Abstract
Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.
Highlights
Organic products with branched tert-butyl groups represent a relatively important number of active compounds [1,2]
Analytical HPLC and semi-preparative HPLC were performed on a 5-μm Prevail C18 column (250 mm × 4.6 mm for the former, and 250 mm × 10 mm for the later), GRACE, Columbia, molecular dynamics (MD), USA
Two tert-butylphenol compounds were firstly isolated from the culture of a bacterium, P. odorifer, associated with the lichen, Rhizocarpon geographicum
Summary
Organic products with branched tert-butyl groups represent a relatively important number of active compounds [1,2]. In the past, this group was already exploited in many organic syntheses due to its chemical reactivity. There are more than 200 compounds containing tert-butyl groups, described as natural products with interesting bioactivities [3]. The tert-butyl moiety can be found in a variety of compounds produced by various sources, such as plants, fungi, algae, cyanobacteria [4,5,6,7,8,9], and especially from bacteria which were admitted as a source of novel and interesting bioactive products [10]. Chemical studies on Paenibacillus odorifer, a bacterium associated with the crustose lichen, Rhizocarpon geographicum, led to the identification of two tert-butylphenol derivatives (1, 2)
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