Abstract
Four new indole-diterpenoids, named penerpenes K-N (1–4), along with twelve known ones (5–16), were isolated from the fermentation broth produced by adding L-tryptophan to the culture medium of the marine-derived fungus Penicillium sp. KFD28. The structures of the new compounds were elucidated extensively by 1D and 2D NMR, HRESIMS data spectroscopic analyses and ECD calculations. Compound 4 represents the second example of paxilline-type indole diterpene bearing a 1,3-dioxepane ring. Three compounds (4, 9, and 15) were cytotoxic to cancer cell lines, of which compound 9 was the most active and showed cytotoxic activity against the human liver cancer cell line BeL-7402 with an IC50 value of 5.3 μM. Moreover, six compounds (5, 7, 10, 12, 14, and 15) showed antibacterial activities against Staphylococcus aureus ATCC 6538 and Bacillus subtilis ATCC 6633.
Highlights
Marine fungi have formed different metabolic pathways and adaptation mechanisms within the peculiar marine environment
As an important class of secondary metabolites produced by marine-derived fungi [3], showed excellent biological activities, including cytotoxic [4], antibacterial [5], quorum sensing inhibitory [6], anti-Zika virus [7], and protein tyrosine phosphatase inhibitory activities [8,9]
Our previous study on the secondary metabolites of this fungus discovered a series of indole alkaloids with novel structures and intriguing bioactivities, e.g., protein tyrosine phosphatase inhibitory activity [8,9]
Summary
Marine fungi have formed different metabolic pathways and adaptation mechanisms within the peculiar marine environment. Marine fungi can produce natural secondary metabolites that are characterized by unique chemical structures and high biological activities [1,2]. Our previous study on the secondary metabolites of this fungus discovered a series of indole alkaloids with novel structures and intriguing bioactivities, e.g., protein tyrosine phosphatase inhibitory activity [8,9]. To find more new alkaloids from marine fungi, adding amino acids to the culture media is becoming a viable. Mar. Drugs 2021, 19, 613 from marine fungi, adding amino acids to the culture media is becoming a viable strategy [12,13].
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