Next Article in Journal
Chitosan Oleate Coated Poly Lactic-Glycolic Acid (PLGA) Nanoparticles versus Chitosan Oleate Self-Assembled Polymeric Micelles, Loaded with Resveratrol
Previous Article in Journal
Bathyptilones: Terpenoids from an Antarctic Sea Pen, Anthoptilum grandiflorum (Verrill, 1879)
Previous Article in Special Issue
New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
Open AccessArticle

Discovery of Bioactive Indole-Diketopiperazines from the Marine-Derived Fungus Penicillium brasilianum Aided by Genomic Information

by Ya-Hui Zhang 1,2,†, Ce Geng 3,†, Xing-Wang Zhang 3, Hua-Jie Zhu 2, Chang-Lun Shao 1,4, Fei Cao 2,* and Chang-Yun Wang 1,4,5,*
1
Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
2
College of Pharmaceutical Sciences, Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Hebei University, Baoding 071002, China
3
Shandong Provincial Key Laboratory of Synthetic Biology, CAS Key Laboratory of Biofuels at Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China
4
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China
5
Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Mar. Drugs 2019, 17(9), 514; https://doi.org/10.3390/md17090514
Received: 2 August 2019 / Revised: 27 August 2019 / Accepted: 29 August 2019 / Published: 1 September 2019
(This article belongs to the Special Issue Marine Microbial Diversity as Source of Bioactive Natural Products)
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 (18), 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 13 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. View Full-Text
Keywords: biosynthetic gene cluster (BGC); indole-diketopiperazine; Penicillium brasilianum; cytotoxicities biosynthetic gene cluster (BGC); indole-diketopiperazine; Penicillium brasilianum; cytotoxicities
Show Figures

Graphical abstract

MDPI and ACS Style

Zhang, Y.-H.; Geng, C.; Zhang, X.-W.; Zhu, H.-J.; Shao, C.-L.; Cao, F.; Wang, C.-Y. Discovery of Bioactive Indole-Diketopiperazines from the Marine-Derived Fungus Penicillium brasilianum Aided by Genomic Information. Mar. Drugs 2019, 17, 514.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop