Kita Masaki, Ohishi Nao, Washida Kazuto, Kondo Mikiko, Koyama Tomoyuki, Yamada Kaoru, Uemura Daisuke
Research Center for Materials Science, Graduate School of Science, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8602, Japan.
Bioorg Med Chem. 2005 Sep 1;13(17):5253-8. doi: 10.1016/j.bmc.2005.05.064.
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.
从培养的共生海洋甲藻共生藻属（Symbiodinium sp.）中分离出两种两性亚胺代谢产物，共生亚胺（1）和新共生亚胺（2）。化合物1和2具有特征性的6,6,6-三环亚胺环结构和芳基硫酸酯部分。1和2可能的生物合成途径可以通过分子内狄尔斯-阿尔德反应继之以亚胺环化来解释。共生亚胺（1）抑制RAW264细胞向破骨细胞的分化（半数有效浓度=44微摩尔），并在10微摩尔时显著抑制环氧合酶-2的活性。因此，共生亚胺是一种有效的抗吸收和抗炎药物。
