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1. (Article ID: 10651)
Pan H, Lundgren LN
Rhododendrol glycosides and phenyl glucoside esters from inner bark of Betula pubescens
Phytochemistry 36 (1994)
79-83
A chemical investigation of the inner bark of Betula pubescens has led to the isolation of rhododendrin, epirhododendrin, apiosylrhododendrin and apiosylepirhododendrin. This is the first observation of both (+)- and (−)-rhododendrol glycosides in the same species. Also, the new compounds 3,4,5-trimethoxyphenyl-6-O-vanilloyl-β-d-glucopyranoside and 3,4,5-trimethoxyphenyl-6-O-syringoyl-β-d-glucopyranoside, and the known 4-O-β-d-glucoside of p-hydroxybenzoic acid, as well as (+)-catechin, catechin 7-O-β-d-xylopyranoside and B1 and B3 procyanidins were found.
4, 3, Betula pubescens, Betulaceae, inner bark, rhododendrin, epirhododendrin, apiosylrhododendrin, apiosylepirhododendrin, 5-trimethoxyphenyl-6-O-vanilloyl-β-d-glucopyranoside, 5-trimethoxyphenyl-6-O-syringoyl-β-d-glucopyranoside, Betulaceae; inner bark
Publication DOI: 10.1016/S0031-9422(00)97017-1Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden
Methods: 13C NMR, 1H NMR, EI-MS, TLC, GLC, HPLC, enzymatic digestion
The publication contains the following compound(s):
- Compound ID: 26319
Structure type: monomer
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39045, CBank-STR:1071
- Compound ID: 26320
|
b-D-Glcp-(1-2)-Subst
Subst = (R)-4-hydroxyphenyl-2-butanol = SMILES C{2}[C@@H](O)CCC1=CC=C(O)C=C1 |
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Structure type: monomer
Trivial name: rhododendrin
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39046, CBank-STR:1118
- Compound ID: 26321
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b-D-Glcp-(1-2)-Subst
Subst = (S)-4-hydroxyphenyl-2-butanol = SMILES C{2}[C@H](O)CCC1=CC=C(O)C=C1 |
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Structure type: monomer
Trivial name: epirhododendrin
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39047, CBank-STR:1118
- Compound ID: 26322
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b-D-Apif-(1-6)-b-D-Glcp-(1-2)-Subst
Subst = (R)-4-hydroxyphenyl-2-butanol = SMILES C{2}[C@@H](O)CCC1=CC=C(O)C=C1 |
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Structure type: oligomer
Trivial name: apiosylrhododendrin
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39048, CBank-STR:3003
- Compound ID: 26323
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b-D-Apif-(1-6)-b-D-Glcp-(1-2)-Subst
Subst = (S)-4-hydroxyphenyl-2-butanol = SMILES C{2}[C@H](O)CCC1=CC=C(O)C=C1 |
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Structure type: oligomer
Trivial name: apiosylepirhododendrin
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39049, CBank-STR:3004
- 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: 26325
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Subst1-(7-6)-b-D-Glcp-(1-5)-Subst2-1Me2Me3Me
Subst1 = vanillic acid = SMILES COC1=CC({7}C(O)=O)=CC={4}C1O;
Subst2 = 5-hydroxypyrogallol = SMILES {1}OC1={2}C(O){3}C(O)=C{5}C(O)=C1 |
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Structure type: monomer
; 496 [M]+
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39051, CBank-STR:2328
- Compound ID: 26326
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Subst1-(7-6)-b-D-Glcp-(1-1)-Subst2-2Me3Me5Me
Subst1 = syringic acid = SMILES O{4}C(C(OC)=CC({7}C(O)=O)=C1)=C1OC;
Subst2 = 5-hydroxypyrogallol = SMILES {1}OC1={2}C(O){3}C(O)=C{5}C(O)=C1 |
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Structure type: monomer
; 526 [M]+
Compound class: glycoside
Reference(s) to other database(s): CCSD:
39052, CBank-STR:2330
- Compound ID: 26327
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b-D-Xylp-(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
Reference(s) to other database(s): CCSD:
39053, CBank-STR:850
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2. (Article ID: 11291)
Wilson IBH, Altmann F
Structural analysis of N-glycans from allergenic grass, ragweed and tree pollens: Core alpha 1,3-linked fucose and xylose present in all pollens examined
Glycoconjugate Journal 15(11) (1998)
1055-1070
The N-glycans from soluble extracts of ten pollens were examined. The pyridylaminated oligosaccharides derived from these sources were subject to gel filtration and reverse-phase HPLC, in conjunction with exoglycosidase digests, and in some cases matrix-assisted laser desorption-ionisation mass spectrometry. In comparison to known structures, it was possible to determine the major structures of the N-glycans derived from Kentucky blue grass (Poa pratensis), rye (Secale cerale), ryegrass (Lolium perenne), short ragweed (Ambrosia elatior), giant ragweed (Ambrosia trifida), birch (Betula alba), hornbeam (Carpinus betulus), horse chestnut (Aesculus hippocastanum), olive (Olea europaea) and snake-skin pine (Pinus leucodermis) pollen extracts. For grass pollens the major glycans detected were identical in properties to: [structure in text] Grass pollens also contained some minor structures with one or two non-reducing terminal N-acetylglucosamine residues. In the ragweed pollens, the major structures carried core alpha1,3-linked fucose with or without the presence of xylose. In tree pollen extracts, the major structures were either xylosylated, with or without fucose and terminal N-acetylglucosamine residues, with also significant amounts of oligomannose structures. These results are compatible with the hypothesis that the carbohydrate structures are another potential source of immunological cross-reaction between different plant allergens.
N-glycans, pollens
NCBI PubMed ID: 10386890Publication DOI: 10.1023/a:1006960401562Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: Altmann F
edv2.boku.ac.at>
Institutions: Institut für Chemie der Universität für Bodenkultur, Wien, Austria
Methods: gel filtration, HPLC, enzymatic digestion, MALDI-TOF, pyridylamination, fluorescence labeling, reverse-phase HPLC
The publication contains the following compound(s):
- Compound ID: 28504
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a-D-Manp-(1-6)-+ a-D-Fucp-(1-3)-+
| |
a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-Glcp2Ac-(1--/(->4) Asn-X-Ser/Thr (protein)/
|
b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1390.2 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G40632TS
- Compound ID: 28508
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a-D-Manp-(1-3)-+
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a-D-Manp-(1-6)-+ |
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a-D-Manp-(1-3)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1336.2 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G55220VL
- Compound ID: 28509
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a-D-Manp-(1-6)-+ a-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
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b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1493.4 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G67193FI
- Compound ID: 28510
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a-D-Manp-(1-3)-+ a-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
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b-Xylp-(1-2)-+ |
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Structure type: oligomer
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G03566WF
- Compound ID: 28511
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b-D-GlcpNAc-(1-2)-a-D-Manp-(1-6)-+ a-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
|
b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1696.5 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G93166VS
- Compound ID: 28512
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a-D-Manp-(1-2)-a-D-Manp-(1-3)-+
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a-D-Manp-(1-6)-+ |
| |
a-D-Manp-(1-3)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1498.4 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G80966KZ
- Compound ID: 28513
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a-D-Manp-(1-2)-a-D-Manp-(1-3)-+
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a-D-Manp-(1-3)-+ |
| |
a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1660.5 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G83161QT
- Compound ID: 28514
|
a-D-Manp-(1-6)-+
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a-D-Manp-(1-3)-a-D-Manp-(1-6)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1660.5 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G68668TB
- Compound ID: 28515
|
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-+
|
a-D-Manp-(1-3)-+ |
| |
a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1822.6 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G40702WU
- Compound ID: 28496
|
a-Fucp-(1-3)-+
|
b-Xylp-(1-2)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 965.9 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G19461FS
- Compound ID: 28498
|
a-Fucp-(1-3)-+
|
a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 995.9 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G38990RA
- Compound ID: 28499
|
b-Xylp-(1-2)-+ a-D-Fucp-(1-3)-+
| |
a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1128.1 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G55167NO
- Compound ID: 28500
|
a-D-Manp-(1-6)-+
|
a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
|
b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1144.1 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G37075ZM
- Compound ID: 28497
|
b-Xylp-(1-2)-+
|
a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 981.9 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G95497LY
- Compound ID: 28502
|
b-Xylp-(1-2)-+ a-D-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1331.2 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G83505HH
- Compound ID: 28505
|
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-6)-+
|
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
|
b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1550.3 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G15866AM
- Compound ID: 28516
|
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-+
|
a-D-Manp-(1-2)-a-D-Manp-(1-6)-+ |
| |
a-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1984.8 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G60230HH
- Compound ID: 28501
|
a-D-Manp-(1-6)-+ a-D-Fucp-(1-3)-+
| |
a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1158.1 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G86601RH
- Compound ID: 28506
|
a-D-Manp-(1-6)-+ a-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1361.3 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G62888VZ
- Compound ID: 28507
|
a-D-Manp-(1-3)-+ a-Fucp-(1-3)-+
| |
a-D-Manp-(1-?)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/ |
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Structure type: oligomer
; 1320.2 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G51942GM
- Compound ID: 28503
|
a-D-Manp-(1-6)-+
|
b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1--/(->4) Asn-X-Ser/Thr (protein)/
|
b-Xylp-(1-2)-+ |
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Structure type: oligomer
; 1347.2 [M+Na]+
Aglycon: (->4) Asn-X-Ser/Thr (protein)
Compound class: N-glycan
Reference(s) to other database(s): GTC:G37246YI
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