Spiro-prorocentrimine

Prorocentrolides and Spiro-prorocentrimine Fast-Acting Toxins with Unknown Molecular Targets... 

Figure 18.7. Chemical structures of prorocentrolide (a), prorocentrolide B (b), and spiro-prorocentrimine (c).

Lu, C.K., Lee, G.H., Huang, R. and Chou, H.N., 2001. Spiro-prorocentrimine, a novel macrocyclic lactone from a benthic Prorocentrum sp. ofTaiwan. Tetrahedron Lett 42, 1713—1716. 

Spiro-prorocentrimine (196) is a polar lipid-soluble toxin isolated from a laboratory-cultured benthic P. lima collected in Taiwan. It was crystallized in methanol and X-ray diffraction analysis of spiro-prorocentrimine (196) revealed a spiro-linked cyclic imine with the 1,1,2,4-tetrasubstituted 3-cyclohexene in addition to its macrolide skeleton. Biogenetically, prorocentrolides and spiro-prorocentrimine might be related to each other. 

Spiro-prorocentrimine was isolated from Prorocentrum cells by Lu et al. [7] by methanolic extraction and subsequent partition against hexane, chloroform, and 1-butanol. Combined chloroform and butanol phases were subjected to flash chromatography on silica, RP-HPLC on ODS, GPC, again silica flash chromatography, and RP-HPLC on ODS. 

Gymnodimines Spirolides Spiro- Prorocentrimine Pinna-/ Weriatoxins Prorocentrolides... 

All of the cyclic imine toxins (except spiro-prorocentrimine) may be structurally classihed as macrocyclic polyethers. Although the elucidation of biosynthetic pathways for polyether dino-flagellates toxins is limited to the ladder frame polyether brevetoxins [40], the linear polyether dinophysistoxins DTX4 and DTX5 [11,41] and the macrocyclic imine des-methyl spirolide C... 

Imines Gymnodimine, Spirolides, Pinnatoxins, Pteriatoxins, Prorocentrolide, Spiro-Prorocentrimine, and Symbioimines... 

Prorocentrolide has been isolated from Japanese and Taiwanese strains of the dinoflagellate Prorocentrum lima [37,38], A congener, prorocentrolide B, was found in a Japanese strain of Prorocentrum maculosum [39], Spiro-prorocentrimine was extracted from an unidentified benthic Prorocentrum species from Taiwan [37], while symbioimine and neosymbioimine were found in a symbiotic marine dinoflagellate of the species Symbiodinium in Japan [40,41],... 

Spiro-prorocentrimine appears to be much less toxic than other cyclic imines. Lu etal. [37] reported an intraperitoneal LD99 of 2500 pg/kg in mice. No information on the symptoms of intoxication with spiro-prorocentrimine has been found or on pathological changes induced by this substance. 

No data on the oral toxicity of prorocentrolide, spiro-prorocentrimine, or symbioimines have been found. 

Lu C.K. et al. Spiro-prorocentrimine, a novel macrocychc lactone from a benthic Prorocentrum spp. of Taiwan, Tetrahedron Lett. 42, 1713, 2001. 

Spiro-prorocentrimine (103) was also isolated from P lima collected in Taiwan [101]. Spiro-prorocentrimine is characterized by a macrocyclic lactone possessing a spiro-linked cyclic imine with an orthoy para-disubstituted 3 -cyclohexene. Its mouse lethality (2.5 mg/kg) is less toxic than that of pro-... 

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