ABSTRACT
Four new isoprenoids, including two norcembranoids sinulerectols A and B (1 and 2), a cembranoid sinulerectol C (3), and a degraded cembranoid sinulerectadione (4), along with three known isoprenoids, an unnamed norcembrene (5), sinularectin (6), and ineleganolide (7), and a known nitrogen-containing compound (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (8), were isolated from an extract of the marine soft coral Sinularia erecta. The structure of sinularectin (6) was revised, too. Compounds 3, 4, and 8 exhibited inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 1, 2, and 8 displayed potent anti-inflammatory activity in fMLP/CB-stimulated human neutrophils.
Subject(s)
Anthozoa/chemistry , Biological Products , Terpenes , Animals , Anti-Inflammatory Agents/pharmacology , Biological Products/chemistry , Biological Products/isolation & purification , Biological Products/pharmacology , Cyclooxygenase 2/metabolism , Diterpenes/chemistry , Drug Screening Assays, Antitumor , Humans , Macrophages/metabolism , Marine Biology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacologyABSTRACT
Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by extensive spectroscopic analysis. Anti-inflammatory activity of new metabolites to inhibit the superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (FMLP/CB)-induced human neutrophil cells and cytotoxicity of both new compounds toward five cancer cell lines were reported.
Subject(s)
Anthozoa/chemistry , Diterpenes/pharmacology , Animals , Carbon-13 Magnetic Resonance Spectroscopy , Diterpenes/chemistry , Humans , Neutrophils/drug effects , Neutrophils/metabolism , Proton Magnetic Resonance Spectroscopy , Superoxides/metabolismABSTRACT
A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and ß-carotene (5) were isolated from the brown alga Homoeostrichus formosana. The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses. Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6). Compounds 1-6 exhibited various levels of cytotoxic, antibacterial, and anti-inflammatory activities. Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 µg/mL) and elastase release (IC50 0.48 ± 0.11 µg/mL) in FMLP/CB-induced human neutrophils.
Subject(s)
Anti-Inflammatory Agents/chemistry , Benzopyrans/chemistry , Benzoquinones/chemistry , Phaeophyceae/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/toxicity , Benzopyrans/pharmacology , Benzopyrans/toxicity , Benzoquinones/pharmacology , Benzoquinones/toxicity , Cell Line, Tumor , Cell Proliferation/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Hep G2 Cells , Humans , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Conformation , Neutrophils/drug effects , Neutrophils/metabolism , Phaeophyceae/metabolism , Superoxides/metabolismABSTRACT
A series of novel pyrimido and other fused quinoline derivatives like 4-methyl pyrimido [5,4-c]quinoline-2,5(1H,6H)-dione (4a), 4-methyl-2-thioxo-1,2-dihydropyrimido [5,4-c]quinoline-5(6H)-one (4b), 2-amino-4-methyl-1,2-dihydropyrimido [5,4-c]quinolin-5(6H)-one (4c), 3-methylisoxazolo [4,5-c]quinolin-4(5H)-one (4d), 3-methyl-1H-pyrazolo [4,3-c]quinoline-4(5H)-one (5e), 5-methyl-1H-[1,2,4] triazepino [6,5-c]quinoline-2,6(3H,7H)-dione (5f), 5-methyl-2-thioxo-2,3-dihydro-1H-[1,2,4]triazepino [6,5-c]quinolin-6(7H)-one (5 g) were synthesized regioselectively from 4-hydroxy-3-acyl quinolin-2-one 3. They were screened for their in vitro antioxidant activities against radical scavenging capacity using DPPH(), Trolox equivalent antioxidant capacity (TEAC), total antioxidant activity by FRAP, superoxide radical (O(2)(°-)) scavenging activity, metal chelating activity and nitric oxide scavenging activity. Among the compounds screened, 4c and 5 g exhibited significant antioxidant activities.
