Asperphenyltones A and B: New Phenylfuropyridinone Skeleton from an Endophytic Aspergillus sp. GXNU-A1

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 23; p. 8160
• Main Authors: Huang, Jiguo, Bo, Xianglong, Wu, Furong, Tan, Meijing, Wei, Youquan, Wang, Lixia, Zhou, Junqiang, Wu, Guiming, Huang, Xishan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 23-11-2022; MDPI
• Subjects: Acanthaceae; anti-inflammatory effects; Aspergillus; Aspergillus - chemistry; Aspergillus sp; asperphenyltone A; Crystallography, X-Ray; Enantiomers; Endophytes; Fermentation; Fungi; Inflammation; Macrophages; mangrove endophytic fungus; Metabolites; Molecular Structure; Nitric oxide; NMR; Nuclear magnetic resonance; Single crystals; Two dimensional analysis; X-ray diffraction; United States > US; China; Japan; anti-inflammatory effects; Aspergillus sp; mangrove endophytic fungus; asperphenyltone A
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27238160

Chemical investigation of the fermentation extract of the mangrove endophytic fungus
sp. GXNU-A1, isolated from
L., discovered an undescribed pair of enantiomers (asperphenyltones A and B (
)), together with four previously described metabolites: nodulisporol (
), isosclerone (
), 2,3,4-trihydroxy-6-(hydroxymethyl)-5-methylbenzyl alcohol (
), and 4,6-dihydroxy-5-methoxy-7-methyl-1,3-dihydroisobenzofuran (
). Analyses of the 1D and 2D NMR spectroscopic data of the compounds supported their structural assignments. The presence of the asperphenyltones A and B, which are a pair of enantiomers, was established by HR-ESI-MS, 1D and 2D NMR data and confirmed by single-crystal X-ray diffraction analysis. Metabolites
-
were evaluated for their anti-inflammatory effects on the production of nitric oxide (NO), and
,
, and
showed significant potential inhibitory activities against NO production in activated macrophages with IC
values of 26-40 μM, respectively.