p-Terphenyls as Anti-HSV-1/2 Agents from a Deep-Sea-Derived Penicillium sp.

Abstract

Guided by Global Natural Products Social molecular networking, two p-terphenyl derivatives and one 4,5-diphenyl-2-pyrone analogue, peniterphenyls A–C (1–3), together with five known p-terphenyl derivatives (4–8) and sulochrin (9), were obtained from a deep-sea-derived Penicillium sp. SCSIO41030. Their structures were elucidated using extensive NMR spectroscopic and HRESIMS data and by comparing the information with literature data. Peniterphenyl B (2) represented the first reported natural product possessing a 4,5-diphenyl-substituted 2-pyrone derivative. The p-terphenyl derivatives displayed inhibitory activities against HSV-1/2 with EC50 values ranging from 1.4 ± 0.6 to 9.3 ± 3.7 μM in Vero cells, which showed that they possessed antiviral activities with low cytotoxicity, superior to the current clinical drug acyclovir (EC50 3.6 ± 0.7 μM). Peniterphenyl A (1) inhibited HSV-1/2 virus entry into cells and may block HSV-1/2 infection through direct interaction with virus envelope glycoprotein D to interfere with virus adsorption and membrane fusion, and thus differs from the nucleoside analogues such as acyclovir. Our study indicated peniterphenyl A (1) could be a promising lead compound against HSV-1/2.

Marine natural products

“…219 Deep-sea sediment and sediment-derived Penicillium strains have been the source of numerous metabolites. Deep-sea-derived compounds include chromone derivatives 597–604 , 220 meroterpenoids 605–607 , 221 p -terphenyls 608–610 , 222 drimane sesquiterpenes 611 and 612 , and polyketides 613–618 . 223 Sesquiterpene lactone 619 , 224 resorcinol-long chain fatty acid derivatives 620–624 , oxygenated polyene 625 , pyridinone derivative 626 , 225 and polyhydroxoxanthones 627–631 , 226 were also isolated from sediment-derived Penicillium strains.…”

Synthesis of Pogostone‐Inspired Dehydroacetic Acid Derivatives and Their Antifungal Activity against Sclerotinia sclerotiorum (Lib.) de Bary

“…2-Pyrones are a unique class of heterocycle, and they were presented as an essential fragment in various natural products with reported biological activities ranging from antiviral, [6] antiinflammatory, [7] antitumor, [8,9] antibacterial, [10,11] to antifungal [12] properties. Of particular interest to our prime concerns with the NPs occurring 2-pyrone motif is pogostone (Figure 1) since it has been demonstrated to exhibit prominent antifungal activities.…”

Aromatic Acids and Leucine Derivatives Produced from the Deep-Sea Actinomycetes Streptomyces chumphonensis SCSIO15079 with Antihyperlipidemic Activities

“…Marine-derived microorganisms have shown promising potential to produce a great number of active substances including antibacterial, antiviral, antioxidant, as well as cytotoxic compounds [13][14][15][16][17][18]. Marine extremophilic microorganisms tend to produce fascinating novel types of bioactive secondary metabolites; therefore deepsea-derived microorganisms seem to be significant sources for discovering lead compounds in drug discovery [19,20].…”