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1. (Article ID: 12116)
De-Eknamkul W, Suttipanta N, Kutchan TM
Purification and characterization of deacetylipecoside synthase from Alangium lamarckii Thw.
Phytochemistry 55(2) (2000)
177-181
Deacetylipecoside synthase (DIS), the enzyme catalyzing the condensation of dopamine and secologanin to form the (R)-epimer of deacetylipecoside, has been purified 570-fold from the leaves of Alangium lamarckii and partially characterized. The isolated enzyme is a single polypeptide with Mr 30,000, and has a pH optimum at 7.5 and a temperature optimum at 45 degrees C. The apparent Km values for dopamine and secologanin are 0.7 and 0.9 mM, respectively. DIS exhibits high substrate specificity toward dopamine, whereas neither tyramine nor tryptamine are utilized. The enzyme activity is not inhibited by its substrate dopamine, but is inhibited by alangimakine and dehydroalangimakine with similar I50 values of 10 μM. DIS presumably provides (R)-deacetylipecoside for the formation of tetrahydroisoquinoline monoterpene glucosides that also possess an (R)-configuration at the same chiral center.
characterization, purification, Alangiaceae, Alangium lamarkii, deacetylipecoside, deacetylipecoside synthase, isoquinoline monoterpenoid biosynthesis
NCBI PubMed ID: 11065292Publication DOI: 10.1016/s0031-9422(00)00260-0Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: De-Eknamkul W
chula.ac.th>
Institutions: Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, Leibniz-Institüt für Pflanzenbiochemie, Halle (Saale), Germany
Methods: SDS-PAGE, inhibition studies, radiolabeling, radioactivity measurement, HPLC, GPC, extraction, CC, enzymatic assay, precipitation, centrifugation
The publication contains the following compound(s):
- Compound ID: 27272
|
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: 31509
|
b-D-Glcp-(1-2)-Subst
Subst = deacetylipecoside aglycon = SMILES O=C(OC)C1=CO{2}[C@@H](O)[C@H](C=C)[C@@H]1C[C@@H]2C3=C{57}C(O)={56}C(O)C=C3CCN2 |
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Structure type: monomer
Trivial name: deacetylipecoside
Compound class: glycoside
- Compound ID: 31510
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b-D-Glcp-(1-2)-Subst
Subst = deacetylisoipecoside aglycon = SMILES O=C(OC)C1=CO{2}[C@@H](O)[C@H](C=C)[C@@H]1C[C@H]2C3=C{57}C(O)={56}C(O)C=C3CCN2 |
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Structure type: monomer
Trivial name: deacetylisoipecoside
Compound class: glycoside
- Compound ID: 31511
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b-D-Glcp-(1-2)-Subst6'Me
Subst = demethylalangiside aglycon = SMILES O{56}C1={57}C(O)C=C2[C@H]3C[C@H]4[C@@H](C=C){2}[C@H](O)OC=C4C(N3CCC2=C1)=O |
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Structure type: monomer
Trivial name: alangiside
Compound class: glycoside
- Compound ID: 31512
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b-D-Glcp-(1-2)-Subst6'Me
Subst = demethylisoalangiside aglycon = SMILES O{56}C1={57}C(O)C=C2[C@@H]3C[C@H]4[C@@H](C=C){2}[C@H](O)OC=C4C(N3CCC2=C1)=O |
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Structure type: monomer
Trivial name: isoalangiside
Compound class: glycoside
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