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Saracoglu I, Kojima K, Sebnem Harput U, Ogihara Y
A new phenylethanoid glycoside from Phlomis pungens Willd. var. pungens
Chemical and Pharmaceutical Bulletin 46(4) (1998)
726-727
|
b-D-Glcp-(1-1)-Subst
Subst = lamiide aglycone = SMILES CO{10}C(=O)/C1=C/O{1}[C@@H](O)C2{8}[C@@](C)(O){7}[C@@H](O)C{5}[C@]12O |
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Phlomis pungens
(later renamed to: Phlomis herba-venti ssp. pungens)
(NCBI TaxID 997721,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
NCBI PubMed ID: 9579050Publication DOI: 10.1248/cpb.46.726Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, Japan
Three known phenylethanoid glycosides, forsythoside B, alyssonoside and leucosceptoside B, and a known iridoid glycoside, lamiide, were isolated from the methanol extract of the aerial parts of Phlomis pungens WILLD. var. pungens (Labiatae) along with one new phenylethanoid glycoside, (4- hydroxyphenyl)ethyl (5-O-syringyl-β-D-apiofuranosyl)-(1→2)-β-D- glucopyranoside, termed hattushoside.
phenylethanoid glycoside, Labiatae, Phlomis pungens, hattushoside
Structure type: monomer
Location inside paper: Chart 1, compound 1
Trivial name: lamiide
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, chromatography, HMBC, HMQC, COSY, MPLC, ioptical rotaion measurement
Related record ID(s): 62056, 62057
NCBI Taxonomy refs (TaxIDs): 997721
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There is only one chemically distinct structure:
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Saracoglu I, Kojima K, Sebnem Harput U, Ogihara Y
A new phenylethanoid glycoside from Phlomis pungens Willd. var. pungens
Chemical and Pharmaceutical Bulletin 46(4) (1998)
726-727
|
/Variants 0/-+
|
b-D-Apif-(1-6)-b-D-Glcp-(1-8)-3,4,8HOPhet-(4-1)-Me
/Variants 0/ is:
Fer-(9-4)-
OR (exclusively)
Caf-(9-4)- |
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Phlomis pungens
(later renamed to: Phlomis herba-venti ssp. pungens)
(NCBI TaxID 997721,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
NCBI PubMed ID: 9579050Publication DOI: 10.1248/cpb.46.726Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, Japan
Three known phenylethanoid glycosides, forsythoside B, alyssonoside and leucosceptoside B, and a known iridoid glycoside, lamiide, were isolated from the methanol extract of the aerial parts of Phlomis pungens WILLD. var. pungens (Labiatae) along with one new phenylethanoid glycoside, (4- hydroxyphenyl)ethyl (5-O-syringyl-β-D-apiofuranosyl)-(1→2)-β-D- glucopyranoside, termed hattushoside.
phenylethanoid glycoside, Labiatae, Phlomis pungens, hattushoside
Structure type: oligomer
Location inside paper: Chart 1, compound 2, compound 3, compound 4
Trivial name: forythoside B, alyssonodie, leucosceptoside B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, chromatography, HMBC, HMQC, COSY, MPLC, ioptical rotaion measurement
Related record ID(s): 62055, 62057
NCBI Taxonomy refs (TaxIDs): 997721
Show glycosyltransferases
There is only one chemically distinct structure:
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Saracoglu I, Kojima K, Sebnem Harput U, Ogihara Y
A new phenylethanoid glycoside from Phlomis pungens Willd. var. pungens
Chemical and Pharmaceutical Bulletin 46(4) (1998)
726-727
|
Gallic3Me5Me-(7-5)-b-D-Apif-(1-2)-b-D-Glcp-(1-8)-Subst
Subst = tyrosol = SMILES O{8}CCC1=CC={4}C(O)C=C1 |
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Phlomis pungens
(later renamed to: Phlomis herba-venti ssp. pungens)
(NCBI TaxID 997721,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperNCBI PubMed ID: 9579050Publication DOI: 10.1248/cpb.46.726Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, Japan
Three known phenylethanoid glycosides, forsythoside B, alyssonoside and leucosceptoside B, and a known iridoid glycoside, lamiide, were isolated from the methanol extract of the aerial parts of Phlomis pungens WILLD. var. pungens (Labiatae) along with one new phenylethanoid glycoside, (4- hydroxyphenyl)ethyl (5-O-syringyl-β-D-apiofuranosyl)-(1→2)-β-D- glucopyranoside, termed hattushoside.
phenylethanoid glycoside, Labiatae, Phlomis pungens, hattushoside
Structure type: oligomer ; 635.1932
C
28H
36O
15Location inside paper: Chart 1, compound 5, table 1
Trivial name: hattushoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, chromatography, HMBC, HMQC, COSY, MPLC, ioptical rotaion measurement
Related record ID(s): 62055, 62056
NCBI Taxonomy refs (TaxIDs): 997721
Show glycosyltransferases
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
8,2,5,3 Me 57.0
8,2,5,5 Me 57.0
8,2,5 xXGallic 121.2 108.6 149.0 142.6 149.0 108.6 168.0
8,2 bDApif 110.1 78.5 79.3 75.5 68.9
8 bDGlcp 103.0 77.9 79.0 71.8 77.9 62.7
Subst 130.4 130.9 116.1 156.8 116.1 130.9 36.5 71.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
8,2,5,3 Me 3.84
8,2,5,5 Me 3.84
8,2,5 xXGallic - 7.35 - - - 7.35 -
8,2 bDApif 5.44 4.00 - 3.80-4.17 4.35-4.46
8 bDGlcp 4.28 3.40 3.48 3.27 3.22 3.64-3.84
Subst - 6.90 6.62 - 6.62 6.90 2.70 3.51-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
8,2,5,3 Me 57.0/3.84
8,2,5,5 Me 57.0/3.84
8,2,5 xXGallic 108.6/7.35 108.6/7.35
8,2 bDApif 110.1/5.44 78.5/4.00 75.5/3.80-4.17 68.9/4.35-4.46
8 bDGlcp 103.0/4.28 77.9/3.40 79.0/3.48 71.8/3.27 77.9/3.22 62.7/3.64-3.84
Subst 130.9/6.90 116.1/6.62 116.1/6.62 130.9/6.90 36.5/2.70 71.8/3.51-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 8,2,5,3 | Me | 3.84 | |
| 8,2,5,5 | Me | 3.84 | |
| 8,2,5 | xXGallic |
| 7.35 |
|
|
| 7.35 |
| |
| 8,2 | bDApif | 5.44 | 4.00 |
| 3.80
4.17 | 4.35
4.46 | |
| 8 | bDGlcp | 4.28 | 3.40 | 3.48 | 3.27 | 3.22 | 3.64
3.84 | |
| | Subst |
| 6.90 | 6.62 |
| 6.62 | 6.90 | 2.70 | 3.51
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 8,2,5,3 | Me | 57.0 | |
| 8,2,5,5 | Me | 57.0 | |
| 8,2,5 | xXGallic | 121.2 | 108.6 | 149.0 | 142.6 | 149.0 | 108.6 | 168.0 | |
| 8,2 | bDApif | 110.1 | 78.5 | 79.3 | 75.5 | 68.9 | |
| 8 | bDGlcp | 103.0 | 77.9 | 79.0 | 71.8 | 77.9 | 62.7 | |
| | Subst | 130.4 | 130.9 | 116.1 | 156.8 | 116.1 | 130.9 | 36.5 | 71.8 |
|
There is only one chemically distinct structure:
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