Strictosidinic acid

Strictosidinic acid V H IJ oYYoh 0 OH HOOC P. myriantha Analgesic, antipyretic, antiinflammatory [136, 138]... 

P. myriantha is common in Southern Brazilian forests [129] and produces the MIA strictosidinic acid, being the major alkaloid present in P. myriantha leaves. Oral administration of strictosidinic acid in mice has analgesic and antipyretic effects [136], and it is also an efficient inhibitor of PMN chemotaxis in vivo [137], having anti-inflammatory properties [138]. 

Sim5es-Pires CA, Farias FM, Marston A, Queiroz EF, Chaves CG, Henriques AT, Hostettmann K (2006) Indole monoterpenes with antichemotactic activity from Psychotria myriantha. chemotaxonomic significance. Nat Prod Commun 1 1101-1106. http //www. naturalproduct.us/content/npcl 12 2006. pdf page=37. Accessed 24 Oct 2011 Farias FM, Passes CS, Arbo MD, Zuanazzi JAS, Steffen VM, Henriques AT (2010) Monoamine levels in rat striatum after acute intraperitoneal injection of strictosidinic acid isolated from Psychotria myriantha Mull. Arg. (Rubiaceae). Phytomedicine 17 289-291. doi 10.1016/j.phymed.2009.05.008... 

Gene transfer from the angiosperm Catharanthus roseus, and over-expression in the bacterium Escherichia coli, yielded the synthase for strictosidine, a known alkaloid of the tryptophan-secologanin class (Scott 1992). A similar strategy has clarifted the biosynthesis of hydrogenobyrinic acid, an advanced precursor of vitamin B,2 (Scott 1994). 

Alkal. indole strictosidine (Catharanthus roseus Ang. Escherichia coli Bact. Scott 1992) corrins hydrogenobyrinic acid (Pseudomonas denitrificans Bact. E. coli. Scott 1994). 

The mechanism of formation of the (19i )-bases was studied by means of 2H and lsO experiments. In D20, at pH 6, strictosidine gives the monodeuterio-compounds (71) and (72), as expected, but whereas the proportion of (72) increases with time, no further deuterium is incorporated. Hence cathenamine does not revert in acid to the dienamine (67). Evidently cathenamine is protonated to... 

MCKNIGHT, T.D., ROESSNER, C.A., DEVAGUPTA, R SCOTT, A.I., NESSLER, C.L., Nucleotide sequence of a cDNA encoding the vacuolar protein strictosidine synthase from Catharanthus roseus. Nucleic Acids Res., 1990, 18, 4939. 

Figure 1.3 Several pathways of secondary metabolites derive from precursors in the shikimate pathway. Abbreviation NPAAs, non-protein amino acids PAL, phenylalanine ammonia lyase TDC, tryptophan decarboxylase STS, strictosidine synthase CHS, chalcone synthase. (See Plate 2 in colour plate section.)...

Figure 7.17 Phyiogenetic reiationships in key enzymes of iater steps in SM pathways, based on amino acid sequences, (a) Chaicone synthase (CHS), (b) Strictosidine synthase (STS), (c) Berberine bridge enzyme (BBE). (d) Codeinone reductase (CR).

Table 7.7 Sequence alignment (amino acids) of strictosidine synthase (STS) of selected taxa from plants, animals and bacteria. Conserved sites are marked by x species with a functional STR are in bold...

The initial preparation of dihydromancunine (Scheme 13) used an N -blocking group to avoid formation of vallesiachotamine derivatives (i.e. cyclization of C-17 onto iVb). Subsequently" it was found that a blocking group is unnecessary if more acidic media are used, but the yield is lower owing to denaturing of the enzyme used. In an extension of these studies to the 3a-H series strictosidine, treated with... 

An amorphous material found in R. orientalis which gave strictosidine on methylation is presumably the corresponding acid (70) (8). 

L-Tryptophan was shown to be incorporated with high efficiency into 5a-carboxystrictosidine (33a) in Rhazya orientalis, from where it was originally isolated. It joins the small group of indole alkaloids which retain the carboxyl of precursor tryptophan. The di-acid (33c) and the acid (33b), corresponding to strictosidine, were also isolated in this study. 

Generation of Engineered Strains of Saccharomyces cerevisiae for Lactic acid, Xylitol, and Strictosidine Production... 

Moreno et al. 136) found that feeding loganin, secologanin, or loganic acid to a C. roseus cell culture resulted in a considerable increase of strictosi-dine and ajmalicine levels, and a concomitant decrease of tryptamine. Also, after these iridoids were fed to elicited cells a decrease of tryptamine levels was observed, but strictosidine and ajmalicine levels were much lower than in the normal cells to which the iridoids were fed, suggesting a rapid turnover of strictosidine. 

The terpenoid indole alkaloids are a group of plant bases derived by multiple variation on the strictosidine [(79) p. 20] skeleton. Arguably the most important work in the past five years has been done on these alkaloids with enzyme preparations from plant tissue cultures, and the research is of great potential significance for other studies in alkaloid biosynthesis. The results have allowed close definition of the early stages of biosynthesis (this Report, p. 19). Use of crude enzyme preparations in this way has been extended to the study of benzylisoquinoline biosynthesis, with enzyme-catalysed formation of norlaudanosoline-1-carboxylic acid [(57) p. 16] this compound had earlier been identified as the first of the benzylisoquinolines (this Report, p. 15). It seems that amino-acids of this general formula (6) are key intermediates in the biosynthesis of all isoquinoline alkaloids. Lophocereine (7) is exceptional in that two routes (from leucine and mevalonate) may lead to it, only one of which potentially involves an acid like (6). ... 

A key step in indole alkaloid biosynthesis is the formation of strictosidine from tryptamine and the aldehyde secologanin [357, 358]. This reactimi is catalyzed by the enzyme strictosidine synthase. The crystal structure of the enzyme has been determined and the binding site identified [359]. Site-directed mutagenesis has been used to identify both the active site amino acids and to modify the substrate specificity of the enzyme [360]. The enzymatic mechanism has been compared with the H -catalyzed reaction in solution and they appear to be similar, based on... 

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