Secologanin
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Names | |
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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 | |
Identifiers | |
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Properties | |
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). |
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
[edit]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
[edit]- ^ 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.