The 50% aqueous methanolic extract from the bark of Betula platyphylla SUKATCHEV var. japonica (MIQ) HARA was found to show potent inhibitory activity on the liver-injury induced by CCl4 or D-galactosamine (D- GalN)/lipopolysaccharide as well as O2- scavenging and antioxidative activities. From the 50% aqueous methanolic extract, two new diarylheptanoids named betulaplatosides Ia (1) and Ib (2) and a new arylbutanoid named betulaplatoside II (3) were isolated together with seventeen known aromatic constituents. 1, 2, and two known diarylheptanoids [(5S)-5-hydroxy-1,7-bis- (4-hydroxyphenyl)-3-heptanone 5-O-β-D-apiofurano-syl-(1→6)-β-D- glucopyranoside (6) and aceroside VIII (7)] showed protective activity against D-GaIN-induced cytotoxicity in primary cultured rat hepatocytes. Furthermore, several aromatic constituents exhibited potent O2- scavenging and antioxidative activities.
NCBI PubMed ID: 9873651Publication DOI: 10.1016/S0960-894X(98)00528-9Journal NLM ID: 9107377Publisher: Elsevier
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Sunstar Inc., Takatsuki, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, enzymatic hydrolysis, acid hydrolysis, GLC, biological assays, HPLC, UV, extraction, optical rotation measurement, CC, antioxidant activities, HMBC, radical scavenging assay, NaNH4 reduction, opitcal rotation measurement, enzymatic hidrolysis
- Compound ID: 26324
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b-D-Glcp-(1-5)-Subst
Subst = platyphyllone = SMILES O{5}[C@H](CC(CCC1=CC={54}C(O)C=C1)=O)CCC2=CC={104}C(O)C=C2 |
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Structure type: monomer
Trivial name: platyphylloside
Compound class: glycoside, diarylheptanoid glycoside
Reference(s) to other database(s): CCSD:
39050, CBank-STR:1019
- Compound ID: 27898
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b-D-Glcp-(1-3a)-Subst
Subst = (+)-lyoniresinol = SMILES O{6}C1=C(OC)C=C2C[C@@H]({152}CO)[C@H]({153}CO)[C@@H](C3=CC(OC)={54}C(O)C(OC)=C3)C2=C1OC |
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Structure type: monomer
Trivial name: (+)-3α-O-(β-D-glucopyranosyl)-lyoniresinol
Compound class: glycoside, lignan glycoside
- Compound ID: 27900
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b-D-Glcp-(1-2a)-Subst
Subst = (-)-lyoniresinol = SMILES O{6}C1=C(OC)C=C2C[C@H]({152}CO)[C@@H]({153}CO)[C@H](C3=CC(OC)={54}C(O)C(OC)=C3)C2=C1OC |
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Structure type: monomer
Trivial name: (-)-2α-O-(β-D-glucopyranosyl)-lyoniresinol
Compound class: glycoside, lignan glycoside
- Compound ID: 29360
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b-D-Glcp-(1-5)-Subst
Subst = hannokinol = SMILES O{104}c2ccc(CC{5}[C@H](O){3}C[C@@H](O)CCc1cc{54}c(O)cc1)cc2 |
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Structure type: monomer
; 479 [M+H]+
C25H34O9
Trivial name: betulaplotoside Ia
Compound class: glycoside
- Compound ID: 29361
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b-D-Glcp-(1-5)-Subst
Subst = meso-hannokinol = SMILES O{104}c2ccc(CC{5}[C@H](O){3}C[C@H](O)CCc1cc{54}c(O)cc1)cc2 |
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Structure type: monomer
; 479 [M+H]+
C25H34O9
Trivial name: betulaplotoside Ib
Compound class: glycoside
- Compound ID: 29362
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a-L-Araf-(1-6)-b-D-Glcp-(1-9)-Subst
Subst = (+)-rhododendrol = SMILES C{9}[C@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: oligomer
C21H32O11
Trivial name: betulaplotoside II
Compound class: glycoside
- Compound ID: 29363
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a-L-Apif-(1-6)-b-D-Glcp-(1-5)-Subst
Subst = platyphyllone = SMILES O{5}[C@H](CC(CCC1=CC={54}C(O)C=C1)=O)CCC2=CC={104}C(O)C=C2 |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 29364
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a-L-Apif-(1-6)-b-D-Glcp-(1-5)-Subst
Subst = centrolobol = SMILES O{54}c2ccc(CCCC{5}[C@@H](O)CCc1cc{104}c(O)cc1)cc2 |
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Structure type: oligomer
Trivial name: aceroside VIII
Compound class: glycoside
- Compound ID: 29365
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b-D-Glcp-(1-9)-Subst
Subst = (-)-rhododendrol = SMILES C{9}[C@@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: monomer
Trivial name: rhododendrin
Compound class: glycoside
- Compound ID: 29366
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b-D-Glcp-(1-9)-Subst
Subst = (+)-rhododendrol = SMILES C{9}[C@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: monomer
Trivial name: epirhododendrin
Compound class: glycoside
- Compound ID: 29367
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a-L-Api-(1-6)-b-D-Glcp-(1-9)-Subst
Subst = (-)-rhododendrol = SMILES C{9}[C@@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: oligomer
Trivial name: apiosylrhododendrin
Compound class: glycoside
- Compound ID: 29368
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a-L-Api-(1-6)-b-D-Glcp-(1-9)-Subst
Subst = (+)-rhododendrol = SMILES C{9}[C@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: oligomer
Trivial name: apiosylepirhododendrin
Compound class: glycoside
- Compound ID: 29369
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a-L-Arap-(1-6)-b-D-Glcp-(1-9)-Subst
Subst = (-)-rhododendrol = SMILES C{9}[C@@H](O)CCc1cc{4}c(O)cc1 |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 29370
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b-D-Xylp-(1-2a)-Subst
Subst = (-)-lyoniresinol = SMILES O{6}C1=C(OC)C=C2C[C@H]({152}CO)[C@@H]({153}CO)[C@H](C3=CC(OC)={54}C(O)C(OC)=C3)C2=C1OC |
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Structure type: monomer
Trivial name: nudiposide
Compound class: glycoside
- Compound ID: 29371
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b-D-Glcp-(1-3a)-Subst
Subst = (+)-5'-methoxyisolariciresinol = SMILES O{6}C1=C(OC)C=C2C[C@@H]({152}CO)[C@H]({153}CO)[C@@H](C3=CC(OC)={54}C(O)C(OC)=C3)C2=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 29372
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b-D-Glcp-(1-7)-Subst
Subst = (+)-catechin = SMILES O{3}[C@@H]1[C@@H](C2=CC={54}C(O){53}C(O)=C2)OC3=C({5}C(O)=C{7}C(O)={8}C3)C1 |
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Structure type: monomer
Compound class: glycoside