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MetaCyc Pathway: lupeol biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: lupeol biosynthesis

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: BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisTriterpenoids Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Betula platyphylla japonica

Expected Taxonomic Range: Viridiplantae

General Background

Thousands of nonsteroidal triterpenes have been identified and, in spite of their elusive functions, the ubiquity of these compounds among higher plants implies that they are essential. Lupeol is a pentacyclic triterpene present in plants but not fungi and animals. Lupeol displays anti-inflammatory properties when administered to rats, yet, unlike other non-steroidal anti-inflammatory drugs, had no antinociceptive, anti-pyretic and ulcerogenic actions [Geetha01]. Lupeol was also reported to be involved in apoptosis [Aratanechemuge04].

Key Notes on the Enzymes:

Lupeol is synthesized by oxidosqualene cyclases from oxidosqualene. These enzymes catalyze the cyclization, rearrangement and deprotonation of oxidosqualene to simultaneously form a variety of triterpene compounds in varying amounts. The first lupeol synthase identified from Arabidopsis thaliana col was thus shown to catalyze the formation of -not only- lupeol but lupan-3β,20-diol, β-amyrin, germanicol, taraxasterol and Ψ-taraxasterol [Segura00].

Citations: [Herrera98]

Unification Links: AraCyc:PWY-112

Reviewed 08-Dec-2008 by Pujar A, Boyce Thompson Institute


Aratanechemuge04: Aratanechemuge Y, Hibasami H, Sanpin K, Katsuzaki H, Imai K, Komiya T (2004). "Induction of apoptosis by lupeol isolated from mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells." Oncol Rep 11(2);289-92. PMID: 14719056

Geetha01: Geetha T, Varalakshmi P (2001). "Anti-inflammatory activity of lupeol and lupeol linoleate in rats." J Ethnopharmacol 76(1);77-80. PMID: 11378285

Herrera98: Herrera JB, Bartel B, Wilson WK, Matsuda SP (1998). "Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene." Phytochemistry 49(7);1905-11. PMID: 9883589

Segura00: Segura MJ, Meyer MM, Matsuda SP (2000). "Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol." Org Lett 2(15);2257-9. PMID: 10930257

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

Basyuni06: Basyuni M, Oku H, Inafuku M, Baba S, Iwasaki H, Oshiro K, Okabe T, Shibuya M, Ebizuka Y (2006). "Molecular cloning and functional expression of a multifunctional triterpene synthase cDNA from a mangrove species Kandelia candel (L.) Druce." Phytochemistry 67(23);2517-24. PMID: 17078982

Basyuni07a: Basyuni M, Oku H, Tsujimoto E, Kinjo K, Baba S, Takara K (2007). "Triterpene synthases from the Okinawan mangrove tribe, Rhizophoraceae." FEBS J 274(19);5028-42. PMID: 17803686

Ebizuka03: Ebizuka Y, Katsube Y, Tsutsumi T, Kushiro T, Shibuya M (2003). "Functional genomics approach to the study of triterpene biosynthesis." Pure and Applied Chemistry 75(2-3);369-374.

Guhling06: Guhling O, Hobl B, Yeats T, Jetter R (2006). "Cloning and characterization of a lupeol synthase involved in the synthesis of epicuticular wax crystals on stem and hypocotyl surfaces of Ricinus communis." Arch Biochem Biophys 448(1-2);60-72. PMID: 16445885

HusselsteinMull01: Husselstein-Muller T, Schaller H, Benveniste P (2001). "Molecular cloning and expression in yeast of 2,3-oxidosqualene-triterpenoid cyclases from Arabidopsis thaliana." Plant Mol Biol 45(1);75-92. PMID: 11247608

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

Shibuya07: Shibuya M, Xiang T, Katsube Y, Otsuka M, Zhang H, Ebizuka Y (2007). "Origin of structural diversity in natural triterpenes: direct synthesis of seco-triterpene skeletons by oxidosqualene cyclase." J Am Chem Soc 129(5);1450-5. PMID: 17263431

Zhang03e: Zhang H, Shibuya M, Yokota S, Ebizuka Y (2003). "Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: molecular evolution of oxidosqualene cyclases in higher plants." Biol Pharm Bull 26(5);642-50. PMID: 12736505

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 Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc13.