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Banskota AH, Tezuka Y, Adnyana IK, Xiong Q, Hase K, Tran KQ, Tanaka K, Saiki I, Kadota S
Hepatoprotective effect of Combretum quadrangulare and its constituents
Biological and Pharmaceutical Bulletin 23(4) (2000)
456-460
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b-D-Glcp-(1-3)-Subst
Subst = β-sitosterol = SMILES O{3}[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@@]2([H])CC[C@@]4(C)[C@]3([H])CC[C@]4([C@@H](C)CC[C@@H](CC)C(C)C)[H] |
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Combretum quadrangulare
(Ancestor NCBI TaxID 99434,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
NCBI PubMed ID: 10784427Publication DOI: 10.1248/bpb.23.456Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: National University Ho Chi Minh City, Ho Chi Minh City, Vietnam, Institute of Narural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Japan, National Research Institute of Police Science, Tokyo, Japan
The MeOH extract of leaves of Combretum quadrangulare showed significant hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced experimental liver injury in mice and on D-GalN/tumor necrosis factor-α (TNF-α)-induced cell death in primary cultured mouse hepatocytes. Phytochemical investigation led to the isolation of thirty cycloartane-type triterpenes together with betulinic acid, beta-sitosterol, beta-sitosterol glucoside, 4 flavones (34-37), and 3 flavone C-glucosides (38-40). These compounds showed various potencies of hepatoprotective effect on D-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. Quadrangularol B (29), methyl quadrangularate I (33), kamatakenin (34), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (35), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (36) and isokaempferide (37) showed strong inhibitory effect on TNF-α-induced cell death with IC50 values of 34.3, 33.7, 13.3, 22.4, 13.4 and 22.8 μM, respectively, whereas clinically-used silibinin had an IC50 value of 39.6 microM and glycyrrhizin showed very weak inhibitory effect. Methyl quadrangularates A (30) and N (32), norquadrangularic acid B (31) and vitexin (40) also showed potent inhibition on TNF-α-induced cell death with IC50 values of 45.7, 89.3, 67.6 and 40.1 μM, respectively. The flavonoids and some of the cycloartane-type triterpenes appeared to be the hepatoprotective principles of the leaves of C. quadrangulare.
flavone, flavone C-glycoside, hepatoprotective effect, Combretum quadrangulare, cycloartane-type triterpene
Structure type: monomer
Location inside paper: p. 457, Chart 1, structure 19
Trivial name: daucosterol, β-daucosterol, β-sitosterol, β-sitosterol-β-D-glucoside, androsine, saxifragifolin B, β-sitosterol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, triterpene glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, biological assays, extraction, column chromatography, evaporation, MTT, RP-PTLC
Related record ID(s): 64820, 64821, 64822
NCBI Taxonomy refs (TaxIDs): 99434Reference(s) to other database(s): GenDB:MK026953.1
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Banskota AH, Tezuka Y, Adnyana IK, Xiong Q, Hase K, Tran KQ, Tanaka K, Saiki I, Kadota S
Hepatoprotective effect of Combretum quadrangulare and its constituents
Biological and Pharmaceutical Bulletin 23(4) (2000)
456-460
Combretum quadrangulare
(Ancestor NCBI TaxID 99434,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
NCBI PubMed ID: 10784427Publication DOI: 10.1248/bpb.23.456Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: National University Ho Chi Minh City, Ho Chi Minh City, Vietnam, Institute of Narural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Japan, National Research Institute of Police Science, Tokyo, Japan
The MeOH extract of leaves of Combretum quadrangulare showed significant hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced experimental liver injury in mice and on D-GalN/tumor necrosis factor-α (TNF-α)-induced cell death in primary cultured mouse hepatocytes. Phytochemical investigation led to the isolation of thirty cycloartane-type triterpenes together with betulinic acid, beta-sitosterol, beta-sitosterol glucoside, 4 flavones (34-37), and 3 flavone C-glucosides (38-40). These compounds showed various potencies of hepatoprotective effect on D-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. Quadrangularol B (29), methyl quadrangularate I (33), kamatakenin (34), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (35), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (36) and isokaempferide (37) showed strong inhibitory effect on TNF-α-induced cell death with IC50 values of 34.3, 33.7, 13.3, 22.4, 13.4 and 22.8 μM, respectively, whereas clinically-used silibinin had an IC50 value of 39.6 microM and glycyrrhizin showed very weak inhibitory effect. Methyl quadrangularates A (30) and N (32), norquadrangularic acid B (31) and vitexin (40) also showed potent inhibition on TNF-α-induced cell death with IC50 values of 45.7, 89.3, 67.6 and 40.1 μM, respectively. The flavonoids and some of the cycloartane-type triterpenes appeared to be the hepatoprotective principles of the leaves of C. quadrangulare.
flavone, flavone C-glycoside, hepatoprotective effect, Combretum quadrangulare, cycloartane-type triterpene
Structure type: monomer
Location inside paper: p. 457, Chart 1, structure 38
Trivial name: isoorientin, homoorientin, isoorientin
Compound class: glycoside, flavonoid glycoside, flavone glycoside
Contained glycoepitopes: IEDB_613439
Methods: 13C NMR, 1H NMR, biological assays, extraction, column chromatography, evaporation, MTT, RP-PTLC
Related record ID(s): 64819, 64821, 64822
NCBI Taxonomy refs (TaxIDs): 99434
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There is only one chemically distinct structure:
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Banskota AH, Tezuka Y, Adnyana IK, Xiong Q, Hase K, Tran KQ, Tanaka K, Saiki I, Kadota S
Hepatoprotective effect of Combretum quadrangulare and its constituents
Biological and Pharmaceutical Bulletin 23(4) (2000)
456-460
Combretum quadrangulare
(Ancestor NCBI TaxID 99434,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
NCBI PubMed ID: 10784427Publication DOI: 10.1248/bpb.23.456Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: National University Ho Chi Minh City, Ho Chi Minh City, Vietnam, Institute of Narural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Japan, National Research Institute of Police Science, Tokyo, Japan
The MeOH extract of leaves of Combretum quadrangulare showed significant hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced experimental liver injury in mice and on D-GalN/tumor necrosis factor-α (TNF-α)-induced cell death in primary cultured mouse hepatocytes. Phytochemical investigation led to the isolation of thirty cycloartane-type triterpenes together with betulinic acid, beta-sitosterol, beta-sitosterol glucoside, 4 flavones (34-37), and 3 flavone C-glucosides (38-40). These compounds showed various potencies of hepatoprotective effect on D-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. Quadrangularol B (29), methyl quadrangularate I (33), kamatakenin (34), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (35), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (36) and isokaempferide (37) showed strong inhibitory effect on TNF-α-induced cell death with IC50 values of 34.3, 33.7, 13.3, 22.4, 13.4 and 22.8 μM, respectively, whereas clinically-used silibinin had an IC50 value of 39.6 microM and glycyrrhizin showed very weak inhibitory effect. Methyl quadrangularates A (30) and N (32), norquadrangularic acid B (31) and vitexin (40) also showed potent inhibition on TNF-α-induced cell death with IC50 values of 45.7, 89.3, 67.6 and 40.1 μM, respectively. The flavonoids and some of the cycloartane-type triterpenes appeared to be the hepatoprotective principles of the leaves of C. quadrangulare.
flavone, flavone C-glycoside, hepatoprotective effect, Combretum quadrangulare, cycloartane-type triterpene
Structure type: monomer
Location inside paper: p. 457, Chart 1, structure 39
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_613414
Methods: 13C NMR, 1H NMR, biological assays, extraction, column chromatography, evaporation, MTT, RP-PTLC
Related record ID(s): 64819, 64820, 64822
NCBI Taxonomy refs (TaxIDs): 99434
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There is only one chemically distinct structure:
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Banskota AH, Tezuka Y, Adnyana IK, Xiong Q, Hase K, Tran KQ, Tanaka K, Saiki I, Kadota S
Hepatoprotective effect of Combretum quadrangulare and its constituents
Biological and Pharmaceutical Bulletin 23(4) (2000)
456-460
Combretum quadrangulare
(Ancestor NCBI TaxID 99434,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
NCBI PubMed ID: 10784427Publication DOI: 10.1248/bpb.23.456Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: National University Ho Chi Minh City, Ho Chi Minh City, Vietnam, Institute of Narural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Japan, National Research Institute of Police Science, Tokyo, Japan
The MeOH extract of leaves of Combretum quadrangulare showed significant hepatoprotective effect on D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced experimental liver injury in mice and on D-GalN/tumor necrosis factor-α (TNF-α)-induced cell death in primary cultured mouse hepatocytes. Phytochemical investigation led to the isolation of thirty cycloartane-type triterpenes together with betulinic acid, beta-sitosterol, beta-sitosterol glucoside, 4 flavones (34-37), and 3 flavone C-glucosides (38-40). These compounds showed various potencies of hepatoprotective effect on D-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. Quadrangularol B (29), methyl quadrangularate I (33), kamatakenin (34), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (35), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (36) and isokaempferide (37) showed strong inhibitory effect on TNF-α-induced cell death with IC50 values of 34.3, 33.7, 13.3, 22.4, 13.4 and 22.8 μM, respectively, whereas clinically-used silibinin had an IC50 value of 39.6 microM and glycyrrhizin showed very weak inhibitory effect. Methyl quadrangularates A (30) and N (32), norquadrangularic acid B (31) and vitexin (40) also showed potent inhibition on TNF-α-induced cell death with IC50 values of 45.7, 89.3, 67.6 and 40.1 μM, respectively. The flavonoids and some of the cycloartane-type triterpenes appeared to be the hepatoprotective principles of the leaves of C. quadrangulare.
flavone, flavone C-glycoside, hepatoprotective effect, Combretum quadrangulare, cycloartane-type triterpene
Structure type: monomer
Location inside paper: p. 457, Chart 1, structure 40
Trivial name: vitexin, vicenin-2
Compound class: glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_613414
Methods: 13C NMR, 1H NMR, biological assays, extraction, column chromatography, evaporation, MTT, RP-PTLC
Related record ID(s): 64819, 64820, 64821
NCBI Taxonomy refs (TaxIDs): 99434
Show glycosyltransferases
There is only one chemically distinct structure:
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