Abstract
Two new (1–2) and three known (3–5) sorbicillinoids were isolated from the deep-sea-derived fungus Penicillium allii-sativi MCCC 3A00580. Compounds 1 and 2, named sorbicatechols C and D, were two new hybrid dihydrosorbillinoids. Their structures were established mainly by spectroscopic analyses and electronic circular dichroism (ECD) calculations. All five isolates were tested for antiproliferative activities against four tumor cell lines of MCF-7, HT-29, HuH-7, and LNCap. Compounds 2 and 5 inhibited HT-29 cells in a good dose-dependent manner. Mechanism investigation uncovered that they could significantly induce cell cycle G2-M phase arresting by increasing the protein levels of p-H3 and cyclin B1.
Highlights
Sorbicillinoids are hexaketide metabolites that possess complex and highly oxygenated frameworks
The high resolution electrospray ionization mass spectroscopy (HRESIMS) spectra were measured on a Waters Xevo G2 Q-TOF (Waters) mass spectrometer
The sodiated molecular ion peak at m/z 495.1951 [M + Na]+ in the HRESIMS indicated its molecular formula as C24H30O6, requiring 10 degrees of unsaturation
Summary
Sorbicillinoids are hexaketide metabolites that possess complex and highly oxygenated frameworks They can be divided into four groups: monomeric, dimeric, trimeric, and hybrid sorbicillinoids (Harned and Volp, 2011; Meng et al, 2016). Three meroterpenoids were obtained and andrastones A showed significant inhibitory effect against HepG2 tumor cells by activating caspase-3 and regulating the transcriptional activation function of RXRα (Xie et al, 2019b). Further investigation on this strain led to the discovery of two new and three known sorbicillinoid derivates (Figure 1). We report the isolation, structures, and bioactivities of these compounds
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