Abstract
Marine-derived fungi are a treasure house for the discovery of structurally novel secondary metabolites with potential pharmaceutical value. In this study, a pair of new nor-bisabolane derivative enantiomers (±)−1 and two new phthalides (4 and 5), as well as four known metabolites, were isolated from the culture filtrate of the marine algal-derived endophytic fungus Penicillium chrysogenum LD-201810. Their structures were established by detailed interpretation of spectroscopic data (1D/2D NMR and ESI-MS). The optical resolution of compound (±)−1 by chiral HPLC successfully afforded individual enantiomers (+)−1 and (−)−1, and their absolute configurations were determined by TDDFT-ECD calculations. Compound (±)−1 represents the first example of bisabolane analogs with a methylsulfinyl substituent group, which is rare in natural products. All of the isolated compounds 1–7 were evaluated for their cytotoxic activity against A549, BT-549, HeLa, HepG2, MCF-7, and THP-1 cell lines, as well as for antifungal activity against four plant pathogenetic fungi (Alternaria solani, Botrytis cinerea, Fusarium oxysporum, and Valsa mali). Compound 2, a bisabolane-type sesquiterpenoid, was shown to possess excellent activity for control of B. cinerea with half-maximal inhibitory concentration (IC50) of 13.6 μg/mL, whereas the remaining investigated compounds showed either weak or no cytotoxic/antifungal activity in this study.
Highlights
Marine-derived fungi that inhabit the marine environment possess the unique metabolic pathways to produce a great diversity of bioactive secondary metabolites, which play an important role in agrochemical and pharmaceutical industries (Xu et al, 2020; Zhang et al, 2020)
We reported the first example of nor-bisabolane analogs with a methylsulfinyl substituent group, which is rare in natural products
The result demonstrated that Penicillium chrysogenum LD-201810 belongs to the Penicillium genus
Summary
Marine-derived fungi that inhabit the marine environment possess the unique metabolic pathways to produce a great diversity of bioactive secondary metabolites, which play an important role in agrochemical and pharmaceutical industries (Xu et al, 2020; Zhang et al, 2020). It is well-known that a large number of new marine natural products have been discovered and reported every year. A follow-up examination of this cultivation yielded a pair of new nor-bisabolane derivative enantiomers (±)−1, two previously reported bisabolenes (2 and 3), and two new phthalides (4 and 5) (Figure 1). The structure elucidation of the new phthalides (4 and 5), as well as the cytotoxicity and antifungal activity of the isolated compounds, are described
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