Brasilianoids A-F, New Meroterpenoids From the Sponge-Associated Fungus Penicillium brasilianum
- PMID: 30101144
- PMCID: PMC6072878
- DOI: 10.3389/fchem.2018.00314
Brasilianoids A-F, New Meroterpenoids From the Sponge-Associated Fungus Penicillium brasilianum
Abstract
3,5-Dimethylorsellinic acid (DMOA) derived meroterpenoids comprise an unique class of natural products with diverse scaffolds and with a broad spectrum of bioactivities. Bioinformatics analysis of the gene clusters in association with the qRT-PCR detection of the amplification of two key genes led to speculate that the sponge associated fungus Penicillium brasilianum WZXY-m122-9 is a potential producer of meroterpenoids. Chromatographic separation of the EtOAc extract of this fungal strain on a large-scale fermentation resulted in the isolation of six new DMOA-related meroterpenoids with trivial names of brasilianoids A-F (1-6), together with preaustinoid D and preaustinoid A2. The structures were determined by extensive analyses of spectroscopic data, including the X-ray diffraction and the ECD data for configurational assignment. Brasilianoids A and F showed an unprecedented skeleton with a γ-lactone in ring A, while brasilianoids B-C featured a 7/6/6/5/5 pentacyclic ring system finding in nature for the first time. The biosynthetic relationship among the isolated compounds was postulated. Compound 1 significantly stimulated the expression of filaggrin and caspase-14 in HaCaT cells in dose-dependent manner, while compounds 2 and 3 showed moderate inhibition against NO production in LPS-induced RAW 264.7 macrophages.
Keywords: Penicillium brasilianum; brasilianoids A–F; inhibition of NO production; sponge-associated fungus; stimulation of filaggrin and caspase-14.
Figures
References
-
- Ahmed S. A., Scott F. E., Stenzel D. J., Simpson T. J., Moore R. N., Trimble L. A., et al. (1989). Studies on te biosynthesis of the mycotoxin austin, a meroterpenoid metabolite of Aspergillus ustus. J. Chem. Soc. Perkin Trans. 1. 4, 807–816.
-
- Duan R., Zhou H., Yang Y., Li H., Dong J., Li X., et al. (2016). Antimicrobial meroterpenoids from the endophytic fungus Penicillium sp. T2-8 associated with Gastrodia elata. Phytochem. Lett. 18, 197–201. 10.1016/j.phytol.2016.10.013 - DOI
LinkOut - more resources
Full Text Sources
Other Literature Sources
