CYP716A Subfamily Members are Multifunctional Oxidases in Triterpenoid Biosynthesis

Achnine, 2005, Genomics-based selection and functional characterization of triterpene glycosyltransferases from the model legume Medicago truncatula, Plant J., 41, 875, 10.1111/j.1365-313X.2005.02344.x

Augustin, 2011, Molecular activities, biosynthesis and evolution of triterpenoid saponins, Phytochemistry, 72, 435, 10.1016/j.phytochem.2011.01.015

Bialy, 2006, Triterpene saponins from the roots of Medicago hybrida, J. Agric. Food Chem., 54, 2520, 10.1021/jf0581628

Bialy, 2004, Triterpene saponins from aerial parts of Medicago arabica L, J. Agric. Food Chem., 52, 1095, 10.1021/jf030446+

Bialy, 1999, Saponins in alfalfa (Medicago sativa L.) root and their structural elucidation, J. Agric. Food Chem., 47, 3185, 10.1021/jf9901237

Broeckling, 2005, Metabolic profiling of Medicago truncatula cell cultures reveals the effects of biotic and abiotic elicitors on metabolism, J. Exp. Bot., 56, 323, 10.1093/jxb/eri058

Carelli, 2011, Medicago truncatula CYP716A12 is a multifunctional oxidase involved in the biosynthesis of hemolytic saponins, Plant Cell, 23, 3070, 10.1105/tpc.111.087312

Croteau, 2000, Natural products: secondary metabolites In, Biochemistry and Molecular Biology of Plants, 1250

Fai, 2009, A review of presence of oleanolic acid in natural products, Natura Proda Medica, 1

Field, 2008, Metabolic diversification-independent assembly of operon-like gene clusters in different plants, Science, 320, 543, 10.1126/science.1154990

Fulda, 2009, Targeting mitochondrial apoptosis by betulinic acid in human cancers, Drug Discov. Today, 14, 885, 10.1016/j.drudis.2009.05.015

Haralampidis, 2002, Biosynthesis of triterpenoid saponins in plants, Adv. Biochem. Eng. Biotechnol., 75, 32

Hayashi, 2004, Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra, Biol. Pharm. Bull., 27, 1086, 10.1248/bpb.27.1086

Herrera, 1998, Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene, Phytochemistry, 49, 1905, 10.1016/S0031-9422(98)00366-5

Huhman, 2005, Quantification of saponins in aerial and subterranean tissues of Medicago truncatula, J. Agric. Food Chem., 53, 1914, 10.1021/jf0482663

Huhman, 2002, Metabolic profiling of saponins in Medicago sativa and Medicago truncatula using HPLC coupled to an electrospray ion-trap mass spectrometer, Phytochemistry, 59, 347, 10.1016/S0031-9422(01)00432-0

Iturbe-Ormaetxe, 2003, Molecular cloning and characterization of triterpene synthases from Medicago truncatula and Lotus japonicus, Plant Mol. Biol., 51, 731, 10.1023/A:1022519709298

Julsing, 2006, Combinatorial biosynthesis of medicinal plant secondary metabolites, Biomol. Eng., 23, 265, 10.1016/j.bioeng.2006.08.001

Kapusta, 2005, Determination of saponins in aerial parts of barrel medic (Medicago truncatula) by liquid chromatography–electrospray ionization/mass spectrometry, J. Agric. Food Chem., 53, 7654, 10.1021/jf051256x

Kapusta, 2005, Triterpene saponins from barrel medic (Medicago truncatula) aerial parts, J. Agric. Food Chem., 53, 2164, 10.1021/jf048178i

Kushiro, 1998, β-Amyrin synthase: cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants, Eur. J. Biochem., 256, 238, 10.1046/j.1432-1327.1998.2560238.x

Marasco, 2007, Exploring and accessing plant natural product biosynthesis in engineered microbial hosts, Medicinal Plant Biotechnology: From Basic Research to Industrial Applications, 287

Mizutani, 1998, Two isoforms of NADPH: cytochrome P450 reductase in Arabidopsis thaliana. Gene structure, heterologous expression in insect cells, and differential regulation, Plant Physiol., 116, 357, 10.1104/pp.116.1.357

Mizutani, 2010, Diversification of P450 genes during land plant evolution, Annu. Rev. Plant Biol., 61, 291, 10.1146/annurev-arplant-042809-112305

Morita, 2000, Molecular cloning and functional expression of triterpene synthases from pea (Pisum sativum): new α-amyrin-producing enzyme is a multifunctional triterpene synthase, Eur. J. Biochem., 267, 3453, 10.1046/j.1432-1327.2000.01357.x

Naoumkina, 2010, Genomic and coexpression analyses predict multiple genes involved in triterpene saponin biosynthesis in Medicago truncatula, Plant Cell, 22, 850, 10.1105/tpc.109.073270

Nelson, 2009, The cytochrome P450 homepage, Hum. Genomics, 4, 59, 10.1186/1479-7364-4-1-59

Nelson, 2011, A P450-centric view of plant evolution, Plant J., 66, 194, 10.1111/j.1365-313X.2011.04529.x

Ohnishi, 2006, Tomato cytochrome P450 CYP734A7 functions in brassinosteroid catabolism, Phytochemistry, 67, 1895, 10.1016/j.phytochem.2006.05.042

Ono, 2010, Functional differentiation of the glycosyltransferases that contribute to the chemical diversity of bioactive flavonol glycosides in grapevines (Vitis vinifera), Plant Cell, 22, 2856, 10.1105/tpc.110.074625

Qi, 2006, A different function for a member of ancient and highly conserved cytochrome P450 family: from essential sterols to plant defense, Proc. Natl Acad. Sci. USA, 103, 18848, 10.1073/pnas.0607849103

Rivero-Cruz, 2008, Antimicrobial constituents of Thompson seedless raisins (Vitis vinifera) against selected oral pathogens, Phytochem. Lett., 1, 151, 10.1016/j.phytol.2008.07.007

Saimaru, 2007, Production of triterpene acids by cell suspension cultures of Olea europaea, Chem. Pharm. Bull., 55, 784, 10.1248/cpb.55.784

Sasazuka, 1995, Water-soluble oleanolic acid. Production, inhibition of insoluble glucan synthesis and antibacterial action, Seito Gijutsu Kenkyu Kaishi, 43, 63

Schliemann, 2008, Metabolite profiling of mycorrhizal roots of Medicago truncatula, Phytochemistry, 69, 112, 10.1016/j.phytochem.2007.06.032

Schuler, 2003, Functional genomics of P450s, Annu. Rev. Plant. Biol., 54, 629, 10.1146/annurev.arplant.54.031902.134840

Seki, 2008, Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin, Proc. Natl. Acad. Sci. USA, 105, 14204, 10.1073/pnas.0803876105

Shibuya, 2006, Identification of β-amyrin and sophoradiol 24-oxidase by expressed sequence tag mining and functional expression assay, FEBS J., 273, 948, 10.1111/j.1742-4658.2006.05120.x

Shimura, 2007, Identification of a biosynthetic gene cluster in rice for momilactones, J. Biol. Chem., 282, 34013, 10.1074/jbc.M703344200

Sparg, 2004, Biological activities and distribution of plant saponins, J. Ethnopharm., 94, 219, 10.1016/j.jep.2004.05.016

Suzuki, 2002, A genomics approach to the early stages of triterpene saponin biosynthesis in Medicago truncatula, Plant J., 32, 1033, 10.1046/j.1365-313X.2002.01497.x

Tamura, 2011, Mol. Biol. Evol., 28, 2731, 10.1093/molbev/msr121

Tava, 2009, New triterpenic saponins from the aerial parts of Medicago arabica (L.) huds, J. Agric. Food Chem., 57, 2826, 10.1021/jf8036984

Thompson, 1994, CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice, Nucleic. Acids Res., 22, 4673, 10.1093/nar/22.22.4673

Usadel, 2009, Co-expression tools for plant biology: opportunities for hypothesis generation and caveats, Plant Cell Environ., 32, 1633, 10.1111/j.1365-3040.2009.02040.x

Werck-Reichhart, 2002, Cytochromes P450, The Arabidopsis Book, 1

Wu, 2009, Grape products and oral health, J. Nutr., 139, 1818S, 10.3945/jn.109.107854

Zhang, 2004, Insulin secretion and cyclooxygenase enzyme inhibition by cabernet sauvignon grape skin compounds, J. Agric. Food. Chem., 52, 228, 10.1021/jf034616u