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1. (Article ID: 11586)
Ida Y, Satoh Y, Katsumata M, Nagasao M, Hirai Y, Kajimoto T, Katada N, Yasuda M, Yamamoto T
Two novel oleanolic acid saponins having a sialyl Lewis X mimetic structure from Achyranthes fauriei root
Bioorganic and Medicinal Chemistry Letters 8(18) (1998)
2555-2558
Two novel triterpene glycosides, achyranthosides E and F, were isolated as methyl esters from the root of Achyranthes fauriei, an antiinflammatory medicinal plant. Their structures were characterized as oleanolic acid glucuronides having unique substituents composed of C6H9O5 and C9H15O7, respectively, at the C-3 position of glucuronic acid. These compounds are active components which can inhibit the excess recruiting of neutrophiles to injured tissues 1,000 times more potently than sialyl Lewis X.
Oligosaccharides, Magnetic Resonance Spectroscopy, antiinflammatory activity, achyranthoside
Publication DOI: 10.1016/S0960-894X(98)00457-0Journal NLM ID: 9107377Publisher: Elsevier
Institutions: School of Pharamaceutical Sciences, Showa University, Shinagawa, Tokyo, Japan
Methods: 13C NMR, NOE, IR, FAB-MS, enzymatic hydrolysis, acid hydrolysis, acetylation, CC, HMBC, COSY, optical rotation
The publication contains the following compound(s):
- Compound ID: 29756
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b-D-Glcp-(1-28)-+
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Gc-(2-3)-Subst2(%)Me-(3-3:2-4)-b-D-GlcpA-(1-3)-Oleanolic
Subst = SMILES O=C(O){2}[C@@](O)(O){3}C(O)O |
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Structure type: oligomer
Trivial name: achyranthoside A, achyranthoside B
Compound class: triterpenoid glycoside
- Compound ID: 29757
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b-D-Glcp-(1-28)-+
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?%b-D-Glcp-(1-2)-+ |
| |
Gc-(2-3)-Subst-(3-3)-b-D-GlcpA-(1-3)-Oleanolic
Subst = SMILES O=C(O)C(O){3}C(O)O |
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Structure type: oligomer
Trivial name: achyranthoside C, achyranthoside D
Compound class: triterpenoid glycoside
- Compound ID: 29758
Structure type: oligomer
Trivial name: chikusetsusaponin IVa
Compound class: triterpenoid glycoside
- Compound ID: 29759
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b-D-Glcp-(1-28)-+
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Gc-(2-2)-Subst-(2-3)-b-D-GlcpA-(1-3)-Oleanolic
Subst = SMILES O={1}C(O){2}C(O)O |
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Structure type: monomer
Trivial name: achyranthoside E
Compound class: triterpenoid glycoside
- Compound ID: 29760
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b-D-Glcp-(1-28)-+
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Gc-(2-3)-Subst-(3-3)-b-D-GlcpA-(1-3)-Oleanolic
Subst = SMILES O={1}C(O)C(O)({4}CO){3}C(O)O |
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Structure type: monomer
Trivial name: achyranthoside F
Compound class: triterpenoid glycoside
- Compound ID: 29761
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b-D-Glcp-(1-28)-+
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Gc1Me-(2-2)-Subst1Me-(2-3)-b-D-GlcpA6Me-(1-3)-Oleanolic
Subst = SMILES O={1}C(O){2}C(O)O |
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Structure type: oligomer
; 991 [M+Na]+
C49H76O19
Trivial name: achyranthoside E methyl ester
Compound class: triterpenoid glycoside
- Compound ID: 29762
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b-D-Glcp2Ac3Ac4Ac6Ac-(1-28)-+
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Gc1Me-(2-2)-Subst1Me-(2-3)-b-D-GlcpA2Ac4Ac6Me-(1-3)-Oleanolic
Subst = SMILES O={1}C(O){2}C(O)O |
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Structure type: oligomer
; 1243 [M+Na]+
C61H88O25
Compound class: triterpenoid glycoside
- Compound ID: 29763
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b-D-Glcp-(1-28)-+
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Gc1Me-(2-3)-Subst1Me4Me-(3-3)-b-D-GlcpA6Me-(1-3)-Oleanolic
Subst = SMILES O={1}C(O)C(O)({4}CO){3}C(O)O |
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Structure type: oligomer
; 1041 [M-H]-
C52H82O21
Trivial name: achyranthoside F methyl ester
Compound class: triterpenoid glycoside
- Compound ID: 29764
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Gc1Me-(2-3)-Subst1Me4Me-(3-3)-b-D-GlcpA6Me-(1-3)-Oleanolic
Subst = SMILES O={1}C(O)C(O)({4}CO){3}C(O)O |
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Structure type: monomer
; 1041 [M-H]-
C52H82O21
Compound class: triterpenoid glycoside
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