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- Title
Discovery of Bioactive Indole-Diketopiperazines from the Marine-Derived Fungus Penicillium brasilianum Aided by Genomic Information.
- Authors
Zhang, Ya-Hui; Geng, Ce; Zhang, Xing-Wang; Zhu, Hua-Jie; Shao, Chang-Lun; Cao, Fei; Wang, Chang-Yun
- Abstract
Identification and analysis of the whole genome of the marine-derived fungus Penicillium brasilianum HBU-136 revealed the presence of an interesting biosynthetic gene cluster (BGC) for non-ribosomal peptide synthetases (NRPS), highly homologous to the BGCs of indole-diketopiperazine derivatives. With the aid of genomic analysis, eight indole-diketopiperazines (1−8), including three new compounds, spirotryprostatin G (1), and cyclotryprostatins F and G (2 and 3), were obtained by large-scale cultivation of the fungal strain HBU-136 using rice medium with 1.0% MgCl2. The absolute configurations of 1−3 were determined by comparison of their experimental electronic circular dichroism (ECD) with calculated ECD spectra. Selective cytotoxicities were observed for compounds 1 and 4 against HL-60 cell line with the IC50 values of 6.0 and 7.9 μM, respectively, whereas 2, 3, and 5 against MCF-7 cell line with the IC50 values of 7.6, 10.8, and 5.1 μM, respectively.
- Subjects
PENICILLIUM; GENE clusters; CIRCULAR dichroism; CELL lines; LIGASES; FUNGI; MARINE debris
- Publication
Marine Drugs, 2019, Vol 17, Issue 9, p514
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md17090514