ABSTRACT
Three pregnane-type steroids, including a new metabolite, 3ß-methoxy-5,20-pregnadiene (1) along with two known analogues, 3ß-acetoxy-5,20-pregnadiene (2) and 5α-pregna-1,20-dien-3-one (3) were isolated from the soft coral Scleronephthya flexilis. Standard spectroscopic techniques were used to determine the structure of new steroid 1. The absolute stereochemistry of steroid 2 was confirmed by X-ray diffraction analysis. Steroid 3 exhibited potent activity against MOLT-4 tumor cells.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/chemistry , Pregnanes/chemistry , Steroids/chemistry , Animals , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cell Line , Humans , Models, Molecular , Neoplasms/drug therapy , Pregnanes/isolation & purification , Pregnanes/pharmacology , Stereoisomerism , Steroids/isolation & purification , Steroids/pharmacology , X-Ray DiffractionABSTRACT
A new norcembranoidal diterpene, 1-epi-sinulanorcembranolide A (1), and a new cembranoidal diterpene, flexibilin D (2), were isolated from the soft corals, Sinularia gaweli and Sinularia flexibilis, respectively. The structures of new metabolites 1 and 2 were elucidated by spectroscopic methods, and compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 proteins of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In addition, S. flexibilis yielded a known cembrane, 5-dehydrosinulariolide (3); the structure, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis.
Subject(s)
Anthozoa/chemistry , Diterpenes/pharmacology , Macrophages/drug effects , Animals , Cyclooxygenase 2/drug effects , Cyclooxygenase 2/metabolism , Diterpenes/chemistry , Diterpenes/isolation & purification , Lipopolysaccharides/pharmacology , Macrophages/metabolism , Mice , Nitric Oxide Synthase Type II/drug effects , Nitric Oxide Synthase Type II/metabolism , Spectrum Analysis , X-Ray DiffractionABSTRACT
Three new cembrane-type diterpenoids, flexibilins A-C (1-3), along with a known cembrane, (-)-sandensolide (4), were isolated from the soft coral, Sinularia flexibilis. The structures of cembranes 1-4 were elucidated by spectroscopic methods. The structure of 4, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis. Cembrane 2 displayed a moderate inhibitory effect on the release of elastase by human neutrophils.
Subject(s)
Anthozoa/chemistry , Diterpenes/pharmacology , Neutrophils/drug effects , Pancreatic Elastase/drug effects , Animals , Diterpenes/chemistry , Diterpenes/isolation & purification , Humans , Neutrophils/metabolism , Pancreatic Elastase/metabolism , Spectrum Analysis , Taiwan , X-Ray DiffractionABSTRACT
Chemical investigations of the Formosan soft coral Cespitularia hypotentaculata ROXAS led to the isolation of two new verticillane diterpenoids, cespitularins R and S (1, 2), along with seven known compounds (3-9). The structures of these isolated compounds were elucidated on the basis of extensive spectroscopic analysis and by comparison with those of reported in literature. The anti-inflammatory activity using RAW 264.7 macrophages of compounds 1-9 were evaluated in vitro.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Macrophages/drug effects , Animals , Anti-Inflammatory Agents/isolation & purification , Cell Line , Diterpenes/isolation & purification , Macrophages/immunologyABSTRACT
A new cembrane diterpenoid, briaviodiol A (1), has been isolated from a soft coral Briareum violacea. The structure of 1 was determined by spectroscopic methods and further confirmed by a single-crystal X-ray diffraction analysis.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/chemistry , Diterpenes/chemistry , Animals , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/toxicity , Cell Line, Tumor , Crystallography, X-Ray , Diterpenes/isolation & purification , Diterpenes/toxicity , Humans , Magnetic Resonance Spectroscopy , Molecular ConformationABSTRACT
Adenocarcinomas in rats and humans frequently contain perivascular, degranulating mast cells that release heparin. Protamine is a low-molecular weight, cationic polypeptide that binds to heparin and neutralizes its anticoagulant properties. A novel magnetic resonance imaging (MRI) contrast agent containing protamine was synthesized. TTDASQ, the derivative of TTDA (3,6,10-tri(carboxymethyl)-3,6,10-triazadodecanedioic acid), was also synthesized and the kinetic stability of [Gd(TTDASQ)]- chelate containing phosphate buffer and ZnCl2 to measure the relaxation rate (R1) at 20 MHz was studied by transmetallation with Zn(II). The water-exchange rate (k(ex)298) of [Gd(TTDASQ)]- is 6.4 x 10(6) s(-1) at 25.0 +/- 0.1 degrees C which was obtained from the reduced 17O relaxation rates (1/T(1r) and 1/T(2r)) and chemical shift (omega(r)) of H(2)17O, and it is compared with that previously reported for the other gadolinium(III) complex, [Gd(DO3ASQ)]. The binding affinity assay showed that the (TTDASQ)3-pro19 has higher activity toward heparin. On the other hand, the effect of heparin on the relaxivity of the [Gd(TTDASQ)3-pro19] conjugate shows the binding strength (K(A)) is 7669 dm3 mol(-1) at pH 7.4 and the relaxivity (r(b)1) of the [Gd(TTDASQ)3-pro19]-heparin adduct is 30.9 dm3 mmol(-1) s(-1).
Subject(s)
Cyclobutanes/chemistry , Gadolinium/chemistry , Glycine/analogs & derivatives , Magnetics , Organometallic Compounds , Protamines/chemistry , Cyclobutanes/chemical synthesis , Glycine/chemical synthesis , Glycine/chemistry , Hydrogen-Ion Concentration , Ligands , Macromolecular Substances/chemistry , Magnetic Resonance Spectroscopy/methods , Molecular Structure , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Sensitivity and Specificity , TemperatureABSTRACT
The solid-state structure of the first reported homoleptic copper di-2-pyridylphosphinate complex shows an extremely large 'z-out' tetragonal distortion, with an axial Cu.O distance of 2.430 (2) A. The title complex, [Cu(C(10)H(8)N(2)O(2)P)(2)].2CH(2)Cl(2) or Cu[py(2)P(O)O](2).2CH(2)Cl(2), comprises two di-2-pyridylphosphinate ligands coordinated to the central copper(II) ion, which sits on an inversion center. The pyridyl rings of one ligand are trans to the pyridyl rings of their symmetry-related counterpart. The two trans py-Cu-py moieties are coplanar, as required by the inversion symmetry. A disordered dichloromethane solvent molecule is cocrystallized in the asymmetric unit cell.