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Berberine isolation from Coscinium fenestratum: optical, electrochemical, and computational studies

Lookup NU author(s): Dr Ben Horrocks

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Abstract

© 2023 The Royal Society of ChemistryBerberine was extracted from Coscinium fenestratum (tree turmeric) and purified by column chromatography. The UV-Vis absorption spectroscopy of berberine was studied in acetonitrile and aqueous media. TD-DFT calculations employing the B3LYP functional were found to reproduce the general features of the absorption and emission spectra correctly. The electronic transitions to the first and second excited singlet states involve a transfer of electron density from the electron donating methylenedioxy phenyl ring to the electron accepting isoquinolium moiety. An estimate of the electrochemical gap (2.64 V) was obtained from microelectrode voltammetry and good agreement was found with quantum chemical calculations using the cc-pVTZ basis set and the B3LYP, CAM-B3LYP and wB97XD functionals. The calculations indicate spin density of the radical dication is delocalised over the molecule. These basic data are useful for assessment of the synthesis of donor-acceptor polymeric materials employing oxidative polymerization or co-polymerisation of berberine.

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Author(s): Rajapakse RMG, Horrocks BR, Malikaramage AU, Gunarathna HMNP, Egodawele MGSAMEWDDK, Jayasinghe JMS, Ranatunga U, Herath WHMRNK, Sandakelum L, Wylie S, Abewardana PGPR, Seneviratne VN, Perera LLK, Velauthapillai D

Publication type: Article

Publication status: Published

Journal: RSC Advances

Year: 2023

Volume: 13

Issue: 25

Pages: 17062-17073

Online publication date: 07/06/2023

Acceptance date: 22/05/2023

Date deposited: 10/07/2023

ISSN (electronic): 2046-2069

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/d3ra01769a

DOI: 10.1039/d3ra01769a

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