Brocaeloid D, a novel compound isolated from a wheat pathogenic fungus, Microdochium majus 99049

Abstract

Microbes serve as the most important resource for drug discovery. During our screening for bioactive compounds from our natural products library, a pathogenic fungus, Microdochium majus strain 99049, from wheat was selected for further investigation. A new alkaloid named brocaeloid D (1), together with six previously characterized compounds (2–7) were identified. Compound 1 belongs to 4-oxoquinoline with C-2 reversed prenylation and a succinimide substructure. All the structures of these newly isolated compounds were determined by different means in spectroscopic experiments. The absolute configurations of 1 was further deduced from comparison of its CD spectrum with that of known compound 2. The bioactivities of these identified compounds were evaluated against several pathogenic microorganisms and cancer cell lines. Compounds 1–5 showed activity against HUH-7 human hepatoma cells with IC50 values of 80 μg/mL. Compound 6 showed mild activity against HeLa cells (IC50 = 51.9 μg/mL), weak anti-MTB activity (MIC = 80 μg/mL), and moderate anti-MRSA activity (MIC = 25 μg/mL), and compound 7 showed weak anti-MRSA activity (MIC = 100 μg/mL).

Antimicrobial potentials of natural products against multidrug resistance pathogens: a comprehensive review

“…(22 E ,24 R )-6β-methoxyergosta-7,22-diene-3β,5α-diol 204, (22 E ,24 R )-6β-methoxyergosta-7,22-diene-3β,5α-diol 205, isolated from a pathogenic fungus, Microdochium majus strain 99 049, from wheat, showed moderate to weak anti-MRSA activity (MIC 25, 100 μg mL −1 , respectively). 110 The antimicrobial epidithiodioxopiperazine, gliotoxin 206, and bisdethiobis (methylthio)gliotxin 207, were isolated from the endophytic fungus Hypocrea virens , from Premna serratifolia , showed MIC 32–35 μg mL −1 against MRSA. 111 Terrenolide S 208, isolated from the endophytic fungus Aspergillus terreus isolated from the roots of Carthamus lanatus , displayed a potent activity towards MRSA with IC 50 2.29 μM.…”

Chemical and biosynthetic potential of Penicillium shentong XL-F41

“…Spectroscopic analysis, including 1 H NMR, 13 C NMR ( Table 1 ), and DEPT, revealed that compound 1 contains three methyl groups, one of which is oxygenated, four methines, three saturated non-protonated carbons, and two ketone carbonyl carbons (δ C 175.94, δ C 194.36). Its NMR data closely resemble those of brocaeloid D [ 23 ], with the notable addition of a methoxy group (δ H 3.20/δ C 53.92). HMBC correlations confirmed the presence of a reversed prenyl group and differentiated compound 1 from brocaeloid D by the substitution of a succinimide substructure at C-14 with a methine at C-16, indicated by the methoxy group.…”

Endophytic Fungi from the Four Staple Crops and Their Secondary Metabolites

“…In addition, two sesquiterpene-xanthenone adducts, bisphenols I and J (39 and 40) (Figure 2), resistant to phytopathogenic fungi (Alternaria solani) were isolated from cultures of the potato endophyte fungus B. eleusines, and they showed potent inhibitory activity against A. solani with MIC values of 8 and 16 µg mL −1 , respectively [97]. The compounds leptosphaeric acid (50) and cillifuranone (51) (Figure 2) were isolated from the wheat endophytic fungus Microdochium majus 99049, which showed activity against the HUH-7 human hepatoma cell with IC 50 values at 80 µg/mL [96]. The compounds (+)-dehydrovomifoliol ( 52) and macrolactin A (53) (Figure 2) were isolated from the maize endophytic fungus Fusarium sp.…”

“…Eight cytochalasins boerechalasins A-G (215-221) and compound 222 were isolated from the potato endophytic fungus B. exigua, and compound 220 exhibited moderate cytotoxicity against the MCF-7 cell line, with an IC50 value of 22.8 µM [120]. 8) were isolated from the wheat endophytic fungus M. majus 99049, and they showed weak inhibitory activity against the HUH-7 human hepatoma cell with IC50 values at 80 µg/mL [96]. The compound caffeine (226) was isolated from the maize endophytic fungus Fusarium sp.…”