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11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid), a pentacyclic triterpenic acid of the oleogum resin, is a natural product isolated from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. The main reason that 11-Keto-beta-boswellic acid has anti-inflammatory properties is because it prevents the production of 5-lipoxygenase, leukotriene, nuclear factor-kappa B (NF-κB), and tumor necrosis factor alpha.
| Targets |
NF-κB; 5-LOX
11-keto-beta-boswellic acid inhibits DPP-4 activity with an IC50 of 1.65 μM[2]. Inhibiting 4-inhibitor pyridine-stimulated amino acid trough release in hippocampal nerve terminals, 11-keto-beta-boswellic acid (10 minutes) (IC50: 31 μM) [3]. |
|---|---|
| ln Vitro |
11-keto-beta-boswellic acid inhibits DPP-4 activity with an IC50 of 1.65 μM[2]. Inhibiting 4-inhibitor pyridine-stimulated amino acid trough release in hippocampal nerve terminals, 11-keto-beta-boswellic acid (10 minutes) (IC50: 31 μM) [3].
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| ln Vivo |
In streptozotocin-induced diabetic signaling, 11-Keto-beta-boswellic acid (1–10 mg/kg, applied topically for 21 days) exhibits antidiabetic activity [2]. The excitotoxicity caused by kainic acid (15 mg/kg, i.p.) is prevented by boswellic acid (10 or 50 mg/kg, i.p.) [3].
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| Enzyme Assay |
High-Performance Liquid Chromatography (HPLC) for quantification of KBA in supplements: A derived HPLC method was used to estimate KBA concentrations within market formulations. The mobile phase consisted of mobile phase A (water-methanol-orthophosphoric acid, 90:9.5:0.5, v/v) and mobile phase B (methanol-acetonitrile-water-orthophosphoric acid, 55:40:4.5:0.5, v/v). A gradient program was used: 0-10 min, 90% B and 10% A; 11–14 min, linear gradient change to 100% B; and 14–15 min, instant change to 90% B and 10% A. Analysis parameters were: 1.0 mL/min flow rate, 50 μL injection volume, and 250 nm detection wavelength. A LiChrospher RP-18 column was used. KBA standard solutions ranging from 10 to 100 μg/mL were prepared in methanol to create a calibration curve by plotting peak area against concentration. The retention time for KBA was 3.1 minutes. The method was validated for linearity (correlation coefficient R² = 0.9907), accuracy (mean recovery of 100.3±3.1% from spiked herbal samples), inter-assay precision (0.12–2.77% difference from the mean), intra-assay precision (0.11–2.87% difference from the mean), and limit of detection (0.11 μg/mL). [1]
Sample Preparation for Supplement Analysis: For tablet formulations, tablets were finely powdered. For capsules, contents were emptied. Powder, powdered tablet, or capsule contents equivalent to 100 mg of claimed Boswellia serrata extract were accurately weighed, transferred to a volumetric flask, and 20 mL methanol was added. The mixture was sonicated for 30 minutes, diluted with an additional 30 mL methanol, then filtered through filter paper followed by ultrafiltration using a 0.45 μm syringe filter. Some samples required further dilution. The final sample solution (50 μL) was injected into the HPLC system in triplicate, and the mean peak area was used to estimate KBA quantity via the calibration curve. [1] |
| Animal Protocol |
Animal/Disease Models: Streptozotocin-induced diabetic rats [2]
Doses: 1-10 mg/kg Route of Administration: Orally for 21 days Experimental Results: diminished blood glucose levels. Reduce serum SGPT, SGOT, ALP and serum creatinine levels. Serum MDA levels diminished and serum SOD levels increased. |
| Toxicity/Toxicokinetics |
The literature provided does not specifically describe KBA. The literature mentions that no adverse event response level (NOAEL) greater than 2500 mg/kg body weight was observed after feeding rats with concentrated AKBA product (Aflapin™), but notes that no similar studies of KBA have been conducted in dogs. [1]
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| References | |
| Additional Infomation |
It has been reported that 11-keto-β-boswellic acid is found in Boswellia sacra, Boswellia serrata, and Boswellia papyrifera. See also: Boswellia sacra (partial). 11-keto-β-boswellic acid (KBA) is one of the main active pentacyclic triterpenoid acids in Boswellia serrata extract (BSE) and has anti-inflammatory effects. [1] In 13 commercially available human and canine formulations containing BSE, the average concentration of KBA was 5.2 mg/g (based on feed), ranging from 0 to 24.8 mg/g. Four of the formulations contained KBA at levels below the detection limit. The concentration of KBA was not indicated in any of the commercially available formulations. [1] The concentrations of active boswellic acid (including KBA) vary widely among the various formulations that claim to contain BSE. [1] The recommended dosage of BSE products by dietary supplement manufacturers is often lower than the effective dosage used in one cited human clinical study, suggesting that underdosing may occur in actual use, although the toxicity risk is considered low based on safety data of the products in rats. [1]
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| Molecular Formula |
C30H46O4
|
|---|---|
| Molecular Weight |
470.6838
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| Exact Mass |
470.34
|
| CAS # |
17019-92-0
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| Related CAS # |
17019-92-0
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| PubChem CID |
9847548
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| Appearance |
White to off-white solid
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| Density |
1.14g/cm3
|
| Boiling Point |
591.8ºC at 760mmHg
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| Melting Point |
190 - 191 °C
|
| Flash Point |
325.8ºC
|
| Vapour Pressure |
0mmHg at 25°C
|
| Index of Refraction |
1.561
|
| LogP |
6.268
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
34
|
| Complexity |
954
|
| Defined Atom Stereocenter Count |
11
|
| SMILES |
O([H])C1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([C@]1(C(=O)O[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])C2([H])C(C([H])=C2C3([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])=O
|
| InChi Key |
YIMHGPSYDOGBPI-YZCVQEKWSA-N
|
| InChi Code |
InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1
|
| Chemical Name |
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
|
| Synonyms |
11-Keto-beta-boswellic acid; 11-Keto-β-boswellic acid
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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 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)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~212.5 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.31 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 (5.31 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1246 mL | 10.6229 mL | 21.2459 mL | |
| 5 mM | 0.4249 mL | 2.1246 mL | 4.2492 mL | |
| 10 mM | 0.2125 mL | 1.0623 mL | 2.1246 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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