Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs

Abstract

2,4-Di-tert-butylphenol or 2,4-bis(1,1-dimethylethyl)-phenol (2,4-DTBP) is a common toxic secondary metabolite produced by various groups of organisms. The biosources and bioactivities of 2,4-DTBP have been well investigated, but the phenol has not been systematically reviewed. This article provides a comprehensive review of 2,4-DTBP and its analogs with emphasis on natural sources and bioactivities. 2,4-DTBP has been found in at least 169 species of bacteria (16 species, 10 families), fungi (11 species, eight families), diatom (one species, one family), liverwort (one species, one family), pteridiphyta (two species, two families), gymnosperms (four species, one family), dicots (107 species, 58 families), monocots (22 species, eight families), and animals (five species, five families). 2,4-DTBP is often a major component of violate or essential oils and it exhibits potent toxicity against almost all testing organisms, including the producers; however, it is not clear why organisms produce autotoxic 2,4-DTBP and its analogs. The accumulating evidence indicates that the endocidal regulation seems to be the primary function of the phenols in the producing organisms.

Evaluation of Phytochemicals and Bioactive Properties in Mangrove Associate Suaeda monoica Forssk. ex J.F.Gmel. of Indian Sundarbans

“…So, at this point, we cannot pinpoint a particular compound or a group of phytochemicals responsible for the highest antimicrobial property present in the n-hexane extract as observed by the MIC assay. GC-MS identified few phenolics compounds including phenol (0.19%), 2,6dimethoxyphenol or syringol (0.31%), 2,4-bis(1,1-dimethylethyl) phenol (1.69%), 2,6-bis(1,1-dimethylethyl)phenol (0.17%), 2,4bis(1,1-dimethylethyl)phenol (0.17%) and 2-methoxy-4-vinylphenol (1.26%) which share reports as potent antioxidants (Foti, 2007;Loo et al, 2008;Jeong and Jeong, 2010;Zhao et al, 2020). In addition, many other molecules present in Table 4, share reports of acting as antioxidant molecules.…”

The faecal metabolome in COVID-19 patients is altered and associated with clinical features and gut microbes

“…Because D-allose and D-arabinose are rare sugars and both Aspergillus and the unclassified species of Ascomycota were depleted, their positive correlation indicates that gut microbes may contribute to D-allose and D-arabinose depletion. In addition, 2,4-di-tert-butylphenol, which has antibacterial, antifungal and anticancer activities and cannot be produced by humans [ 28 ], strongly and positively correlated with Fusarium proliferatum and an unclassified species of Didymellaceae , both of which were depleted in the faeces of COVID-19 patients, further indicating the important role of gut microbes in the depletion of metabolites rarely occurring in nature.…”

Scrutinizing pharmacological efficiency for Acacia auriculiformis by experimental and computational approach

“…This outcome confirms that 2-4-ditert-butylphenol can directly bind with targeted enzymes and decrease enzymatic activities and reveal potential activity. Hence, in earlier, this compound expressed interaction with COX2, interleukin IL-6, IL-1b and TNF-α in RAW 264.7 cells and MCF-7 cell line activation of P53 gene has observed [49]. However, 3-hydroxy-β-damascone exhibited the best interaction score against helminthic (PDB ID: 1SA0), inflammatory and pyretic (PDB ID: 3DWW).…”