Secologanin

In this article, we will explore the fascinating world of Secologanin and how it has impacted our lives in unimaginable ways. Secologanin has been the object of study, controversy and admiration throughout history, and its influence extends to practically all aspects of our society. From its origins to its modern evolution, Secologanin has left an indelible mark on humanity, challenging our perceptions and provoking deep reflections on who we are and where we are headed. Join us on this journey to discover the importance of Secologanin in our lives and in the world around us.

Secologanin
Names
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-{oxy}-3,4-dihydro-2H-pyran-5-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1 InChI Key = CSKKDSFETGLMSB-NRZPKYKESA-N
  • COC(=O)C1=CO((1CC=O)C=C)O2((((O2)CO)O)O)O
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 , 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

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. 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.

References

  1. ^ Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; van der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle (7 April 2014). "The seco-iridoid pathway from Catharanthus roseus". Nature Communications. 5 (1): 3606. doi:10.1038/ncomms4606. PMC 3992524. PMID 24710322.
  2. ^ "Secologanin Biosynthesis". Retrieved 31 May 2011.
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