New Chromones from a Marine-Derived Fungus, Arthrinium sp., and Their Biological Activity

Abstract

Five new chromone derivatives, arthones A–E (1–5), together with eight known biogenetically related cometabolites (6–13), were isolated from a deep-sea-derived fungus Arthrinium sp. UJNMF0008. Their structures were assigned by detailed analyses of spectroscopic data, while the absolute configurations of 1 and 5 were established by electronic circular dichroism (ECD) calculations and that of 2 was determined by modified Mosher ester method. Compounds 3 and 8 exhibited potent antioxidant property with DPPH and ABTS radical scavenging activities, with IC50 values ranging from 16.9 to 18.7 μM. Meanwhile, no compounds indicated obvious bioactivity in our antimicrobial and anti-inflammatory assays at 50.0 μM.

Diversity and Ecology of Marine Algicolous Arthrinium Species as a Source of Bioactive Natural Products

“…Filamentous fungi produce a wide range of secondary metabolites, and many polyphenolic compounds have been reported to exhibit high radical-scavenging abilities against ROS and free radicals [25]. In the case of marine Arthrinium spp., arthone C and 2,3,4,6,8-pentahydroxy-1-methylxanthone were reported as antioxidants [17]. Our ABTS assay results imply that marine-derived Arthrinium spp.…”

“…They have been discovered to produce natural compounds such as arthrinone, arthrichitin, terpestacin, (1 R ,2 S ,3a S ,8a R )-3a,6-dimethyl-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulene-1,2-diol (CAF-603), norlichexanthone, myrocins, libertellenones, spiroarthrinols, and griseofulvin derivatives [12,13,14,15]. However, a limited number of bioactive compounds were reported: arthpyrones F–I and apiosporamide (antibacterial) [16]; arthrinins A–D (antitumoral and antiproliferative) [13]; decarboxyhydroxycitrinone, myrocin A, libertellenone C, and cytochalasin E (antiangiogenic); arthone C and 2,3,4,6,8-pentahydroxy-1-methylxanthone (antioxidant) [17]; and cytochalasin K and 10-phenyl-[12]-cytochalasin Z 16 (cytotoxic) [18]. In this regard, it was suggested that marine Arthrinium spp.…”

Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

“…Phenylpropanoids contain many chemical structure types, such as chromone, coumarin, flavone and lignin, which possess various biological activities including antioxidant, cytotoxic, antimicrobial, and enzyme inhibitory activities. For example, arthone C, a chromone derivative isolated from a deep-sea-derived fungus Arthrinium sp., exhibited potent antioxidant activity (Bao et al 2018). Two tetracyclic coumarin derivatives and two coumarin dimers isolated from the marine-derived fungus Eurotium rubrum showed significant tyrosinase inhibitory activity (Kamauchi et al 2018).…”

Arthpyrone L, a New Pyridone Alkaloid from a Deep‐Sea Arthrinium sp., Inhibits Proliferation of MG63 Osteosarcoma Cells by Inducing G0/G1 Arrest and Apoptosis

“…UJNMF0008) came to our attention during the initial chemical profiling and antimicrobial assays. A subsequent chemical investigation into the ethanol extract of this fungus afforded a series of antibacterial pyridone alkaloids [8] and antiradical chromones [9] . Among them, a known alkaloid named apiosporamide exhibited moderate growth inhibition against two OS cells (U2OS and MG63), and a preliminary mechanism study was also performed, since there had no relevant work reported in the literature [10] .…”