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1. (Article ID: 10029)
Mimaki Y, Kuroda M, Nakamura O, Sashida Y, Satou T, Koike K, Nikaido T
New polyhydroxylated steroidal saponins from the tubers of Brodiaea californica
Chemical and Pharmaceutical Bulletin 45 (1997)
558-560
New polyhydroxylated steroidal saponins (1,2) were isolated from the tubers of Brodiaea californica. The structures were determined by spectroscopic analysis and acid-catalyzed hydrolysis. The bisdesmosidic saponin (2) is unique in structure, and is the first representative of a steroidal saponin bearing 6-deoxy-D-gulopyranose among both the steroidal and triterpene saponins reported up to the present.
Liliaceae, Brodiaea californica, polyhydroxylated steroidal saponin, bisdesmosidic saponin, 6-deoxy-D-gulopyranose
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003616526Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Tokyo, Japan, School of Pharmaceutical Sciences, Toho University, Japan
Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, HPLC
The publication contains the following compound(s):
- Compound ID: 24365
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b-D-Xylp-(1-3)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
Reference(s) to other database(s): CCSD:
15185, CBank-STR:10914
- Compound ID: 24366
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b-D-Quip-(1-24)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
Reference(s) to other database(s): CCSD:
15193, CBank-STR:10926
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2. (Article ID: 11129)
Mimaki Y, Kuroda M, Nakamura O, Sashida Y
Brodiosaponins A-F, six new polyhydroxylated steroidal saponins from the tubers of Brodiaea californica
Journal of Natural Products 60(6) (1997)
592-597
The constituents of the tubers of Brodiaea californica have been analyzed as part of a systematic study of plants of the subfamily Allioideae in Liliaceae. Six new polyhydroxylated steroidal saponins designated as brodiosaponins A-F (1-6) were isolated, and their structures were elucidated on the basis of spectroscopic analysis, including 2D NMR techniques, and acid- and alkaline-catalyzed hydrolysis. The bisdesmosidic saponins, brodiosaponins D-F (4-6) contain 6-deoxy-D-gulopyranose, which has been shown for the first time as a saccharide component among the steroidal and triterpene saponins reported to date.
Publication DOI: 10.1021/np960749gJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: mimakiy
.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi 1432-1, Hachioji, Tokyo 192-03, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, sugar analysis, TLC, acid hydrolysis, HPLC, alkaline hydrolysis, extraction
The publication contains the following compound(s):
- Compound ID: 27801
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b-D-Fucp-(1-24)-+
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b-D-Xylp-(1-3)-+ |
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a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1063 [M-H]-
C50H80O24
Trivial name: brodiosaponin B
Compound class: saponin glycoside
- Compound ID: 27802
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b-D-Fucp-(1-24)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap4Ac-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1105 [M-H]-
Trivial name: brodiosaponin C
Compound class: saponin glycoside
- Compound ID: 27803
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b-D-Xylp-(1-3)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 917 [M-H]-
C44H70O20
Trivial name: brodiosaponin A
Compound class: saponin glycoside
- Compound ID: 27804
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b-D-6dGul-(1-24)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1093 [M-H]-
C51H82O25
Trivial name: brodiosaponin D
Compound class: saponin glycoside
- Compound ID: 27805
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b-D-6dGul-(1-24)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1063 [M-H]-
C50H80O24
Trivial name: brodiosaponin E
Compound class: saponin glycoside
- Compound ID: 27806
|
b-D-6dGul-(1-24)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap4Ac-(1-2)-b-D-Glcp-(1-1)-Subst
Subst = 23S,24S,25R-spirost-5-en-1β,3β,12β,23,24-pentol = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C){24}[C@H](O){23}[C@@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])C{12}[C@@H](O)[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1105 [M-H]-
C52H82O25
Trivial name: brodiosaponin F
Compound class: saponin glycoside
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