Secologanin
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IUPAC name Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate | |
Systematic IUPAC name Methyl (4S,5R,6S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate | |
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Properties | |
Chemical formula | C17H24O10 |
Molar mass | 388.369 g·mol−1 |
Density | 1.42 g/mL |
Boiling point | 595.5 °C (1,103.9 °F; 868.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.
Biosynthesis
Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoids. Recent efforts have characterized the entire secologanin biosynthetic pathway.[1] Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids.[2]
References
- ^ Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, et al. (April 2014). "The seco-iridoid pathway from Catharanthus roseus". Nature Communications. 5 (1): 3606. doi:10.1038/ncomms4606. PMC 3992524. PMID 24710322.
- ^ "Secologanin Biosynthesis". Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Retrieved 31 May 2011 – via School of Physical and Chemical Sciences, Queen Mary University of London.