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MetaCyc Pathway: secologanin and strictosidine biosynthesis

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Nitrogen-Containing Secondary Compounds Biosynthesis Alkaloids Biosynthesis Indole Alkaloids Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Nitrogen-Containing Secondary Compounds Biosynthesis Alkaloids Biosynthesis Terpenoid Alkaloids Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Terpenoid Alkaloids Biosynthesis

Some taxa known to possess this pathway include ? : Catharanthus roseus , Rauvolfia serpentina

Expected Taxonomic Range: Apocynaceae , Loganiaceae , Rubiaceae

Summary:
Strictosidine is the central branch point metabolite leading to the biosynthesis of a variety of terpenoid indole alkaloids. Terpenoid indole alkaloids are found in a number of plants belonging to the families Apocynaceae, Loganiaceae, Rubiaceae, and Nyssaceae. Several terpenoid indole alkaloids are used in modern medicine. Vinblastine and vincristine are widely used as anticancer drugs, ajmalicine and reserpine as anti-hypertension drugs, and ajmaline as an anti-arrhythmic drug.

It is interesting to note that the biosynthesis of terpenoid indole alkaloids in Catharanthus roseus displays striking intercellular locations. The so-called early-stage enzymes such as tryptophan decarboxylase and strictosidine synthase, for strictosidine biosynthesis, are expressed specifically in the upper and lower epidermis of young leaves. The late-stage enzymes such as desacetoxyvindoline 4-hydroxylase and deacetylvindoline 4-O-acetyltransferase, for vindoline biosynthesis, are expressed in the laticifer and idioblast cells in the leaf mesophyll [StPierre99, Murata05].

Citations: [Collu01, Irmler00, De89a, deWaal95, Facchini05, Ziegler08, Ikeda91]

Credits:
Revised 25-Apr-2008 by Zhang P
Revised 07-Jan-2014 by Caspi R , SRI International


References

Collu01: Collu G, Unver N, Peltenburg-Looman AM, van der Heijden R, Verpoorte R, Memelink J (2001). "Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis." FEBS Lett 508(2);215-20. PMID: 11718718

De89a: De Luca V, Marineau C, Brisson N (1989). "Molecular cloning and analysis of cDNA encoding a plant tryptophan decarboxylase: comparison with animal dopa decarboxylases." Proc Natl Acad Sci U S A 86(8);2582-6. PMID: 2704736

deWaal95: de Waal A, Meijer AH, Verpoorte R (1995). "Strictosidine synthase from Catharanthus roseus: purification and characterization of multiple forms." Biochem J 306 ( Pt 2);571-80. PMID: 7887913

Facchini05: Facchini, Peter (2005). "Regulation of alkaloid biosynthesis in plants." The alkaloids, vol 62: 1-50.

Ikeda91: Ikeda H, Esaki N, Nakai S, Hashimoto K, Uesato S, Soda K, Fujita T (1991). "Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols." J Biochem 109(2);341-7. PMID: 1864846

Irmler00: Irmler S, Schroder G, St-Pierre B, Crouch NP, Hotze M, Schmidt J, Strack D, Matern U, Schroder J (2000). "Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase." Plant J 24(6);797-804. PMID: 11135113

Murata05: Murata J, Luca VD (2005). "Localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus." Plant J 44(4);581-94. PMID: 16262708

StPierre99: St-Pierre B, Vazquez-Flota FA, De Luca V (1999). "Multicellular compartmentation of catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate." Plant Cell 11(5);887-900. PMID: 10330473

Ziegler08: Ziegler J, Facchini PJ (2008). "Alkaloid Biosynthesis: Metabolism and Trafficking." Annu Rev Plant Biol NIL. PMID: 18251710

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

Asada13: Asada K, Salim V, Masada-Atsumi S, Edmunds E, Nagatoshi M, Terasaka K, Mizukami H, De Luca V (2013). "A 7-deoxyloganetic Acid glucosyltransferase contributes a key step in secologanin biosynthesis in madagascar periwinkle." Plant Cell 25(10);4123-34. PMID: 24104568

Bertoldi00: Bertoldi M, Borri Voltattorni C (2000). "Reaction of dopa decarboxylase with L-aromatic amino acids under aerobic and anaerobic conditions." Biochem J 352 Pt 2;533-8. PMID: 11085948

Buki85: Buki KG, Vinh DQ, Horvath I (1985). "Partial purification and some properties of tryptophan decarboxylase from a Bacillus strain." Acta Microbiol Hung 32(1);65-73. PMID: 4036551

Burkhard01: Burkhard P, Dominici P, Borri-Voltattorni C, Jansonius JN, Malashkevich VN (2001). "Structural insight into Parkinson's disease treatment from drug-inhibited DOPA decarboxylase." Nat Struct Biol 8(11);963-7. PMID: 11685243

Fernandez89: Fernandez, J.A., Owen, T.G., Kurz, W.G.W., De Luca, V.D. (1989). "Immunological detection and quantitation of tryptophan decarboxylase in developing Catharanthus roseus seedlings." Plant Physiol. 91: 79-84.

Fountzilas05: Fountzilas G, Pectasides D, Kalogera-Fountzila A, Skarlos D, Kalofonos HP, Papadimitriou C, Bafaloukos D, Lambropoulos S, Papadopoulos S, Kourea H, Markopoulos C, Linardou H, Mavroudis D, Briasoulis E, Pavlidis N, Razis E, Kosmidis P, Gogas H (2005). "Paclitaxel and carboplatin as first-line chemotherapy combined with gefitinib (IRESSA) in patients with advanced breast cancer: a phase I/II study conducted by the Hellenic Cooperative Oncology Group." Breast Cancer Res Treat 92(1);1-9. PMID: 15980985

Ichinose85: Ichinose H, Kojima K, Togari A, Kato Y, Parvez S, Parvez H, Nagatsu T (1985). "Simple purification of aromatic L-amino acid decarboxylase from human pheochromocytoma using high-performance liquid chromatography." Anal Biochem 150(2);408-14. PMID: 4091266

Iijima04: Iijima Y, Gang DR, Fridman E, Lewinsohn E, Pichersky E (2004). "Characterization of geraniol synthase from the peltate glands of sweet basil." Plant Physiol 134(1);370-9. PMID: 14657409

Ito07: Ito M, Honda G (2007). "Geraniol synthases from perilla and their taxonomical significance." Phytochemistry 68(4);446-53. PMID: 17187833

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

LopezMeyer97: Lopez-Meyer M, Nessler CL (1997). "Tryptophan decarboxylase is encoded by two autonomously regulated genes in Camptotheca acuminata which are differentially expressed during development and stress." Plant J 11(6);1167-75. PMID: 9225462

Lu09: Lu Y, Wang H, Wang W, Qian Z, Li L, Wang J, Zhou G, Kai G (2009). "Molecular characterization and expression analysis of a new cDNA encoding strictosidine synthase from Ophiorrhiza japonica." Mol Biol Rep 36(7);1845-52. PMID: 18987991

Madyastha73: Madyastha KM, Guarnaccia R, Baxter C, Coscia CJ (1973). "S-Adenosyl-L-methionine: loganic acid methyltransferase. A carboxyl-alkylating enzyme from Vinca rosea." J Biol Chem 248(7);2497-501. PMID: 4698228

Moore96: Moore PS, Dominici P, Borri Voltattorni C (1996). "Cloning and expression of pig kidney dopa decarboxylase: comparison of the naturally occurring and recombinant enzymes." Biochem J 315 ( Pt 1);249-56. PMID: 8670114

Murata08: Murata J, Roepke J, Gordon H, De Luca V (2008). "The Leaf Epidermome of Catharanthus roseus Reveals Its Biochemical Specialization." Plant Cell NIL. PMID: 18326827

Nakazawa77: Nakazawa, H., Sano, K., Kumagai, H., Yamada, H. (1977). "Distribution and formation of aromatic L-amino acid decarboxylase in bacteria." Agric. Biol.. Chem. 41(11):2241-2247.

Noe84: Noe, W., Mollenschott, C., Berlin, J. (84). "Tryptophan decarboxylase from Catharanthus roseus cell suspension cultures: purification, molecular and kinetic data of the homogeneous protein." Plant Mol Biol 3: 281-288.

Pasquali92: Pasquali G, Goddijn OJ, de Waal A, Verpoorte R, Schilperoort RA, Hoge JH, Memelink J (1992). "Coordinated regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors." Plant Mol Biol 18(6);1121-31. PMID: 1600148

Schnee02: Schnee C, Kollner TG, Gershenzon J, Degenhardt J (2002). "The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-beta-farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage." Plant Physiol 130(4);2049-60. PMID: 12481088

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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 Sun Dec 21, 2014, biocyc11.