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18,19-dihydrostrictosidine + H2O
D-glucose + 18,19-dihydrostrictosidine aglycone
-
-
-
?
5-methylstrictosidine + H2O
D-glucose + 5-methylstrictosidine aglycone
-
-
-
-
?
5alpha-carboxystrictosidine + H2O
D-glucose + 5alpha-carboxystrictosidine aglycone
-
-
-
?
6-fluorostrictosidine + H2O
D-glucose + 6-fluorostrictosidine aglycone
-
-
-
-
?
6-methoxystrictosidine + H2O
D-glucose + 6-methoxystrictosidine aglycone
-
-
-
-
?
6-methylstrictosidine + H2O
D-glucose + 6-methylstrictosidine aglycone
-
-
-
-
?
7-fluorostrictosidine + H2O
D-glucose + 7-fluorostrictosidine aglycone
-
-
-
-
?
7-methoxystrictosidine + H2O
D-glucose + 7-methoxystrictosidine aglycone
-
-
-
-
?
7-methylstrictosidine + H2O
D-glucose + 7-methylstrictosidine aglycone
-
-
-
-
?
8-methylstrictosidine + H2O
D-glucose + 8-methylstrictosidine aglycone
-
-
-
-
?
dolichantoside + H2O
?
-
-
-
-
?
dolichantoside + H2O
D-glucose + dolichantoside aglycone
Nbeta-acetylstrictosidine + H2O
D-glucose + Nbeta-acetylstrictosidine aglycone
weak substrate
-
-
?
Nbeta-methylstrictosidine + H2O
D-glucose + Nbeta-methylstrictosidine aglycone
weak substrate
-
-
?
palicoside + H2O
D-glucose + palicoside aglycone
strictosidine + H2O
D-glucose + strictosidine aglycone
vincoside + H2O
?
-
hydrolyzed at less than 10% of strictosidine
-
-
?
vincoside + H2O
D-glucose + vincoside aglycone
-
-
-
-
?
vincoside pent-4-yn-1-yl ester + H2O
D-glucose + vincoside pent-4-yn-1-yl ester aglycone
-
-
-
-
?
additional information
?
-
dolichantoside + H2O
D-glucose + dolichantoside aglycone
-
-
-
-
?
dolichantoside + H2O
D-glucose + dolichantoside aglycone
-
-
-
?
dolichantoside + H2O
D-glucose + dolichantoside aglycone
-
-
-
-
?
palicoside + H2O
?
-
-
-
-
?
palicoside + H2O
?
-
-
-
-
?
palicoside + H2O
D-glucose + palicoside aglycone
-
-
-
-
?
palicoside + H2O
D-glucose + palicoside aglycone
-
-
-
-
?
strictosidine
?
-
-
-
-
?
strictosidine
?
-
the enzyme may play an important role in steering the monoterpenoid indole alkaloid biosynthesis in a specific direction
-
-
?
strictosidine
?
enzyme in terpenoid indole alkaloid biosynthesis
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
i.e. hemiacetal
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
specific substrate
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
The structural diversity of monoterpenoid indole alkaloids comes first from the deglucosylation of strictosidine by strictosidine beta-glucosidase. The unstable and versatile aglycone is biochemically converted by mostly uncharacterized enzyme reactions to the Corynanthe, Iboga and Aspidosperma classes of alkaloids such as ajmalicine, catharanthine and tabersonine, respectively
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
specific substrate
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
-
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
the major intermediate after rearrangement of the strictosidine aglycone is thought to be 21-hydroxyajmalicine
?
strictosidine + H2O
D-glucose + strictosidine aglycone
-
-
-
?
additional information
?
-
-
involved In the indole alkaloid biosynthesis by hydrolyzing strictosidine to cathenamine
-
-
?
additional information
?
-
no substrates: strictosidine pentaacetate, vincoside, strictosidine lactam, vincoside lactam, raucafficrine, 1,2-dihydrocafficrine, 1-methyl-1,2-dihydrocarcafficrine, secologanin, loganin, 4-nitrophenylglucoside, arbutin, vanillin-glucoside, isatinoxim-glucoside, prunasin, rhapontin, rutin, sinigrin and zeatin-glucoside
-
-
?
additional information
?
-
-
no substrates: strictosidine pentaacetate, vincoside, strictosidine lactam, vincoside lactam, raucafficrine, 1,2-dihydrocafficrine, 1-methyl-1,2-dihydrocarcafficrine, secologanin, loganin, 4-nitrophenylglucoside, arbutin, vanillin-glucoside, isatinoxim-glucoside, prunasin, rhapontin, rutin, sinigrin and zeatin-glucoside
-
-
?
additional information
?
-
the enzyme does not accept raucaffricine as substrate
-
-
?
additional information
?
-
-
no activity with secologanin, strictosamide or p-nitrophenyl-beta-D-glucopyranoside
-
-
?
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Luijendijk, T.J.C.; Nowak, A.; Verpoorte, R.
Strictosidine glucosidase from suspension cultured cells of Tabernaemontana divaricata
Phytochemistry
41
1451-1456
1996
Tabernaemontana divaricata
-
brenda
Luijendijk, T.J.C.; Stevens, L.H.; Verpoorte, R.
Purification and characterization of strictosidine beta-D-glucosidase from Catharanthus roseus cell suspension cultures
Plant Physiol. Biochem.
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1998
Catharanthus roseus
-
brenda
Brandt, V.; Geerlings, A.; Tits, M.; Delaude, C.; van der Heijden, R.; Verpoorte, R.; Angenot, L.
New strictosidine beta-glucosidase from Strychnos mellodora
Plant Physiol. Biochem.
38
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2000
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-
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Stevens, L.H.; Blom, T.J.M.; Verpoorte, R.
Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and Tabernaemontana divaricata
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Geerlings, A.; Martinez-Lozano Ibanez, M.; Memlink, J.; van der Heijden, R.; Verpoorte, R.
Molecular cloning and analysis of strictosidine beta-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus
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275
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2000
Catharanthus roseus (Q9M7N7), Catharanthus roseus
brenda
Hemscheid, T.; Zenk, M.H.
Glucosidases involved in indole alkaloid biosynthesis of Catharanthus cell culture
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110
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1980
Amsonia salicifolia, Catharanthus ovalis, Catharanthus pusillus, Catharanthus roseus, Catharanthus trichophyllus, Rauvolfia vomitoria, Amsonia orientalis, Vinca major
brenda
Gerasimenko, I.; Sheludko, Y.; Ma, X.; Stockigt, J.
Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids
Eur. J. Biochem.
269
2204-2213
2002
Rauvolfia serpentina (Q8GU20), Rauvolfia serpentina
brenda
Zarate, R.; Bonavia, M.; Geerlings, A.; van der Heijden, R.; Verpoorte, R.
Expression of strictosidine beta-D-glucosidase cDNA from Catharanthus roseus, involved in the monoterpene indole alkaloid pathway, in a transgenic suspension culture of Nicotiana tabacum
Plant Physiol. Biochem.
39
763-769
2001
Catharanthus roseus
-
brenda
Barleben, L.; Ma, X.; Koepke, J.; Peng, G.; Michel, H.; Stoeckigt, J.
Expression, purification, crystallization and preliminary X-ray analysis of strictosidine glucosidase, an enzyme initiating biosynthetic pathways to a unique diversity of indole alkaloid skeletons
Biochim. Biophys. Acta
1747
89-92
2005
Rauvolfia serpentina
brenda
Murata, J.; De Luca, V.
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
Plant J.
44
581-594
2005
Catharanthus roseus
brenda
Yerkes, N.; Wu, J.X.; McCoy, E.; Galan, M.C.; Chen, S.; OConnor, S.E.
Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis
Bioorg. Med. Chem. Lett.
18
3095-3098
2007
Catharanthus roseus
brenda
Stockigt, J.; Hammes, B.; Ruppert, M.
Construction and expression of a dual vector for chemo-enzymatic synthesis of plant indole alkaloids in Escherichia coli
Nat. Prod. Res.
24
759-766
2010
Rauvolfia serpentina
brenda
Shukla, A.K.; Shasany, A.K.; Verma, R.K.; Gupta, M.M.; Mathur, A.K.; Khanuja, S.P.
Influence of cellular differentiation and elicitation on intermediate and late steps of terpenoid indole alkaloid biosynthesis in Catharanthus roseus
Protoplasma
242
35-47
2010
Catharanthus roseus
brenda
Xia, L.; Ruppert, M.; Wang, M.; Panjikar, S.; Lin, H.; Rajendran, C.; Barleben, L.; Stoeckigt, J.
Structures of alkaloid biosynthetic glucosidases decode substrate specificity
ACS Chem. Biol.
7
226-234
2012
Rauvolfia serpentina (Q8GU20)
brenda
Guirimand, G.; Courdavault, V.; Lanoue, A.; Mahroug, S.; Guihur, A.; Blanc, N.; Giglioli-Guivarch, N.; St-Pierre, B.; Burlat, V.
Strictosidine activation in Apocynaceae: Towards a nuclear time bomb?
BMC Plant Biol.
10
182
2010
Rauvolfia serpentina (Q8GU20), Rauvolfia serpentina, Catharanthus roseus (Q9M7N7), Catharanthus roseus
brenda
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.
Strictosidine-related enzymes involved in the alkaloid biosynthesis of Uncaria tomentosa root cultures grown under oxidative stress
Biotechnol. Prog.
29
621-630
2013
Uncaria tomentosa (I6ZQ42), Uncaria tomentosa
brenda
Nejat, N.; Vadamalai, G.; Dickinson, M.
Expression patterns of genes involved in the defense and stress response of Spiroplasma citri infected Madagascar periwinkle Catharanthus roseus
Int. J. Mol. Sci.
13
2301-2313
2012
Catharanthus roseus
brenda
Xia, L.; Lin, H.; Staniek, A.; Panjikar, S.; Ruppert, M.; Hilgers, P.; Williardt, J.; Rajendran, C.; Wang, M.; Warzecha, H.; Jger, V.; Stckigt, J.
Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours
J. Enzyme Inhib. Med. Chem.
30
472-478
2015
Rauvolfia serpentina (Q8GU20)
brenda
Sun, J.; Peebles, C.A.
Engineering overexpression of ORCA3 and strictosidine glucosidase in Catharanthus roseus hairy roots increases alkaloid production
Protoplasma
253
1255-1264
2016
Catharanthus roseus (Q9M7N7), Catharanthus roseus
brenda