Five monodesmosidic serjanic acid saponins and a monodesmosidic spergulagenic acid saponin were isolated from an aqueous extract of the berries of Phytolacca icosandra. A methanol extract of the berries furnished three bidesmosidic serjanic acid glycosides. Their structures were established by spectroscopic (ES-MS, 1H NMR, COSY, HSQC, HMBC, 13C NMR) and chemical methods. The molluscicidal, spermicidal and haemolytic properties of the saponins were investigated.
NCBI PubMed ID: 11130671Publication DOI: 10.1016/s0031-9422(00)00233-8Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: kurt.hostettmann
ipp.unil.ch
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, Switzerland, Fakultas Pascasarjana, Universitas Airlangga, Surabaya, Indonesia
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, biological assays, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
- Compound ID: 33062
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b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: monomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33063
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b-D-Galp-(1-3)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33064
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33065
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b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33066
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a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33067
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a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33068
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b-D-Glcp-(1-28)-+
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b-D-Galp-(1-3)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33069
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b-D-Glcp-(1-28)-+
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33070
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b-D-Glcp-(1-28)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst30Me
Subst = spergulagenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@]({30}C(O)=O)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Found