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Ligand strictosidine

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Biosynthesis of alkaloids derived from shikimate pathway, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, Indole alkaloid biosynthesis

MetaCyc

ajmaline and sarpagine biosynthesis, camptothecin biosynthesis, cinchona alkaloids biosynthesis, secologanin and strictosidine biosynthesis, strychnine biosynthesis, vindoline, vindorosine and vinblastine biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.105

strictosidine + H2O = D-glucose + strictosidine aglycone

731951, 751210, 729484, 710520

-

3.2.1.105

strictosidine = ?

135715, 135711, 135714

-

3.2.1.105

2 entries

4.3.3.2

3-alpha(S)-strictosidine + H2O = tryptamine + secologanin

679162, 679175, 680382, 679176

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine

648725, 648726, 393871, 648717, 648723, 648713, 648714, 648715, 648716, 648718, 648720, 648721, 648728, 648729, 648719, 648722, 648730, 648727

-

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine + H2O

-

-

4.3.3.2

2 entries

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.219

strictosidine + UDP = ?

488938

-

3.2.1.105

strictosidine + H2O = cathenamine

670558

-

3.2.1.105

strictosidine + H2O = D-glucose + strictosidine aglycone

135711, 135713, 678705, 731951, 135712, 655431, 713606, 751210, 135714, 729484, 135710, 710520, 714624

-

3.2.1.105

strictosidine = ?

135715, 135711, 135714

-

3.2.1.125

strictosidine + H2O = ?

682286, 488938

-

3.2.1.125

strictosidine + H2O = strictosidine aglycone + D-glucose

713606

-

3.2.1.105

3 entries

3.2.1.125

2 entries

3.2.1.21

strictosidine + H2O = ?

698851

-

4.3.3.2

3-alpha(S)-strictosidine + H2O = tryptamine + secologanin

679162, 679175, 680382, 679176

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.3.2

secologanin + tryptamine = 3-alpha(S)-strictosidine + H2O

-

-

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine

648723, 648714, 648715, 648716, 648718, 648720, 648721, 648725, 648726, 648728, 648729, 648713, 393871, 648719, 648722, 648717, 648730, , 648727

-

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine + H2O

-

-

4.3.3.2

tryptamine + secologanin = 3alpha(S)-strictosidine

-

-

4.3.3.2

4 entries

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.105

enzyme I shows substrate inhibition at 1 mM, enzyme II not

135715

-

4.3.3.2

-

648723

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.2.1.21

2.1

-

pH 5.0, 30°C

698851

K_M Value (16 results)

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Show KM Value (16 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.219

1.8

-

-

488938

3.2.1.105

0.01

0.018

-

135712

3.2.1.105

0.018

-

-

135711

3.2.1.105

0.1

-

enzyme II

135715

3.2.1.105

0.12

-

-

135712

3.2.1.105

0.12

-

pH 5, 30°C

655431

3.2.1.105

0.12

-

pH 6.3, 30°C

135712

3.2.1.105

0.12

-

pH and temperature not specified in the publication

713606

3.2.1.105

0.2

-

enzyme I

135715

3.2.1.105

0.22

-

pH 6.0, 37°C

678705

3.2.1.105

0.25

0.33

enzyme form SGIII

135710

3.2.1.105

1

-

above, enzyme form SGII

135710

3.2.1.105

10

-

pH 6.3, 30°C

135712

3.2.1.125

1.8

-

pH 5, 28°C, recombinant RG

488938

3.2.1.125

1.8

-

wild type enzyme, pH and temperature not specified in the publication

713606

3.2.1.105

12 entries

3.2.1.125

2 entries

3.2.1.21

0.19

-

pH 5.0, 30°C

698851

References & Links

Literature References (40)

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Show Reference (40 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

135710

-

Strictosidine glucosidase from suspension cultured cells of Tabernaemontana divaricata

1996

Luijendijk, T.J.C.; Nowak, A.; Verpoorte, R.

Phytochemistry

41

1451-1456

135711

-

Purification and characterization of strictosidine beta-D-glucosidase from Catharanthus roseus cell suspension cultures

1998

Luijendijk, T.J.C.; Stevens, L.H.; Verpoorte, R.

Plant Physiol. Biochem.

36

419-425

135712

-

New strictosidine beta-glucosidase from Strychnos mellodora

2000

Brandt, V.; Geerlings, A.; Tits, M.; Delaude, C.; van der Heijden, R.; Verpoorte, R.; Angenot, L.

Plant Physiol. Biochem.

38

187-192

135713

24201788

Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and Tabernaemontana divaricata

1993

Stevens, L.H.; Blom, T.J.M.; Verpoorte, R.

Plant Cell Rep.

12

573-576

135714

10652285

Molecular cloning and analysis of strictosidine beta-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus

2000

Geerlings, A.; Martinez-Lozano Ibanez, M.; Memlink, J.; van der Heijden, R.; Verpoorte, R.

J. Biol. Chem.

275

3051-3056

135715

6768587

Glucosidases involved in indole alkaloid biosynthesis of Catharanthus cell culture

1980

Hemscheid, T.; Zenk, M.H.

FEBS Lett.

110

187-191

393871

7764480

Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture

1994

Kutchan, T.M.; Bock, A.; Dittrich, H.

Phytochemistry

35

353-360

488938

10975500

Molecular cloning and functional bacterial expression of a plant glucosidase specifically involved in alkaloid biosynthesis

2000

Warzecha, H.; Gerasimenko, I.; Kutchan, T.M.; Stockigt, J.

Phytochemistry

54

657-666

648713

510306

Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation

1979

Treimer, J.F.; Zenk, M.H.

Eur. J. Biochem.

101

225-233

648714

476085

Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cell

1979

Mizukami, H.; Nordlov, H.; Lee, S.L.; Scott, A.I.

Biochemistry

18

3760-3763

648715

-

Strictosidine synthase from cell cultrues of Apocynaceae plants

1979

Treimer, J.F.; Zenk, M.H.

FEBS Lett.

97

159-162

648716

17396930

Immobilization of strictosidine synthase from Catharanthus cell cultures and preparative synthesis of strictosidine

1982

Pfitzner, U.; Zenk, M.H.

Planta Med.

46

10-14

648717

-

Tryptophan decarboxylase, strictosidine synthase and alkaloid production by Cinchona ledgerinana suspension cultures

1987

Skinner, S.E.; Walton, N.J.; Robins, R.J.; Rhodes, M.J.C.

Phytochemistry

26

721-725

648718

-

Isoation and immobilization of strictosidine synthase

1987

Pfitzner, U.; Zenk, M.H.

Methods Enzymol.

136

342-350

648719

-

Homogeneous strictosidine synthase from cell suspension cultures of Rauvolfia serpentina

1988

Hampp, N.; Zenk, M.H.

Phytochemistry

27

3811-3815

648720

2742131

Assay of trictosidine synthase from plant cell cultures by high-performance liquid chromatography

1989

Pennings, E.J.M.; Van den Bosch, R.A.; Van der Heijden, R.; Stevens, L.H.; Duine, J.A.; Verpoorte, R.

Anal. Biochem.

176

412-415

648721

1330135

Purification of an indole alkaloid biosynthetic enzyme, strictosidine synthase, from a recombinant strain of Escherichia coli

1992

Roessner, C.A.; Devagupta, R.; Hasan, M.; Williams, H.J.; Scott, A.I.

Protein Expr. Purif.

3

295-300

648722

1567228

Strictosidine synthase from Rauvolfia serpentina: analysis of a gene involved in indole alkaloid biosynthesis

1992

Bracher, D.; Kutchan, T.M.

Arch. Biochem. Biophys.

294

717-723

648723

-

Purification and characterization of strictosidine synthase from a suspension culture of Cinchona robusta

1993

Stevens, L.H.; Giroud, C.; Pennings, E.J.M.; Verpoorte, R.

Phytochemistry

33

99-106

648725

7887913

Strictosidine synthase from Catharanthus roseus: purification and characterization of multiple forms

1995

de Waal, A.; Meijer, A.H.; Verpoorte, R.

Biochem. J.

306

571-580

648726

30732419

Suspension cultured transgenic cells of Nicotiana tabacum expressing tryptophan decarboxylase and strictosidine synthase cDNAs from Catharanthus roseus produce strictosidine upon secologanin feeding.

1997

Hallard, D.; Van der Heijden, R.; Verpoorte, R.; Lopes Cardoso, M.I.; Pasquali, G.; Memelink, J.; Hoge, J.H.C.

Plant Cell Rep.

17

50-54

648727

9640666

Effects of over-expression of strictosidine synthase and tryptophan decarboxylase on alkaloid production by cell cultures of Catharanthus roseus

1998

Canel, C.; Lopes-Cardoso, M.I.; Whitmer, S.; van der Fits, L.; Pasquali, G.; van der Heijden, R.; Hoge, J.H.; Verpoorte, R.

Planta

205

414-419

648728

10380815

The promoter of the strictosidine synthase gene from periwinkle confers elicitor-inducible expression in transgenic tobacco and binds nuclear factors GT-1 and GBF

1999

Pasquali, G.; Erven, A.S.; Ouwerkerk, P.B.; Menke, F.L.; Memelink, J.

Plant Mol. Biol.

39

1299-1310

648729

-

Effect of precursor feeding on alkaloid accumulation by a strictosidine synthase over-expressing transgenic cell line S1 of Catharanthus roseus

2002

Whitmer, S.; van der Heijden, R.; Verpoorte, R.

Plant Cell Tissue Organ Cult.

69

85-93

648730

12620359

Metabolite profiling of alkaloids and strictosidine synthase activity in camptothecin producing plants

2003

Yamazaki, Y.; Urano, A.; Sudo, H.; Kitajima, M.; Takayama, H.; Yamazaki, M.; Aimi, N.; Saito, K.

Phytochemistry

62

461-470

655431

11985599

Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids

2002

Gerasimenko, I.; Sheludko, Y.; Ma, X.; Stockigt, J.

Eur. J. Biochem.

269

2204-2213

670558

16262708

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

2005

Murata, J.; De Luca, V.

Plant J.

44

581-594

678705

18061449

Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis

2007

Yerkes, N.; Wu, J.X.; McCoy, E.; Galan, M.C.; Chen, S.; OConnor, S.E.

Bioorg. Med. Chem. Lett.

18

3095-3098

679162

17113995

Redesign of a central enzyme in alkaloid biosynthesis

2006

Chen, S.; Galan, M.C.; Coltharp, C.; OConnor, S.E.

Chem. Biol.

13

1137-1141

679175

17719488

Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle

2007

Bernhardt, P.; McCoy, E.; OConnor, S.E.

Chem. Biol.

14

888-897

679176

17884630

Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries

2007

Loris, E.A.; Panjikar, S.; Ruppert, M.; Barleben, L.; Unger, M.; Schuebel, H.; Stoeckigt, J.

Chem. Biol.

14

979-985

680382

18081287

Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme

2008

Maresh, J.J.; Giddings, L.A.; Friedrich, A.; Loris, E.A.; Panjikar, S.; Trout, B.L.; Stoeckigt, J.; Peters, B.; OConnor, S.E.

J. Am. Chem. Soc.

130

710-723

682286

-

The molecular architecture of major enzymes from ajmaline biosynthetic pathway

2007

Stoeckigt, J.; Panjikar, S.; Ruppert, M.; Barleben, L.; Ma, X.; Loris, E.; Hill, M.

Phytochem. Rev.

6

15-34

698851

18927081

The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha

2008

Nomura, T.; Quesada, A.L.; Kutchan, T.M.

J. Biol. Chem.

283

34650-34659

710520

20217156

Influence of cellular differentiation and elicitation on intermediate and late steps of terpenoid indole alkaloid biosynthesis in Catharanthus roseus

2010

Shukla, A.K.; Shasany, A.K.; Verma, R.K.; Gupta, M.M.; Mathur, A.K.; Khanuja, S.P.

Protoplasma

242

35-47

713606

22004291

Structures of alkaloid biosynthetic glucosidases decode substrate specificity

2012

Xia, L.; Ruppert, M.; Wang, M.; Panjikar, S.; Lin, H.; Rajendran, C.; Barleben, L.; Stoeckigt, J.

ACS Chem. Biol.

7

226-234

714624

20723215

Strictosidine activation in Apocynaceae: Towards a nuclear time bomb?

2010

Guirimand, G.; Courdavault, V.; Lanoue, A.; Mahroug, S.; Guihur, A.; Blanc, N.; Giglioli-Guivarch, N.; St-Pierre, B.; Burlat, V.

BMC Plant Biol.

10

182

729484

23606578

Strictosidine-related enzymes involved in the alkaloid biosynthesis of Uncaria tomentosa root cultures grown under oxidative stress

2013

Vera-Reyes, I.; Huerta-Heredia, A.A.; Ponce-Noyola, T.; Flores-Sanchez, I.J.; Esparza-Garcia, F.; Cerda-Garcia-Rojas, C.M.; Trejo-Tapia, G.; Ramos-Valdivia, A.C.

Biotechnol. Prog.

29

621-630

731951

22408455

Expression patterns of genes involved in the defense and stress response of Spiroplasma citri infected Madagascar periwinkle Catharanthus roseus

2012

Nejat, N.; Vadamalai, G.; Dickinson, M.

Int. J. Mol. Sci.

13

2301-2313

751210

25140865

Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours

2015

Xia, L.; Lin, H.; Staniek, A.; Panjikar, S.; Ruppert, M.; Hilgers, P.; Williardt, J.; Rajendran, C.; Wang, M.; Warzecha, H.; Jäger, V.; Stöckigt, J.

J. Enzyme Inhib. Med. Chem.

30

472-478

Links to other databases for strictosidine

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Show Links (1 entry)

ChEBI

PubChem

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