One pot two-step borylation/fluorination reaction of dysobinin from Chisocheton macrophyllus and its cytotoxicity against cancer cell

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DOI: https://doi.org/10.21924/cst.9.2.2024.1514
Keywords:
Fluorine, boron, selecflour, cancer cell, dysobinin, limonoid

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Muhammad Badrul Huda
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia; Department of Chemistry, Diponegoro University, Semarang 50275, Indonesia
Nurlelasari
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia
Wahyu Safriansyah
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia
Mohamad Fajar
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia
Iis Intan Widiyowati
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia; Department of Chemical Education, Mulawarman University, Samarinda 75123, Indonesia
Unang Supratman
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia; Central Laboratory, Padjadjaran University, Sumedang 45363, Indonesia
Yessi Permana
Department of Chemistry, Bandung Institute of Technology, Bandung 40132, Indonesia
Yudha P. Budiman
Department of Chemistry, Padjadjaran University, Sumedang 45363, Indonesia

Abstract

Dysobinin is a naturally occurred limonoid, which is a specific form of triterpenoid, mostly found in certain plants, particularly the Meliaceae family. Overall, it has been found that limonoids have a wide range of biological functions. Typically, the compound comprises anticancer, antimicrobial, and anti-inflammatory properties. Even though dysobinin has shown some effectiveness, its potential in pharmacology, so far, is found limited. This study, therefore, aims to enhance the pharmacological properties of dysobinin through the addition of fluorine. To do this, a one-pot, two-step reaction comprising C-H borylation and selectfluor was used to turn dysobinin into two new compounds:  1,2-dihydro-6?-acetoxyazadirone (5) and 1?-fluorodysobinin (6). After the transformation, various spectroscopic methods, including UV (Ultraviolet), IR (infrared), MS (mass spectra), as well as NMR (1D and 2D) were applied to figure out the structures of the new compounds. Accordingly, of the derived compounds, 1?-fluorodysobinin showed significantly higher cytotoxicity against A549 lung cancer cells when compared to dysobinin.

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Huda, M. B., Nurlelasari, Safriansyah, W., Fajar, M., Widiyowati, I. I., Supratman, U., Permana, Y., & Budiman, Y. P. (2024). One pot two-step borylation/fluorination reaction of dysobinin from Chisocheton macrophyllus and its cytotoxicity against cancer cell. Communications in Science and Technology, 9(2), 366-371. https://doi.org/10.21924/cst.9.2.2024.1514
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Vol. 9 No. 2 (2024)
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