ABSTRACT
Ten new (1-10) and 26 known (11-36) compounds were isolated from Penicillium griseofulvum MCCC 3A00225, a deep sea-derived fungus. The structures of the new compounds were determined by detailed analysis of the NMR and HRESIMS spectroscopic data. The absolute configurations were established by X-ray crystallography, Marfey's method, and the ICD method. All isolates were tested for in vitro anti-food allergic bioactivities in immunoglobulin (Ig) E-mediated rat basophilic leukemia (RBL)-2H3 cells. Compound 13 significantly decreased the degranulation release with an IC50 value of 60.3 µM, compared to that of 91.6 µM of the positive control, loratadine.
Subject(s)
Anti-Allergic Agents/pharmacology , Basophils/drug effects , Cell Degranulation/drug effects , Food Hypersensitivity/drug therapy , Penicillium/metabolism , Animals , Anti-Allergic Agents/isolation & purification , Basophils/immunology , Cell Line, Tumor , Food Hypersensitivity/immunology , Geologic Sediments/microbiology , Immunoglobulin E/immunology , Molecular Structure , Rats , Structure-Activity RelationshipABSTRACT
From the deep-sea-derived fungus Aspergillus candidus, one novel (1) and three known (2-4) p-terphenyl derivates were isolated. The structure of the new compound was established mainly on the basis of extensive analysis of 1D and 2D NMR data. All four isolates were tested for in vitro anti-food allergic and antitumor bioactivities. Compounds 3 and 4 showed potent antiproliferative effect against four cancer cells of Hela, Eca-109, Bel-7402, and PANC-1 with IC50 values ranging from 5.5 µM to 9.4 µM.
Subject(s)
Aspergillus/chemistry , Oceans and Seas , Terphenyl Compounds/pharmacology , Antineoplastic Agents/pharmacology , Carbon-13 Magnetic Resonance Spectroscopy , Cell Death/drug effects , Cell Line, Tumor , Humans , Proton Magnetic Resonance Spectroscopy , Terphenyl Compounds/chemistry , Terphenyl Compounds/isolation & purificationABSTRACT
Four new (penigrisacids A-D, 1-4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6-9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 µM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 µM).
Subject(s)
Aquatic Organisms/chemistry , Penicillium/chemistry , Sesquiterpenes/chemistry , Cell Line, Tumor , Circular Dichroism , HeLa Cells , Humans , Magnetic Resonance Spectroscopy/methods , Oceans and Seas , Sesquiterpenes/pharmacologyABSTRACT
A novel ergostane, sarocladione (1), was isolated from the deep-sea-derived fungus Sarocladium kiliense, along with 20 known compounds. The structure of 1 was determined mainly by a detailed analysis of its experimental and calculated NMR spectroscopic data. It is worth noting that 1 was the first steroid bearing a 5,10:8,9-diseco moiety. All 21 compounds were tested for in vitro antitumor activities against five cancer cell lines. ß-Sitostenone (7) and 4,6-dihydroxyeudesmane (20) showed significant effects on HeLa-S3 cells with the IC50 values of 9.2 µM and 9.3 µM, respectively.
