Shamil Sh. Afiyatullov

Secondary metabolites from a marine-derived fungus Aspergillus carneus Blochwitz

Prenylated indole alkaloids, carneamides A-C (1-3), quinazolinone derivatives, carnequinazolines A-C (5-7), aryl C-glycosides, carnemycin A, B (8, 9) and a drimane sesquiterpenoid (10), together with known compounds (11-21) were isolated from the marine-derived fungus Aspergillus carneus (Trichocomaceae) KMM 4638. The antimicrobial and cytotoxic activities of the several alkaloids were examined.

Mycaloside A, a new steroid oligoglycoside with an unprecedented structure from the Caribbean sponge Mycale laxissima

Abstract The structure of mycaloside A ( 1 ) isolated from the Caribbean sponge Mycale laxissima has been established as (22 E ,20 R ,24 S )-3- O -{α- d -Galp(1→2)-β- d -Arap(1→3)-[β- d -Galp(1→4)]-β- d -Glcp}-3β,4β,15α,21-tetrahydroxy-24-methylcholesta-5,22-diene by interpretation of spectral data and chemical transformations.

Meroterpenoids from the alga-derived fungi Penicillium thomii maire and Penicillium lividum westling

Ten new austalide meroterpenoids (1-10) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The absolute configurations of some of the metabolites were assigned by the modified Moshers method and CD data. Compounds 1, 2, 8, and 9 were able to inhibit AP-1-dependent transcriptional activity in JB6 Cl41 cell lines at noncytotoxic concentrations. Austalides 1-5, 8, and 9 exhibited significant inhibitory activity against endo-1,3-β-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis.

Oxirapentyns F-K from the marine-sediment-derived fungus Isaria felina KMM 4639

Six new highly oxygenated chromene derivatives, oxirapentyns F-K (2-7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2-9 were determined using spectroscopic methods. The relative configurations of compounds 2-7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Moshers method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells.

Decumbenone C, a new cytotoxic decaline derivative from the marine fungus Aspergillus sulphureus KMM 4640

A new decaline derivative, decumbenone C (1) along with four known compounds, decumbenones A (2) and B (3), diorcinol (4), and brevianamide F (5) were isolated from the marine fungus Aspergillus sulphureus KMM 4640. Decumbenone C shows potent cytotoxic activity against SK-MEL-5 human melanoma cells with IC50 values of 0.9 μM.

Sargassopenillines A-G, 6,6-Spiroketals from the Alga-Derived Fungi Penicillium thomii and Penicillium lividum

Seven new 6,6-spiroketals, sargassopenillines A–G (1–7) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR. The absolute configurations of compounds 1, 5 and 6 were assigned by the modified Mosher’s method and by CD data. Sargassopenilline C (3) inhibited the transcriptional activity of the oncogenic nuclear factor AP-1 with an IC50 value of 15 µM.

Isolation, structures, and biological activities of triterpenoids from a Penares sp. marine sponge.

Six new triterpenoids (1-6) and the previously known penasterone, acetylpenasterol, and ergosta-4,24(28)-dien-3-one were isolated from a Penares sp. sponge collected from Vietnamese waters. Structures of the obtained compounds were established by extensive 1D and 2D NMR spectroscopy and mass spectrometry. Configurations of the triterpene epoxy lactones (1-4) were determined on the basis of NOESY and CD data and calculation of spin coupling constants and confirmed by X-ray crystallographic analysis of compound 2. The isolated triterpenoid 6 was cytotoxic against human leukemia HL-60 cells (IC₅₀ = 9.7 μM).

New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber.

Three new diterpene glycosides, virescenosides V (1), W (2), and X (3) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of high resolution mass spectrometry, 1D and 2D NMR (1H, 13C, DEPT, COSY 45, COSY RCT, HSQC, HMBC, and NOESY spectra) as 19-O-β-D-altropyranosyl-7-oxo-isopimara-8(14),15-diene-2α,3β-diol (1), 19-O-β-D-altropyranosyl-isopimara-7,15-diene-2α,3β,6α-triol (2), and 19-O-β-D-altropyranosyl-isopimara-8,15-diene-2α,3β,7α-triol (3).

Pretrichodermamides D–F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Three new epidithiodiketopiperazines pretrichodermamides D–F (1–3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1–5 were determined based on spectroscopic methods. The absolute configuration of pretrichodermamide D (1) was established by a combination of modified Mosher′s method, NOESY data, and biogenetic considerations. N-Methylpretrichodermamide B (5) showed strong cytotoxicity against 22Rv1 human prostate cancer cells resistant to androgen receptor targeted therapies.

Pallidopenillines: Polyketides from the Alga-Derived Fungus Penicillium thomii Maire KMM 4675

Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Moshers method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively.