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MedKoo Cat#: 558358 | Name: Oxyberberine
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Description:

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

Oxyberberine is isolated from the methanol extract of A. mexicana. Oxyberberine has been used to study the SW480 human colon cancer cell line. Oxyberberine is seen to possess hepatoprotective properties.

Chemical Structure

Oxyberberine
Oxyberberine
CAS#549-21-3

Theoretical Analysis

MedKoo Cat#: 558358

Name: Oxyberberine

CAS#: 549-21-3

Chemical Formula: C20H17NO5

Exact Mass: 351.1100

Molecular Weight: 351.36

Elemental Analysis: C, 68.37; H, 4.88; N, 3.99; O, 22.77

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 675.00 2 Weeks
10mg USD 1,000.00 2 Weeks
25mg USD 1,400.00 2 Weeks
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Related CAS #
No Data
Synonym
Oxyberberine; Ketoberberine; Berlambine; 8-Oxyberberine; 8 Oxyberberine; 8Oxyberberine;
IUPAC/Chemical Name
8-Berbinone, 13,13a-didehydro-9,10-dimethoxy-2,3-(methylenedioxy)-
InChi Key
ZHYQCBCBTQWPLC-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H17NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9H,5-6,10H2,1-2H3
SMILES Code
O=C1N2CCC3=CC4=C(OCO4)C=C3C2=CC5=C1C(OC)=C(OC)C=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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 351.36 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
1: Mukhtar M, Khan HA, Ibisanmi TA, Faleti AI, Zaidi NUSS. Computational Exploration of Berberis lycium Royle: A Hidden Treasure Trove for Antiviral Development. Bioinform Biol Insights. 2024 Jul 27;18:11779322241264144. doi: 10.1177/11779322241264144. PMID: 39072259; PMCID: PMC11283669. 2: Chen T, Li Q, Ai G, Huang Z, Liu J, Zeng L, Su Z, Dou Y. Enhancing hepatoprotective action: oxyberberine amorphous solid dispersion system targeting TLR4. Sci Rep. 2024 Jun 28;14(1):14924. doi: 10.1038/s41598-024-65190-2. PMID: 38942824; PMCID: PMC11213902. 3: Pan F, Wang CN, Yu ZH, Wu ZR, Wang Z, Lou S, Li WH, Liu GX, Li T, Zhao YZ, Tang Y. NADPHnet: a novel strategy to predict compounds for regulation of NADPH metabolism via network-based methods. Acta Pharmacol Sin. 2024 Jun 20. doi: 10.1038/s41401-024-01324-6. Epub ahead of print. PMID: 38902503. 4: Huang Z, Zhang S, Qin Z, Ai G, Li M, Gong S, Liu Y, Zeng H, Chen J, Su Z, Lai Z. Supersaturated Drug Delivery System of Oxyberberine Based on Cyclodextrin Nanoaggregates: Preparation, Characterization, and in vivo Application. Int J Nanomedicine. 2024 Jun 6;19:5297-5316. doi: 10.2147/IJN.S464994. PMID: 38859955; PMCID: PMC11164094. 5: Chen T, Ai G, Liang G, Zeng L, Zhao D, Liu J, Dou Y. Mitigation of inflammatory bowel disease-related osteoporosis by oxyberberine: Insights into the RANKL/NF-κB signaling pathway. Biomed Pharmacother. 2024 May;174:116523. doi: 10.1016/j.biopha.2024.116523. Epub 2024 Apr 3. PMID: 38574627. 6: Sun L, He M, Li F, Wu D, Zheng P, Zhang C, Liu Y, Liu D, Shan M, Yang M, Ma Y, Lian J, Xiong H. Oxyberberine sensitizes liver cancer cells to sorafenib via inhibiting NOTCH1-USP7-c-Myc pathway. Hepatol Commun. 2024 Mar 29;8(4):e0405. doi: 10.1097/HC9.0000000000000405. PMID: 38573832; PMCID: PMC10997235. 7: Rahman Z, Shaikh AS, Rao KV, Dandekar MP. Oxyberberine protects middle cerebral artery occlusion triggered cerebral injury through TLR4/NLRP3 pathway in rats. J Chem Neuroanat. 2024 Mar;136:102393. doi: 10.1016/j.jchemneu.2024.102393. Epub 2024 Jan 19. PMID: 38246265. 8: Tentu PM, Bazaz MR, Pasam T, Shaikh AS, Rahman Z, Mourya A, Kaki VR, Madan J, Dandekar MP. Oxyberberine an oxoderivative of berberine confers neuroprotective effects in controlled-cortical impact mouse model of traumatic brain injury. Int J Neurosci. 2023 Nov 20:1-16. doi: 10.1080/00207454.2023.2286209. Epub ahead of print. PMID: 37982448. 9: Zhao S, Li J, Xing X, Chen J, Zhou Q, Sun J. Oxyberberine suppressed the carbon tetrachloride-induced liver fibrosis by inhibiting liver inflammation in a sirtuin 3-dependent manner in mice. Int Immunopharmacol. 2023 Mar;116:109876. doi: 10.1016/j.intimp.2023.109876. Epub 2023 Feb 13. PMID: 37599565. 10: Xue A, Zhao D, Zhao C, Li X, Yang M, Zhao H, Zhao C, Lei X, Wu J, Zhang N. Study on the neuroprotective effect of Zhimu-Huangbo extract on mitochondrial dysfunction in HT22 cells induced by D-galactose by promoting mitochondrial autophagy. J Ethnopharmacol. 2024 Jan 10;318(Pt B):117012. doi: 10.1016/j.jep.2023.117012. Epub 2023 Aug 9. PMID: 37567426. 11: Li C, Liu M, Deng L, Luo D, Ma R, Lu Q. Oxyberberine ameliorates TNBS- induced colitis in rats through suppressing inflammation and oxidative stress via Keap1/Nrf2/NF-κB signaling pathways. Phytomedicine. 2023 Jul 25;116:154899. doi: 10.1016/j.phymed.2023.154899. Epub 2023 May 23. PMID: 37247589. 12: Huang Z, Li M, Qin Z, Ma X, Huang R, Liu Y, Xie J, Zeng H, Zhan R, Su Z. Intestines-erythrocytes-mediated bio-disposition deciphers the hypolipidemic effect of berberine from Rhizoma Coptidis: A neglected insight. J Ethnopharmacol. 2023 Oct 5;314:116600. doi: 10.1016/j.jep.2023.116600. Epub 2023 May 15. PMID: 37196811. 13: Lin X, Chen J, Li X, Chen D, Luo K, Deng Y, Yang D, Huang Z, Tao C. Dimeric oxyberberine CT4-1 targets LINC02331 to induce cytotoxicity and inhibit chemoresistance via suppressing Wnt/β-catenin signaling in hepatocellular carcinoma. Arch Toxicol. 2023 Jun;97(6):1627-1647. doi: 10.1007/s00204-023-03501-8. Epub 2023 Apr 30. PMID: 37120773. 14: Chen R, Li F, Zhou K, Xing M, Zhang X, Zhao X, Wu C, Han Z, Zhou Y, Yan L, Xia D. Component identification of modified sanmiao pills by UPLC-Xevo G2-XS QTOF and its anti-gouty arthritis mechanism based on network pharmacology and experimental verification. J Ethnopharmacol. 2023 Jul 15;311:116394. doi: 10.1016/j.jep.2023.116394. Epub 2023 Mar 20. PMID: 36940736. 15: Laurindo LF, Santos AROD, Carvalho ACA, Bechara MD, Guiguer EL, Goulart RA, Vargas Sinatora R, Araújo AC, Barbalho SM. Phytochemicals and Regulation of NF- kB in Inflammatory Bowel Diseases: An Overview of In Vitro and In Vivo Effects. Metabolites. 2023 Jan 7;13(1):96. doi: 10.3390/metabo13010096. PMID: 36677021; PMCID: PMC9862976. 16: Savova MS, Mihaylova LV, Tews D, Wabitsch M, Georgiev MI. Targeting PI3K/AKT signaling pathway in obesity. Biomed Pharmacother. 2023 Mar;159:114244. doi: 10.1016/j.biopha.2023.114244. Epub 2023 Jan 11. PMID: 36638594. 17: He F, Huang YF, Dai W, Qu XY, Lu JG, Lao CC, Luo WH, Sun DM, Wei M, Xiao SY, Xie Y, Liu L, Zhou H. The localization of the alkaloids in Coptis chinensis rhizome by time-of-flight secondary ion mass spectrometry. Front Plant Sci. 2022 Dec 23;13:1092643. doi: 10.3389/fpls.2022.1092643. PMID: 36618650; PMCID: PMC9816869. 18: Li M, Qin Z, Yu Q, Huang Z, Cheng J, Zhong L, Liu Y, Xie J, Li Y, Chen J, Zhan R, Su Z. Anti-Inflammatory Activation of Phellodendri Chinensis Cortex is Mediated by Berberine Erythrocytes Self-Assembly Targeted Delivery System. Drug Des Devel Ther. 2022 Dec 23;16:4365-4383. doi: 10.2147/DDDT.S385301. PMID: 36583113; PMCID: PMC9793729. 19: Zhao WY, Xiang Q, Wang C, Wu XY, Zhu YH, Yang DY, Chen YX, Xiao XL, Gong QF, Yu H. [Mechanism of Euodiae Fructus stir-fried with water decoction of Coptidis Rhizoma in treatment of chronic colitis based on UPLC-Q-TOF-MS, network pharmacology and experimental verification]. Zhongguo Zhong Yao Za Zhi. 2022 Oct;47(19):5316-5326. Chinese. doi: 10.19540/j.cnki.cjcmm.20220314.402. PMID: 36472039. 20: Luo G, Lin J, Cheng W, Liu Z, Yu T, Yang B. UHPLC-Q-Orbitrap-MS-Based Metabolomics Reveals Chemical Variations of Two Types of Rhizomes of Polygonatum sibiricum. Molecules. 2022 Jul 22;27(15):4685. doi: 10.3390/molecules27154685. PMID: 35897876; PMCID: PMC9331047.
Zhao R, Wang B, Wang D, Wu B, Ji P, Tan D. Oxyberberine Prevented Lipopolysaccharide-Induced Acute Lung Injury through Inhibition of Mitophagy. Oxid Med Cell Longev. 2021 Feb 26;2021:6675264. doi: 10.1155/2021/6675264. PMID: 33728026; PMCID: PMC7937471.