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|
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].
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
De89: 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
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
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
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
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
Lu09a: 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
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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