Tabersonine | CAS#4429-63-4 | Amyloid Fibril Formation Inhibitor

MedKoo Cat#: 562396 | Name: Tabersonine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tabersonine is an inhibitor of Amyloid Fibril Formation and Cytotoxicity of Aβ(1-42) that is able to permeate the blood-brain barrier. Tabersonine has been investigated for its role in modulating inflammation-associated pathways in various diseases.

Chemical Structure

Tabersonine

CAS#4429-63-4

Theoretical Analysis

MedKoo Cat#: 562396

Name: Tabersonine

CAS#: 4429-63-4

Chemical Formula: C22H24N2O4

Exact Mass: 380.1736

Molecular Weight: 380.44

Elemental Analysis: C, 69.46; H, 6.36; N, 7.36; O, 16.82

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 600.00

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Related CAS #

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Synonym

Tabersonine;

IUPAC/Chemical Name

Methyl (5alpha,19alpha)-16-methoxy-8-oxo-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate

InChi Key

ULVYAIAFWAUMLF-FDFHNCONSA-N

InChi Code

InChI=1S/C22H24N2O4/c1-4-21-8-7-17(25)24-10-9-22(20(21)24)15-6-5-13(27-2)11-16(15)23-18(22)14(12-21)19(26)28-3/h5-8,11,20,23H,4,9-10,12H2,1-3H3/t20-,21-,22+/m0/s1

SMILES Code

CC[C@]1(C=CC(N2CC[C@@]34[C@@]21[H])=O)CC(C(OC)=O)=C4NC5=C3C=CC(OC)=C5

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 380.44 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.

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

1: Kamileen MO, Nakamura Y, Luck K, Heinicke S, Hong B, Colinas M, Lichman BR, O'Connor SE. Streamlined screening platforms lead to the discovery of pachysiphine synthase from Tabernanthe iboga. New Phytol. 2024 Sep 16. doi: 10.1111/nph.20133. Epub ahead of print. PMID: 39285533. 2: da Silva YC, da Silva Gomes G, Antonio ADS, Pimentel Rosado C, Pereira HMG, Kazumy de Lima Yamaguchi K, Teodoro AJ, da Veiga Júnior VF. Chemical composition and antioxidant activity of the Amazonian fruit Ambelania acida Aubl. Nat Prod Res. 2024 May 20:1-5. doi: 10.1080/14786419.2024.2354861. Epub ahead of print. PMID: 38767203. 3: Chen X, Yan Y, Liu Y, Yi Q, Xu Z. Tabersonine enhances cisplatin sensitivity by modulating Aurora kinase A and suppressing epithelial-mesenchymal transition in triple-negative breast cancer. Pharm Biol. 2024 Dec;62(1):394-403. doi: 10.1080/13880209.2024.2351934. Epub 2024 May 13. PMID: 38739003; PMCID: PMC11095288. 4: Li X, Li X, Chen L, Deng Y, Zheng Z, Ming Y. Tabersonine Induces the Apoptosis of Human Hepatocellular Carcinoma In vitro and In vivo. Anticancer Agents Med Chem. 2024;24(10):764-772. doi: 10.2174/0118715206286612240303172230. PMID: 38465429; PMCID: PMC11327752. 5: Chen X, Yan Y, Liu Y, Yi Q, Xu Z. Tabersonine Enhances Olaparib Sensitivity through FHL1-Mediated Epithelial-Mesenchymal Transition in an Ovarian Tumor. J Nat Prod. 2024 Apr 26;87(4):837-848. doi: 10.1021/acs.jnatprod.3c01056. Epub 2024 Feb 28. PMID: 38417401. 6: DeMars MD 2nd, O'Connor SE. Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis. Proc Natl Acad Sci U S A. 2024 Feb 13;121(7):e2318586121. doi: 10.1073/pnas.2318586121. Epub 2024 Feb 6. PMID: 38319969; PMCID: PMC10873640. 7: Cao J, Yang B, Zhang M, Yu F. Regulation of T16H subcellular localization for promoting its catalytic efficiency in yeast cells. Biotechnol Lett. 2024 Feb;46(1):29-35. doi: 10.1007/s10529-023-03442-3. Epub 2023 Nov 16. PMID: 37971563. 8: Etit D, Ögmundarson Ó, Zhang J, Krogh Jensen M, Sukumara S. Early-stage economic and environmental impact assessment for optimized bioprocess development: Monoterpenoid indole alkaloids. Bioresour Technol. 2024 Jan;391(Pt B):130005. doi: 10.1016/j.biortech.2023.130005. Epub 2023 Nov 10. PMID: 37952588. 9: Sandenon Seteyen AL, Guiraud P, Gasque P, Girard-Valenciennes E, Sélambarom J. In Vitro Analyses of the Multifocal Effects of Natural Alkaloids Berberine, Matrine, and Tabersonine against the O'nyong-nyong Arthritogenic Alphavirus Infection and Inflammation. Pharmaceuticals (Basel). 2023 Aug 9;16(8):1125. doi: 10.3390/ph16081125. PMID: 37631040; PMCID: PMC10459185. 10: Yu Y, Wu J, Bao MF, Schinnerl J, Cai XH. Diverse aspidosperma-type alkaloids from the leaves of Tabernaemontana bovina with anti-hepatoma activity. Fitoterapia. 2023 Sep;169:105588. doi: 10.1016/j.fitote.2023.105588. Epub 2023 Jun 17. PMID: 37336417. 11: Habib MA, Islam MM, Islam MM, Hasan MM, Baek KH. Current Status and De Novo Synthesis of Anti-Tumor Alkaloids in Nicotiana. Metabolites. 2023 Apr 30;13(5):623. doi: 10.3390/metabo13050623. PMID: 37233664; PMCID: PMC10222625. 12: Qian C, Wang J, Lin W, Chen Y, Yang J, Liu M, Sun X, Wu H, Zhang M, Wang Y, Cao S. Tabersonine attenuates obesity-induced renal injury via inhibiting NF-κB- mediated inflammation. Phytother Res. 2023 Jun;37(6):2353-2363. doi: 10.1002/ptr.7756. Epub 2023 Feb 8. PMID: 36752025. 13: Xu HW, Li WF, Hong SS, Shao JJ, Chen JH, Chattipakorn N, Wu D, Luo W, Liang G. Tabersonine, a natural NLRP3 inhibitor, suppresses inflammasome activation in macrophages and attenuate NLRP3-driven diseases in mice. Acta Pharmacol Sin. 2023 Jun;44(6):1252-1261. doi: 10.1038/s41401-022-01040-z. Epub 2023 Jan 10. PMID: 36627344; PMCID: PMC10203108. 14: Shahsavarani M, Utomo JC, Kumar R, Paz-Galeano M, Garza-García JJO, Mai Z, Ro DK, Qu Y. Improved protein glycosylation enabled heterologous biosynthesis of monoterpenoid indole alkaloids and their unnatural derivatives in yeast. Metab Eng Commun. 2022 Dec 5;16:e00215. doi: 10.1016/j.mec.2022.e00215. PMID: 36569379; PMCID: PMC9772838. 15: Grzech D, Hong B, Caputi L, Sonawane PD, O'Connor SE. Engineering the Biosynthesis of Late-Stage Vinblastine Precursors Precondylocarpine Acetate, Catharanthine, Tabersonine in Nicotiana benthamiana. ACS Synth Biol. 2023 Jan 20;12(1):27-34. doi: 10.1021/acssynbio.2c00434. Epub 2022 Dec 14. PMID: 36516122; PMCID: PMC9872167. 16: Chen Y, Lin W, Chen P, Ye B, Luo W, Wang X, Huang W, Wu G, Liang G. Tabersonine alleviates obesity-induced cardiomyopathy by binding to Transforming growth factor activated kinase 1 (TAK1) and inhibiting TAK1-mediated inflammation. Phytother Res. 2023 Mar;37(3):860-871. doi: 10.1002/ptr.7666. Epub 2022 Nov 24. PMID: 36420902. 17: Shi J, Wang C, Sang C, Nsanzamahoro S, Chai T, Wang J, Yang A, Yang J. Tabersonine Inhibits the Lipopolysaccharide-Induced Neuroinflammatory Response in BV2 Microglia Cells via the NF-κB Signaling Pathway. Molecules. 2022 Nov 3;27(21):7521. doi: 10.3390/molecules27217521. PMID: 36364344; PMCID: PMC9654763. 18: Cuello C, Stander EA, Jansen HJ, Dugé de Bernonville T, Lanoue A, Giglioli- Guivarc'h N, Papon N, Dirks RP, Jensen MK, O'Connor SE, Besseau S, Courdavault V. Genome Assembly of the Medicinal Plant Voacanga thouarsii. Genome Biol Evol. 2022 Nov 4;14(11):evac158. doi: 10.1093/gbe/evac158. PMID: 36300641; PMCID: PMC9673491. 19: Jiang M, Wang Z, Ren W, Yan S, Xing N, Zhang Z, Li H, Ma W. Identification of the bZIP gene family and regulation of metabolites under salt stress in isatis indigotica. Front Plant Sci. 2022 Oct 4;13:1011616. doi: 10.3389/fpls.2022.1011616. PMID: 36267941; PMCID: PMC9576947. 20: Kamileen MO, DeMars MD 2nd, Hong B, Nakamura Y, Paetz C, Lichman BR, Sonawane PD, Caputi L, O'Connor SE. Recycling Upstream Redox Enzymes Expands the Regioselectivity of Cycloaddition in Pseudo-Aspidosperma Alkaloid Biosynthesis. J Am Chem Soc. 2022 Nov 2;144(43):19673-19679. doi: 10.1021/jacs.2c08107. Epub 2022 Oct 14. PMID: 36240425; PMCID: PMC9634793.