The synthesis of shogaols and investigation of their antibacterial activity Haseeb Ahmed Sayeed Khadas 1 , Liew Yun Khoon 2 , Then Yoon Yee 3 , Wong Lai Chun 3 1 School of Postgraduate Studies, International Medical University, Malaysia, 2 Department of Life Sciences, School of Pharmacy, International Medical University, Malaysia, 3 Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Malaysia Ginger is a natural dietary rhizome of the Zingiber officinale Roscoe and is one of the most consumed dietary condiments in the world. It is an herbaceous tropical monocotyledon perennial plant of the family Zingiberaceae and subfamily Zingiberoideae. There are numerous commercial kinds of ginger available around the world, and about 25 species of Zingiberaceae are used as spices and natural remedies for a variety of ailments owing to its rich chemical constituents. Gingerols, gingerdiols, shogaols, paradols, and zingerones are some of the bioactive components found in ginger. Antibiotic resistance is widely acknowledged as a major public health problem. The escalating threat of antibiotic resistance underscores the urgent need for new antibacterial agents. Plant natural products, such as ginger, are a promising source of antibacterial lead molecules. The antibacterial property of ginger has been majorly attributed to two of its bioactive components, 6-gingerol and 6-shogaol. Shogaol is a phenolic compound that is derived from gingerol conversions through thermal processing of ginger. It has an alkyl side chain consisting of an α, β-unsaturated ketone moiety, giving various components such as 4-, 6-, 8-, 10-, and 12-shogaol. However, apart from 6-shogaol, antibacterial study on shogaols with other alkyl side chain lengths are limited. Hence, in this proposed work we aim to study the antibacterial property of 3-, 4-, 5- and 6- shogaol. The shogaols were synthesized using aldehyde, zingerone and dimethylammonium dimethyl carbamate as the starting materials. The progress of the reaction was monitored by thin layer chromatography. The crude product obtained was purified by column chromatography over silica gel (200–400 mesh). A total of four ATCC strains bacteria was tested for the shogaols, which including Gram positive ( Staphylococcus aureus ATCC 43300, Enterococcus faecalis ATCC 51299) and Gram-negative bacteria ( Acinetobacter baumannii ATCC 19606, Klebsiella pneumoniae ATCC BAA 1705). Antibacterial screening of the shogaols between concentration 250 ug/ mL – 5000 ug/mL were performed by disk diffusion method in Mueller Hinton Agar plates. 3-shogaol were found to be the most potent, exhibiting zone inhibition with Staphylococcus aureus. Hence, our results suggest that apart from 6-shogaol, shogaols with other side chain lengths may also present potential as a source of antibacterial lead molecules and warrant further investigation.
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© The Author(s), 2023
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