During the course of a study of leguminous plants, cytotoxicity was demonstrated by the crude saponin fraction of Albizia julibrissin. Following chromatographic purification, the structures of three novel saponins, julibrosides I-III (1-3), inclusive of a cytotoxic principle, were elucidated. A comparison of the cytotoxicity of julibrosides (1-3) and their prosapogenins (4-15) prepared by alkaline hydrolysis clearly indicated that both an α-L-arabinofuranosyl-(1→4)-[β-D-glucopyranosyl--(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester unit and a monoterpene-quinovopyranosyl moiety are crucial substituents for cytotoxicity among this class of compounds. The hydroxy group at C-16 of aglycon may play an important role in mediating cytotoxicity, and the N-acetyl-glucosamine moiety at C-3 seems to enhance activity because 3 showed the strongest cytotoxicity.
NCBI PubMed ID: 9051910Publication DOI: 10.1021/np960556tJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: none
kumamoto-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-Honmachi, Kumamoto 862, Japan,
Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, GC, chemical methods, biological assays, alkaline hydrolysis, extraction, CC
- Compound ID: 28119
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b-D-Quip-(1-6)-S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-S-Menthiafolic
Subst1 = 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 |
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Structure type: oligomer
Trivial name: julibroside II
Compound class: saponin glycoside
- Compound ID: 28120
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b-D-Quip-(1-6)-S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-GlcpNAc-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-S-Menthiafolic
Subst1 = 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 |
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Structure type: oligomer
Trivial name: julibroside III
Compound class: saponin glycoside
- Compound ID: 28121
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b-D-Quip-(1-6)-+
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b-D-Glcp-(1-2)-+ |
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-S-Menthiafolic
Subst1 = 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 |
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Structure type: oligomer
Trivial name: prosapogenin-8
Compound class: saponin glycoside
- Compound ID: 28122
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b-D-Quip-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-S-Menthiafolic
Subst1 = 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 |
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Structure type: oligomer
; 1841 [M-H]-
Trivial name: prosapogenin-9
Compound class: saponin glycoside
- Compound ID: 28123
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b-D-Quip-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Subst
Subst1 = 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;
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 |
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Structure type: oligomer
; 1857 [M-H]-
Trivial name: prosapogenin-10
Compound class: saponin glycoside
- Compound ID: 28124
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b-D-Quip-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Subst
Subst1 = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C;
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 |
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Structure type: oligomer
; 1825 [M-H]-
Trivial name: prosapogenin-11
Compound class: saponin glycoside
- Compound ID: 28125
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b-D-Quip-(1-6)-+
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b-D-Glcp-(1-2)-+ |
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Subst
Subst1 = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C;
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 |
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Structure type: oligomer
; 1987 [M-H]-
Trivial name: prosapogenin-12
Compound class: saponin glycoside
- Compound ID: 28126
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-Subst1
Subst1 = 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 |
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Structure type: oligomer
; 951 [M+Na]+
Trivial name: prosapogenin-1
Compound class: saponin glycoside
- Compound ID: 28127
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b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-GlcpNAc-(1-3)-Subst1
Subst1 = 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 |
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Structure type: oligomer
; 978 [M+Na]+
Trivial name: prosapogenin-2
Compound class: saponin glycoside
- Compound ID: 28128
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b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-GlcpNAc-(1-3)-Subst1
Subst1 = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 960 [M+Na]+
Trivial name: prosapogenin-4
Compound class: saponin glycoside
- Compound ID: 28129
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b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-Glcp-(1-3)-Subst1
Subst1 = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 919 [M+Na]+
Trivial name: prosapogenin-3
Compound class: saponin glycoside
- Compound ID: 28130
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b-D-Glcp-(1-2)-+
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-Subst1
Subst1 = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: prosapogenin-5 (julibroside A1)
Compound class: saponin glycoside
- Compound ID: 28131
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-Subst1
Subst1 = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: prosapogenin-6 (julibroside A2)
Compound class: saponin glycoside
- Compound ID: 28132
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-GlcpNAc-(1-3)-Subst1
Subst1 = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: prosapogenin-7 (julibroside A3)
Compound class: saponin glycoside
- Compound ID: 28118
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b-D-Quip-(1-6)-S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-+
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b-D-Glcp-(1-2)-+ |
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b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ |
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a-L-Araf-(1-4)-+ | |
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-S-Menthiafolic
Subst1 = 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 |
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Structure type: oligomer
Trivial name: julibroside I
Compound class: saponin glycoside
Found