Abstract
Cytoglobosins H (1) and I (2), together with seven known cytochalasan alkaloids (3–9), were isolated from the deep-sea-derived fungus Chaetomium globosum. The structures of new compounds 1 and 2 were elucidated by extensive 1D and 2D NMR and mass spectroscopic data. All the compounds were evaluated for their antiproliferative activities against MDA-MB-231 human breast cancer cells, LNCaP human prostate cancer cells, and B16F10 mouse melanoma cells. Compound 6 showed significant antiproliferative activity against LNCaP and B16F10 cell lines with IC50 values of 0.62 and 2.78 μM, respectively. Further testing confirmed that compound 6 inhibited the growth of LNCaP cells by inducing apoptosis.
Highlights
Marine microbes have been recognized as a rich source of pharmacologically active metabolites, and a growing number of marine fungi have been reported to produce metabolites with unique structures and interesting biological activities [1]
Repeated flash column chromatography and semi-preparative HPLC of EtOAc extract of Chaetomium globosum led to the isolation of nine cytoglobosins, including two new compounds, cytoglobosins H (1), and I (2), together with seven known ones, cytoglobosin B (3) [8], chaetoglobosinFex (4) [15], chaetoglobosin F (5) [16], chaetoglobosin E (6) [17], cytoglobosin C (7) [8], chaetoglobosin B (8) [16], and isochaetoglobosin D (9) (Figure 1)
In B16F10 cells, compounds 3–8 possessed considerable antiproliferative effects, with inhibit cell growth by 50% (IC50) ranging from 2.10 μM
Summary
Marine microbes have been recognized as a rich source of pharmacologically active metabolites, and a growing number of marine fungi have been reported to produce metabolites with unique structures and interesting biological activities [1]. The genus Chaetomium, which includes both terrestrial- and marine-derived species, is well-known for producing structurally complex natural products with antioxidant, antimicrobial, and cytotoxic bioactivities [4,5,6,7,8]. Cytochalasans are an important class of fungal alkaloids with a wide range of structural diversity and biological activities; they have been an important chemical tool in cell and molecular biology and represent an ambitious target for total synthesis. In our continuing search for novel bioactive natural compounds from marine fungi [11,12,13,14], we investigated the chemical constituents of Chaetomium globosum, a fungus obtained from a deep-sea sediment sample (−2500 m depth) of the Indian Ocean. Compound 6 inhibited the growth of LNCaP cells by inducing apoptosis
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