Found 4 records.
Displayed records from 1 to 4
Expand all records
Collapse all records
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C
Studies on the Constituents of Leaves of Citrus unshiu Markov.
Chemical and Pharmaceutical Bulletin 36(12) (1988)
5004-5008
|
b-D-Glcp-(1-2)-Subst1
Subst1 = icariside B1 aglycone = SMILES CC(=O)C=C=C1C(C)(C)C{4}[C@H](O)C{2}[C@@]1(C)O |
Show graphically |
Citrus unshiu
(NCBI TaxID 55188,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.36.5004Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, 2-2-1, Oshika, Shizuoka 422, Japan, Citrus Experiment Station, Shizuoka Prefecture, 2712, Komagoe, Shimizu 424, Japan
Two new glycosides citroside A (3) and B (4), together with 2-phenylethyl β-D-glucopyranoside (1) and 2-phenylethyl D-rutinoside (2), were isolated from the methanol extract of leaves of Citrus unshiu, in addition to two known terpenoids, limonin (5) and friedelin (6).On the basis of spectral and chemical evidence the structures of the new glycosides were determined as (5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside (3) and a (5-dehydroxy-allenic ketodiol-5-yl) 5-β-D-glucopyranoside (4).
Rutaceae, Citrus unshiu, citroside A, citroside B, 2-phenylethyl β-D-glucopyranoside, 2-phenylethyl D-rutinoside, limonin, friedelin
Structure type: monomer
C
19H
30O
8Location inside paper: compound 3, chart 1(3), table I(3), table II(3)
Trivial name: citroside A
Compound class: sesquiterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC, HPLC, UV, optical rotation measurement, acetylation, sulfuric acid hydrolysis, acetic acid hydrolysis, photo-epimerization
Comments, role: NMR temperature was not specified; aglycon dienic carbon has R configuration in citroside A
Related record ID(s): 62780, 62781, 62782
NCBI Taxonomy refs (TaxIDs): 55188
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13
2 bDGlcp 98.4 75.1 79.0 71.7 78.0 62.8
Subst1 36.4 50.1 62.5 47.5 78.1 118.7 197.6 100.8 211.4 26.5 27.0 29.7 32.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13
2 bDGlcp 5.04 ? ? ? ? ?
Subst1 - ? ? ? - - - 6.00 - 2.20 1.17-1.62 1.17-1.62 1.17-1.62
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13
2 bDGlcp 98.4/5.04 75.1/? 79.0/? 71.7/? 78.0/? 62.8/?
Subst1 50.1/? 62.5/? 47.5/? 100.8/6.00 26.5/2.20 27.0/1.17-1.62 29.7/1.17-1.62 32.3/1.17-1.62
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 |
|---|
| 2 | bDGlcp | 5.04 | ? | ? | ? | ? | ? | |
| | Subst1 |
| ? | ? | ? |
|
|
| 6.00 |
| 2.20 | 1.17
1.62 | 1.17
1.62 | 1.17
1.62 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 |
|---|
| 2 | bDGlcp | 98.4 | 75.1 | 79.0 | 71.7 | 78.0 | 62.8 | |
| | Subst1 | 36.4 | 50.1 | 62.5 | 47.5 | 78.1 | 118.7 | 197.6 | 100.8 | 211.4 | 26.5 | 27.0 | 29.7 | 32.3 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C
Studies on the Constituents of Leaves of Citrus unshiu Markov.
Chemical and Pharmaceutical Bulletin 36(12) (1988)
5004-5008
|
b-D-Glcp-(1-2)-Subst2
Subst2 = icariside B1 aglycone = SMILES CC(=O)C=C=C1C(C)(C)C{4}[C@H](O)C{2}[C@@]1(C)O |
Show graphically |
Citrus unshiu
(NCBI TaxID 55188,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.36.5004Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, 2-2-1, Oshika, Shizuoka 422, Japan, Citrus Experiment Station, Shizuoka Prefecture, 2712, Komagoe, Shimizu 424, Japan
Two new glycosides citroside A (3) and B (4), together with 2-phenylethyl β-D-glucopyranoside (1) and 2-phenylethyl D-rutinoside (2), were isolated from the methanol extract of leaves of Citrus unshiu, in addition to two known terpenoids, limonin (5) and friedelin (6).On the basis of spectral and chemical evidence the structures of the new glycosides were determined as (5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside (3) and a (5-dehydroxy-allenic ketodiol-5-yl) 5-β-D-glucopyranoside (4).
Rutaceae, Citrus unshiu, citroside A, citroside B, 2-phenylethyl β-D-glucopyranoside, 2-phenylethyl D-rutinoside, limonin, friedelin
Structure type: monomer
C
19H
30O
8Location inside paper: compound 4, chart 1(4), table I(4), table II(4)
Trivial name: citroside B
Compound class: sesquiterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC, HPLC, UV, optical rotation measurement, acetylation, sulfuric acid hydrolysis, acetic acid hydrolysis, photo-epimerization
Comments, role: NMR temperature was not specified; aglycon dienic carbon has S configuration in citroside B
Related record ID(s): 62779, 62781, 62782
NCBI Taxonomy refs (TaxIDs): 55188
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13
2 bDGlcp 98.4 75.2 79.1 71.7 78.0 62.8
Subst2 36.2 50.1 62.4 46.8 78.6 118.8 199.0 100.9 211.2 27.1 27.60 29.6 32.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13
2 bDGlcp 5.16 ? ? ? ? ?
Subst2 - ? ? ? - - - 6.10 - 2.28 1.12 1.62 1.66
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13
2 bDGlcp 98.4/5.16 75.2/? 79.1/? 71.7/? 78.0/? 62.8/?
Subst2 50.1/? 62.4/? 46.8/? 100.9/6.10 27.1/2.28 27.60/1.12 29.6/1.62 32.5/1.66
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 |
|---|
| 2 | bDGlcp | 5.16 | ? | ? | ? | ? | ? | |
| | Subst2 |
| ? | ? | ? |
|
|
| 6.10 |
| 2.28 | 1.12 | 1.62 | 1.66 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 |
|---|
| 2 | bDGlcp | 98.4 | 75.2 | 79.1 | 71.7 | 78.0 | 62.8 | |
| | Subst2 | 36.2 | 50.1 | 62.4 | 46.8 | 78.6 | 118.8 | 199.0 | 100.9 | 211.2 | 27.1 | 27.60 | 29.6 | 32.5 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C
Studies on the Constituents of Leaves of Citrus unshiu Markov.
Chemical and Pharmaceutical Bulletin 36(12) (1988)
5004-5008
|
b-D-Glcp-(1-1)-Subst
Subst = phenylethanol = SMILES O{1}CCC1=CC=CC=C1 |
Show graphically |
Citrus unshiu
(NCBI TaxID 55188,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.36.5004Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, 2-2-1, Oshika, Shizuoka 422, Japan, Citrus Experiment Station, Shizuoka Prefecture, 2712, Komagoe, Shimizu 424, Japan
Two new glycosides citroside A (3) and B (4), together with 2-phenylethyl β-D-glucopyranoside (1) and 2-phenylethyl D-rutinoside (2), were isolated from the methanol extract of leaves of Citrus unshiu, in addition to two known terpenoids, limonin (5) and friedelin (6).On the basis of spectral and chemical evidence the structures of the new glycosides were determined as (5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside (3) and a (5-dehydroxy-allenic ketodiol-5-yl) 5-β-D-glucopyranoside (4).
Rutaceae, Citrus unshiu, citroside A, citroside B, 2-phenylethyl β-D-glucopyranoside, 2-phenylethyl D-rutinoside, limonin, friedelin
Structure type: monomer
C
14H
20O
6Location inside paper: compound 1, chart 1(1), table I(1)
Compound class: glycoside, phenylethanoid glycoside, sesquiterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC, HPLC, UV, optical rotation measurement, acetylation, sulfuric acid hydrolysis, acetic acid hydrolysis, photo-epimerization
Comments, role: NMR temperature was not specified
Related record ID(s): 62779, 62780, 62782
NCBI Taxonomy refs (TaxIDs): 55188Reference(s) to other database(s): CCSD:
50059, CBank-STR:1046
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
1 bDGlcp 104.6 75.0 78.3 70.5 78.3 62.8
Subst 139.3 128.6 129.3 126.4 129.3 128.6 36.6 71.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
1 bDGlcp 4.82 ? ? ? ? ?
Subst - 7.25 7.25 7.25 7.25 7.25 3.00 ?
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
1 bDGlcp 104.6/4.82 75.0/? 78.3/? 70.5/? 78.3/? 62.8/?
Subst 128.6/7.25 129.3/7.25 126.4/7.25 129.3/7.25 128.6/7.25 36.6/3.00 71.6/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 1 | bDGlcp | 4.82 | ? | ? | ? | ? | ? | |
| | Subst |
| 7.25 | 7.25 | 7.25 | 7.25 | 7.25 | 3.00 | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 1 | bDGlcp | 104.6 | 75.0 | 78.3 | 70.5 | 78.3 | 62.8 | |
| | Subst | 139.3 | 128.6 | 129.3 | 126.4 | 129.3 | 128.6 | 36.6 | 71.6 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C
Studies on the Constituents of Leaves of Citrus unshiu Markov.
Chemical and Pharmaceutical Bulletin 36(12) (1988)
5004-5008
|
a-L-Rhap-(1-6)-b-D-Glcp-(1-1)-Subst
Subst = phenylethanol = SMILES O{1}CCC1=CC=CC=C1 |
Show graphically |
Citrus unshiu
(NCBI TaxID 55188,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.36.5004Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, 2-2-1, Oshika, Shizuoka 422, Japan, Citrus Experiment Station, Shizuoka Prefecture, 2712, Komagoe, Shimizu 424, Japan
Two new glycosides citroside A (3) and B (4), together with 2-phenylethyl β-D-glucopyranoside (1) and 2-phenylethyl D-rutinoside (2), were isolated from the methanol extract of leaves of Citrus unshiu, in addition to two known terpenoids, limonin (5) and friedelin (6).On the basis of spectral and chemical evidence the structures of the new glycosides were determined as (5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside (3) and a (5-dehydroxy-allenic ketodiol-5-yl) 5-β-D-glucopyranoside (4).
Rutaceae, Citrus unshiu, citroside A, citroside B, 2-phenylethyl β-D-glucopyranoside, 2-phenylethyl D-rutinoside, limonin, friedelin
Structure type: monomer
C
20H
30O
10Location inside paper: compound 2, chart 1(2), table I(2)
Compound class: sesquiterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GC, HPLC, UV, optical rotation measurement, acetylation, sulfuric acid hydrolysis, acetic acid hydrolysis, photo-epimerization
Comments, role: NMR temperature was not specified
Related record ID(s): 62779, 62780, 62781
NCBI Taxonomy refs (TaxIDs): 55188
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
1,6 aLRhap 102.3 72.1 72.7 74.0 69.7 18.6
1 bDGlcp 104.5 74.9 78.4 70.5 77.0 68.2
Subst 139.4 128.6 129.4 126.4 129.4 128.6 36.6 71.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
1,6 aLRhap ? ? ? ? ? 1.60
1 bDGlcp 4.81 ? ? ? ? ?
Subst - 7.25 7.25 7.25 7.25 7.25 3.00 ?
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
1,6 aLRhap 102.3/? 72.1/? 72.7/? 74.0/? 69.7/? 18.6/1.60
1 bDGlcp 104.5/4.81 74.9/? 78.4/? 70.5/? 77.0/? 68.2/?
Subst 128.6/7.25 129.4/7.25 126.4/7.25 129.4/7.25 128.6/7.25 36.6/3.00 71.7/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 1,6 | aLRhap | ? | ? | ? | ? | ? | 1.60 | |
| 1 | bDGlcp | 4.81 | ? | ? | ? | ? | ? | |
| | Subst |
| 7.25 | 7.25 | 7.25 | 7.25 | 7.25 | 3.00 | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 1,6 | aLRhap | 102.3 | 72.1 | 72.7 | 74.0 | 69.7 | 18.6 | |
| 1 | bDGlcp | 104.5 | 74.9 | 78.4 | 70.5 | 77.0 | 68.2 | |
| | Subst | 139.4 | 128.6 | 129.4 | 126.4 | 129.4 | 128.6 | 36.6 | 71.7 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Total list of record IDs on all result pages of the current query:
Execution: 8 sec
report error