Symbioimine and neosymbioimine, amphoteric iminium metabolites from the symbiotic marine dinoflagellate Symbiodinium sp.
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.
Kita
Masaki
M
Research Center for Materials Science, Graduate School of Science, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8602, Japan.
Ohishi
Nao
N
Washida
Kazuto
K
Kondo
Mikiko
M
Koyama
Tomoyuki
T
Yamada
Kaoru
K
Uemura
Daisuke
D
D000818:Animals; D002460:Cell Line; D004141:Dinoflagellida / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization
D006575:Heterocyclic Compounds, 3-Ring; C505669:neosymbioimine; C505668:symbioimine