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An Unusual Spiro-Fused Indole Alkaloid-Terrein Hybrid From Marine-Derived Fungus Aspergillus chevalieri HK-56
WanJuan Xie1, XuHua Nong1, YiLin Kuang1
1Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education and Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, Hainan, China.
Abstract:
One previously undescribed alkaloid variecoterrein (1) and seven known compounds (2-8) were obtained from the solid-state fermentation culture of the marine-derived fungus Aspergillus chevalieri HK-56. The planar and stereochemical structures of 1 was unambiguously elucidated by comprehensive spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HRESIMS), DP4+ probability analysis, and electronic circular dichroism (ECD) spectroscopy. Compound 1 represents a structurally unique hybrid molecule, constituting the first naturally occurring conjugate that incorporates both indole 2,5-diketopiperazine alkaloid and terrein structural scaffolds. All isolated compounds were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophage cells. Among them, compound 2 exhibited potent in vitro anti-inflammatory activity, with an IC50 value of 22.72 ± 0.22 µM, comparable to the positive control quercetin (IC50 = 13.81 ± 0.35 µM).
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