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1. (Article ID: 12248)
Huang J, Ogihara Y, Zhang H, Shimizu N, Takeda T
Ardisimamillosides C-F, four new triterpenoid saponins from Ardisia mamillata
Chemical and Pharmaceutical Bulletin 48(10) (2000)
1413-1417
Four new triterpenoid saponins, ardisimamilloside C (1), 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β, 16α, 28, 30-tetrahydroxy-olean 12-en, ardisimamilloside D (2), 3-Or-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β, 15α, 28, 30-tetrahydroxy-olean-12-en, ardisimamilloside E (3), 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-13β, 28-epoxy-3β, 16α, 29-oleananetriol, and ardisimamilloside F (4), 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β, 16α-dihydroxy-13β, 28-epoxy-oleanan-30-oic acid were isolated from the roots of Ardisia mamillata HANCE. Structure assignments were established on the basis of highresolution (HR)-FAB-MS, 1H-, 13C-, and two-dimensional (2D)-NMR spectra, and on the chemical evidence.
D, triterpenoid saponin, E, F, Myrsinaceae, Ardisia mamillata, ardisimamilloside C
NCBI PubMed ID: 11045441Publication DOI: 10.1248/cpb.48.1413Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: takeda-td
kyoritsu-ph.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan, Kyoritsu College of Pharmacy, Tokyo, Japan, School of Pharmaceutical Sciences, West China University of Medical Sciences, Chengdu, China
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, GC, MALDI-TOF MS, HPLC, extraction, optical rotation measurement, acetylation, reduction, CC, precipitation, derivatization, evaporation, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 31839
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b-D-Glcp-(1-2)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = pridentigenin E = SMILES O{3}[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4C[C@@](C)({29}CO)CC5)C1(C)C |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31840
|
b-D-Glcp-(1-2)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = ardisimamilloside D aglycon = SMILES O{3}[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C){15}[C@@H](O)C[C@]5({28}CO)[C@H]4C[C@@](C)({29}CO)CC5)C1(C)C |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31841
|
b-D-Glcp-(1-2)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = ardisimamilloside E aglycon = SMILES O{3}[C@H]1CC[C@]2(C)[C@H]3CC[C@@]45[C@@H]6C[C@](C)({29}CO)CC[C@@]6({16}[C@H](O)C[C@@]5(C)[C@]3(C)CC[C@H]2C1(C)C)CO4 |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31842
|
b-D-Glcp-(1-2)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = ardisimamilloside F aglycon = SMILES O{3}[C@H]1CC[C@]2(C)[C@H]3CC[C@@]45[C@@H]6C[C@]({29}C(O)=O)(C)CC[C@@]6({16}[C@H](O)C[C@@]5(C)[C@]3(C)CC[C@H]2C1(C)C)CO4 |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31843
|
b-D-Glcp-(1-2)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = 3β,13β,28-epoxy-16α,30-oleananetriol = SMILES CC1(C){3}[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@]23OC[C@@]4(CC[C@](C)({30}CO)C[C@H]42){16}[C@H](O)C[C@]31C |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31844
|
b-D-Glcp-(1-2)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = cyclamiretin D = SMILES O{3}[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4C[C@@](C)(C=O)CC5)C1(C)C |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31845
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a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = cyclamiretin A = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]45[C@]6([H])C[C@@](C)(C=O)CC[C@@](CO5)6{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
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2. (Article ID: 12249)
Huang J, Ogihara Y, Zhang H, Shimizu N, Takeda T
Triterpenoid saponins from Ardisia mamillata
Phytochemistry 54(8) (2000)
817-822
Two saponins were isolated from the roots of Ardisia mamillata HANCE. Their structures were established on the basis of MALDI-TOFMS, 1H, 13C NMR and 2D NMR (COSY, HOHAHA, HETCOR, HMBC and ROESY) spectra, and on chemical evidence, to be ardisimamilloside A, 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β, 16α,28α-trihydroxy-13β,28-epoxy-oleanan-30-al; and ardisimamilloside B, 3-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-3β-hydroxy-13β,28-epoxy-oleanan-16-oxo-30-al.
triterpenoid saponin, Myrsinaceae, Ardisia mamillata, ardisimamilloside A, ardisimamilloside B
NCBI PubMed ID: 11014272Publication DOI: 10.1016/s0031-9422(00)00173-4Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: takeda-td
kyoritsu-ph.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan, School of Pharmaceutical Sciences, West China University of Medical Sciences, Chengdu, China, Department of Pharmacognosy, Kyoritsu College of Pharmacy, Tokyo, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, GC, MALDI-TOF MS, HPLC, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, CC, melting point determination, precipitation, derivatization, evaporation
The publication contains the following compound(s):
- Compound ID: 30042
|
b-D-Glcp-(1-2)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = cyclamiretin A = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]45[C@]6([H])C[C@@](C)(C=O)CC[C@@](CO5)6{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: ardisiacrispin B
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
- Compound ID: 30986
|
b-D-Glcp-(1-3)-Subst
Subst = stigmast-7-en-3β-ol = SMILES CC[C@@H](C(C)C)CC[C@@H](C)[C@H]1CC[C@@]2([H])C3=CCC4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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Structure type: monomer
Trivial name: stigmast-7-en-3β-ol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
- Compound ID: 31846
|
b-D-Glcp-(1-2)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = ardisimamilloside A aglycon = SMILES O{3}[C@H]1CC[C@]2(C)[C@H]3CC[C@]45[C@@H]6C[C@@](C)(C=O)CC[C@]6({28}C(O)O5){16}[C@H](O)C[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31847
|
b-D-Glcp-(1-2)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-a-L-Arap-(1-3)-Subst
Subst = cyclamigenin B = SMILES O{3}[C@H]1CC[C@]2(C)[C@H]3CC[C@]45[C@@H]6C[C@@](C)(C=O)CC[C@]6(CO5)C(C[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)=O |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 31848
|
b-D-Glcp-(1-4)-+
|
b-D-Glcp-(1-2)-a-L-Arap-(1-3)-Subst
Subst = cyclamiretin A = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]45[C@]6([H])C[C@@](C)(C=O)CC[C@@](CO5)6{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
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