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

Jiguo Huang; Xianglong Bo; Furong Wu; Meijing Tan; Youquan Wei; Lixia Wang; Junqiang Zhou; Guiming Wu; Xishan Huang

doi:10.3390/molecules27238160

Molecules (Nov 2022)

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

Jiguo Huang,
Xianglong Bo,
Furong Wu,
Meijing Tan,
Youquan Wei,
Lixia Wang,
Junqiang Zhou,
Guiming Wu,
Xishan Huang

Affiliations

Jiguo Huang: School of Chemical Engineering and Technology, Guangdong Industry Polytechnic, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangzhou 510275, China
Xianglong Bo: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541000, China
Furong Wu: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541000, China
Meijing Tan: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541000, China
Youquan Wei: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541000, China
Lixia Wang: School of Chemical Engineering and Technology, Guangdong Industry Polytechnic, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangzhou 510275, China
Junqiang Zhou: School of Chemical Engineering and Technology, Guangdong Industry Polytechnic, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangzhou 510275, China
Guiming Wu: School of Chemical Engineering and Technology, Guangdong Industry Polytechnic, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangzhou 510275, China
Xishan Huang: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541000, China

DOI: https://doi.org/10.3390/molecules27238160
Journal volume & issue: Vol. 27, no. 23
p. 8160

Abstract

Read online

Chemical investigation of the fermentation extract of the mangrove endophytic fungus Aspergillus sp. GXNU-A1, isolated from Acanthus ilicifolius L., discovered an undescribed pair of enantiomers (asperphenyltones A and B (±1)), together with four previously described metabolites: nodulisporol (2), isosclerone (3), 2,3,4-trihydroxy-6-(hydroxymethyl)-5-methylbenzyl alcohol (4), and 4,6-dihydroxy-5-methoxy-7-methyl-1,3-dihydroisobenzofuran (5). 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 1–5 were evaluated for their anti-inflammatory effects on the production of nitric oxide (NO), and 1, 3, and 4 showed significant potential inhibitory activities against NO production in activated macrophages with IC50 values of 26–40 μM, respectively.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

About the journal

Abstract

Keywords