The marine fireworm, Eurythoe complanata, is known as a dangerous animal for humans because it induces skin inflammation through its small setae. Here, the inflammation-inducing substance was successfully isolated from the whole body using a methanolic extraction, and the inflammatory activity was determined using a bioassay. The structure was spectroscopically revealed to be a trimethylammonium with an unsaturated carbon chain and was named complanine. Complanine enhanced PKC activity in combination with TPA in vitro. This may explain the molecular mechanism behind its inflammation-inducing activity.
SummaryThe synthesis of (−)-complanine, an inflammatory substance of Eurythoe complanata, was accomplished by a “chiral synthon” approach. The absolute configuration of this molecule was determined to be R.
Two new members of the complanine family, neocomplanines A (2) and B (3), were isolated as minor components of the methanolic extract of the "marine fireworm" Eurythoe complanata. The structures of the neocomplanines were revealed spectroscopically to be a trimethylammonium unit with a saturated carbon chain. The planar structures of neocomplanines A and B were confirmed successfully through total syntheses that used epichlorohydrin as a starting material. The neocomplanines show inflammatory activity and also enhanced PKC activity in combination with TPA in the presence of Ca(2+) in vitro; both are similar to the effects of complanine (1). The molecular mechanism of the effects of complanine-related compounds is discussed.
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