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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: salidroside biosynthesis

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis

Some taxa known to possess this pathway include ? : Rhodiola rosea , Rhodiola sachalinensis

Expected Taxonomic Range: Viridiplantae

Summary:
salidroside is an important pharmaceutical compound isolated from Rhodiola species. These species are mainly found in alpine regions of Asia and Scandinavia. salidroside is an adaptogen with medicinal properties such as anti-fatigue, anti-senescence and anti-radiation effects. Natural habitats are limiting for its continuous supply and the cultivation of this plant requires 4-5 years, therefore, alternate ways to produce salidroside have been explored using in vitro studies.

salidroside is a phenylethanoid glycoside and is derived from phenylalanine or L-tyrosine. Over expression of PAL gene did not increase salidroside production as shown in this study [Ma08]. salidroside production, using Rhodiola sachalinensis hairy roots induced by Agrobacterium rhizogenes gave promising yields. The optimal concentration of the precursors; 4-tyrosol, phenylalanine and L-tyrosine along with elicitor concentration was established in this study [Zhou07a].

salidroside is mainly found in the roots. The glycosylation of 4-tyrosol is the final step of the biosynthesis of salidroside, the glycosyltransferases responsible for salidroside biosynthesis have been isolated [Yu11a] and [Ma07a]. The biosynthesis of 4-tyrosol was worked out latter; its precursor was thought to be tyramine, which is synthesized from L-tyrosine. The isolation and over expression of a tyrosine decarboxylase resulted in the increase in 4-tyrosol and salidroside production, indicating its role in the biosynthesis of salidroside [Zhang11d]. Further, in this study [Yan04] it has been shown that red light promotes salidroside production but decreases the plant biomass.

Credits:
Created 29-Apr-2011 by Pujar A , Boyce Thompson Institute


References

Chen11c: Chen B, Zhang L, Chen G (2011). "Determination of salidroside and tyrosol in Rhodiola by capillary electrophoresis with graphene/poly(urea-formaldehyde) composite modified electrode." Electrophoresis 32(8);870-6. PMID: 21374630

Ma07a: Ma LQ, Liu BY, Gao DY, Pang XB, Lu SY, Yu HS, Wang H, Yan F, Li ZQ, Li YF, Ye HC (2007). "Molecular cloning and overexpression of a novel UDP-glucosyltransferase elevating salidroside levels in Rhodiola sachalinensis." Plant Cell Rep 26(7);989-99. PMID: 17333022

Ma08: Ma LQ, Gao DY, Wang YN, Wang HH, Zhang JX, Pang XB, Hu TS, Lu SY, Li GF, Ye HC, Li YF, Wang H (2008). "Effects of overexpression of endogenous phenylalanine ammonia-lyase (PALrs1) on accumulation of salidroside in Rhodiola sachalinensis." Plant Biol (Stuttg) 10(3);323-33. PMID: 18426479

Yan04: Yan X, Wang Y, Guo S, Shang X (2004). "[Seasonal variations in biomass and salidroside content in roots of Rhodiola sachalinensis as affected by gauze and red film shading]." Ying Yong Sheng Tai Xue Bao 15(3);382-6. PMID: 15227984

Yu11a: Yu HS, Ma LQ, Zhang JX, Shi GL, Hu YH, Wang YN (2011). "Characterization of glycosyltransferases responsible for salidroside biosynthesis in Rhodiola sachalinensis." Phytochemistry. PMID: 21497865

Zhang11d: Zhang JX, Ma LQ, Yu HS, Zhang H, Wang HT, Qin YF, Shi GL, Wang YN (2011). "A tyrosine decarboxylase catalyzes the initial reaction of the salidroside biosynthesis pathway in Rhodiola sachalinensis." Plant Cell Rep. PMID: 21538102

Zhou07a: Zhou X, Wu Y, Wang X, Liu B, Xu H (2007). "Salidroside production by hairy roots of Rhodiola sachalinensis obtained after transformation with Agrobacterium rhizogenes." Biol Pharm Bull 30(3);439-42. PMID: 17329834

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Arcos10: Arcos M, Olivera ER, Arias S, Naharro G, Luengo JM (2010). "The 3,4-dihydroxyphenylacetic acid catabolon, a catabolic unit for degradation of biogenic amines tyramine and dopamine in Pseudomonas putida U." Environ Microbiol 12(6);1684-704. PMID: 20482587

Cole05: Cole SH, Carney GE, McClung CA, Willard SS, Taylor BJ, Hirsh J (2005). "Two functional but noncomplementing Drosophila tyrosine decarboxylase genes: distinct roles for neural tyramine and octopamine in female fertility." J Biol Chem 280(15);14948-55. PMID: 15691831

Diaz01: Diaz E, Ferrandez A, Prieto MA, Garcia JL (2001). "Biodegradation of aromatic compounds by Escherichia coli." Microbiol Mol Biol Rev 65(4);523-69, table of contents. PMID: 11729263

Dickinson03: Dickinson JR, Salgado LE, Hewlins MJ (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278(10);8028-34. PMID: 12499363

Facchini94a: Facchini, Peter, De Luca, Vincenzo "Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in Opium poppy." The journal of biological chemistry (1994) 269(43):26684-26690.

Facchini95: Facchini PJ, De Luca V (1995). "Expression in Escherichia coli and partial characterization of two tyrosine/dopa decarboxylases from opium poppy." Phytochemistry 38(5);1119-26. PMID: 7766394

Gyorgy09: Gyorgy Z, Jaakola L, Neubauer P, Hohtola A (2009). "Isolation and genotype-dependent, organ-specific expression analysis of a Rhodiola rosea cDNA encoding tyrosine decarboxylase." J Plant Physiol 166(14);1581-6. PMID: 19487048

Jornvall77: Jornvall H (1977). "The primary structure of yeast alcohol dehydrogenase." Eur J Biochem 72(3);425-42. PMID: 320000

Kezmarsky05: Kezmarsky ND, Xu H, Graham DE, White RH (2005). "Identification and characterization of a L-tyrosine decarboxylase in Methanocaldococcus jannaschii." Biochim Biophys Acta 1722(2);175-82. PMID: 15715981

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

Roh94: Roh JH, Suzuki H, Azakami H, Yamashita M, Murooka Y, Kumagai H (1994). "Purification, characterization, and crystallization of monoamine oxidase from Escherichia coli K-12." Biosci Biotechnol Biochem 58(9);1652-6. PMID: 7765483


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Dec 19, 2014, biocyc14.