Chemical Constituents of the Deep‐sea Gammarid Shrimp‐Derived Fungus Penicillium citrinum XIA‐16

Abstract

One new alkaloid, (S)‐2‐acetamido‐4‐(2‐(methylamino)phenyl)‐4‐oxobutanoic acid (1), was isolated from the deep‐sea‐derived Penicillium citrinum XIA‐16, together with 25 known compounds including ten polyketones (2‐11), eight alkaloids (12‐19), six steroids (20‐25), and a fatty acid (26). Their planar and relative structures were determined by an analysis of 1D and 2D nuclear magnetic resonance (NMR) as well as high resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of 1 was determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Penicitrinol B (6) significantly inhibited RSL3‐induced ferroptosis (EC50 = 2.0 μM) by reducing lipid peroxidation and heme oxygenase 1 (HMOX1) expression. Under the concentration of 10 μM, penicitrinol A (7) was able to inhibit cuproptosis with the cell viabilities of 68.2 % compared to the negative control (copper and elesclomol) with the cell viabilities of 14.8 %.

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

“…SCSIO 41038 [83]. (S)-2-acetamido-4-(2-(methylamino)phenyl)-4-oxobutanoic acid (257) (Figure 6) was isolated from the deepsea-gammarid-shrimp-derived P. citrinum XIA-16 [84]. A pentacyclic alkaloid, citrinadin C (258) (Figure 6), was isolated from the deep-sea-sediment-derived P. citrinum and showed cytotoxic activity against human liver cancer cell line MHCC97H, with an IC 50 value of 16.7 µM [85].…”