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1. (Article ID: 10724)
Ohashi K, Kojima H, Tanikawa T, Okumura Y, Kawazoe K, Tatara N, Shibuya H, Kitagawa I
Indonesian medicinal plants. IX. Chemical structures of gongganosides A, B, and C, three new quinovic acid glycosides from the bark of Bhesa paniculata (Celastraceae)
Chemical and Pharmaceutical Bulletin 42 (1994)
1596-1600
Three new quinovic acid glycosides, named gongganosides A (1), B (2), and C (3), were isolated from the bark of Bhesa paniculata (Celastraceae), an Indonesian medicinal plant collected in Sumatra Island. The chemical structures have been elucidated on the basis of chemical and physicochemical evidence as quinovic acid 3-O-β-D-xylopyranosyl(1→3)-α-L-rhamnopyranoside for 1,28-O-β-D-glucopyranosylquinovic acid 3-O-α-L-rhamnopyranoside for 2,and 28-O-β-D-glucopyranosyl-quinovic acid 3-O-β-D-xylopyranosyl(1→3)-α-L-rhamnopyranoside for 3.
Indonesian medicinal plant, Bhesa paniculata, Celastraceae, quinovic acid glycoside, gongganoside
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003631194Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Japan, Faculty of Science, Shizuoka University, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, GLC, HPLC, methylation analysis, CC
The publication contains the following compound(s):
- Compound ID: 26663
|
b-D-Xylp-(1-3)-a-L-Rhap-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 787 [M+Na]+
C41H64O13
Trivial name: gongganoside A
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40152, CBank-STR:3199
- Compound ID: 26664
|
a-L-Rhap-(1-3)-+
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b-D-Glcp-(1-28)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 817 [M+Na]+
C42H66O14
Trivial name: gongganoside B
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40153, CBank-STR:2398
- Compound ID: 26665
|
b-D-Glcp-(1-28)-+
|
b-D-Xylp-(1-3)-a-L-Rhap-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 949 [M+Na]+
C47H74O18
Trivial name: gongganoside C
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40154, CBank-STR:6141
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2. (Article ID: 10725)
Ohashi K, Tanikawa T, Okumura Y, Kawazoe K, Tatara N, Minato M, Shibuya H, Kitagawa I
Indonesian medicinal plants. X. Chemical structures of four new triterpene-glycosides, gongganosides D, E, F, and G, and two secoiridoid- glucosides from the bark of Bhesa paniculata (Celastraceae)
Chemical and Pharmaceutical Bulletin 42 (1994)
1791-1797
Four new triterpene-glycosides, named gongganosides D (4), E (5), F (6), and G (7), and two new secoiridoid-glucosides, (7R)-7-caffeoyloxysweroside (8) and (7S)-7-caffeoyloxysweroside (9), were isolated from the bark of the Indonesian medicinal plant Bhesa paniculata (Celastraceae). The chemical structures have been elucidated on the bases of their chemical and physicochemical properties.
Indonesian medicinal plant, Bhesa paniculata, Celastraceae, triterpene-glycoside, secoiridoid-glucoside, 27-oxoursolic acid
NCBI PubMed ID: 7954929Publication DOI: 10.1248/cpb.42.1791Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003631236Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Japan, Faculty of Science, Shizuoka University, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis, enzymatic digestion, CC, partial alkaline hydrolysis
The publication contains the following compound(s):
- Compound ID: 26666
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 941 [M-H]-
C48H78O18
Trivial name: gongganoside D
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40173, CBank-STR:7604
- Compound ID: 26667
|
b-D-Xylp-(1-3)-a-L-Rhap-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
Trivial name: gongganoside A
Compound class: saponin glycoside
- Compound ID: 26668
|
a-L-Rhap-(1-3)-+
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b-D-Glcp-(1-28)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
Trivial name: gongganoside B
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
- Compound ID: 26669
|
b-D-Glcp-(1-28)-+
|
b-D-Xylp-(1-3)-a-L-Rhap-(1-3)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
Trivial name: gongganoside C
Compound class: saponin glycoside
- Compound ID: 26670
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1103 [M-H]-
C54H88O23
Trivial name: gongganoside E
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40174, CBank-STR:10788
- Compound ID: 26671
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = ursolic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 1111 [M+Na]+
C54H88O22
Trivial name: gongganoside F
Compound class: saponin glycoside
- Compound ID: 26672
|
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: oligomer
Trivial name: vogeloside
- Compound ID: 26673
|
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: oligomer
Trivial name: epi-vogeloside
- Compound ID: 26674
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = 27-oxoursolic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 1101 [M-H]-
C54H86O23
Trivial name: gongganoside G
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40175, CBank-STR:10790
- Compound ID: 26675
|
Caf-(9-3)-+
|
b-D-Glcp-(1-6)-Subst
Subst = 3R-desmethylvogeloside aglycon = SMILES O=C1C2=CO{6}[C@@H](O)[C@H](C=C)[C@]2([H])C{3}[C@H](O)O1 |
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Structure type: monomer
; 559 [M+Na]+
C25H28O13
Trivial name: (7R)-7-caffeoyloxysweroside
Compound class: glycoside
Reference(s) to other database(s): CCSD:
40176, CBank-STR:1268
- Compound ID: 26676
|
Caf-(9-3)-+
|
b-D-Glcp-(1-6)-Subst
Caf = caffeic acid;
Subst = 3S-desmethylvogeloside aglycon = SMILES O=C1C2=CO{6}[C@@H](O)[C@H](C=C)[C@]2([H])C{3}[C@@H](O)O1 |
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Structure type: monomer
; 559 [M+Na]+
C25H28O13
Trivial name: (7S)-7-caffeoyloxysweroside
Compound class: glycoside
Reference(s) to other database(s): CCSD:
40177, CBank-STR:1269
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