Anti-inflammatory activity of synthetic and natural glucoraphanin

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Published: Jun 4, 2019
DOI: https://doi.org/10.2298/JSC180518108V
Keywords:
broccoli TNF-α sulforaphane glucosinolates synthesis THP-1

Main Article Content

Quan V. Vo
Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City and Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City
Pham Cam Nam
Department of Chemical Engineering, The University of Da Nang – University of Science and Technology
Thuc Ngoc Dinh
Faculty of Natural Sciences, Hong Duc University, Thanh Hoa
Adam Mechler
La Trobe Institute for Molecular Science, La Trobe University, Melbourne
Thi Thi Van Tran
Department of Chemistry, Hue University of Science, 77 Nguyen Hue, Hue

Abstract

Glucoraphanin is one of the best known glucosinolates because of its health benefits. The compound is known to eliminate carcinogens in tissue and hence is frequently studied for its cancer preventative properties. In this work, the total synthesis of α- and β-glucoraphanin epimers was attempted. β-Glu­coraphanin potassium salt was successfully synthesized in high overall yield, whereas the α-epimer was found to be unstable as it decomposed in the final step of the total synthesis. The anti-inflammatory activity of the synthetic glu­co­raphanin was det­ermined by inhibition of the release of tumor necrosis factor alpha (TNF-α) sec­retion in lipopolysaccharide-stimulated THP-1 cells. It was shown that in the pre­sence of either the synthetic or natural glucoraphanin, TNF-α secretion was sig­nificantly reduced (≈52 % inhibition) at a concen­tration of 15 μM.

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How to Cite
[1]
Q. V. Vo, P. C. Nam, T. N. Dinh, A. Mechler, and T. T. V. Tran, “Anti-inflammatory activity of synthetic and natural glucoraphanin”, J. Serb. Chem. Soc., vol. 84, no. 5, pp. 445–453, Jun. 2019.
Issue
Vol. 84 No. 5 (2019)
Section
Organic Chemistry

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