Two Decarestrictine Analogs from the Soil-Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata.

Two new decarestrictine analogs decarestrictine P and penicitone, together with eight known homologous compounds were isolated from the soil fungus from the rhizosphere of Penicillium sp. YUD18003 related to Gastrodia elata. Their different structures include a decanolides decartestridine P and a long-chain polyhydroxyketone penicitone. The structures of new compounds were determined by nuclear magnetic resonance (NMR) spectroscopic analysis and high resolution electrospray ionization mass spectrometry (HR-ESI-MS), while their absolute configurations were determined by spectroscopic methods, DP4+ probability analysis, modified Snatzke's method and electron circular dichroism (ECD) calculations. All compounds were evaluated for antimicrobial activities.

Fungal polyketides from a rhizospheric soil-derived Penicillium sp. YUD17004 associated with Gastrodia elata.

Five unprecedented polyketide metabolites were isolated and characterized from a rhizospheric soil-derived Penicillium sp. YUD17004. Their diverse structures included two indanone-type polyketides penicillyketides A and B, a phthalide-like polyketides penicillyketide C, a symmetrical chromone dimer penicillyketide D, along with a pyrone derivative pyranlyketide, which were elucidated by spectroscopic data interpretation and quantum chemical electronic circular dichroism calculation. Notably, the structures of penicillyketides A and B feature a highly functionalized indanone ring nucleus, but differ from other indanone-containing polyketides by the alkyl substitution pattern. The structure of penicillyketide C comprises a furanone ring instead of the hydroxycyclopentenone ring characteristic for penicillyketides A and B, and represents an undescribed arrangement within C17 polyketides. Penicillyketide D represented the first example of a chromone homodimer with the bridge at C-2/2'. Penicillyketide B exhibited weak anti-inflammatory activity with an IC50 value of 32 ± 1.0 µM. Penicillyketide D displayed weak cytotoxicity against MCF-7 cell line with an IC50 value of 25 ± 0.9 µM.

Altereporenes A-E, five epoxy octa-hydronaphthalene polyketides produced by an endophytic fungus Alternaria sp. YUD20002.

Five previously undescribed epoxy octa-hydronaphthalene polyketides, altereporenes A-E (1-5) were isolated from rice culture of the endophytic fungus Alternaria sp. YUD20002 derived from the tubers of Solanum tuberosum. Their structures were determined on the basis of comprehensive spectroscopic analyses, while the absolute configurations were elucidated by the comparison of experimental and calculated specific rotations. Meanwhile, the antimicrobial, cytotoxic, anti-inflammatory and acetylcholinesterase inhibitory activities of compounds 1-5 were also investigated.

Phialocetones A-J, C12 lactones from the rhizospheric soil-derived fungus Phialocephala sp. YUD18001 associated with Gastrodia elata.

Ten undescribed C12 polyketide phialocetones A-J, featuring twelve-, six- and five-membered lactone moieties, were isolated from a rhizospheric soil-derived Phialocephala sp. YUD18001 associated with Gastrodia elata. Their structures were established by NMR spectroscopic analysis and HRMS, while their absolute configurations were determined by computational methods and chemical reactions. All isolated compounds were evaluated for their anti-inflammatory and cytotoxic activities. As a result, phialocetone D exhibited moderate effects against NO production in lipopolysaccharide (LPS)-induced RAW264.7 cells with an IC50 value of 14.77 µM, while phialocetone E showed cytotoxicity against HL-60 and SW480 cell lines with IC50 values of 19.04 and 10.22 µM, respectively.