Assay
In vitro assays for Gibberellin A4's anti-inflammatory activity typically involve culturing macrophage cell lines, such as RAW 264.7 cells, and stimulating them with lipopolysaccharide (LPS) to induce an inflammatory response. The cells are then treated with Gibberellin A4, and the inhibition of NF-κB activation is measured using reporter gene assays or by quantifying the expression of NF-κB target genes. Antioxidant activity can be assessed using standard cell-based ROS detection assays.
Cell Assay
Cellular assays for Gibberellin A4 are conducted using mammalian cell lines like RAW 264.7 macrophages. The general protocol involves seeding cells, treating them with varying concentrations of Gibberellin A4, and then stimulating with LPS. After incubation, cells are harvested, and the levels of NF-κB activation are measured through methods such as Western blotting for phosphorylated IκB or by using NF-κB luciferase reporter constructs.
Animal Protocol
In vivo studies for Gibberellin A4 in animal models are not detailed in the available research literature. As a plant hormone, its primary in vivo applications are in botanical research. For biomedical applications, the compound's documented anti-inflammatory mechanism suggests that it could be evaluated in standard animal models of inflammation, such as the carrageenan-induced paw edema model or models of periodontitis, but such studies have not been reported in the provided sources.
ADME/Pharmacokinetics
Pharmacokinetic data for Gibberellin A4 are not available in the provided sources. The compound has a molecular weight of 332.39 g/mol and is typically stored as a powder at -20°C for up to 3 years. It is soluble in DMSO. For research purposes, it can be dissolved in appropriate solvents for in vitro assays. No specific information regarding its absorption, distribution, metabolism, or excretion is provided.
Toxicity/Toxicokinetics
Toxicity data for Gibberellin A4 are not reported in the available sources. As a naturally occurring plant hormone, it is generally considered to have a favorable safety profile. The compound is intended for research use only and is not approved for human therapeutic use. Specific toxicological studies have not been described in the provided literature.
References

[1]. Rademacher W, Graebe JE. Gibberellin A4 produced by Sphaceloma manihoticola, the cause of the superelongation disease of cassava (Manihot esculenta). Biochem Biophys Res Commun. 1979 Nov 14;91(1):35-40.

Additional Infomation
Gibberellin A4 is a C19-gibberellin, initially discovered in Gibberella fujikuroi, differing from gibberellin A1 in that the hydroxyl group at the C-7 position (gibberellin number) is replaced by a hydrogen atom. It is a plant metabolite. It is a lactone, belonging to the gibberellin monocarboxylic acid family, and is also a C19-gibberellin. It is the conjugate acid of gibberellin A4(1-). Gibberellin A4 has been reported to exist in Fusarium fujikuroi, citrus (Citrus reticulata), and several other organisms with relevant data.
Gibberellin A4 is a plant hormone with emerging biomedical research applications due to its anti-NF-κB and antioxidant activities. It is a useful tool for studying inflammatory pathways. The compound is available from commercial suppliers for research purposes only. It is not an approved therapeutic agent. Its mechanism of action, involving the modulation of NF-κB signaling, makes it a compound of interest for investigating inflammation-related diseases.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H24O5
Molecular Weight
332.39
Exact Mass
332.162
CAS #
468-44-0
Related CAS #
Gibberellin A4-13C,d3;Gibberellin A4-d2
PubChem CID
92109
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
574.2±50.0 °C at 760 mmHg
Melting Point
201 - 205ºC
Flash Point
210.4±23.6 °C
Vapour Pressure
0.0±3.6 mmHg at 25°C
Index of Refraction
1.615
LogP
1.7
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Heavy Atom Count
24
Complexity
685
Defined Atom Stereocenter Count
8
SMILES
C[C@@]12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@H](C4)C(=C)C5)C(=O)O)OC2=O)O
InChi Key
RSQSQJNRHICNNH-NFMPGMCNSA-N
InChi Code
InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1
Chemical Name
(1R,2R,5R,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~300.85 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0085 mL 15.0426 mL 30.0851 mL
5 mM 0.6017 mL 3.0085 mL 6.0170 mL
10 mM 0.3009 mL 1.5043 mL 3.0085 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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