New Trichothecenes Isolated from the Marine Algicolous Fungus Trichoderma brevicompactum

Abstract

Eight trichothecenes, including four new compounds 1–4 and four known entities 5–8, together with one known cyclonerane (9) were isolated from the solid-state fermentation of Trichoderma brevicompactum NTU439 isolated from the marine alga Mastophora rosea. The structures of 1–9 were determined by 1D/2D NMR (nuclear magnetic resonance), MS (mass spectrometry), and IR (infrared spectroscopy) spectroscopic data. All of the compounds were evaluated for cytotoxic activity against HCT-116, PC-3, and SK-Hep-1 cancer cells by the SRB assay, and compound 8 showed promising cytotoxic activity against all three cancer cell lines with the IC50 values of 3.3 ± 0.3, 5.3 ± 0.3, and 1.8 ± 0.8 μM, respectively. Compounds 1–2, 4–6, and 7–8 potently inhibited LPS-induced NO production, and compounds 5 and 8 showed markedly inhibited gelatinolysis of MMP-9 in S1 protein-stimulated THP-1 monocytes.

Structures and Biological Activities of Secondary Metabolites from the Trichoderma genus (Covering 2018–2022)

“…Four previously undescribed trichothecenes (113−116) were produced by a solid-state culture of T. brevicompactum NTU439, collected from the marine alga Mastophora rosea. 69 Compounds 113, 114, and 116 exhibited a potent inhibition of LPS-induced NO production in BV-2 cells. However, trichothecenes 113−116 showed no obvious cytotoxic activity against three cancer cell lines (IC 50 > 10 μM), possibly due to the hydrolysis of the C-12,13-epoxy ring and the absence of the double bond between C-9 and C-10 in the A ring, as previously observed in SAR research.…”

“…Trichothecene sesquiterpenes typically feature a tetracyclic system with a 12,13-epoxytrichothec-9-ene ring, which is known for its diverse activities including antifungal, cytotoxic, antimicroalgal, and anti-inflammatory properties. − …”

“…Four previously undescribed trichothecenes ( 113 – 116 ) were produced by a solid-state culture of T. brevicompactum NTU439, collected from the marine alga Mastophora rosea . Compounds 113 , 114 , and 116 exhibited a potent inhibition of LPS-induced NO production in BV-2 cells.…”

Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction

“…Trichoderma ( Hypocreaceae ) was described by Christian Hendrik Persoon in 1794 [ 1 ], and currently represents one of the genera with the largest number of described species in the Fungi kingdom [ 2 ], with more than 500 valid species, according to the Index Fungorum ( (accessed on 30 December 2022)). Species of the genus Trichoderma can inhabit innumerable ecosystems, both terrestrial and aquatic, and can be isolated from the interior of other organisms, such as plants (endophytes), insects, marine organisms and even humans (facultative pathogens), which reveals its high adaptability to different conditions [ 3 , 4 , 5 , 6 , 7 , 8 ].…”

“…In addition to agricultural applications, Trichoderma is also a valuable source of secondary metabolites, and contributes to several carbon skeletons that have the most diverse biological activities [ 7 , 17 ]. Among the classes of metabolites that are produced by species of Trichoderma , alkaloids [ 18 ], terpenes [ 19 ], and peptides [ 20 , 21 ] stand out.…”