Abstract
Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively.
Highlights
Since the ocean covers over 70% of the Earth’s surface, marine organisms are regarded as a prolific and under-explored resource of bioactive natural products [1,2]
Comparing the high-resolution electrospray ionization mass spectra (HRESIMS) and NMR data with previously reported C27 meroterpenoids from the Penicillium species [7,8,9,10,11], these data were indicative of a breviane spiroditerpenoid, and interpretations of the 1 H–1 H COSY and HMBC spectra (Figure 2)
Ultraviolet (UV), and electronic circular dichroism (ECD) data were recorded on a PerkinElmer 341 polarimeter (Waltham, MA, USA), a Varian Cary 50 (Santa Clara, CA, USA), and a JASCO-810 CD
Summary
Since the ocean covers over 70% of the Earth’s surface, marine organisms are regarded as a prolific and under-explored resource of bioactive natural products [1,2]. Over the past few decades, with the discovery of plenty of new chemicals, marine-derived fungi have increasingly attracted the attention of natural product chemists and biologists, largely due to their surprising potentials for drug discovery [3,4,5]. Breviane spiroditerpenoids, which are biosynthesized from geranylgeranyl and pyrone derived from three molecules of acetyl CoA and one methyl from methionine, are an important group of architecturally complex and bioactive meroterpenoids [6].
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