AKBA
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MedKoo CAT#: 526492

CAS#: 67416-61-9

Description: AKBA is an antiangiogenic and neuroprotective agent, reducing the impact of proliferative retinopathies, protecting neurons against ischemic injury involving the Nrf2/HO-1 pathway. AKBA is a naturally occurring pentacyclic triterpene isolated from the gum resin exudate from the stem of the tree B. serrata (frankincense). It selectively inhibits 5-lipoxygenase (IC50 = 1.5 µM) in an enzyme-directed, nonredox, and noncompetitive manner. 2 3-acetyl-11-keto-β-Boswellic acid and other members of the boswellic acid family have been studied for potential use in the control of inflammatory diseases, including arthritis and cancer.

Chemical Structure

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AKBA
CAS# 67416-61-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526492
Name: AKBA
CAS#: 67416-61-9
Chemical Formula: C32H48O5
Exact Mass: 512.35
Molecular Weight: 512.730
Elemental Analysis: C, 74.96; H, 9.44; O, 15.60

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3750 Ready to ship
2g USD 6250 Ready to ship
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Synonym: AKBA; 3-O-acetyl-11-keto-β-Boswellic acid; 3-acetyl-11-keto-β-Boswellic acid; Acetylketo-β-boswellic acid;

IUPAC/Chemical Name: (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-acetyloxy-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

InChi Key: HMMGKOVEOFBCAU-BCDBGHSCSA-N

InChi Code: InChI=1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1

SMILES Code: O=C([C@@]([C@]1([H])CC[C@@]2(C)[C@]3(C)CC[C@@]4(C)CC[C@@H](C)[C@H](C)[C@@]4([H])C3=C5)(C)[C@H](OC(C)=O)CC[C@]1(C)[C@@]2([H])C5=O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: 3-acetyl-11-keto-β-Boswellic acid is a naturally occurring pentacyclic triterpene isolated from the gum resin exudate from the stem of the tree B. serrata (frankincense).1 It selectively inhibits 5-lipoxygenase (IC50 = 1.5 µM) in an enzyme-directed, nonredox, and noncompetitive manner.2 3-acetyl-11-keto-β-Boswellic acid and other members of the boswellic acid family have been studied for potential use in the control of inflammatory diseases, including arthritis and cancer.

Biological target: AKBA (Acetyl-11-keto-β-boswellic acid) is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator.
In vitro activity: bEND.3 cells were subjected to OGD/reperfusion to investigate the protective role of AKBA in this model. It was found that AKBA treatment attenuated endothelial cell death and oxidative stress assessed by means of TUNEL assay, cleaved-caspase-3, and dihydroethidium (DHE) staining. Furthermore, OGD downregulated tight junction proteins ZO-1 and Occludin levels, and increased the expressions of inflammatory cytokines TNF-α, ICAM-1, and complement C3a receptor (C3aR). It was also noticed that the increased phosphorylation of ERK 1/2 in bEND.3 cells in OGD group. AKBA treatment significantly attenuated expression levels of these inflammatory proteins and prevented the degradation of ZO-1 and Occludin following OGD. In conclusion, AKBA treatment provides protection against endothelial cell dysfunction following OGD by attenuating oxidative stress and inflammation. Reference: Neuromolecular Med. 2019 Dec;21(4):505-516. https://dx.doi.org/10.1007/s12017-019-08569-z
In vivo activity: A developmental toxicity assay in zebrafish embryos/larvae from 4 to 96 hours post-fertilization (hpf) was performed and a cardiotoxicity assay was designed from 48 to 72 hpf. Markers of oxidative stress and related genes were selected to access the possible mechanisms. According to the results, AKBA induced pericardium edema, yolk-sac edema, abnormal melanin, spinal curvature, hatching inhibition and shortened body length. Further, increased SV-BA distance, reduced heart rate, increased pericardium area and decreased blood flow velocity were detected in AKBA treated groups. The inhibition of cardiac progenitor gene expression, such as Nkx2.5 and Gata4, may be related to cardiotoxicity. The activities of antioxidant enzymes were decreased and the content of MDA was increased. In addition, AKBA treatment decreased the expression levels of Mn-Sod, Cat, and Gpx. These results suggested that AKBA induced developmental toxicity and cardiotoxicity through oxidative stress. Reference: Drug Chem Toxicol. 2019 Oct 28:1-8. https://www.tandfonline.com/doi/full/10.1080/01480545.2019.1663865

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.2 10.14

Preparing Stock Solutions

The following data is based on the product molecular weight 512.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Ahmad S, Khan SA, Kindelin A, Mohseni T, Bhatia K, Hoda MN, Ducruet AF. Acetyl-11-keto-β-boswellic acid (AKBA) Attenuates Oxidative Stress, Inflammation, Complement Activation and Cell Death in Brain Endothelial Cells Following OGD/Reperfusion. Neuromolecular Med. 2019 Dec;21(4):505-516. doi: 10.1007/s12017-019-08569-z. Epub 2019 Sep 12. PMID: 31515728.
In vivo protocol: 1. Han L, Xia Q, Zhang L, Zhang X, Li X, Zhang S, Wang L, Liu C, Liu K. Induction of developmental toxicity and cardiotoxicity in zebrafish embryos/larvae by acetyl-11-keto-β-boswellic acid (AKBA) through oxidative stress. Drug Chem Toxicol. 2019 Oct 28:1-8. doi: 10.1080/01480545.2019.1663865. Epub ahead of print. PMID: 31656113.

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1: Rybakovsky E, Valenzano MC, Deis R, DiGuilio KM, Thomas S, Mullin JM. Improvement of Human-Oral-Epithelial-Barrier Function and of Tight Junctions by Micronutrients. J Agric Food Chem. 2017 Dec 7. doi: 10.1021/acs.jafc.7b04203. [Epub ahead of print] PubMed PMID: 29172516.

2: Ranzato E, Martinotti S, Volante A, Tava A, Masini MA, Burlando B. The major Boswellia serrata active 3-acetyl-11-keto-β-boswellic acid strengthens interleukin-1α upregulation of matrix metalloproteinase-9 via JNK MAP kinase activation. Phytomedicine. 2017 Dec 1;36:176-182. doi: 10.1016/j.phymed.2017.09.010. Epub 2017 Sep 25. PubMed PMID: 29157812.

3: Sayed AS, Gomaa IEO, Bader M, El Sayed NSED. Role of 3-Acetyl-11-Keto-Beta-Boswellic Acid in Counteracting LPS-Induced Neuroinflammation via Modulation of miRNA-155. Mol Neurobiol. 2017 Oct 27. doi: 10.1007/s12035-017-0801-2. [Epub ahead of print] PubMed PMID: 29079998.

4: Rehman NU, Ali L, Al-Harrasi A, Mabood F, Al-Broumi M, Khan AL, Hussain H, Hussain J, Csuk R. Quantification of AKBA in Boswellia sacra Using NIRS Coupled with PLSR as an Alternative Method and Cross-Validation by HPLC. Phytochem Anal. 2017 Sep 7. doi: 10.1002/pca.2721. [Epub ahead of print] PubMed PMID: 28881407.

5: Niphadkar SS, Rathod VK. Adsorption kinetics, isotherm, and thermodynamics studies of acetyl-11-keto-β-boswellic acids (AKBA) from Boswellia serrata extract using macroporous resin. Prep Biochem Biotechnol. 2017 Sep 14;47(8):804-812. doi: 10.1080/10826068.2017.1342263. Epub 2017 Jun 29. PubMed PMID: 28662360.

6: Beghelli D, Isani G, Roncada P, Andreani G, Bistoni O, Bertocchi M, Lupidi G, Alunno A. Antioxidant and Ex Vivo Immune System Regulatory Properties of Boswellia serrata Extracts. Oxid Med Cell Longev. 2017;2017:7468064. doi: 10.1155/2017/7468064. Epub 2017 Mar 13. PubMed PMID: 28386311; PubMed Central PMCID: PMC5366763.

7: Yang S, Zhou B, Xu W, Xue F, Nisar MF, Bian C, Huang X, Yang L, Zhang Y, Bartsch JW, Zhong JL. Nrf2- and Bach1 May Play a Role in the Modulation of Ultraviolet A-Induced Oxidative Stress by Acetyl-11-Keto-β-Boswellic Acid in Skin Keratinocytes. Skin Pharmacol Physiol. 2017;30(1):13-23. doi: 10.1159/000452744. Epub 2017 Feb 1. PubMed PMID: 28142143.

8: Meka B, Ravada SR, Murali Krishna Kumar M, Purna Nagasree K, Golakoti T. Synthesis of new analogs of AKBA and evaluation of their anti-inflammatory activities. Bioorg Med Chem. 2017 Feb 15;25(4):1374-1388. doi: 10.1016/j.bmc.2016.12.045. Epub 2016 Dec 29. PubMed PMID: 28110820.

9: Shang P, Liu W, Liu T, Zhang Y, Mu F, Zhu Z, Liang L, Zhai X, Ding Y, Li Y, Wen A. Acetyl-11-Keto-β-Boswellic Acid Attenuates Prooxidant and Profibrotic Mechanisms Involving Transforming Growth Factor-β1, and Improves Vascular Remodeling in Spontaneously Hypertensive Rats. Sci Rep. 2016 Dec 23;6:39809. doi: 10.1038/srep39809. PubMed PMID: 28009003; PubMed Central PMCID: PMC5180224.

10: Li K, Li L, Wang S, Li X, Ma T, Liu D, Jing Y, Zhao L. Design and synthesis of novel 2-substituted 11-keto-boswellic acid heterocyclic derivatives as anti-prostate cancer agents with Pin1 inhibition ability. Eur J Med Chem. 2017 Jan 27;126:910-919. doi: 10.1016/j.ejmech.2016.09.089. Epub 2016 Sep 28. PubMed PMID: 27997878.

11: Li T, Fan P, Ye Y, Luo Q, Lou H. Ring A-modified Derivatives from the Natural Triterpene 3-O-acetyl-11-keto-β-Boswellic Acid and their Cytotoxic Activity. Anticancer Agents Med Chem. 2017;17(8):1153-1167. doi: 10.2174/1871520616666161207144031. PubMed PMID: 27928954.

12: Mannino G, Occhipinti A, Maffei ME. Quantitative Determination of 3-O-Acetyl-11-Keto-βBoswellic Acid (AKBA) and Other Boswellic Acids in Boswellia sacra Flueck (syn. B. carteri Birdw) and Boswellia serrata Roxb. Molecules. 2016 Oct 6;21(10). pii: E1329. PubMed PMID: 27782055.

13: Riva A, Morazzoni P, Artaria C, Allegrini P, Meins J, Savio D, Appendino G, Schubert-Zsilavecz M, Abdel-Tawab M. A single-dose, randomized, cross-over, two-way, open-label study for comparing the absorption of boswellic acids and its lecithin formulation. Phytomedicine. 2016 Nov 15;23(12):1375-1382. doi: 10.1016/j.phymed.2016.07.009. Epub 2016 Jul 27. PubMed PMID: 27765357.

14: Ammon HP. Boswellic Acids and Their Role in Chronic Inflammatory Diseases. Adv Exp Med Biol. 2016;928:291-327. Review. PubMed PMID: 27671822.

15: Xue X, Chen F, Liu A, Sun D, Wu J, Kong F, Luan Y, Qu X, Wang R. Reversal of the multidrug resistance of human ileocecal adenocarcinoma cells by acetyl-11-keto-β-boswellic acid via downregulation of P-glycoprotein signals. Biosci Trends. 2016 Nov 15;10(5):392-399. Epub 2016 Aug 19. PubMed PMID: 27545217.

16: Forouzanfar F, Hosseinzadeh H, Ebrahimzadeh Bideskan A, Sadeghnia HR. Aqueous and Ethanolic Extracts of Boswellia serrata Protect Against Focal Cerebral Ischemia and Reperfusion Injury in Rats. Phytother Res. 2016 Dec;30(12):1954-1967. doi: 10.1002/ptr.5701. Epub 2016 Aug 12. PubMed PMID: 27515127.

17: Rajabian A, Boroushaki MT, Hayatdavoudi P, Sadeghnia HR. Boswellia serrata Protects Against Glutamate-Induced Oxidative Stress and Apoptosis in PC12 and N2a Cells. DNA Cell Biol. 2016 Nov;35(11):666-679. Epub 2016 Aug 5. PubMed PMID: 27494534.

18: Cui Y, Tian X, Ning J, Wang C, Yu Z, Wang Y, Huo X, Jin L, Deng S, Zhang B, Ma X. Metabolic Profile of 3-Acetyl-11-Keto-β-Boswellic Acid and 11-Keto-β-Boswellic Acid in Human Preparations In Vitro, Species Differences, and Bioactivity Variation. AAPS J. 2016 Sep;18(5):1273-88. doi: 10.1208/s12248-016-9945-7. Epub 2016 Jun 21. PubMed PMID: 27329304.

19: Chen M, Wang M, Yang Q, Wang M, Wang Z, Zhu Y, Zhang Y, Wang C, Jia Y, Li Y, Wen A. Antioxidant effects of hydroxysafflor yellow A and acetyl-11-keto-β-boswellic acid in combination on isoproterenol-induced myocardial injury in rats. Int J Mol Med. 2016 Jun;37(6):1501-10. doi: 10.3892/ijmm.2016.2571. Epub 2016 Apr 20. PubMed PMID: 27121241; PubMed Central PMCID: PMC4866969.

20: Meins J, Artaria C, Riva A, Morazzoni P, Schubert-Zsilavecz M, Abdel-Tawab M. Survey on the Quality of the Top-Selling European and American Botanical Dietary Supplements Containing Boswellic Acids. Planta Med. 2016 Apr;82(6):573-9. doi: 10.1055/s-0042-103497. Epub 2016 Apr 7. PubMed PMID: 27054914.