WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H558358
CAS#: 549-21-3
Description: Oxyberberine is isolated from the methanol extract of A. mexicana. It has been used to study the SW480 human colon cancer cell line.
Hodoodo Cat#: H558358
Name: Oxyberberine
CAS#: 549-21-3
Chemical Formula: C20H17NO5
Exact Mass: 351.11
Molecular Weight: 351.360
Elemental Analysis: C, 68.37; H, 4.88; N, 3.99; O, 22.77
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
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.
| 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: | |
| In vivo protocol: |
1: Singh S, Verma M, Malhotra M, Prakash S, Singh TD. Cytotoxicity of alkaloids isolated from Argemone mexicana on SW480 human colon cancer cell line. Pharm Biol. 2016;54(4):740-5. doi: 10.3109/13880209.2015.1073334. Epub 2015 Oct 6. PubMed PMID: 26439487.
2: Singh S, Singh TD, Singh VP, Pandey VB. Quaternary alkaloids of Argemone mexicana. Pharm Biol. 2010 Feb;48(2):158-60. doi: 10.3109/13880200903062622. PubMed PMID: 20645832.
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5: Moniot JL, Kravetz TM, Abd el Rahman AH, Shamma M. Chemistry of 8-chloroberberine. J Pharm Sci. 1979 Jun;68(6):705-8. PubMed PMID: 458568.
6: Qian XC, Zhang L, Tao Y, Huang P, Li JS, Chai C, Li W, Di LQ, Cai BC. Simultaneous determination of ten alkaloids of crude and wine-processed Rhizoma Coptidis aqueous extracts in rat plasma by UHPLC-ESI-MS/MS and its application to a comparative pharmacokinetic study. J Pharm Biomed Anal. 2015 Feb;105:64-73. doi: 10.1016/j.jpba.2014.11.049. Epub 2014 Dec 5. PubMed PMID: 25543284.
7: Liang YD, Yu CX. Determination of berberine in pharmaceutical preparations using acidic hydrogen peroxide-nitrite chemiluminescence system. Drug Test Anal. 2013 Mar;5(3):150-5. doi: 10.1002/dta.282. Epub 2011 Apr 16. PubMed PMID: 21500372.
8: Wu WN, Beal JL, Leu RP, Doskotch RW. Alkaloids of Thalictrum. XXI. Isolation and characterization of alkaloids from the roots of Thalictrum podocarpum. Lloydia. 1977 Jul-Aug;40(4):384-94. PubMed PMID: 331006.
9: Wu WN, Beal JL, Mitscher LA, Salman KN, Patil P. Alkaloids of Thalictrum. XV. Isolation and identification of the hypotensive alkaloids of the root of Thalictrum lucidum. Lloydia. 1976 Jul-Aug;39(4):204-12. PubMed PMID: 957909.
10: Wu WN, Beal JL, Leu RP, Doskotch RW. Alkaloids of thalictrum. XX. Isolation, identification and structural elucidation of the alkaloids of the root of Thalictrum longistylum. Lloydia. 1977 May-Jun;40(3):281-9. PubMed PMID: 895386.
11: Yang TC, Chao HF, Shi LS, Chang TC, Lin HC, Chang WL. Alkaloids from Coptis chinensis root promote glucose uptake in C2C12 myotubes. Fitoterapia. 2014 Mar;93:239-44. doi: 10.1016/j.fitote.2014.01.008. Epub 2014 Jan 18. PubMed PMID: 24444890.
12: Chen HY, Ye XL, Cui XL, He K, Jin YN, Chen Z, Li XG. Cytotoxicity and antihyperglycemic effect of minor constituents from Rhizoma Coptis in HepG2 cells. Fitoterapia. 2012 Jan;83(1):67-73. doi: 10.1016/j.fitote.2011.09.014. Epub 2011 Sep 24. PubMed PMID: 21968062.
13: Min YD, Yang MC, Lee KH, Kim KR, Choi SU, Lee KR. Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino. Arch Pharm Res. 2006 Sep;29(9):757-61. PubMed PMID: 17024849.
14: Min YD, Kwon HC, Yang MC, Lee KH, Choi SU, Lee KR. Isolation of limonoids and alkaloids from Phellodendron amurense and their multidrug resistance (MDR) reversal activity. Arch Pharm Res. 2007 Jan;30(1):58-63. PubMed PMID: 17328243.
15: Zhang MY, Yu YY, Wang SF, Zhang Q, Wu HW, Wei JY, Yang W, Li SY, Yang HJ. Cardiotoxicity evaluation of nine alkaloids from Rhizoma Coptis. Hum Exp Toxicol. 2018 Feb;37(2):185-195. doi: 10.1177/0960327117695633. Epub 2017 Mar 1. PubMed PMID: 29233041.
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.
