ABSTRACT
Seven previously undescribed meroterpenoids, peniscmeroterpenoids H - N (1-7), were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03-2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid H was a 6/6/6/5/6 rearranged pentacyclic meroterpenoid, featuring a unique 2-oxaspiro[5.5] undeca-4,7-dien-3-one motif. Peniscmeroterpenoids I and J (2 and 3) owned rare 6(D)/5(E) fused rings were not common in natural products, and compound 2 was the second example of a berkeleyone analogue stripped of the methyl ester fragment. Peniscmeroterpenoid K (4) was the first case where the C-24 was oxidized. In bioassay, compound 5 showed moderate anti-inflammatory activity.
Subject(s)
Fungi , Penicillium , Molecular Structure , Penicillium/chemistry , Circular DichroismABSTRACT
Four new chromone compounds diaporspchromanones A-C (1-3) and diaporspchromanone H (4), together with three known compounds (5-7) were separated from the marine derived fungus Diaporthe sp. XW12-1. The structures of the new compounds, including their absolute configurations, were elucidated by extensive spectroscopic analysis and the Mosher's ester method. Among them, diaporspchromanones A-C (1-3) possess a 3-substituted-chroman-4-one skeleton, which are rarely found in natural sources. In the bioassays, all compounds were evaluated for their inhibitory activity against lipopolysaccharide-activated nitric oxide (NO) production in RAW264.7 cells. Compounds 2 and 3 showed potent anti-inflammatory effects than the positive control (indomethacin, IC50, 70.33 ± 0.95 µM) (p < 0.05) with IC50 values of 19.06 ± 3.60 and 9.56 ± 0.18 µM, respectively.
Subject(s)
Chromones , Fungi , Animals , Mice , Chromones/pharmacology , Molecular Structure , Fungi/chemistry , RAW 264.7 CellsABSTRACT
Seven undescribed meroterpenoids, peniscmeroterpenoids A - G, were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03-2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid A possessed an unprecedented and highly oxidized 6/7/6/5/5 pentacyclic system, featuring a unique tetrahydrofuro [2,3-b]furan-2(3H)-one motif. Peniscmeroterpenoids B - E owned rare 6(D)/5(E) fused rings were not common in natural products, and peniscmeroterpenoid E is the first example of a berkeleyone analogue stripped of the methyl ester fragment. In bioassays, peniscmeroterpenoids A and D inhibited the production of nitric oxide (NO) in RAW264.7 cells with IC50 values of 26.60 ± 1.15 and 8.79 ± 1.22 µM. Moreover, peniscmeroterpenoid D significantly suppressed the production of pro-inflammatory mediators (COX-2, IL-1ß and IL-6) and the protein expression of the enzyme iNOS.
Subject(s)
Penicillium , Animals , Anti-Inflammatory Agents/chemistry , Fungi , Mice , Molecular Structure , Penicillium/chemistry , RAW 264.7 CellsABSTRACT
Nine previously undescribed butyrolactone and sesquiterpene derivatives, named cyclopentanone A (1), subamolides F and G (2 and 3), secosubamolide F (4), rupestonic acids J - L (5-7), linderaguaianols A and B (8 and 9), together with six known ones 10-15 were isolated from the roots of Lindera glauca. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and Mo2(AcO)4-induced circular dichroism. Compound 1 that possessed a unique five-membered cyclopentane skeleton with a side chain was rarely found from natural sources. The biogenetic pathway for 1-4 was postulated. Secosubamolide F (4) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells with IC50 value of 1.73 ± 0.18 µM and also significantly suppressed the production of iNOS. The binding interactions between 4 and iNOS were investigated using docking analyses.