New azaphilones from mangrove endophytic fungus Penicillium sclerotiorin SCNU-F0040

Abstract

：Two new sclerotioramines (1 and 2) and a new natural product of sclerotioramine analog (3), together with seven known compounds have been isolated from the mangrove endophytic fungus Penicillium sclerotiorin SCNU-F0040. Their structures were identified based on the 1D, 2D NMR and HRESIM spectra. The absolute configurations of new compounds were deduced by specific rotation data and electronic circular dichroism spectra. All the isolated new compounds were tested on anti-diabetes activity by using aglucosidase inhibition assay and anti-inflammatory activity by using cyclooxygenase inhibition assay, respectively. Compounds 1 and 2 have a-glucosidase inhibition activity with IC50 values of 102.3 and 217.5 μM.Compound 2 shows a moderate cyclooxygenase-2 inhibitory activity with an IC50 value of 47.8 μM.

Azaphilones Pigments from the Fungus Penicillium hirayamae

“…Indeed, combined annotations from GNPS databases and SIRIUS version 5.5.5 highlighted the presence of various ions identified as azaphilones (Figure 1). Among the annotated azaphilones, penazaphilone D [8], isochromophilone VI [7], and sclerketide E [6] were fully chemically characterized by 2D NMR after isolation from the Penicillium hirayamae crude extract, reinforcing the GNPS and SIRIUS predictions. Among the known compounds produced by P. hirayamae, only the sclerotiorin was identified from GNPS and Sirius (Figure S1).…”

“…The UV spectrum displayed an absorption maximum of 371 nm. The 1 H NMR and 13 C NMR spectra were identified to have the same planar structures as the sclerotionamine dimer [6,8].…”

“…Using this approach, we identified the fungus Penicillium hirayamae as a producer of novel azaphilones. Three new azaphilones named penazaphilones J-L (1-3), along with three known ones, penazaphilone D, isochromophilone VI, and sclerketide E [6][7][8] were isolated and identified from the ethyl acetate extract of the solid culture of the strain Penicillium hirayamae. Here, the isolation, structure elucidation, and biological activities of these compounds were described.…”

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

“…160 Three new sclerotioramines (334−336) are found in the mangrove endophytic fungus Penicillium sclerotiorin SCNU-FOO40. 161 A review on the biosynthesis of azaphilones has appeared, 162 and the production of halogenated azaphilones and ilicicolins in the termite symbiotic fungi, Penicillium sclerotiorum and Neonectria discophora is demonstrated using a combination of metabolomics and genomic methods. 163 The Australian mud dauber wasp nest is associated with the fungus Penicillium sp.…”

“…Both compounds exhibit antibacterial activity against MRSA (MIC 12.5 and 25 μg/mL, respectively) and four other germs . Three new sclerotioramines ( 334 – 336 ) are found in the mangrove endophytic fungus Penicillium sclerotiorin SCNU-FOO40 …”