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| 1mg | ||
| 5mg | ||
| Other Sizes |
| Targets |
Isogarcinol (cambogin) was evaluated for leishmanicidal activity against Leishmania donovani axenic amastigotes and for anticholinesterase activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). [1]
AChE (IC50 = 1.13 ± 0.0 μM); BChE (IC50 = 8.30 ± 0.0 μM); Leishmania (IC50 = 0.33 μM) |
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| ln Vitro |
Isogarcinol (cambogin, compound 3) was tested for in vitro leishmanicidal activity against Leishmania donovani axenic amastigotes. At a screening concentration of 0.8 μg/mL, it showed parasite growth inhibition of 13.3%; at 4.8 μg/mL, it showed 57.4% inhibition. [1]
Cambogin was subsequently assayed for IC₅₀ determination against L. donovani, showing an IC₅₀ of 0.33 μM. Its cytotoxicity against rat skeletal myoblast L6 cells was 2.7 μM, giving a selectivity index of 6.1. [1] For anticholinesterase activity, cambogin showed an IC₅₀ of 1.13 μM against AChE and 8.30 μM against BChE. [1] |
| Enzyme Assay |
Leishmanicidal Activity Assay: Leishmania donovani axenic amastigotes (strain MHOM/ET/67/L82) were cultured in a 1:1 mixture of SM and SDM-79 medium (pH 5.4) with 10% heat-inactivated fetal bovine serum. Compounds were serially diluted (30 to 0.041 μg/mL) in 96-well plates. Then 10⁵ amastigotes in 50 μL medium were added per well and incubated at 37°C under 5% CO₂ for 72 hours. Resazurin solution (12.5 mg in 100 mL distilled water, 10 μL) was added and incubated for 2-4 hours. Fluorescence was measured at 536 nm excitation and 588 nm emission. Miltefosine was used as a positive control. IC₅₀ values were calculated from sigmoidal inhibition curves. [1]
Cytotoxicity Assay (L6 cells): Rat skeletal muscle myoblasts (L6 cells) were seeded in 96-well plates at 2 × 10³ cells/100 μL in MEM with 10% heat-inactivated FBS. Three-fold serial dilutions of compounds (90 to 0.13 μg/mL) were added. Plates were incubated at 37°C with 5% CO₂ for 72 hours. Resazurin was added as a viability indicator, and fluorescence was measured at 536 nm excitation and 588 nm emission. Podophyllotoxin was used as a positive control. IC₅₀ values were calculated using Softmax Pro software. [1] Cholinesterase Inhibition Assay: A slightly modified spectrophotometric method was used. Acetylthiocholine iodide and butyrylthiocholine chloride were used as substrates for AChE and BChE, respectively. DTNB was used to measure cholinesterase activity. A 100 mM sodium phosphate buffer (pH 8.0, 140 μL), DTNB (10 μL), test compound solution (20 μL), and enzyme solution (20 μL) were mixed and incubated for 15 minutes at 25°C. The reaction was initiated by adding 10 μL of substrate. Hydrolysis was monitored by formation of the yellow 5-thio-2-nitrobenzoate anion at 412 nm for 15 minutes. All reactions were performed in triplicate in 96-well plates. IC₅₀ values were calculated using EZ-Fit Enzyme Kinetics software. [1] |
| Toxicity/Toxicokinetics |
Isogarcinol (cambogin) showed cytotoxicity against rat skeletal myoblast L6 cells with an IC₅₀ of 2.7 μM. The selectivity index (cytotoxicity/leishmanicidal activity) was 6.1. [1]
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| References | |
| Additional Infomation |
Isogarcinol (cambogin) is a polyisoprenylated benzophenone isolated from the fruits of Allanblackia monticola (Clusiaceae family). It was obtained as a yellow powder (110 mg) from the methanolic extract of A. monticola fruits after flash chromatography and repeated column chromatography on silica gel eluted with n-hexane-EtOAc mixtures. [1]
In this study, cambogin showed moderate leishmanicidal activity (IC₅₀ = 0.33 μM) compared to guttiferone A (0.16 μM) and guttiferone F (0.20 μM). Its anticholinesterase activity against AChE (IC₅₀ = 1.13 μM) was less potent than garcinol (0.66 μM) and guttiferone A (0.88 μM). [1] Isogarcinol has been reported in gamboge, garcinia cochinchinensis, and other organisms with available data. |
| Molecular Formula |
C38H50O6
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|---|---|
| Molecular Weight |
602.8
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| Exact Mass |
602.36
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| Elemental Analysis |
C, 75.71; H, 8.36; O, 15.92
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| CAS # |
71117-97-0
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| PubChem CID |
11135781
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
710.2±60.0 °C at 760 mmHg
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| Flash Point |
213.4±26.4 °C
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| Vapour Pressure |
0.0±2.3 mmHg at 25°C
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| Index of Refraction |
1.579
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| LogP |
11.07
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
44
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| Complexity |
1310
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| Defined Atom Stereocenter Count |
4
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| SMILES |
CC(=CCC1CC23CC(C(OC2=C(C(=O)C(C3=O)(C1(C)C)CC=C(C)C)C(=O)C4=CC(=C(C=C4)O)O)(C)C)CC=C(C)C)C
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| InChi Key |
KXTNVBQRLRYVCO-LPSZMIQCSA-N
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| InChi Code |
InChI=1S/C38H50O6/c1-22(2)11-14-26-20-37-21-27(15-12-23(3)4)36(9,10)44-33(37)30(31(41)25-13-16-28(39)29(40)19-25)32(42)38(34(37)43,35(26,7)8)18-17-24(5)6/h11-13,16-17,19,26-27,39-40H,14-15,18,20-21H2,1-10H3/t26-,27+,37+,38+/m1/s1
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| Chemical Name |
(1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-enyl)-5-oxatricyclo[7.3.1.01,6]tridec-6-ene-8,13-dione
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| Synonyms |
Isogarcinol; (1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-enyl)-5-oxatricyclo[7.3.1.01,6]tridec-6-ene-8,13-dione; DTXSID801318189; (1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-enyl)-5-oxatricyclo(7.3.1.01,6)tridec-6-ene-8,13-dione; 71117-97-0;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6589 mL | 8.2946 mL | 16.5893 mL | |
| 5 mM | 0.3318 mL | 1.6589 mL | 3.3179 mL | |
| 10 mM | 0.1659 mL | 0.8295 mL | 1.6589 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.
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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