Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp. TZP29.

Two new C12 polyketides, cladospolides E and F (1 and 2), together with four known derivatives seco-patulolides A and C (3 and 4), 11-hydroxy-γ-dodecalactone (5) and iso-cladospolide B (6), were isolated from a soft coral-derived fungus Cladosporium sp. TZP-29. Their structures, including the absolute configurations, were elucidated by spectroscopic analysis, modified Mosher's method, and the analysis of their biogenesis. All compounds were non-cytotoxic while compounds 1 and 3-5 showed potent lipid-lowering activity in HepG2 hepatocytes.

Psychrophilins E-H and versicotide C, cyclic peptides from the marine-derived fungus Aspergillus versicolor ZLN-60.

Four new cyclic peptides, psychrophilins E-H (1-4), possessing a rare amide linkage between the carboxylic acid in anthranilic acid (ATA) and the nitrogen from an indole moiety, along with a new ATA-containing hexapeptide, versicotide C (5), were obtained from the culture of the marine-derived fungus Aspergillus versicolor ZLN-60. The structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, TDDFT ECD calculations, and Marfey's method. Versicotide C (5) is the first natural cyclic hexapeptide containing two anthranilic acids. Compounds 1-5 were not cytotoxic, and compound 3 showed potent lipid-lowering effects.

Prenylated indole diketopiperazines from the marine-derived fungus Aspergillus versicolor.

Seven new prenylated indole diketopiperazines, versicamides A-G (1-7) and a novel chemical derivative from 7, versicamide H (8), along with three known analogic diketopiperazines (9-11) were obtained from the marine-derived fungus Aspergillus versicolor HDN08-60. Their structures were determined by spectroscopic techniques, including 2D NMR, ECD calculations, and single-crystal X-ray diffraction analysis, together with the assistance of further chemical conversions. The cytotoxicities of 1-8 were tested against the HeLa, HCT-116, HL-60, and K562 cell lines, but only 8 exhibited moderate activity against HL-60 cells, with an IC50 value of 8.7 µM. Further investigation with target screening showed that 8 exhibited selective PTK inhibitory activities.

Two new meroterpenoids produced by the endophytic fungus Penicillium sp. SXH-65.

Two new meroterpenoids, arisugacins I (1) and J (2), together with five known meroterpenoids including arisugacin B (3), arisugacin F (4), arisugacin G (5), territrem B (6) and territrem C (7) were isolated from an endophytic fungus Penicillium sp. SXH-65. Their structures were determined by extensive spectroscopic experiments and comparison with literature data. Their cytotoxicities were evaluated against Hela, HL-60 and K562 cell lines, and only 3 and 4 exhibited weak cytotoxicities against Hela, HL-60 and K562 cell lines with IC50 values ranging from 24 to 60 µM.

Diorcinols B-E, new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60.

Four new prenylated diphenyl ethers (1-4), diorcinols B-E, together with one known diorcinol (5), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures were established on the basis of chemical and spectroscopic data. The absolute configurations of compounds 1 and 2 were determined by Mosher's ester and specific rotation analysis. Their cytotoxicities were evaluated using A-549, Hela, BEL-7402 and K562 cell lines. Compound 3 exhibited moderate cytotoxicities against the Hela and K562 cell lines with the IC50 values of 31.5 and 48.9 µM, respectively, and compound 4 exhibited moderate cytotoxicity only against the Hela cell line with the IC50 value of 36.5 µM.

Prenylated indole diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1.

One new prenylated indole diketopiperazine alkaloid, named dihydroneochinulin B (1), one known spiro-polyketide-diketopiperazine hybrid cryptoechinuline D (2) and three related known metabolites didehydroechinulin B (3), neoechinulin B (4) and auroglaucin (5) were isolated from the mangrove rhizosphere soil derived fungus, Aspergillus effuses H1-1. The structures were assigned by detailed spectroscopic analysis. The enantiomers of cryptoechinuline D (2) were separated to be (+)-cryptoechinuline D (2a) and (-)-cryptoechinuline D (2b) by chiral HPLC, and their absolute configurations were determined by ECD analysis. The cytotoxic effects of the compounds were preliminarily evaluated on P388, HL-60, BEL-7402 and A-549 cell lines by SRB or MTT methods, and compounds 2, 2a and 3 showed significant activities.

Aspulvinones from a mangrove rhizosphere soil-derived fungus Aspergillus terreus Gwq-48 with anti-influenza A viral (H1N1) activity.

A new butenolide isoaspulvinone E (1), together with two known butenolides aspulvinone E (2) and pulvic acid (3) were isolated from the marine-derived fungus, Aspergillus terreus Gwq-48. They showed significant anti-influenza A H1N1 virus activities, with IC50 values of 32.3, 56.9, and 29.1µg/mL, respectively. Moreover, only compound 1 exhibited effective inhibitory activity against H1N1 viral neuraminidase (NA), and docking of two isomers (1-2) into the active sites of NA showed that the E double bond Δ(5(10)) was essential to achieve activity.

Diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1.

Effusin A (1), a spirobicyclic N,O-acetal derivative with an unprecedented 3',3a',5',6'-tetrahydrospiro[piperazine-2,2'-pyrano[2,3,4-de]chromene] ring system, and a spiro-polyketide-diketopiperazine hybrid dihydrocryptoechinulin D (2) were isolated from a mangrove rhizosphere soil derived fungus, Aspergillus effuses H1-1. Their structures were determined by detailed spectroscopic analysis. Effusin A (1) and dihydrocryptoechinulin D (2) occurred as racemates, the enantiomers of which were separated and characterized by online HPLC-ECD analysis and their absolute configurations were determined by the solution TDDFT ECD calculation approach. The cytotoxic effects of 1 and 2 were preliminarily evaluated and 2 showed potent activity on P388 cells with an IC(50) value of 1.83 µM. The target of racemic 2 was also investigated and the (12R,28S,31S)-2 enantiomer showed selectivity against topoisomerase I.

Unusual pyrrolyl 4-quinolinone alkaloids from the marine-derived fungus Penicillium sp. ghq208.

One new pyrrolyl 4-quinolinone alkaloid, penicinoline E (1), together with three known deriverites, methyl-penicinoline (2), penicinoline (3), and quinolactacide (4), were isolated from the marine-derived fungus Penicillium sp. ghq208. The structures of these isolated compounds were elucidated by spectroscopic methods. Compounds (2, 3) exhibited moderate cytotoxicities against the HepG2 cell line with IC(50) values of 11.3 and 13.2 µM, respectively.