Dihydroisocoumarins from the Mangrove-Derived Fungus Penicillium citrinum

Abstract

Three new dihydroisocoumarin penicimarins G–I (1–3), together with one known dihydroisocoumarin (4) and three known meroterpenoids (5–7), were obtained from a fungus Penicillium citrinum isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of spectroscopic data. The absolute configuration of 1 was determined by the X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of 2 and 3 were determined by comparison of their circular dichroism (CD) spectra with the literature. All compounds were evaluated for their antibacterial activities and cytotoxic activities.

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

“…Phomasatin (141) showed no cytotoxicity (IC 50 > 50 µM) against Molm 1, HL-60, and PC-3 cell lines using MTT assay [84]. Compounds 154 and 155 had no cytotoxic potential against HeLa, MCF-7, and A549 cells (IC 50 > 50 µM) [56]. Compounds 157-159, dihydroisocoumarin derivatives reported from Penicillium simplicissimum were examined against Artemia salina (brine shrimp lethality).…”

Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

“…In our ongoing research on mangrove-derived fungi, we have found some new bioactive metabolites (including metabolites with inhibitory activity against α-glucosidase) [9][10][11][12][13][14].…”

“…A mangrove-derived fungus Daldinia eschscholtzii HJ004 attracted our attention due to the inhibitory activity against α-glucosidase of its EtOAc extract, and three polyketide derivatives with strong inhibitory activity against α-glucosidase have been isolated [9]. A further chemical investigation of the fermentation broth resulted in the identification of two new polyketides 8-O-methylnodulisporin F (1) [15] and nodulisporin H (2) [15], two new naphthoquinones 5-hydroxy-2-methoxy-6,7-dimethyl-1,4-naphthoquinone (3), and 5-hydroxy-2-methoxynaphtho [9-c]furan-1,4-dione (4), and a new naphthofuran 1,3,8-trimethoxynaphtho [9-c] furan (5), together with five known compounds, 4-O-methyl eleutherol (6) [16], 2-acetyl-7-methoxybenzofuran (7) [17], (-)-orthosporin (8) [18], diaporthin (9) [18], and 6-hydroxymellein (10) [19] (Figure 1). The electronic circular dichroism (ECD) calculation method was used to establish the absolute configurations of the stereogenic carbons in 1 and 2.…”

“…Mangrove-derived fungi can produce secondary metabolites with novel structures and biological activities [8]. In our ongoing research on mangrove-derived fungi, we have found some new bioactive metabolites (including metabolites with inhibitory activity against α-glucosidase) [9][10][11][12][13][14]. A mangrove-derived fungus Daldinia eschscholtzii HJ004 attracted our attention due to the inhibitory activity against α-glucosidase of its EtOAc extract, and three polyketide derivatives with strong inhibitory activity against α-glucosidase have been isolated [9].…”

Four New Insecticidal Xanthene Derivatives from the Mangrove-Derived Fungus Penicillium sp. JY246

“…In our search for new bioactive compounds from fungal sources [6,8,9], the fungus Penicillium sp. JY246 was isolated from the mangrove's stem Ceriops tagal, collected from the South China Sea.…”