Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

Abstract

Microbial studies of the Mediterranean sponge Tethya aurantium led to the isolation of the fungus Bartalinia robillardoides strain LF550. The strain produced a number of secondary metabolites belonging to the chloroazaphilones. This is the first report on the isolation of chloroazaphilones of a fungal strain belonging to the genus Bartalinia. Besides some known compounds (helicusin A (1) and deacetylsclerotiorin (2)), three new chloroazaphilones (helicusin E (3); isochromophilone X (4) and isochromophilone XI (5)) and one new pentaketide (bartanolide (6)) were isolated. The structure elucidations were based on spectroscopic analyses. All isolated compounds revealed different biological activity spectra against a test panel of four bacteria: three fungi; two tumor cell lines and two enzymes.

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…Albeit an IC 50 for enzyme or receptor inhibition is provided, no mechanism of action studies were reported at the time of publication: alotaketal C ( 224 ) [215]; aspergentisyl A ( 225 ) [216]; A. terreus butyrolactone ( 226 ) [217]; caulerpine ( 227 ) [218]; conicasterol F ( 228 ) [219]; D. avara sesquiterpene ( 229 ) [220]; D. gigantea sterols ( 230 , 231 ) [221]; dysidavarone A ( 232 ) [222]; galvaquinone B ( 233 ) [223]; halicloic acids A and B ( 234 , 235 ) [224]; isochromophilone XI ( 236 ) [225]; leucettamols A and B ( 237 , 238 ) [226]; manadosterol A ( 239 ) [227]; marilines A1 and A2 ( 240 , 241 ) [228]; methyl sarcotroate B ( 242 ) [229]; P. citrinum sorbicillinoid ( 243 ) [230]; phosphoiodyn A ( 244 ) [231]; purpuroines A and D ( 245 , 246 ) [232]; santacruzamate A ( 247 ) [233]; sarcophytonolide N ( 248 ) [234]; sargassumol ( 249 ) [235]; sesquibastadin 1 ( 250 ) [236]; S. glaucum cembranoids ( 251 – 253 ) [237]; symplocin A ( 254 ) [238]; tsitsikammamine A derivative ( 255 ) [239]; V. lanosa bromophenol ( 256 ) [240] ; and X. testudinaria fatty acid ( 257 ) [241]. …”

Biscogniauxone, a New Isopyrrolonaphthoquinone Compound from the Fungus Biscogniauxia mediterranea Isolated from Deep-Sea Sediments

“…The bioassays with the clinically relevant bacterial strains Staphylococcus epidermidis (DSM 20044), methicillin-resistant Staphylococcus aureus (MRSA) (DSM 18827), and the causative agent of acne, Propionibacterium acnes (DSM 1897 T ), were performed as described by Silber et al [32]. The phytopathogenic fungus Septoria tritici and the dermatophytic fungus Trichophyton rubrum as well as the cytotoxic effect on the human hepatocellular liver carcinoma cell line HepG2 were tested according to Jansen et al [33]. Inhibition of the enzymes glycogen synthase kinase (GSK-3β), acetylcholinesterase (AchE), phosphodiesterase (PDE-4B2), and protein tyrosine phosphatase (PTP1B) was determined according to Baki et al [34], Ohlendorf et al [31], Schulz et al [35], and Silber et al [36], respectively.…”

Recent advances in the chemistry and biology of azaphilones

“…co-cultured with Bacillus subtilis 41 Peniazaphilin A (77) Penicillium sp. CPCC 400786 13 Antiviral (HIV: 60.4 mM) Monapilosusazaphilone (78) Monascus pilosus 103 Monascusazaphilone A (79) Monascus purpureus BCRC 38108 43 Anti-inammatory (inhibit NO production: 4.6 mg mL À1 ); cytotoxic (LPS-induced RAW264.7: cell viability 83%) Monascusazaphilone B (80) Monascus purpureus BCRC 38108 43 Anti-inammatory (inhibit NO production: 8.88 mg mL À1 ); cytotoxic (LPS-induced RAW264.7: cell viability 85%) Berkchaetoazaphilone C (81) Pleurostomophora sp. 49…”

“…77 The fungus Bartalinia robillardoides strain LF550, obtained from the Mediterranean sponge Tethya aurantium, metabolized two novel chloroazaphilones, helicusin E (175) and isochromophilone XI (176). 78 Inducing the Mediterranian sponge Agelas oroides derived fungus Penicillium canescens by using 5% NaBr, resulted in two new brominated azaphilones, bromophilones A and B (177-178). Notably, 178 showed moderate cytotoxicity against the mouse lymphoma cell line L5178Y and the human ovarian cancer cell line A2780 with IC 50 values of 8.9 and 2.7 mM, respectively, while 177 was less active.…”

“…69,77 Bartalinia robillardoides LF550 metabolized a cytotoxic compound, isochromophilone X (223), which showed inhibitory activity against PDE4 (IC 50 ¼ 11.7 mM). 78 In 2019, Tang's group described the isolation and characterization of nine new azaphilone alkaloids, penazaphilones A-I (224-232), which were isolated from the rice solid fermented culture of Penicillium sclerotiorum cib-411. Meanwhile, structures of 228 and 231 were conrmed by X-ray diffraction analysis.…”