Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete <i>Nocardiopsis</i> sp. KMF-001

Abstract

Three new 3,6-disubstituted α-pyrones, nocapyrones H-J (1-3), were isolated from the marine actinomycete Nocardiopsis sp. KMF-001. Their structures were assigned to be 3-alkylated 6-(1-methyl-1-propenyl)-2H-pyran-2-ones on the basis of UV, MS, NMR, and high resolution (HR)-FAB-MS analyses. Nocapyrone H (1) reduced the pro-inflammatory factor such as nitric oxide (NO), prostaglandin E 2 (PGE 2 ) and interleukin-1β (IL-1β). Moreover, nocapyrone H showed 5.82% stronger inhibitory effect on NO production than chrysin at a concentration of 10 µm in lipopolysaccharide (LPS)-stimulated BV-2 microglial cells.

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

“…A large number of pyrone–containing marine natural products are known [26,27,28,29,30,31,32]. Specifically, a series of nocapyrones (A–Q) have been continuously reported from marine-derived Nocardiopsis strains with a wide range of bioactivity (Figure 8).…”

Marine Compounds and Cancer

“…KMF-001 reduced the pro-inflammatory factors such as nitric oxide (NO), prostaglandin E-2 (PGE(2)) and interleukin-1 (IL-1 ). Moreover, nocapyrone H showed a 5.8% stronger inhibitory effect on NO production than chrysin at a concentration of 10 M in lipopolysaccharide (LPS)-stimulated BV-2 microglial cells [136].…”

“…The mechanisms of action for the chemopreventive properties of -3 fatty acids are presumably five [125]: (1) suppression of arachidonic acid-derived eicosanoid biosynthesis [128]; (2) influence on transcription factor activity [129]; (3) increased or decreased production of free radicals and radical pathology [136]. This type of drugs has been reported to be beneficial, since they reduce the risk of developing solid tumors in breast, colon, lung, and prostate cancers [137,138].…”

“…They contain a great variety of polysaccharide compounds, including glycosaminoglycans, fucans, and galactans [23,[128][129][130]]. These compounds demonstrate diverse biological properties, including anticoagulant and antitrombotic [131][132][133], antioxidative [134], neuroprotective [135,136], and antiviral activity as well [8,137]. However, anticancer and cancer preventive activities of the polysaccharides from marine animals have been studied insufficiently.…”

Draft Genome Sequence of Marine-Derived Actinomycete Nocardiopsis sp. Strain TP-A0876, a Producer of Polyketide Pyrones

“…We assume that this cluster is responsible for nocapyrone biosynthesis in strain TP-A0876. Interestingly, a variety of pyrone derivatives were isolated from marine-derived Nocardiopsis strains (11–14). The actual products of the remaining four PKS and NRPS gene clusters have not been isolated or characterized from our strain.…”