Bioactive Steroid Derivatives and Butyrolactone Derivatives from a Gorgonian‐Derived Aspergillus sp. Fungus

Abstract

Six steroid derivatives, 1-6, and five butyrolactone derivatives, 7-11, were isolated from the fermentation broth of a gorgonian-derived Aspergillus sp. fungus. Their structures were elucidated on the basis of NMR and MS spectral data. Compound 1 is a new, highly conjugated steroid. The NMR and MS data of 7 and 8 are reported for the first time, as their structures were listed in SciFinder Scholar with no associated reference. Compounds 1, 4, 5, and 8-11 inhibited the larval settlement of barnacle Balanus amphitrite with EC50 values ranging from 0.63 to 18.4 μg ml(-1) . Butyrolactone derivatives 7 and 8 showed pronounced antibacterial activities against Staphylococcus aureus with the same MIC values as the positive control ciprofloxacin (MIC 1.56 μM for all three compounds).

Screening Fungal Endophytes Derived from Under-Explored Egyptian Marine Habitats for Antimicrobial and Antioxidant Properties in Factionalised Textiles

“…Moreover, GNPS identified a cluster containing butyrolactone I ( m / z 425.145, [M+H] + ), II ( m / z 357.083, [M+H] + ) and III ( m / z 441.142, [M+H] + ), which were observed in two strains of Aspergillus terreus (7S4, 15F6) and in one isolate of Penicillium crustosum , M35 ( Figure 3 B). Butyrolactones are commonly found in fungal strains and have exhibited a wide range of biological activities [ 50 , 51 ]. Our identifications were based on matching spectra in the GNPS library, although the mass error of the pertaining molecular formulae was relatively high (data not shown).…”

“…Aspergillus calidoustus strain M113 produced previously reported emericellamide derivatives [ 48 ] but also two potentially new congeners. The second strain with promising antimicrobial textile functionality and the third for UV protection was Aspergillus terreus strain 7S4, which produces a suite of known butyrolactones and aspernolides [ 49 , 50 , 51 , 52 , 53 ] besides one potentially new derivative. However, its skin toxicity precluded further analysis.…”

Potential Pharmacological Resources: Natural Bioactive Compounds from Marine-Derived Fungi

“…The fungus was isolated from the inner part of the fresh gorgonian M. abnormalis , which was collected from the Xisha Islands coral reef of the South China Sea. Compound 28 inhibited the larval settlement of barnacle Balanus amphitrite with EC 50 18.40 ± 2.0 μg/mL ( Figure 7 ) [ 20 ].…”

Marine Pharmacology in 2014–2015: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, Antiviral, and Anthelmintic Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…[35]; a butyrolactone derivative (17), isolated from the fermentation broth of a South China sea gorgonian Muricella abnormalis-derived Aspergillus sp. XS-20090B15 fungus [36]; a meroditerpene aszonapyrone A (18), isolated from the Thai marine sponge Chondrilla asutraliensis-associated fungus Neosartorya paulistensis (KUFC 7897) [37]; a new meroterpenoid, austalide R (19), from a fungus Aspergillus sp. isolated from the Mediterranean sponge Tethya aurantium [38]; a novel citrifelin B (20) with a unique tetracyclic framework was characterized from a co-culture of marine-derived fungi Penicillium citrinum and Beauveria felina [39]; a novel cyclohexadepsipeptide desmethylisaridin C1 (21) identified from a marine bryozoan-derived fungus Beauveria felina EN-135 [40]; two novel polybrominated diphenyl ethers (22,23), isolated from the cosmopolitan marine sponge Dysidea spp.…”

“…[45]; a terpenoid fuscoside E peracetate (29) and a lipid batyl alcohol (30), isolated from the Colombian soft coral Eunicea sp. [46]; a new aromatic butyrolactone flavipesin A (31), isolated from a marine-derived endophytic fungus Aspergillus flavipes [47]; new non-cytotoxic lipopeptides gageopeptides A-D (32,33,34,35) [48] and gageotetrins A-C (36,37,38) [49], isolated from a Korean marine-derived Bacillus subtilis strain 109GGC020; a new cyclic depsipeptide hormaomycin B (39), isolated from a Korean marine mudflat-derived actinomycete Streptomyces sp. strain SNM55 [50]; a new glycolipid ieodoglucomide C (40) from the Korean marine-derived bacterium Bacillus licheniformis strain 09IDYM23 [51]; a new polycyclic tetramic acid macrolactam isoikarugamycin (41) from Equatorial Guinean Streptomyces zhaozhouensis strain CA-185989 [52]; a bromopyrrole alkaloid keramadine (42), isolated from the Okinawan marine sponge Agelas sp.…”