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1. (Article ID: 11969)
Abe F, Yamauchi T
An androstane bioside and 3'-thiazolidinone derivatives of doubly-linked cardenolide glycosides from the roots of Asclepias tuberosa
Chemical and Pharmaceutical Bulletin 48(7) (2000)
991-993
Steroidal compounds in the roots of Asclepias tuberosa were investigated and 17α-hydroxyandrosta-4,6,15-trien-3-one 17-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside, termed ascandroside, was isolated from the CHCl3-soluble fraction. Among five doubly-linked cardenolide glycosides, two were identified as 3'-spiro-linked thiazolidinone (4) and S-oxythiazolidinone derivatives (5) of Δ5-calotropin. The stereochemistry at the C-3' in these two cardenolides is discussed. 3'-O-β-D-glucopyranosyl-Δ5-calotropin (3) was also isolated along with Δ5-calotropin and its 3'-acetate. Nine glycosides of uzarigenin, coroglaucigenin and corotoxigenin were identified.
Asclepias tuberosa, androstane bioside, thiazolidinone-linked Δ5-calotropin, pleurisy root
NCBI PubMed ID: 10923828Publication DOI: 10.1248/cpb.48.991Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: abefumi
fukuoka-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Fukuoka, Japan
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, CC, melting point determination, derivatization, HR-FAB-MS
The publication contains the following compound(s):
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2. (Article ID: 11972)
Abe F, Yamauchi T
Pregnane glycosides from the roots of Asclepias tuberosa
Chemical and Pharmaceutical Bulletin 48(7) (2000)
1017-1022
Sixteen glycosides of pregnanes, including ikemagenin, lineolon, and a new pregnane, 3β,8β,14β,15β,16α-pentahydroxy-5α-pregnan-20-one, termed pleurogenin, were isolated from the roots of Asclepias tuberosa. Among ikemagenin and lineolon glycosides, one (1) was a known glycoside, and eight (2-7, 10, 13) were glycosides with new combinations of ikemagenin or lineolon and known sugar sequences composed of D-cymarose, D-oleandrose, D-thevetose and D-glucose. The structures of four new glycosides of ikemagenin (8, 9, 11, 12) and three of pleurogenin (14-16) were determined. The new glycosides have sugar sequences ranging from tetraoside to heptaosides.
Asclepiadaceae, pregnane glycoside, 3β, Asclepias tuberosa, pleurisy root, 8β, 14β, 15β, 16α-pentahydroxy-5α-pregnan-20-one, ikemagenin
NCBI PubMed ID: 10923833Publication DOI: 10.1248/cpb.48.1017Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: abefumi
fukuoka-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Fukuoka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, extraction, optical rotation measurement, CC, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 31121
|
Cin-(9-12)-+
|
b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31122
|
Cin-(9-12)-+
|
b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 949.4910 [M+Na]+
C51H74O15
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31123
|
Cin-(9-12)-+
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b-Tyvp-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 1109.5664 [M+Na]+
C58H86O19
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31124
|
Cin-(9-12)-+
|
b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
Show graphically |
Structure type: oligomer
; 1093.5717 [M+Na]+
C58H86O18
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31125
|
Cin-(9-12)-+
|
b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 1093.5717
C58H86O18
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31126
|
Cin-(9-12)-+
|
b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
Show graphically |
Structure type: oligomer
; 1237.6500 [M+Na]+
C65H96O21
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31127
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
Show graphically |
Structure type: oligomer
; 1399.7025 [M+Na]+
C71H108O26
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31128
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp-(1-4)-b-D-Olip-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 1357.6566 [M+Na]+
C68H102O26
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31129
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp-(1-4)-b-D-Olip-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
Show graphically |
Structure type: oligomer
; 1371.6713
C69H104O26
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31130
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
Show graphically |
Structure type: oligomer
; 1273.5985 [M+Na]+
C63H94O25
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31131
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 1417.6780 [M+Na]+
C70H106O28
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31132
|
Cin-(9-12)-+
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 1561.7535
C77H118O31
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31133
|
b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
; 963.5295 [M+Na]+
C49H80O17
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31134
|
b-D-Digp3Me-(1-4)-b-D-Olip-(1-4)-b-D-Olip-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = pleurogenin = SMILES CC([C@H]1{16}[C@H](O){15}[C@@H](O){14}[C@@]2(O)[C@]1(C)CC[C@H]3{8}[C@@]2(O)CC[C@@H]4[C@]3(C)CC{3}[C@H](O)C4)=O |
Show graphically |
Structure type: oligomer
; 953.5088 [M+Na]+
C49H80O17
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31135
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Olip-(1-4)-b-D-Olip-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = pleurogenin = SMILES CC([C@H]1{16}[C@H](O){15}[C@@H](O){14}[C@@]2(O)[C@]1(C)CC[C@H]3{8}[C@@]2(O)CC[C@@H]4[C@]3(C)CC{3}[C@H](O)C4)=O |
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Structure type: oligomer
; 1115.5613 [M+Na]+
C53H88O23
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31136
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Olip-(1-4)-b-D-Olip-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = pleurogenin = SMILES CC([C@H]1{16}[C@H](O){15}[C@@H](O){14}[C@@]2(O)[C@]1(C)CC[C@H]3{8}[C@@]2(O)CC[C@@H]4[C@]3(C)CC{3}[C@H](O)C4)=O |
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Structure type: oligomer
; 1421.6929 [M+Na]+
C66H110O31
Compound class: glycoside, triterpenoid glycoside
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