Found 10 structures.
Displayed structures from 1 to 10
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 27872
Structure type: monomer
; 329 [M-H]-
C16H25O7
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
2. Compound ID: 27873
Structure type: monomer
; 329 [M-H]-
C16H25O7
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
3. Compound ID: 27874
Structure type: monomer
; 315 [M-H]-
C15H23O7
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
4. Compound ID: 27875
Structure type: monomer
; 315 [M-H]-
C15H23O7
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
5. Compound ID: 27876
|
b-D-Quip-(1-6)-Subst
Subst = 6R-hydroxy-2-hydroxymethyl-6-methyl-2E,7-octadienoic acid = SMILES C=C{6}[C@](C)(O)CC/C=C({9}CO)/{1}C(O)=O |
Show graphically |
Structure type: monomer
; 383 [M+Na]+
C17H29O8
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
6. Compound ID: 27877
|
b-D-Quip-(1-6)-Subst
Subst = 6S-hydroxy-2-hydroxymethyl-6-methyl-2E,7-octadienoic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C({9}CO)/{1}C(O)=O |
Show graphically |
Structure type: monomer
; 383 [M+Na]+
C17H29O8
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 11144
Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" -
Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.
13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside
Publication DOI: 10.1248/cpb.45.807Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
Expand this compound
Collapse this compound
7. Compound ID: 33040
|
Subst1-(1-4)-b-D-Quip-(1-6)-Subst2-(1-21)-+
|
a-L-Araf-(1-4)-+ |
| |
b-D-Glcp-(1-2)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst
|
a-L-Arap-(1-6)-+ |
| |
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES O{1}C(/C({9}CO)=C/CC{6}C(C)(O)C=C)=O;
Subst2 = 6R-hydroxy-2-hydroxymethyl-6-methyl-2E,7-octadienoic acid = SMILES C=C{6}[C@](C)(O)CC/C=C({9}CO)/{1}C(O)=O |
Show graphically |
Structure type: oligomer
Trivial name: kinmoonoside A
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_136907,IEDB_140628,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12757
Tezuka Y, Honda K, Banskota AH, Thet MM, Kadota S "Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar" -
Journal of Natural Products 63(12) (2000) 1658-1664
Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.
cytotoxicity, Acacia concinna, kinmoonosides A-C, HT-1080 fibrosarcoma
NCBI PubMed ID: 11141109Publication DOI: 10.1021/np000347fJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kadota@ms.toyama-mpu.ac.jp
Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Expand this compound
Collapse this compound
8. Compound ID: 33041
|
Subst1-(1-4)-b-D-Quip-(1-6)-Subst2-(1-21)-+
|
a-L-Araf-(1-4)-+ |
| |
b-D-Glcp-(1-2)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst
|
a-L-Arap-(1-6)-+ |
| |
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES O{1}C(/C({9}CO)=C/CC{6}C(C)(O)C=C)=O;
Subst2 = 6S-hydroxy-2-hydroxymethyl-6-methyl-2E,7-octadienoic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C({9}CO)/{1}C(O)=O |
Show graphically |
Structure type: oligomer
Trivial name: kinmoonoside B
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_136907,IEDB_140628,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12757
Tezuka Y, Honda K, Banskota AH, Thet MM, Kadota S "Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar" -
Journal of Natural Products 63(12) (2000) 1658-1664
Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.
cytotoxicity, Acacia concinna, kinmoonosides A-C, HT-1080 fibrosarcoma
NCBI PubMed ID: 11141109Publication DOI: 10.1021/np000347fJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kadota@ms.toyama-mpu.ac.jp
Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Expand this compound
Collapse this compound
9. Compound ID: 33042
|
a-L-Arap-(1-6)-+
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
|
a-L-Araf-(1-4)-+ |
| |
b-D-Glcp-(1-2)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst
|
Subst1-(1-21)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES O{1}C(/C({9}CO)=C/CC{6}C(C)(O)C=C)=O |
Show graphically |
Structure type: oligomer
Trivial name: kinmoonoside C
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_136907,IEDB_140628,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12757
Tezuka Y, Honda K, Banskota AH, Thet MM, Kadota S "Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar" -
Journal of Natural Products 63(12) (2000) 1658-1664
Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.
cytotoxicity, Acacia concinna, kinmoonosides A-C, HT-1080 fibrosarcoma
NCBI PubMed ID: 11141109Publication DOI: 10.1021/np000347fJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kadota@ms.toyama-mpu.ac.jp
Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Expand this compound
Collapse this compound
10. Compound ID: 33043
|
Subst-(1-4)-D-Quip
Subst = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES O{1}C(/C({9}CO)=C/CC{6}C(C)(O)C=C)=O |
Show graphically |
Structure type: monomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 12757
Tezuka Y, Honda K, Banskota AH, Thet MM, Kadota S "Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar" -
Journal of Natural Products 63(12) (2000) 1658-1664
Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.
cytotoxicity, Acacia concinna, kinmoonosides A-C, HT-1080 fibrosarcoma
NCBI PubMed ID: 11141109Publication DOI: 10.1021/np000347fJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kadota@ms.toyama-mpu.ac.jp
Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Expand this compound
Collapse this compound
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: <1 sec