Isolation of Novel 6-methylideneoxecane-3,4,5,7,8,9-hexol from the Leaves of Rauwolfia vomitoria, Apocynaceae

Azibanasamesa D.C Owaba, Raji O. Rafiu, Arueniobebh Frank, Darlington D. Eboh, Samuel J. Bunu

Abstract


Rauwolfia vomitoria (Wennberg) belongs to the family Apocynaceae, the dried leaves were extracted successively using n-hexane, dichloromethane, and 70% methanol, concentrated in vacuo. Extracts were subjected to antibacterial assay and the butanol fraction was subjected to chromatographic purification to obtain NBF12 which was subjected to spectral analysis. The antibacterial of n-Hexane, dichloromethane, and 70% methanol extracts was inactive against the screened organisms assessed (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa). NBF12 is yellowish crystals (10.5 mg), Rf (0.69), UV, max Abs (248) The carbon 13C-NMR spectrum displayed ten carbon atoms; one methylene, two methylene oxide carbon, 6-carbinolic carbon (Sp3) and a quaternary carbon (SP2). The spectrum showed a tertiary carbon at δ131.09 ppm, due to C-6 and at δ 114.74 ppm due to exocyclic methylidene carbon (Sp2) (C=CH2) linked to the C-6position. Based on the spectral data NBF12 is 6-methylideneoxecane-3,4,5,7,8,9-hexol with a molecular formula C10H18O7, molecular weight 250 g/mol.

Keywords


Isolation; Rauwolfia vomitoria; antibacterial; 6-methylideneoxecane-3,4,5,7,8,9-hexol

Full Text:

PDF

References


Ajayi OA. (2021). Phytochemical and GCMS analysis of bioactive components in ethanolic extract of Rauvolfia vomitoria leaves. Journal of Chemical Society of Nigeria, 46(4): 0656-0660.

Azogu CP. (2010). Laboratory Organic Chemistry. 2nd Edition. Maybinson Book Publishers, New Jersey, USA. 269p.

Balogun OD and Akintude SL. (2022). Antimicrobial activities of Rauwolfia vomitoria against selected organisms. International Journal of Innovative and Advanced Studies, 9(3): 73-77.

Bubb WA (2003). NMR Spectroscopy in the study of carbohydrates: characterizing the structural Complexity. Wiley Periodicals, Inc Concepts Magn Reson Part A:19A (1): 1-19, DOI: 10.1002/cmr.a.10080.

Dhital S, Amatya SP, Aryal S, Neupane P, Tamang NPM, Thanait P. (2024). Synthesis of Manganese Oxide nanoparticles using co-precipitation method and its antimicrobial activity. International Journal of New Chemistry, 11 (3), 243-253.

Emencheta SC, Enweani BI, Oli AN, Ibezim EC, Imanyikwa IEO. (2020). Antimicrobial Evaluation of Plants Parts of Rauwolfia vomitoria. Journal of Complementary and Alternative Medical Research, 12(1); 11-20.

Etim E I, Johnson EC, Bassey US, and Nwafor PA. (2018). Phytochemical and aphrodisiac studies of ethanol root extract of Rauwolfia vomitoria Afzel (Apocynaceae), Journal of Pharmacy and Bioresources, 15(2): 160 – 165.

Fannang SV, Kuete V, Mbazoa CD, Momo JI, Van-Dufat HT, Tillequin, F, Seguin E, Chosson, E, Wandji J. (2011). A new acylated triterpene with antimicrobial activity from the leaves of Rauvolfia vomitoria, Chemistry of Natural Compounds, 47 (3): 20-25.

Kalsi PS. (2004). Spectroscopy of Organic Compounds. 3rd Edition. New Age International Publishers, New Delhi, India, 183p.

Kamentani S, Mizuno H, Shiga Y, Akunuma H. (1995). NMR of all-Carbon-13 sugars: An application in the development of an analytical method for a novel natural sugar, 1,5-Anhydrofructose. Journal of Biochemistry 119, 180-185.

Karim M, Khan S, Ullah I, Gamaryani A, Hasnain M, Abbas SH, Nawaz H, Saeed Z, Zafar I, Ur R, Saeed SY and Malik, MUA. (2023). Etiology and antibiotic resistant pattern of urinary tract bacterial pathogen in district Mardan. Biomed Journal of Scientific and Technical Research, 52(5): 44207-44211. DOI: 10.26717/BJSTR.2023.52.008330.

Oyeniran OH, Ademiluyi AO, Oboh G. (2020). Phenolic constituents and inhibitory effects of the leaf of Rauvolfia vomitoria, Afzel on free radicals, cholinergic and monoaminergic enzymes in rat's brain in vitro, J Basic Clin Physiol Pharmacol; 32(5):987-994, doi: 10.1515/jbcpp-2020-0144.

Sharma YR. (2015). Elementary Organic Spectroscopy: Principles and Chemical Application. S. Chand and Company PVT. Ltd., New York, 162p.




DOI: https://doi.org/10.14421/biomedich.2024.131.135-139

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2024 Azibanasamesa D.C Owaba, Raji O. Rafiu, Arueniobebh Frank, Darlington D. Eboh, Samuel J. Bunu



Biology, Medicine, & Natural Product Chemistry
ISSN 2089-6514 (paper) - ISSN 2540-9328 (online)
Published by Sunan Kalijaga State Islamic University & Society for Indonesian Biodiversity.

CC BY NC
This work is licensed under a CC BY-NC