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1. (Article ID: 12015)
Bak S, Olsen CE, Halkier BA, Møller BL
Transgenic tobacco and Arabidopsis plants expressing the two multifunctional Sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in dhurrin biosynthesis
Plant Physiology 123(4) (2000)
1437-1448
Novel cyanogenic plants have been generated by the simultaneous expression of the two multifunctional sorghum (Sorghum bicolor [L.] Moench) cytochrome P450 enzymes CYP79A1 and CYP71E1 in tobacco (Nicotiana tabacum cv Xanthi) and Arabidopsis under the regulation of the constitutive 35S promoter. CYP79A1 and CYP71E1 catalyze the conversion of the parent amino acid tyrosine to p-hydroxymandelonitrile, the aglycone of the cyanogenic glucoside dhurrin. CYP79A1 catalyzes the conversion of tyrosine to p-hydroxyphenylacetaldoxime and CYP71E1, the subsequent conversion to p-hydroxymandelonitrile. p-Hydroxymandelonitrile is labile and dissociates into p-hydroxybenzaldehyde and hydrogen cyanide, the same products released from dhurrin upon cell disruption as a result of pest or herbivore attack. In transgenic plants expressing CYP79A1 as well as CYP71E1, the activity of CYP79A1 is higher than that of CYP71E1, resulting in the accumulation of several p-hydroxyphenylacetaldoxime-derived products in the addition to those derived from p-hydroxymandelonitrile. Transgenic tobacco and Arabidopsis plants expressing only CYP79A1 accumulate the same p-hydroxyphenylacetaldoxime-derived products as transgenic plants expressing both sorghum cytochrome P450 enzymes. In addition, the transgenic CYP79A1 Arabidopsis plants accumulate large amounts of p-hydroxybenzylglucosinolate. In transgenic Arabidopsis expressing CYP71E1, this enzyme and the enzymes of the pre-existing glucosinolate pathway compete for the p-hydroxyphenylacetaldoxime as substrate, resulting in the formation of small amounts of p-hydroxybenzylglucosinolate. Cyanogenic glucosides are phytoanticipins, and the present study demonstrates the feasibility of expressing cyanogenic compounds in new plant species by gene transfer technology to improve pest and disease resistance.
NCBI PubMed ID: 10938360Publication DOI: 10.1104/pp.123.4.1437Journal NLM ID: 0401224Publisher: American Society of Plant Biologists
Correspondence: Møller BL
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Institutions: Plant Biochemistry Laboratory, Department of Plant Biology, , Royal Veterinary and Agricultural University, Copenhagen, Denmark, Department of Chemistry, Royal Veterinary and Agricultural University, Copenhagen, Denmark, Center of Molecular Plant Physiology (PlaCe), Royal Veterinary and Agricultural University, Copenhagen, Denmark
Methods: GC-EI-MS, DNA techniques, TLC, radiolabeling, enzymatic digestion, colorimetry, extraction, GC-CI-MS, centrifugation, radiography
The publication contains the following compound(s):
- Compound ID: 31273
|
b-D-Glcp-(1-8)-Subst
Subst = (Z)-2-(4-hydroxyphenyl)-N-(sulfooxy)ethanimidothioic acid = SMILES OC1=CC=C(C/{8}C(S)=N/OS(=O)(O)=O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31274
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b-D-Glcp-(1-4)-Subst
Subst = tyrosol = SMILES O{8}CCC1=CC={4}C(O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31275
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b-D-Glcp-(1-4)-Subst
Subst = 2-(4-hydroxyphenyl)acetonitrile = SMILES O{4}C1=CC=C(CC#N)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31276
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b-D-Glcp-(1-8)-Subst
Subst = (Z)-2-(4-hydroxyphenyl)acetaldehyde oxime = SMILES O{4}C1=CC=C(C/C=N\{8}O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31277
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b-D-Glcp-(1-4)-Subst
Subst = 4-hydroxybenzaldehyde = SMILES O{4}C1=CC=C(C=O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31278
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b-D-Glcp-(1-4)-Subst
Subst = 4-(hydroxymethyl)phenol = SMILES O{4}C1=CC=C({7}CO)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31279
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b-D-Glcp-(1-7)-Subst
Subst = 4-hydroxybenzoic acid = SMILES O{4}C1=CC=C({7}C(O)=O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31280
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b-D-Glcp-(1-4)-Subst
Subst = 4-hydroxybenzoic acid = SMILES O{4}C1=CC=C({7}C(O)=O)C=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 31281
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b-D-Glcp-(1-4)-Subst
Subst = 2-hydroxy-2-(4-hydroxyphenyl)acetonitrile = SMILES O{4}C1=CC=C({7}C(C#N)O)C=C1 |
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Structure type: monomer
Trivial name: dhurrin
Compound class: glycoside
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2. (Article ID: 12396)
Kakuda R, Imai M, Yaoita Y, Machida K, Kikuchi M
Secoiridoid glycosides from the flower buds of Lonicera japonica
Phytochemistry 55(8) (2000)
879-881
Two secoiridoid glycosides, loniceracetalides A and B, were isolated in very small amounts, together with 10 known iridoid glycosides, from the flower buds of Lonicera japonica. The structures of loniceracetalides A and B were determined by spectroscopic analysis.
Caprifoliaceae, flower buds, secoiridoid glycoside, Lonicera japonica, loniceracetalide A, loniceracetalide B
NCBI PubMed ID: 11140518Publication DOI: 10.1016/s0031-9422(00)00279-xJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of 2nd Analytical Chemistry, Tohoku Pharmaceutical University, Sendai, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, UV, extraction, optical rotation measurement, CC, evaporation
The publication contains the following compound(s):
- Compound ID: 27207
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b-D-Glcp-(1-1)-Subst
Subst = 8-epiloganin aglycon = SMILES O=C(C1=CO{1}[C@@H](O)[C@@]2([H])[C@]1([H])C{7}[C@H](O)[C@H]2C)OC |
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Structure type: monomer
Trivial name: 8-epiloganin
Compound class: glycoside, iridoid glycoside
Reference(s) to other database(s): CCSD:
49801, CBank-STR:1110
- Compound ID: 27269
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b-D-Glcp-(1-1)-Subst11Me
Subst = loganic acid aglycon = SMILES O={11}C(C1=CO{1}[C@@H](O)[C@@]2([H])[C@]1([H])C{7}[C@H](O)[C@@H]2C)O |
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Structure type: monomer
Trivial name: loganin
Compound class: saponin glycoside, glycoside, iridoid glycoside
Reference(s) to other database(s): CCSD:
49946, CBank-STR:1937
- Compound ID: 27272
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b-D-Glcp-(1-1)-Subst
Subst = secologanin aglycon = SMILES O=C(C1=CO{1}[C@@H](O)[C@H](C=C)[C@@H]1CC=O)OC |
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Structure type: monomer
Trivial name: secologanin
Compound class: glycoside, iridoid glycoside
Reference(s) to other database(s): CCSD:
49947, CBank-STR:5157
- Compound ID: 27273
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b-D-Glcp-(1-1)-Subst7Me7Me
Subst = secologanin aglycon diacetal = SMILES O=C(C1=CO{1}[C@@H](O)[C@H](C=C)[C@@H]1C{7}C(O){57}O)OC |
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Structure type: monomer
Trivial name: secologanin dimethyl acetal
Compound class: glycoside, iridoid glycoside
Reference(s) to other database(s): CCSD:
49948, CBank-STR:1277
- Compound ID: 27274
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b-D-Glcp-(1-1)-Subst
Subst = sweroside aglycon = SMILES O=C1C2=CO{1}[C@@H](O)[C@H](C=C)[C@]2([H])CCO1 |
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Structure type: monomer
Trivial name: sweroside
Compound class: saponin glycoside, glycoside, iridoid glycoside
Reference(s) to other database(s): CCSD:
49949, CBank-STR:1079
- Compound ID: 31796
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b-D-Glcp-(1-6)-Subst
Subst = vogeloside aglycon = SMILES O=C1C2=CO{6}[C@@H](O)[C@H](C=C)[C@]2([H])C[C@@H](OC)O1 |
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Structure type: monomer
Trivial name: vogeloside
Compound class: glycoside, iridoid glycoside
- Compound ID: 31797
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b-D-Glcp-(1-6)-Subst
Subst = epi-vogeloside aglycon = SMILES O=C1C2=CO{6}[C@@H](O)[C@H](C=C)[C@]2([H])C[C@H](OC)O1 |
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Structure type: monomer
Trivial name: epi-vogeloside
Compound class: glycoside, iridoid glycoside
- Compound ID: 32158
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b-D-Glcp-(1-1)-Subst
Subst = loniceracetalide A aglycon = SMILES C[C@@H]1[C@@H](O[C@H](O1)C[C@H]2[C@H]({1}[C@@H](OC=C2C(OC)=O)O)C=C)C |
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Structure type: monomer
Trivial name: loniceracetalide A
Compound class: glycoside, iridoid glycoside
- Compound ID: 32159
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b-D-Glcp-(1-1)-Subst
Subst = loniceracetalide B aglycon = SMILES C[C@H]1[C@H](O[C@H](O1)C[C@H]2[C@H]({1}[C@@H](OC=C2C(OC)=O)O)C=C)C |
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Structure type: monomer
Trivial name: loniceracetalide B
Compound class: glycoside, iridoid glycoside
- Compound ID: 32160
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b-D-Glcp-(1-2)-Subst9Me
Subst = secologanoside aglycon = SMILES C=C[C@@H]1[C@H](C{9}C(O)=O)C({7}C(O)=O)=CO{2}[C@H]1O |
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Structure type: monomer
Compound class: glycoside, iridoid glycoside
- Compound ID: 32161
Structure type: monomer
Trivial name: kingiside
Compound class: glycoside, iridoid glycoside
- Compound ID: 32162
Structure type: monomer
Trivial name: morroniside
Compound class: glycoside, iridoid glycoside
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