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1. (Article ID: 11871)
Tamaki A, Otsuka H, Ide T
Platanionosides A-C, megastigmane diglycosides from the leaves of Alangium platanifolium
Journal of Natural Products 62(7) (1999)
1074-1076
From the leaves of Alangium platanifolium var. platanifolium collected in Fukuoka Prefecture, Japan, three megastigmane diglycosides (1-3) were isolated, along with two known compounds, benzyl alcohol 7-O-β-D-(6'-O-β-D-xylopyranosyl)glucopyranoside and Z-hex-3-en-1-ol 1-O-β-D-glucopyranoside. The structures of the new compounds, named platanionosides A (1), B (2), and C(3) were elucidated by spectroscopic evidence to be 3S,5R,6R,9R,7E-megastigma-3,9-diol 3,9-di-O-β-D-glucopyranoside, 3R,9R,7E-megastigma-5,7-diene-3,9-diol 3,9-di-O-β-D-glucopyranoside, and 5R,6S,7E-megastigma-3-on-7-en-9-ol 9-O-β-D-(6'-O-β-D-xylopyranosyl)glucopyranoside, respectively.
megastigmane diglycoside, platanionosides A-C, Alangium platanifolium var. platanifolium
NCBI PubMed ID: 10425149Publication DOI: 10.1021/np990050lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Ide T
pharm.hiroshima-u.ac.jp>
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University Faculty of Medicine, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
Methods: 13C NMR, 1H NMR, IR, HPLC, optical rotation measurement, CD, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 26100
Structure type: oligomer
Trivial name: benzyl β-primeveroside
Compound class: saponin glycoside, glycoside
Reference(s) to other database(s): CCSD:
34652, CBank-STR:4010
- Compound ID: 26459
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b-D-Glcp-(1-1)-Subst
Subst = aoba alcohol = SMILES CC/C=C\C{1}CO |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 30716
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b-D-Glcp-(1-9)-+
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b-D-Glcp-(1-3)-Subst
Subst = (1S,4R,5R)-4-[(1E,3R)-3-hydroxy-1-buten-1-yl]-3,3,5-trimethylcyclohexanol = SMILES C{9}[C@@H](O)/C=C/[C@H]1[C@H](C)C{3}[C@H](O)CC1(C)C |
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Structure type: oligomer
; 535.2727 [M-H]-
C25H44O12
Trivial name: platanionoside A
Compound class: sesquiterpenoid glycoside
- Compound ID: 30717
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b-D-Glcp-(1-9)-+
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b-D-Glcp-(1-3)-Subst
Subst = (1R)-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-3-en-1-ol = SMILES CC1=C(/C=C/{9}[C@@H](C)O)C(C)(C)C{3}[C@H](O)C1 |
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Structure type: oligomer
; 533.2577 [M-H]-
C25H41O12
Trivial name: platanionoside B
Compound class: sesquiterpenoid glycoside
- Compound ID: 30718
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b-D-Xylp-(1-6)-b-D-Glcp-(1-9)-Subst
Subst = 4,5-dihydroblumenol = SMILES C{9}[C@@H](O)/C=C/{6}[C@@]1(O)[C@H](C)CC(=O)CC1(C)C |
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Structure type: oligomer
; 519.2439 [M-H]-
C24H39O12
Trivial name: platanionoside C
Compound class: sesquiterpenoid glycoside
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2. (Article ID: 12745)
Tamaki A, Ide T, Otsuka H
Phenolic glycosides from the leaves of Alangium platanifolium var. platanifolium
Journal of Natural Products 63(10) (2000)
1417-1419
Chemical investigation of Alangiumplatanifolium var. platanifolium has resulted in the isolation of nine phenolic glycosides that were identified by means of 1D and 2D NMR experiments. Among them, catechol and salicinol O- and 1-O-β-d-(6-O-β-d-apiofuranosyl)glucopyranosides, respectively 1 and 2, and two compounds characterized as adducts of 2,6-dihydroxybenzoic acid with salicin (plataplatanoside, 3) and 4-hydroxysalicin (4-hydroxyalangifolioside, 4) were determined structurally as new compounds.
phenolic glycosides, Alangium platanifolium var. platanifolium, catechol, salicinol
NCBI PubMed ID: 11076566Publication DOI: 10.1021/np000119lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Otsuka H
pharm.hiroshima-u.ac.jp>
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
The publication contains the following compound(s):
- 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: 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: 33010
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b-D-Apif-(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, phenolic glycoside
- Compound ID: 33011
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b-D-Apif-(1-6)-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
Compound class: glycoside, phenolic glycoside
- Compound ID: 33012
|
b-D-Glcp-(1-2)-Subst-(7-2)-Subst1
Subst = salicyl alcohol = SMILES O{2}C1=CC=CC=C1{7}CO;
Subst1 = 2,6-dihydroxybenzoic acid = SMILES C1=C{6}C(=C({2}C(=C1)O){7}C(=O)O)O |
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Structure type: monomer
Compound class: glycoside, phenolic glycoside
- Compound ID: 33013
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b-D-Glcp-(1-1)-Subst
Subst = 4-hydroxyalangifolioside aglycon = SMILES O{4}C1=CC(CC2={52}C(O)C({57}C(O)=O)={56}C(O)C=C2)={1}C(O)C=C1 |
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Structure type: monomer
Compound class: glycoside, phenolic glycoside
- Compound ID: 33014
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b-D-Glcp-(1-2)-+
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b-D-Glcp-(1-2')-Subst
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b-D-Glcp-(1-6)-+
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
Compound class: glycoside, phenolic glycoside
- Compound ID: 33015
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b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-Subst
Subst = alangifolioside aglycon |
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Structure type: oligomer
Trivial name: alangifolioside
Compound class: glycoside, phenolic glycoside
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