KEGG ENZYME: 5.4.99.41

ENZYME: 5.4.99.41

Entry

EC 5.4.99.41                Enzyme

Name

lupeol synthase;
LUPI;
BPW;
RcLUS

Class

Isomerases;
Intramolecular transferases;
Transferring other groups

Sysname

(3S)-2,3-epoxy-2,3-dihydrosqualene mutase (cyclizing, lupeol-forming)

Reaction(IUBMB)

(3S)-2,3-epoxy-2,3-dihydrosqualene = lupeol [RN:R06466]

Reaction(KEGG)

R06466

Substrate

(3S)-2,3-epoxy-2,3-dihydrosqualene [CPD:C01054]

Product

lupeol [CPD:C08628]

Comment

Also forms some beta-amyrin. The recombinant enzyme from Arabidopsis thaliana [3] gives a 1:1 mixture of lupeol and lupan-3beta,20-diol with small amounts of beta-amyrin, germanicol, taraxasterol and psi-taraxasterol. See EC 4.2.1.128 (lupan-3beta,20-diol synthase).

History

EC 5.4.99.41 created 2011

Pathway

ec00909

Sesquiterpenoid and triterpenoid biosynthesis

ec01110

Biosynthesis of secondary metabolites

Orthology

K15815

lupeol synthase 2

K15816

lupeol synthase 1

K20659

lupeol synthase

Genes

ATH:	AT1G78960(LUP2) AT1G78970(LUP1)

CRB:	17894179 17894180

EUS:	EUTSA_v10018166mg EUTSA_v10022563mg

BRP:	103830506 103832374

BNA:

106354658

CPAP:

110811355

PVY:	116105893 116140120

MINC:

123194247 123194248 123194249 123199220

TCC:	18589606 18595384

GRA:	105772660 105774382

GHI:	107901998 107944512 107962932

GAB:	108486269 108486446 108486699

HSYR:

120130362 120182577 120202777

DZI:	111284967 111318516

EGR:	104437295 104454355

GMX:	100794151 100810400

GSJ:	114402293 114421101

PVU:	PHAVU_002G302200g PHAVU_004G178500g

VRA:	106765073 106766643

VAR:	108322906 108345867

VUN:	114178348 114181519

VUM:	124839344 124848881

CCAJ:

109799472 109803947 109804015

APRC:

113867241

MTR:	25496085 25497034

TPRA:

123907319

CAM:

101514106

PSAT:

127118562

VVO:

131594267

ADU:	107474563 107490028 107490080 107490082 107490083 107490087 107490112

AIP:	107641335 107641345 107642153 107644502 107644510 107644513

AHF:	112729284 112747247 112747248 112751369 112751374 112751378 112799770 112801977 112801978 112801979 112801982 112801990

LANG:

109344416 109351963

PCIN:

129311120

QSA:	O6P43_003869

FVE:

101308521

RCN:	112197150 112198241

PPER:

18771897

PMUM:

103339316

PDUL:

117620888

ZJU:

107417569

MNT:	21387439 21394590 21396873

CSAV:

115695836

RCU:

8280320

JCU:

105634775

HBR:	110650225 110651734

MESC:

110613016

POP:

7496060

PEU:

105132608

JRE:	108989535 108989538 108989546 108993024 108993142 108993143 108993144 118343676

CILL:

122295685 122296515 122296516 122296517 122298490 122299869 122300163 122300164

CAVE:

132183717 132184114 132184115 132184327 132185383 132185454 132185455 132185907

QSU:	111991790 112005544 112005545

QLO:	115966272 115967540 115969538

TWL:

120001583

VVI:

100241546

VRI:

117925485

SLY:

101265842

SPEN:

107024535

SOT:

102583547

SSTN:

125877043

SDUL:

129892499

CANN:

107877838

LBB:	132616727 132636945

NTA:

107822584

NSY:

104234415

INI:	109170366 109184947

ITR:

116033081

EGT:	105969755 105970991

SSPL:

121796209

SMIL:

130988388

SHIS:

125195713 125197478

APAN:

127264905

HAN:

110940172

ECAD:

122606550

LSV:

111880217

CCAV:

112507013

RVL:

131320946

AEW:

130784273

BVG:

104886793

SOE:

110783899

CQI:

110683768

ATRI:

130800896

MOF:	131166294 131166295

NNU:

104593853

» show all

Reference

1 [PMID:9883589]

Authors

Herrera JB, Bartel B, Wilson WK, Matsuda SP

Title

Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene.

Journal

Phytochemistry 49:1905-11 (1998)
DOI:10.1016/S0031-9422(98)00366-5

Sequence

[ath:AT1G78970]

Reference

2 [PMID:10542078]

Authors

Shibuya M, Zhang H, Endo A, Shishikura K, Kushiro T, Ebizuka Y

Title

Two branches of the lupeol synthase gene in the molecular evolution of plant oxidosqualene cyclases.

Journal

Eur J Biochem 266:302-7 (1999)
DOI:10.1046/j.1432-1327.1999.00875.x

Reference

3 [PMID:10930257]

Authors

Segura MJ, Meyer MM, Matsuda SP

Title

Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol.

Journal

Org Lett 2:2257-9 (2000)
DOI:10.1021/ol006016b

Sequence

[ath:AT1G78970]

Reference

4 [PMID:12736505]

Authors

Zhang H, Shibuya M, Yokota S, Ebizuka Y

Title

Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: molecular evolution of oxidosqualene cyclases in higher plants.

Journal

Biol Pharm Bull 26:642-50 (2003)
DOI:10.1248/bpb.26.642

Sequence

[ag:BAB83087]

Reference

5 [PMID:15256745]

Authors

Hayashi H, Huang P, Takada S, Obinata M, Inoue K, Shibuya M, Ebizuka Y

Title

Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra.

Journal

Biol Pharm Bull 27:1086-92 (2004)
DOI:10.1248/bpb.27.1086

Sequence

[ag:BAD08587]

Reference

6 [PMID:16445885]

Authors

Guhling O, Hobl B, Yeats T, Jetter R

Title

Cloning and characterization of a lupeol synthase involved in the synthesis of epicuticular wax crystals on stem and hypocotyl surfaces of Ricinus communis.

Journal

Arch Biochem Biophys 448:60-72 (2006)
DOI:10.1016/j.abb.2005.12.013

Sequence

[ag:ABB76766]

Reference

7 [PMID:17803686]

Authors

Basyuni M, Oku H, Tsujimoto E, Kinjo K, Baba S, Takara K

Title

Triterpene synthases from the Okinawan mangrove tribe, Rhizophoraceae.

Journal

FEBS J 274:5028-42 (2007)
DOI:10.1111/j.1742-4658.2007.06025.x