TL;DR: Complanine enhanced PKC activity in combination with TPA in vitro in vitro may explain the molecular mechanism behind the inflammation-inducing activity of the marine fireworm.
Abstract: 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.
TL;DR: Two new members of the complanine family, neocomplanines A and B, were isolated as minor components of the methanolic extract of the "marine fireworm" Eurythoe complanata and show inflammatory activity and also enhanced PKC activity in combination with TPA in the presence of Ca(2+) in vitro.
Abstract: 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.
TL;DR: The synthesis of (−)-complanine, an inflammatory substance of Eurythoe complanata, was accomplished by a “chiral synthon” approach by determining the absolute configuration of this molecule to be R.
Abstract: The 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.
TL;DR: A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation.
Abstract: A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.