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de Mesquita ML, Grellier P, Blond A, Brouard JP, de Paula JE, Espindola LS, Mambu L
New ether diglycosides from Matayba guianensis with antiplasmodial activity
Bioorganic and Medicinal Chemistry 13(14) (2005)
4499-4506
Matayba guianensis
(NCBI TaxID 557007,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root bark
The structure was elucidated in this paperJournal NLM ID: 9413298WWW link: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15908216Publisher: Elsevier
Institutions: Laboratorio de Farmacognosia, Faculdade de Ciencias da Saude, Universidade de Brasilia, Brasilia, Brazil
Four new ether diglycosides (1-4), named matayosides A-D, were isolated from the root bark of Matayba guianensis, a plant exhibiting in vitro antiplasmodial activity. They were identified as hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-palmi toyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-4,6-di-O- acetyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O- acetyl-β-D-glucopyranoside and hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-acety l-β-D-glucopyranoside, respectively. Their structures were established using one- and two-dimensional NMR techniques, mass spectrometry (MS) and MS/MS experiments. The compounds were found to inhibit the growth of Plasmodium falciparum in vitro with IC50 values ranging from 2.5 to 8.9 microg/mL
chemistry, Carbohydrate Conformation, glycosides, in vitro, isolation & purification, Spectrum Analysis, drug effects, pharmacology, Animals, Plasmodium falciparum, Sapindaceae, Antimalarials, Ethers
Structure type: oligomer
Location inside paper: Structure 1
Trivial name: matayoside A
Contained glycoepitopes: IEDB_130422,IEDB_136105,IEDB_141181,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: NMR, TLC, MS-MS, Haemolysis assay
Biological activity: antiplasmodial activity
Related record ID(s): 14412, 14512, 14612
NCBI Taxonomy refs (TaxIDs): 557007
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There is only one chemically distinct structure:
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de Mesquita ML, Grellier P, Blond A, Brouard JP, de Paula JE, Espindola LS, Mambu L
New ether diglycosides from Matayba guianensis with antiplasmodial activity
Bioorganic and Medicinal Chemistry 13(14) (2005)
4499-4506
Matayba guianensis
(NCBI TaxID 557007,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root bark
The structure was elucidated in this paperJournal NLM ID: 9413298WWW link: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15908216Publisher: Elsevier
Institutions: Laboratorio de Farmacognosia, Faculdade de Ciencias da Saude, Universidade de Brasilia, Brasilia, Brazil
Four new ether diglycosides (1-4), named matayosides A-D, were isolated from the root bark of Matayba guianensis, a plant exhibiting in vitro antiplasmodial activity. They were identified as hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-palmi toyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-4,6-di-O- acetyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O- acetyl-β-D-glucopyranoside and hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-acety l-β-D-glucopyranoside, respectively. Their structures were established using one- and two-dimensional NMR techniques, mass spectrometry (MS) and MS/MS experiments. The compounds were found to inhibit the growth of Plasmodium falciparum in vitro with IC50 values ranging from 2.5 to 8.9 microg/mL
chemistry, Carbohydrate Conformation, glycosides, in vitro, isolation & purification, Spectrum Analysis, drug effects, pharmacology, Animals, Plasmodium falciparum, Sapindaceae, Antimalarials, Ethers
Structure type: oligomer
Location inside paper: Structure 2
Trivial name: matayoside B
Contained glycoepitopes: IEDB_130422,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: NMR, TLC, MS-MS, Haemolysis assay
Biological activity: antiplasmodial activity
Related record ID(s): 11412, 14512, 14612
NCBI Taxonomy refs (TaxIDs): 557007
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There is only one chemically distinct structure:
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de Mesquita ML, Grellier P, Blond A, Brouard JP, de Paula JE, Espindola LS, Mambu L
New ether diglycosides from Matayba guianensis with antiplasmodial activity
Bioorganic and Medicinal Chemistry 13(14) (2005)
4499-4506
Matayba guianensis
(NCBI TaxID 557007,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root bark
The structure was elucidated in this paperJournal NLM ID: 9413298WWW link: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15908216Publisher: Elsevier
Institutions: Laboratorio de Farmacognosia, Faculdade de Ciencias da Saude, Universidade de Brasilia, Brasilia, Brazil
Four new ether diglycosides (1-4), named matayosides A-D, were isolated from the root bark of Matayba guianensis, a plant exhibiting in vitro antiplasmodial activity. They were identified as hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-palmi toyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-4,6-di-O- acetyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O- acetyl-β-D-glucopyranoside and hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-acety l-β-D-glucopyranoside, respectively. Their structures were established using one- and two-dimensional NMR techniques, mass spectrometry (MS) and MS/MS experiments. The compounds were found to inhibit the growth of Plasmodium falciparum in vitro with IC50 values ranging from 2.5 to 8.9 microg/mL
chemistry, Carbohydrate Conformation, glycosides, in vitro, isolation & purification, Spectrum Analysis, drug effects, pharmacology, Animals, Plasmodium falciparum, Sapindaceae, Antimalarials, Ethers
Structure type: oligomer
Location inside paper: Structure 3
Trivial name: matayoside C
Contained glycoepitopes: IEDB_130422,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: NMR, TLC, MS-MS, Haemolysis assay
Biological activity: antiplasmodial activity
Related record ID(s): 11412, 14412, 14612
NCBI Taxonomy refs (TaxIDs): 557007
Show glycosyltransferases
There is only one chemically distinct structure:
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de Mesquita ML, Grellier P, Blond A, Brouard JP, de Paula JE, Espindola LS, Mambu L
New ether diglycosides from Matayba guianensis with antiplasmodial activity
Bioorganic and Medicinal Chemistry 13(14) (2005)
4499-4506
Matayba guianensis
(NCBI TaxID 557007,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root bark
The structure was elucidated in this paperJournal NLM ID: 9413298WWW link: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15908216Publisher: Elsevier
Institutions: Laboratorio de Farmacognosia, Faculdade de Ciencias da Saude, Universidade de Brasilia, Brasilia, Brazil
Four new ether diglycosides (1-4), named matayosides A-D, were isolated from the root bark of Matayba guianensis, a plant exhibiting in vitro antiplasmodial activity. They were identified as hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-palmi toyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-4,6-di-O- acetyl-β-D-glucopyranoside, hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O- acetyl-β-D-glucopyranoside and hexadecyl-[O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)]-6-O-acety l-β-D-glucopyranoside, respectively. Their structures were established using one- and two-dimensional NMR techniques, mass spectrometry (MS) and MS/MS experiments. The compounds were found to inhibit the growth of Plasmodium falciparum in vitro with IC50 values ranging from 2.5 to 8.9 microg/mL
chemistry, Carbohydrate Conformation, glycosides, in vitro, isolation & purification, Spectrum Analysis, drug effects, pharmacology, Animals, Plasmodium falciparum, Sapindaceae, Antimalarials, Ethers
Structure type: oligomer
Location inside paper: Structure 4
Trivial name: matayoside D
Contained glycoepitopes: IEDB_130422,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: NMR, TLC, MS-MS, Haemolysis assay
Biological activity: antiplasmodial activity
Related record ID(s): 11412, 14412, 14512
NCBI Taxonomy refs (TaxIDs): 557007
Show glycosyltransferases
There is only one chemically distinct structure:
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