From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6‘-O-galloylsalicin (1); 4‘,6‘-di-O-galloylsalicin (2); 4‘,6‘-O-(S)-hexahydroxydiphenoylsalicin (3); 4‘,6‘-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-β-d-xylopyranosyl(1→6)-β-d-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods.
NCBI PubMed ID: 10650086Publication DOI: 10.1021/np990391zJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: tanahash
kobepharma-u.ac.jp
Institutions: Kobe Pharmaceutical University, Kobe, Japan, Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Higashiosaka, Japan, Yunnan Pharmaceutical Group Corporation, Kunming, China
Methods: 13C NMR, 1H NMR, deacetylation, NMR-2D, IR, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, evaporation, SI-MS, RP-MPLC, PTLC, HR-SI-MS
- Compound ID: 21989
Structure type: monomer
Trivial name: hyperoside, hyperin, hyperoside, hyperin, baohuoside-II, quercetin 3-galactoside, vulgarsaponin B
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside, flavanone glycoside
Reference(s) to other database(s): CCSD:
49969, CBank-STR:1983
- Compound ID: 26431
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b-D-Glcp-(1-9)-Subst
Subst = vomifoliol = SMILES O=C1CC(C)({6}[C@@](C(C)=C1)(O)/C=C/{9}[C@@H](C)O)C |
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Structure type: monomer
C19H30O8
Trivial name: (6S,9R)-roseoside, roseoside, (6S,9R)-releoside
Compound class: saponin glycoside, glycoside
Reference(s) to other database(s): CCSD:
50060, CBank-STR:971
- Compound ID: 26457
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b-D-Glcp-(1-1)-Subst
Subst = phenylethanol = SMILES O{1}CCC1=CC=CC=C1 |
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Structure type: monomer
C14H20O6
Compound class: glycoside, phenylethanoid glycoside, sesquiterpenoid glycoside
Reference(s) to other database(s): CCSD:
50059, CBank-STR:1046
- Compound ID: 27833
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b-D-Glcp-(1-1)-Subst
Subst = loganic acid aglycon = SMILES O={11}C(C1=CO{1}[C@@H](O)[C@@]2([H])[C@]1([H])C{7}[C@H](O)[C@@H]2C)O |
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Structure type: monomer
Trivial name: loganic acid
Compound class: saponin glycoside, glycoside, iridoid glycoside
- Compound ID: 27945
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b-D-Glcp-(1-6)-+
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b-D-Glcp-(1-2')-Subst
Subst = 2,6-dihydroxybenzoic acid 2'-hydroxybenzyl ester = SMILES O=C(OCC1=CC=CC={52}C1O)C2={2}C(O)C=CC={6}C2O |
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Structure type: oligomer
Trivial name: henryoside
Compound class: saponin glycoside, glycoside, phenolic glycoside
- Compound ID: 29194
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b-D-Glcp-(1-2)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO |
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Structure type: monomer
Trivial name: salicin
Compound class: glycoside, phenolic glycoside
- Compound ID: 30477
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside, flavanone glycoside
- Compound ID: 30478
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside, flavanone glycoside
- Compound ID: 32123
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Gallic-(7-6)-b-D-Glcp-(1-7)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32124
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Gallic-(7-6)-+
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Gallic-(7-4)-b-D-Glcp-(1-7)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32125
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Subst1-(7'-6:7-4)-b-D-Glcp-(1-2)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO;
Subst1 = hexahydroxydiphenic acid = SMILES O{3}C1={4}C(O){5}C(O)=C(C2={55}C(O){54}C(O)={53}C(O)C=C2{57}C(O)=O)C({7}C(O)=O)=C1 |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32126
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b-D-Xylp-(1-6)-b-D-Glcp-(1-1)-Subst
Subst = catechol = SMILES O{1}C1=CC=CC={2}C1O |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 32127
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b-D-Glcp-(1-2)-Subst
Subst = demethylalangiside aglycon = SMILES O{56}C1={57}C(O)C=C2[C@H]3C[C@H]4[C@@H](C=C){2}[C@H](O)OC=C4C(N3CCC2=C1)=O |
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Structure type: monomer
Trivial name: demethylalangiside
Compound class: glycoside, phenolic glycoside
- Compound ID: 32128
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b-D-Glcp-(1-1)-Subst
Subst = catechol = SMILES O{1}C1=CC=CC={2}C1O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32129
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Caf-(9-6)-b-D-Glcp-(1-7)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32130
Structure type: monomer
Compound class: glycoside
- Compound ID: 32131
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b-D-Xylp-(1-7)-Subst
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32132
Structure type: oligomer
Compound class: glycoside
- Compound ID: 32133
Structure type: oligomer
Compound class: glycoside
Found