MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Arabidopsis thaliana col: lupeol/lupan-3β,20-diol synthaseInferred from experiment: LUP1
multifunctional triterpene synthaseInferred from experiment: PEN6
Betula platyphylla japonica: lupeol synthaseInferred from experiment: OSCBPW
Bruguiera gymnorhiza: lupeol synthaseInferred from experiment: BgLUS
Kandelia candel: triterpene synthaseInferred from experiment: KcMS
Rhizophora stylosa: triterpene synthaseInferred from experiment: RsM1
triterpene synthaseInferred from experiment: RsM2

In Pathway: mangrove triterpenoid biosynthesis, pentacyclic triterpene biosynthesis, lupeol biosynthesis

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the Enzyme Commission system.

Mass balance status: Balanced.

Enzyme Commission Primary Name: lupeol synthase

Enzyme Commission Synonyms: LUPI, BPW, RcLUS

Standard Gibbs Free Energy (ΔrG in kcal/mol): -120.3Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
Also forms some β-amyrin. The recombinant enzyme from Arabidopsis thaliana [Segura00] gives a 1:1 mixture of lupeol and lupan-3β,20-diol with small amounts of β-amyrin, germanicol, taraxasterol and Ψ-taraxasterol. See EC (lupan-3β,20-diol synthase).

Citations: [Guhling06, Herrera98, Shibuya99, Zhang03i, Hayashi04, Basyuni07]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R06466, Rhea:31386

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:

Revised 11-Apr-2011 by Caspi R, SRI International


Basyuni07: 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

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

Hayashi04: Hayashi H, Huang P, Takada S, Obinata M, Inoue K, Shibuya M, Ebizuka Y (2004). "Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra." Biol Pharm Bull 27(7);1086-92. PMID: 15256745

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

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

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

Shibuya99: Shibuya M, Zhang H, Endo A, Shishikura K, Kushiro T, Ebizuka Y (1999). "Two branches of the lupeol synthase gene in the molecular evolution of plant oxidosqualene cyclases." Eur J Biochem 266(1);302-7. PMID: 10542078

Zhang03i: 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

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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
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