Identification of Unknown Compound in Apocynum cannabinum by High Resolution Mass Spectrometry (HRMS) and 600 MHz NMR
DOI:
https://doi.org/10.21423/JRS-V04N03P014Keywords:
Apocynum cannabinum, LC-MS, NMR, 4’-hydroxyacetophenoneAbstract
High resolution mass spectrometry (HRMS) was able to determine that the m/z of the [M+H]+ ion formed by an unknown compound that was purified by preparative scale liquid chromatography (LC) was 137.05966. This was done rapidly and easily by direct infusion. Neither a column nor chromatography was needed. This is within 0.4 ppm of the mass calculated by ThermoFisher’s exact mass calculator for the protonated version of C8H8O2. Based on this, the compound could have been 2’-, 3’- or 4’-hydroxyacetophenone or 2’-, 3’- or 4’-methoxybenzaldehyde. However, 1H- and 13C-NMR spectra of the isolated compound showed that it was 4’-hydroxyacetophenone, without needing a standard. Neither mass spectrometry (MS) nor NMR could have identified this compound by itself. Finally, HRMS was also able to verify that another peak isolated by preparative scale LC was apocynin, or 4’-hydroxy-3’-methoxyacetophenone.
https://doi.org/10.21423/jrs-v04n03p014 (DOI assigned 5/31/2019)
References
USDA. INDIAN HEMP Apocynum cannabinum L. URL http://plants.usda.gov/plantguide/pdf/cs_apca.pdf
S. Ram, A bibliometric assessment of apocynin (Apocynum cannabinum) research, Ann. Library Information Sci. 60.
A. Simonyi, et al., The neuroprotective eect of apocynin, Front. Biosci. (Elite Ed) 4 (2014) 2183.
R. F. Klees, et al., Apocynin derivatives interrupt intercellular signaling resulting in decreased migration in breast cancer cells, J. Biomed. Biotechnol. 2006 (2006) 1.
Chemical Book. 4’-hydroxyacetophenone 13CNMR. URL http://www.chemicalbook.com/SpectrumEN_99-93-4_13CNMR.htm
R. Luchtefeld, et al., Dose Formulation and Analysis of Diapocynin, J. Agr. Food Chem. 56 (2008) 301.
J. Stolk, T. Hilterman, J. Dijkman, Characteristics of the inhibition of NADPH oxidase activation in neutrophils by apocynin, a methoxysubstituted catechol, Am. J. Respir. Cell Mol.Biol. 11 (1994) 95.
A. Boorem, R. Smith, R. Luchtefeld, D. Monroe, R. Luo, Analysis of products of coupling reactions with sulfate radicals, Missouri J. Undergrad. Chem. Res. 10 (2010) 9.
R. Matthews, V. Massey, C. Sweeley, Identification of phydroxybenzaldehyde as the ligand in the green form of old yellow enzyme, J. Biol. Chem. 250 (1975) 9294.
M. Moonen, et al., Elucidation of the 4-hydroxyacetophenone catabolic pathway in Pseudomonas fluorescens ACB, J. bacteriol. 190 (2008) 5190.
J.-N. Han, et al., Artemisia capillaris extract protects against bile duct ligation-induced liver fibrosis in rats, Exp. Toxicol. Pathol. 65 (2013) 837.
H. Koo, et al., An ethanol root extract of Cynanchum wilfordii containing acetophenones suppresses the expression of VCAM-1 and ICAM-1 in TNF--stimulated human aortic smooth muscle cells through the NF-B pathway, Int. J. Mol. Med. 35 (2015) 915.
H. Baxter , J.B. harborne , Moss, G., eds. Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants, 2nd ed. Taylor & Francis, Philadelphia, 1999, p. 1943.
Downloads
Published
Issue
Section
License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
By submitting content to the Journal of Regulatory Science (JRS), authors agree to the following terms:
- Authors retain copyright and grant the JRS the right of first publication. Authors retain patent, trademark, and other intellectual property rights (including research data) and grant third parties the right to use, reproduce, and share the article according to the Creative Commons — Attribution-NonCommercial 4.0 International — CC BY-NC 4.0 license agreement. The JRS is an open access journal and, as a result, articles are free to use with proper acknowledgment of the work's authorship and initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process.
- If excerpts from other copyrighted works are included, the author(s) must obtain written permission from the copyright owners and credit the source(s) in the article.
- The publication of the submission has been approved by all co-authors and responsible authorities at the institute or organization where the work has been carried out.
- Copyright has not been breached in seeking publication of the submission.
