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Literature summary extracted from

  • Hannemann, L.; Lucaciu, C.R.; Sharma, S.; Rattei, T.; Mayer, K.F.X.; Gierl, A.; Frey, M.
    A promiscuous beta-glucosidase is involved in benzoxazinoid deglycosylation in Lamium galeobdolon (2018), Phytochemistry, 156, 224-233 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.2.1.182 gene Bglu1, quantitative RT-PCR expression analysis Lamium galeobdolon
3.2.1.182 gene Bglu2, quantitative RT-PCR expression analysis Lamium galeobdolon
3.2.1.182 gene Bglu3, quantitative RT-PCR expression analysis Lamium galeobdolon
3.2.1.182 gene Bglu4, quantitative RT-PCR expression analysis Lamium galeobdolon

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.21 1.9
-
 Dhurrin isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 2.5
-
 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 4.1
-
 oleuropein isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.182 DIBOA beta-D-glucoside + H2O Lamium galeobdolon i.e. benzoxazinoid GDIBOA, a DIBOA glucoside DIBOA + beta-D-glucose
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.21 Lamium galeobdolon A0A3G1VCA8
-
-
3.2.1.21 Lamium galeobdolon A0A3G1VCA9
-
-
3.2.1.21 Lamium galeobdolon A0A3G1VCB1
-
-
3.2.1.21 Lamium galeobdolon A0A3G1VCB6
-
-
3.2.1.182 Lamium galeobdolon A0A3G1VCA8 i.e. Galeopsis galeobdolon
-
3.2.1.182 Lamium galeobdolon A0A3G1VCA9 i.e. Galeopsis galeobdolon
-
3.2.1.182 Lamium galeobdolon A0A3G1VCB1 i.e. Galeopsis galeobdolon
-
3.2.1.182 Lamium galeobdolon A0A3G1VCB6 i.e. Galeopsis galeobdolon
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.2.1.21 leaf
-
 Lamium galeobdolon
-
3.2.1.182 flower
-
 Lamium galeobdolon
-
3.2.1.182 leaf
-
 Lamium galeobdolon
-
3.2.1.182 additional information quantitative tissue expression analysis of LgGLU isozymes, LgGLU1-4, overview. Isozyme LgGLU3 shows the highest expression, LgGLU4 the lowest Lamium galeobdolon
-
3.2.1.182 root
-
 Lamium galeobdolon
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
3.2.1.21 0.002
-
 isoform GLU2, with phloridzin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.005
-
 isoform GLU4, with 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.013
-
 isoform GLU1, with trans-zeatin-O-glucoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.053
-
 isoform GLU2, with daidzin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.065
-
 isoform GLU1, with phloridzin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.071
-
 isoform GLU1, with geniposide as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.077
-
 isoform GLU4, with oleuropein as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.078
-
 isoform GLU4, with genistin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.086
-
 isoform GLU2, with 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.104
-
 isoform GLU2, with 4-nitrophenyl beta-D-fucopyranoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.104
-
 isoform GLU4, with 4-nitrophenyl beta-D-fucopyranoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.149
-
 isoform GLU4, with daidzin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.283
-
 isoform GLU1, with 4-nitrophenyl beta-D-cellobioside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.291
-
 isoform GLU2, with 4-nitrophenyl beta-D-cellobioside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.291
-
 isoform GLU4, with 4-nitrophenyl beta-D-cellobioside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.34
-
 isoform GLU4, with dhurrin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.472
-
 isoform GLU2, with 4-nitrophenyl beta-D-glucopyranoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.58
-
 isoform GLU2, with oleuropein as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 0.949
-
 isoform GLU2, with dhurrin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 1.933
-
 isoform GLU1, with genistin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 2.436
-
 isoform GLU1, with daidzin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 5.814
-
 isoform GLU4, with 4-nitrophenyl beta-D-glucopyranoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 7.139
-
 isoform GLU1, with dhurrin as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 7.967
-
 isoform GLU1, with oleuropein as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 8.66
-
 isoform GLU1, with 4-nitrophenyl beta-D-glucopyranoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 34.083
-
 isoform GLU1, with 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside as substrate, at pH 5.5 and 30°C Lamium galeobdolon

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.21 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside + H2O
-
 Lamium galeobdolon ?
-
 ?
3.2.1.21 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside + H2O best substrate for isoform GLU1 Lamium galeobdolon ?
-
 ?
3.2.1.21 4-nitrophenyl beta-D-cellobioside + H2O about 10% activity compared to 4-nitrophenyl beta-D-glucopyranoside Lamium galeobdolon 4-nitrophenol + D-cellobiose
-
 ?
3.2.1.21 4-nitrophenyl beta-D-fucopyranoside + H2O
-
 Lamium galeobdolon 4-nitrophenol + D-fucopyranose
-
 ?
3.2.1.21 4-nitrophenyl beta-D-glucopyranoside + H2O
-
 Lamium galeobdolon 4-nitrophenol + beta-D-glucopyranose
-
 ?
3.2.1.21 4-nitrophenyl beta-D-glucopyranoside + H2O best substrate for isoform GLU4 Lamium galeobdolon 4-nitrophenol + beta-D-glucopyranose
-
 ?
3.2.1.21 daidzin + H2O
-
 Lamium galeobdolon daidzein + D-glucose
-
 ?
3.2.1.21 dhurrin + H2O
-
 Lamium galeobdolon (S)-4-hydroxymandelonitrile + D-glucose
-
 ?
3.2.1.21 dhurrin + H2O best substrate for isoform GLU2 Lamium galeobdolon (S)-4-hydroxymandelonitrile + D-glucose
-
 ?
3.2.1.21 geniposide + H2O
-
 Lamium galeobdolon geniposide aglycone + D-glucose
-
 ?
3.2.1.21 genistin + H2O
-
 Lamium galeobdolon genistein + D-glucose
-
 ?
3.2.1.21 additional information 4-nitrophenyl beta-D-fucopyranoside, 4-nitrophenyl beta-D-mannopyranoside, harpagide, arbutin, and trans-zeatin-O-glucoside are no substrates Lamium galeobdolon ?
-
 ?
3.2.1.21 additional information 4-nitrophenyl beta-D-mannopyranoside, harpagide, arbutin, geniposide, genistin, and trans-zeatin-O-glucoside are no substrates Lamium galeobdolon ?
-
 ?
3.2.1.21 additional information 4-nitrophenyl beta-D-mannopyranoside, harpagide, geniposide, arbutin, and trans-zeatin-O-glucoside are no substrates Lamium galeobdolon ?
-
 ?
3.2.1.21 oleuropein + H2O
-
 Lamium galeobdolon oleuropein aglycone + D-glucose
-
 ?
3.2.1.21 phloridzin + H2O
-
 Lamium galeobdolon phloridzin aglycone + D-glucose
-
 ?
3.2.1.182 4-nitrophenyl-beta-D-cellobioside + H2O
-
 Lamium galeobdolon 4-nitrophenol + D-cellobiose
-
 ?
3.2.1.182 4-nitrophenyl-beta-D-fucopyranoside + H2O
-
 Lamium galeobdolon 4-nitrophenol + D-fucopyranose
-
 ?
3.2.1.182 4-nitrophenyl-beta-D-glucopyranoside + H2O
-
 Lamium galeobdolon 4-nitrophenol + D-glucopyranose
-
 ?
3.2.1.182 7-methoxy-2,4-dihydroxy-1,4-benzoxazin-3-one beta-D-glucoside + H2O i.e. benzoxazinoid GDIMBOA, a DIBOA glucoside Lamium galeobdolon 2-hydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin + beta-D-glucose
-
 ?
3.2.1.182 DIBOA beta-D-glucoside + H2O i.e. benzoxazinoid GDIBOA, a DIBOA glucoside Lamium galeobdolon DIBOA + beta-D-glucose
-
 ?
3.2.1.182 additional information GDIBOA BGLUs of the dicots are promiscuous enzymes Lamium galeobdolon ?
-
 ?
3.2.1.182 additional information substrate specificity of LgGLU isozymes with different substrates: artificial p-nitrophenyl glycoside substrates, benzoxazinoids, iridoids, cyanogenic glycoside, isoflavonoid glucosides, hydroquinone glucoside, and cytokinin glucoside, overview. Besides benzoxazinoid GDIBOA, the enzyme catalyzes the hydrolsis of oleuropein, dhurrin, daidzin, and genistin. The enzyme does not catalyze the hydrolysis of benzoxazinoid GDIMBOA, harpagide, arbutin, geniposide, trans-zeatin-O-glucoside, phloridzin, and 4-nitrophenyl-beta-D-mannopyranoside. GDIBOA BGLUs of the dicots are promiscuous enzymes Lamium galeobdolon ?
-
 ?
3.2.1.182 additional information substrate specificity of LgGLU isozymes with different substrates: artificial p-nitrophenyl glycoside substrates, benzoxazinoids, iridoids, cyanogenic glycoside, isoflavonoid glucosides, hydroquinone glucoside, and cytokinin glucoside, overview. Besides benzoxazinoid GDIBOA, the enzyme catalyzes the hydrolsis of oleuropein, dhurrin, daidzin, and phloridzin. The enzyme does not catalyze the hydrolysis of benzoxazinoid GDIMBOA, harpagide, arbutin, genistin, geniposide, trans-zeatin-O-glucoside, and 4-nitrophenyl-beta-D-mannopyranoside. GDIBOA BGLUs of the dicots are promiscuous enzymes Lamium galeobdolon ?
-
 ?
3.2.1.182 additional information substrate specificity of LgGLU isozymes with different substrates: artificial p-nitrophenyl glycoside substrates, benzoxazinoids, iridoids, cyanogenic glycoside, isoflavonoid glucosides, hydroquinone glucoside, and cytokinin glucoside, overview. Besides the benzoxazinoids, the enzyme catalyzes the hydrolsis of oleuropein, geniposide, dhurrin, daidzin, phloridzin, genistin, and trans-zeatin-O-glucoside. The enzyme does not catalyze the hydrolysis of harpagide, arbutin, 4-nitrophenyl-beta-D-mannopyranoside, and 4-nitrophenyl-beta-D-fucopyranoside. GDIBOA BGLUs of the dicots are promiscuous enzymes Lamium galeobdolon ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.21 BGLU
-
 Lamium galeobdolon
3.2.1.21 Glu1 isoform Lamium galeobdolon
3.2.1.21 Glu2 isoform Lamium galeobdolon
3.2.1.21 GLU3 isoform Lamium galeobdolon
3.2.1.21 GLU4 isoform Lamium galeobdolon
3.2.1.182 LgGLU1
-
 Lamium galeobdolon
3.2.1.182 LgGLU2
-
 Lamium galeobdolon
3.2.1.182 LgGLU3
-
 Lamium galeobdolon
3.2.1.182 LgGLU4
-
 Lamium galeobdolon
3.2.1.182 More cf. EC 3.2.1.21 Lamium galeobdolon

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.2.1.21 104.4
-
 oleuropein isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 112.5
-
 Dhurrin isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 211.1
-
 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon

General Information

EC Number General Information Comment Organism
3.2.1.182 evolution the enzyme belongs to the glycosyl hydrolase family 1, GH1. Benzoxazinoids are characteristic defence compounds of the Poales but are also found in some unrelated dicots. The benzoxazinoid specific BGLUs have recently been identified for the grasses maize, wheat, rye and the Ranunculaceae Consolida orientalis. All enzymes share a general substrate ambiguity but differ in detailed substrate pattern. The isolation of the second dicot GDIBOA glucosidase LgGLU1 allowed it to analyse the phylogenetic relation of the distinct BGLUs also within dicots. The data revealed long periods of independent sequence evolution before speciation Lamium galeobdolon
3.2.1.182 evolution the enzyme belongs to the glycosyl hydrolase family 1, GH1. Benzoxazinoids are characteristic defence compounds of the Poales but are also found in some unrelated dicots. The benzoxazinoid specific BGLUs have recently been identified for the grasses maize, wheat, rye and the Ranunculaceae Consolida orientalis. All enzymes share a general substrate ambiguity but differ in detailed substrate pattern. The isolation of the second dicot GDIBOA glucosidase LgGLU1 allows it to analyse the phylogenetic relation of the distinct BGLUs also within dicots. The data reveals long periods of independent sequence evolution before speciation Lamium galeobdolon
3.2.1.182 physiological function the beta-glucosidases (BGLUs) of the glycosidase hydrolase family 1 in Lamium galeobdolon are involved in hydrolysis of the benzoxazinoid GDIBOA (2,4-dihydroxy-1,4-benzoxazin-3-one glucoside) Lamium galeobdolon

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.2.1.21 25.5
-
 oleuropein isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 59
-
 Dhurrin isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon
3.2.1.21 81.6
-
 2,4-dihydroxy-1,4-benzoxazin-3-one glucoside isoform GLU1, at pH 5.5 and 30°C Lamium galeobdolon