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Chemical Compound Review:

Secologanin methyl(4S,5S,6S)-5-ethenyl-4- (2-oxoethyl)...

Synonyms: loniceroside, CHEMBL1235867, CHEBI:18002, ZINC04095728, AR-1J3362, ...

De-Eknamkul, W. et al., Giroud, C. et al., Treimer, J.F. et al., Mizukami, H. et al., Irmler, S. et al., et al.

Contin, van der Heijden, Lefeber, Verpoorte,

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High impact information on Secologanin

Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase [1].
Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells [2].
In the suspension cultures of CATHARANTHUS ROSEUS secologanin and tryptophan were detected [3].
In order to determine whether 5-methoxytryptamine was a precursor of the methoxylated quinolines, this indole was incubated with secologanin and several CINCHONA ROBUSTA crude protein extracts [4].
The pH optimum was 6.8, apparent Km values for tryptamine and secologanin were 2.3 mM and 3.4 mM respectively for the enzyme to synthesize strictosidine [5].

Biological context of Secologanin

Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast [6].

Anatomical context of Secologanin

The over-expression of Tdc causes this cell line to produce quite large quantities of alkaloids after feeding loganin or secologanin [7].

Associations of Secologanin with other chemical compounds

The isolated enzyme is a single polypeptide with Mr 30,000, and has a pH optimum at 7.5 and a temperature optimum at 45 degrees C. The apparent Km values for dopamine and secologanin are 0.7 and 0.9 mM, respectively [8].

Analytical, diagnostic and therapeutic context of Secologanin

After [1-(13)C]glucose feeding to a cell culture of Catharanthus roseus, its incorporation into secologanin was studied by 13C NMR spectroscopy [9].

References

Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Irmler, S., Schröder, G., St-Pierre, B., Crouch, N.P., Hotze, M., Schmidt, J., Strack, D., Matern, U., Schröder, J. Plant J. (2000) [Pubmed]
Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells. Mizukami, H., Nordlöv, H., Lee, S.L., Scott, A.I. Biochemistry (1979) [Pubmed]
Analysis of several iridoid and indole precursors of terpenoid indole alkaloids with a single HPLC run. Dagnino, D., Schripsema, J., Verpoorte, R. Planta Med. (1996) [Pubmed]
Thermospray Liquid Chromatography/Mass Spectrometry (TSP LC/MS) Analysis of the Alkaloids from Cinchona in vitro Cultures. Giroud, C., van der Leer, T., van der Heijden, R., Verpoorte, R., Heeremans, C.E., Niessen, W.M., Vander Greef, J. Planta Med. (1991) [Pubmed]
Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation. Treimer, J.F., Zenk, M.H. Eur. J. Biochem. (1979) [Pubmed]
Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast. Geerlings, A., Redondo, F.J., Contin, A., Memelink, J., van der Heijden, R., Verpoorte, R. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
Effect of precursor feeding on alkaloid accumulation by a tryptophan decarboxylase over-expressing transgenic cell line T22 of Catharanthus roseus. Whitmer, S., van der Heijden, R., Verpoorte, R. J. Biotechnol. (2002) [Pubmed]
Purification and characterization of deacetylipecoside synthase from Alangium lamarckii Thw. De-Eknamkul, W., Suttipanta, N., Kutchan, T.M. Phytochemistry (2000) [Pubmed]
The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture. Contin, A., van der Heijden, R., Lefeber, A.W., Verpoorte, R. FEBS Lett. (1998) [Pubmed]

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