Symbioimine exhibiting inhibitory effect of osteoclast differentiation, from the symbiotic marine dinoflagellate Symbiodinium sp.
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.
Kita
Masaki
M
Research Center for Materials Science, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8602, Japan.
Kondo
Mikiko
M
Koyama
Tomoyuki
T
Yamada
Kaoru
K
Matsumoto
Tsuyosi
T
Lee
Kun-Hyung
KH
Woo
Je-Tae
JT
Uemura
Daisuke
D
D000818:Animals; D002454:Cell Differentiation / Q000187:drug effects; D002460:Cell Line; D004141:Dinoflagellida / Q000737:chemistry*; D007097:Imines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D051379:Mice; D008958:Models, Molecular; D008970:Molecular Weight; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D010010:Osteoclasts / Q000166:cytology / Q000187:drug effects*; D021241:Spectrometry, Mass, Electrospray Ionization
D007097:Imines