Strictosidine

from Wikipedia, the free encyclopedia
Structural formula
Structure of strictosidine
General
Surname Strictosidine
other names
  • 3-α ( S ) -trictosidine
  • Isovincoside
Molecular formula C 27 H 34 N 2 O 9
External identifiers / databases
CAS number 20824-29-7
PubChem 161336
Wikidata Q2356148
properties
Molar mass 530.55 g · mol -1
Physical state

firmly

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Strictosidin is a vinca alkaloid from Rhazya stricta and the Madagascar periwinkle ( Catharanthus roseus ) from the dog venom family . In the synthesis of indole alkaloids Strictosidine plays an important role, it is the presumed precursor of over 1400 different indole - terpene - alkaloids .

biosynthesis

It arises through Mannich-like condensation of tryptamine and the C-7 of the secologanin . This reaction is catalyzed by the enzyme strictosidine synthase .

Strictosidine synthesis: tryptamine (left), secologanin (middle), strictosidine (right).

chemistry

The specific angle of rotation of the hydrochloride in methanol is −143 ° at 25 ° C in sodium light.

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ There are various stereoisomers of strictosidine , of which the 3-α ( S ) -isomer is the biologically active one and is discussed in this article.
  3. ↑ R. Hansel, O. Sticher, E. Steinegger: Pharmakognosie - Phytopharmazie . 6th edition. tape 1 . Springer, Berlin / Heidelberg 1999, ISBN 978-3-662-09269-9 , pp. 1029 , doi : 10.1007 / 978-3-662-09269-9 ( limited preview in Google book search).
  4. ↑ Rimpler: Biogenic Medicinal Products (2nd edition). Pp. 307-308.
  5. ↑ Bayer: Characterization of the vinorine synthase from Rauvolfia serpentina through purification, expression, mutation and crystallization , dissertation in the chemistry and pharmacy department of the Johannes Gutenberg University in Mainz (2003), p. 9.
  6. ↑ Entry on strictosidine. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.