RESUMO
Two amphoteric iminium metabolites, symbioimine (1) and neosymbioimine (2), were isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Compounds 1 and 2 have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 and 2 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts (EC50 = 44 microM), and significantly inhibited cyclooxygenase-2 activity at 10 microM. Thus, symbioimine is a potent anti-resorptive and anti-inflammatory drug.
Assuntos
Dinoflagellida/química , Compostos Heterocíclicos com 3 Anéis/isolamento & purificação , Animais , Linhagem Celular , Compostos Heterocíclicos com 3 Anéis/química , Compostos Heterocíclicos com 3 Anéis/farmacologia , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
An amphoteric iminium metabolite, symbioimine (1), was isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Its structure was deduced by spectroscopic analysis and X-ray crystallographic analysis. Symbioimine (1) has a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts, whereas its cell viability was not affected. Thus, symbioimine (1) is an antiresorptive drug candidate for the prevention and treatment of osteoporosis in postmenopausal women.
Assuntos
Dinoflagellida/química , Iminas/isolamento & purificação , Iminas/farmacologia , Osteoclastos/efeitos dos fármacos , Animais , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular , Iminas/química , Camundongos , Modelos Moleculares , Peso Molecular , Ressonância Magnética Nuclear Biomolecular , Rotação Ocular , Osteoclastos/citologia , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Protein polymorphisms of the crab-eating macaque (Macaca fascicularis) on the island of Mauritius in the southwest Indian Ocean were examined electrophoretically for 201 blood samples. All of the variant types detected were those found previously in the Asian populations. Genetic variability of the island population was estimated to be Ppoly = 16% and H = 6.5%, which was lower than that of the Asian populations. A tendency that a small number of loci were highly polymorphic was observed. These results may reflect the establishment of the island population from a small number of introduced ancestors, or the existence of the bottleneck effect. For the origin of the Mauritian monkeys, comparison of electrophoretic variants suggested that they originated from the Malay Peninsula or the Greater Sunda Islands, especially from Java. Though the homozygous individuals exceeded in number as a whole, a significant subdivision was not detected in the population. © 1993 Wiley-Liss, Inc.
