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Ganoderenic acid A

Cat No.:V21504 Purity: ≥98%
Ganoderenic acid A is a triterpenoid.
Ganoderenic acid A
Ganoderenic acid A Chemical Structure CAS No.: 100665-40-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Ganoderenic acid A is a triterpenoid. Ganoderenic acid A is a potent β-glucuronidase inhibitor. Ganoderenic acid A has a protective effect on CCl4-induced liver injury.
Ganoderenic acid A (CAS#: 100665-40-5, molecular weight 514.7, molecular formula C30H42O7) is a lanostane-type triterpene isolated from the fruiting body of Ganoderma lucidum (Lingzhi). The compound functions as a potent inhibitor of β-glucuronidase. It demonstrates significant hepatoprotective properties, particularly in mitigating liver injury induced by carbon tetrachloride (CCl4). Ganoderenic acid A also shows inhibitory activity against human aldose reductase in vitro. The compound exhibits cytotoxic effects in addition to its hepatoprotective activities.
Biological Activity I Assay Protocols (From Reference)
Targets
Ganoderenic acid A targets β-glucuronidase, an enzyme involved in the hydrolysis of glucuronides. By inhibiting this enzyme, the compound may modulate the metabolism and elimination of various endogenous and exogenous compounds. The compound also inhibits human aldose reductase, an enzyme involved in the polyol pathway that converts glucose to sorbitol. Aldose reductase inhibition is relevant for preventing diabetic complications. The hepatoprotective effects are attributed to the compound's ability to mitigate oxidative stress and inflammation in the liver.
ln Vitro
Ganoderenic acid A is a potent inhibitor of β-glucuronidase in vitro. The compound demonstrates inhibitory activity against human aldose reductase in cell-free assays. Its cytotoxic effects have been observed in various cell lines. The compound's ability to inhibit these enzymes contributes to its diverse biological activities. Its hepatoprotective effects are also evident in vitro, protecting hepatocytes from toxic injury.
ln Vivo
Ganoderenic acid A has a potent hepatoprotective effect against CCl4-induced liver injury in vivo. The compound protects the liver from toxic damage, likely through its antioxidant and anti-inflammatory properties. Its hepatoprotective activity has been demonstrated in animal models of liver injury. The compound's cytotoxic effects suggest potential applications in cancer research. Its inhibition of aldose reductase may have implications for diabetic complications.
Enzyme Assay
In vitro enzyme assays for ganoderenic acid A involve measuring the inhibition of β-glucuronidase activity using purified enzyme preparations and appropriate substrates. The compound is incubated with β-glucuronidase and a chromogenic or fluorogenic substrate, and the rate of enzymatic hydrolysis is measured spectrophotometrically or fluorometrically. Aldose reductase inhibition assays are performed using purified aldose reductase enzyme and NADPH as cofactor, with the decrease in NADPH absorbance monitored spectrophotometrically. These cell-free assays provide quantitative data on the compound's inhibitory potency against its molecular targets.
Cell Assay
In vitro cell-based assays for ganoderenic acid A involve treating hepatocytes or other cell lines with the compound to assess its hepatoprotective and cytotoxic effects. Hepatocytes are exposed to toxic agents such as CCl4 in the presence or absence of the compound, and cell viability is measured using MTT or similar assays. Cytotoxicity against cancer cell lines is assessed by treating cells with varying concentrations of the compound and measuring cell viability. The compound's effects on apoptosis, oxidative stress, and inflammatory markers can be studied in these cellular models.
Animal Protocol
In vivo animal experiments for ganoderenic acid A have been conducted in models of CCl4-induced liver injury. Mice or rats are treated with CCl4 to induce acute liver damage, and ganoderenic acid A is administered concurrently or prophylactically. Liver injury is assessed by measuring serum transaminase levels (ALT, AST), histopathological examination of liver tissues, and assessment of oxidative stress markers. The compound's hepatoprotective effects are demonstrated by reduced liver enzyme elevations and improved histology. Dose-response relationships are established in these models.
ADME/Pharmacokinetics
Ganoderenic acid A has a molecular weight of 514.7 and a molecular formula of C30H42O7. It is a lanostane-type triterpene with a complex polycyclic structure characteristic of compounds from Ganoderma lucidum. The compound is typically extracted from the fruiting body of Ganoderma lucidum using chloroform. Its solubility properties are characteristic of triterpenoid compounds. The compound is stable under recommended storage conditions. Specific pharmacokinetic data such as absorption, distribution, metabolism, and elimination have not been extensively reported in the available literature.
Toxicity/Toxicokinetics
Specific toxicity data for ganoderenic acid A is not extensively reported in the literature. As a natural compound from Ganoderma lucidum, which has a long history of use in traditional medicine, it is generally considered to have a favorable safety profile. However, the compound exhibits cytotoxic effects against certain cell lines, indicating potential for selective toxicity. Comprehensive toxicological studies would be required for therapeutic development. Standard safety precautions should be taken when handling the compound in research settings.
References

[1]. Beta-glucuronidase-inhibitory activity and hepatoprotective effect of Ganoderma lucidum. Biol Pharm Bull. 1999 Feb;22(2):162-4.

Additional Infomation
Ganoderma lucidum has been reported to contain ganoderic acid A, and relevant data are available. The RN given in the text refers to the (7β,15α,20E)-isomer; its structure can be found in the first reference.
Ganoderenic acid A is a lanostane-type triterpene isolated from Ganoderma lucidum that functions as a potent inhibitor of β-glucuronidase. The compound demonstrates significant hepatoprotective effects against CCl4-induced liver injury. It also shows inhibitory activity against human aldose reductase in vitro. Ganoderenic acid A exhibits cytotoxic effects in addition to its hepatoprotective activities. The compound is isolated from the CHCl3 extract of the fruiting body of Ganoderma lucidum.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H42O7
Molecular Weight
514.6503
Exact Mass
514.293
CAS #
100665-40-5
PubChem CID
131751730
Appearance
White to off-white solid powder
Density
1.24g/cm3
Boiling Point
700.3ºC at 760mmHg
Flash Point
391.3ºC
Vapour Pressure
1.12E-22mmHg at 25°C
Index of Refraction
1.575
LogP
4.051
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
5
Heavy Atom Count
37
Complexity
1130
Defined Atom Stereocenter Count
0
SMILES
CC(CC(=O)/C=C(/C)\C1CC(C2(C1(CC(=O)C3=C2C(CC4C3(CCC(=O)C4(C)C)C)O)C)C)O)C(=O)O
InChi Key
OVUOUFPIPZJGME-GDNBJRDFSA-N
InChi Code
InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h10,16,18-19,21,23,32,35H,8-9,11-14H2,1-7H3,(H,36,37)/b15-10-
Chemical Name
(Z)-6-(7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-4-oxohept-5-enoic 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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9431 mL 9.7153 mL 19.4307 mL
5 mM 0.3886 mL 1.9431 mL 3.8861 mL
10 mM 0.1943 mL 0.9715 mL 1.9431 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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