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Ismailov AÉ, Kuliev ZA, Vdovin AD, Abdullaev ND, Murzubraimov BM
Oligomeric proanthocyanidin glycosides of Rhodiola pamiroalaica. II
Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(1) (1999)
33-38
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-5)-+
|
Gallic-(7-3)-+ Gallic-(7-3)-+ |
| | |
Gallic-(7-6)-b-D-Glcp-(1-7)-Subst1-(4C-8)-Subst2-(4C-8)-Subst1-(4C-8)-Subst3
Subst1 = (2R,3R,4S)-2-(3,4,5-trihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2c{55}c(O){54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst2 = (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2cc{54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst3 = (+)-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 |
Show graphically |
Rhodiola pamiroalaica
(previously named: Rhodiola pamiro-alaica)
(NCBI TaxID 1439920,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperPublication DOI: 10.1007/BF02238206Journal NLM ID: 0151571Publisher: Tashkent: Izdatelstvo Fan
Institutions: Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan, Osh State University, Osh, USSR
In a continuation of investigations of proanthocyanidins of the roots of Rhodiola pamiroalaica, we have isolated proanthocyanidins RP-3 and RP-4. Their compositions, structures, and relative configurations have been investigated: RP-3 is 7-O-(6-O-galloyl-β-D-Glcp)-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[(-)-epicatechin-(4β-8)-(3-O-galloyl-(-)-epigallocatechin)]2-(4β-8)-[5-O-(β-D-Glcp→O-β-D-Glcp)-(+)-catechin], and RP-4 is 7-O-(6-O-galloyl-β-D-Glcp-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)-galloyl-5-(β-D-Glcp→O-β-D-Glcp)-(-)-epigallocatechin
Rhodiola pamiroalaica, proanthocyanidin glycoside, epigallocatechin, epicatechin, catehin
Structure type: oligomer ; 2872
C
136H
120O
70Location inside paper: table 1, RP-3, p. 35 (fig.)
Compound class: tannin
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, IR, TLC, enzymatic hydrolysis, MS, alkaline hydrolysis, UV, optical rotation measurement, methylation analysis, reduction, PC, HCl hydrolysis, sulfuric acid hydrolysis, thiolylic cleavage
Comments, role: NMR temperature was not specified
Related record ID(s): 62880, 62881, 62882
NCBI Taxonomy refs (TaxIDs): 1439920
Show glycosyltransferases
NMR conditions: in vol 50%D2O / vol 50%DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
5,6 bDGlcp 101.3 75.8 77.1 72.9 77.1 60.4
5 bDGlcp 101.3 75.8 77.1 71.7 75.8 64.4
8,3 xXGallic 120.3 109.9 144.7 139.1 144.7 109.9 166.4
8,8,8,3 xXGallic 120.3 109.9 144.7 139.1 144.7 109.9 166.4
8,8,8,7,6 xXGallic 120.3 109.9 144.7 139.1 144.7 109.9 166.4
8,8,8,7 bDGlcp 101.3 75.8 77.1 71.7 75.8 62.3
8,8,8 Subst1 75.8 74.3 34.6 153.2-155.4 95.4 153.2-155.4 93.1 153.2-155.4 101.3 130.5 109.9 144.7 132.4 144.7 109.9
8,8 Subst2 77.1 71.3 36.4 153.2-155.4 95.4 153.2-155.4 106.8 153.2-155.4 101.3 130.5 116.2 144.7 144.7 116.2 120.3
8 Subst1 75.8 74.3 34.6 153.2-155.4 95.4 153.2-155.4 106.8 153.2-155.4 101.3 130.5 109.9 144.7 132.4 144.7 109.9
Subst3 81.2 65.9 27.1 153.2-155.4 95.4 153.2-155.4 106.8 153.2-155.4 101.3 130.5 116.2 144.7 144.7 116.2 120.3
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 5,6 | bDGlcp | 101.3 | 75.8 | 77.1 | 72.9 | 77.1 | 60.4 | |
| 5 | bDGlcp | 101.3 | 75.8 | 77.1 | 71.7 | 75.8 | 64.4 | |
| 8,3 | xXGallic | 120.3 | 109.9 | 144.7 | 139.1 | 144.7 | 109.9 | 166.4 | |
| 8,8,8,3 | xXGallic | 120.3 | 109.9 | 144.7 | 139.1 | 144.7 | 109.9 | 166.4 | |
| 8,8,8,7,6 | xXGallic | 120.3 | 109.9 | 144.7 | 139.1 | 144.7 | 109.9 | 166.4 | |
| 8,8,8,7 | bDGlcp | 101.3 | 75.8 | 77.1 | 71.7 | 75.8 | 62.3 | |
| 8,8,8 | Subst1 | 75.8 | 74.3 | 34.6 | 153.2
155.4 | 95.4 | 153.2
155.4 | 93.1 | 153.2
155.4 | 101.3 | 130.5 | 109.9 | 144.7 | 132.4 | 144.7 | 109.9 |
| 8,8 | Subst2 | 77.1 | 71.3 | 36.4 | 153.2
155.4 | 95.4 | 153.2
155.4 | 106.8 | 153.2
155.4 | 101.3 | 130.5 | 116.2 | 144.7 | 144.7 | 116.2 | 120.3 |
| 8 | Subst1 | 75.8 | 74.3 | 34.6 | 153.2
155.4 | 95.4 | 153.2
155.4 | 106.8 | 153.2
155.4 | 101.3 | 130.5 | 109.9 | 144.7 | 132.4 | 144.7 | 109.9 |
| | Subst3 | 81.2 | 65.9 | 27.1 | 153.2
155.4 | 95.4 | 153.2
155.4 | 106.8 | 153.2
155.4 | 101.3 | 130.5 | 116.2 | 144.7 | 144.7 | 116.2 | 120.3 |
|
There is only one chemically distinct structure:
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Ismailov AÉ, Kuliev ZA, Vdovin AD, Abdullaev ND, Murzubraimov BM
Oligomeric proanthocyanidin glycosides of Rhodiola pamiroalaica. II
Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(1) (1999)
33-38
|
b-D-Glcp-(1-5)-+
|
Gallic-(7-3)-+ |
| |
Gallic-(7-3)-+ | |
| | |
Gallic-(7-3)-+ | | |
| | | |
Gallic-(7-3)-+ | | | |
| | | | |
Gallic-(7-6)-b-D-Glcp-(1-7)-Subst1-(4C-8)-Subst2-(4C-8)-Subst1-(4C-8)-Subst2-(4C-8)-Subst3
|
Gallic-(7-3)-+
Subst1 = (2R,3R,4S)-2-(3,4,5-trihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2c{55}c(O){54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst2 = (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2cc{54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst3 = (-)-epicatechin = SMILES O{7}C1=C{5}C(O)=C2C{3}[C@H]([C@H](OC2={8}C1)C3=C{53}C(O)={54}C(O)C=C3)O |
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Rhodiola pamiroalaica
(previously named: Rhodiola pamiro-alaica)
(NCBI TaxID 1439920,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperPublication DOI: 10.1007/BF02238206Journal NLM ID: 0151571Publisher: Tashkent: Izdatelstvo Fan
Institutions: Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan, Osh State University, Osh, USSR
In a continuation of investigations of proanthocyanidins of the roots of Rhodiola pamiroalaica, we have isolated proanthocyanidins RP-3 and RP-4. Their compositions, structures, and relative configurations have been investigated: RP-3 is 7-O-(6-O-galloyl-β-D-Glcp)-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[(-)-epicatechin-(4β-8)-(3-O-galloyl-(-)-epigallocatechin)]2-(4β-8)-[5-O-(β-D-Glcp→O-β-D-Glcp)-(+)-catechin], and RP-4 is 7-O-(6-O-galloyl-β-D-Glcp-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)-galloyl-5-(β-D-Glcp→O-β-D-Glcp)-(-)-epigallocatechin
Rhodiola pamiroalaica, proanthocyanidin glycoside, epigallocatechin, epicatechin, catehin
Structure type: oligomer ; 2726
C
129H
106O
67Location inside paper: table 2, RP-4, p. 36 (fig.)
Compound class: tannin
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, IR, TLC, enzymatic hydrolysis, MS, alkaline hydrolysis, UV, optical rotation measurement, methylation analysis, reduction, PC, HCl hydrolysis, sulfuric acid hydrolysis, thiolylic cleavage
Comments, role: NMR temperature was not specified
Related record ID(s): 62879, 62881, 62882
NCBI Taxonomy refs (TaxIDs): 1439920
Show glycosyltransferases
NMR conditions: in vol 50%D2O / vol 50%DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
3 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 164.9
5 bDGlcp 103.4 74.0 76.2 71.9 76.2 60.4
8,3 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 162.5
8,8,3 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 164.9
8,8,8,3 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 164.9
8,8,8,8,3 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 164.9
8,8,8,8,7,6 xXGallic 119.2 111.5 142.6 138.8 142.6 111.6 164.9
8,8,8,8,7 bDGlcp 103.4 74.0 76.2 72.5 74.0 62.7
8,8,8,8 Subst1 74.0 74.0 33.4 151.2-153.7 97.0 151.2-153.7 94.2 151.2-153.7 100.1 130.2 111.6 142.6 131.8 142.6 111.6
8,8,8 Subst2 74.0 74.0 33.4 151.2-153.7 94.0 151.2-153.7 106.8 151.2-153.7 103.4 130.2 117.4 142.6 142.6 117.4 119.2
8,8 Subst1 74.0 74.0 33.4 151.2-153.7 94.0 151.2-153.7 106.8 151.2-153.7 103.4 130.2 111.6 142.6 131.8 142.6 111.6
8 Subst2 74.0 74.0 33.4 151.2-153.7 94.0 151.2-153.7 106.8 151.2-153.7 103.4 130.2 117.4 142.6 142.6 117.4 119.2
Subst3 76.2 69.2 26.4 151.2-153.7 94.0 151.2-153.7 106.8 151.2-153.7 103.4 130.2 111.6 142.6 131.8 142.6 111.6
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 164.9 | |
| 5 | bDGlcp | 103.4 | 74.0 | 76.2 | 71.9 | 76.2 | 60.4 | |
| 8,3 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 162.5 | |
| 8,8,3 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 164.9 | |
| 8,8,8,3 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 164.9 | |
| 8,8,8,8,3 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 164.9 | |
| 8,8,8,8,7,6 | xXGallic | 119.2 | 111.5 | 142.6 | 138.8 | 142.6 | 111.6 | 164.9 | |
| 8,8,8,8,7 | bDGlcp | 103.4 | 74.0 | 76.2 | 72.5 | 74.0 | 62.7 | |
| 8,8,8,8 | Subst1 | 74.0 | 74.0 | 33.4 | 151.2
153.7 | 97.0 | 151.2
153.7 | 94.2 | 151.2
153.7 | 100.1 | 130.2 | 111.6 | 142.6 | 131.8 | 142.6 | 111.6 |
| 8,8,8 | Subst2 | 74.0 | 74.0 | 33.4 | 151.2
153.7 | 94.0 | 151.2
153.7 | 106.8 | 151.2
153.7 | 103.4 | 130.2 | 117.4 | 142.6 | 142.6 | 117.4 | 119.2 |
| 8,8 | Subst1 | 74.0 | 74.0 | 33.4 | 151.2
153.7 | 94.0 | 151.2
153.7 | 106.8 | 151.2
153.7 | 103.4 | 130.2 | 111.6 | 142.6 | 131.8 | 142.6 | 111.6 |
| 8 | Subst2 | 74.0 | 74.0 | 33.4 | 151.2
153.7 | 94.0 | 151.2
153.7 | 106.8 | 151.2
153.7 | 103.4 | 130.2 | 117.4 | 142.6 | 142.6 | 117.4 | 119.2 |
| | Subst3 | 76.2 | 69.2 | 26.4 | 151.2
153.7 | 94.0 | 151.2
153.7 | 106.8 | 151.2
153.7 | 103.4 | 130.2 | 111.6 | 142.6 | 131.8 | 142.6 | 111.6 |
|
There is only one chemically distinct structure:
Expand this record
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Matamarova KN, Kuliev ZA, Vdovin AD, Abdullaev ND, Murzubraimov MB
Oligomeric proanthocyanidin glycosides of Clementsia semenovii. II
Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(1) (1999)
39-45
|
Gallic-(7-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-7)-Subst1-(4C-8)-Subst2-(4C-8)-Subst1-(4C-8)-Subst2-(4C-8)-Subst3
Subst1 = (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2cc{54}c(O){53}c(O)c2){3}[C@@H](O){4}[C@@H]3O;
Subst2 = (2R,3R,4S)-2-(3,4,5-trihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2c{55}c(O){54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst3 = (-)-epicatechin = SMILES O{7}C1=C{5}C(O)=C2C{3}[C@H]([C@H](OC2={8}C1)C3=C{53}C(O)={54}C(O)C=C3)O |
Show graphically |
Clementsia semenovii
(previously named: Sedum semenovii; later renamed to: Rhodiola semenovii)
(NCBI TaxID 666566,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperPublication DOI: 10.1007/BF02238207Journal NLM ID: 0151571Publisher: Tashkent: Izdatelstvo Fan
Institutions: Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan, Osh State University, Osh, USSR
The structures of proanthocyanidins CS-3 and CS-4, isolated from the roots of Clementsia semenovii have been established on the basis of chemical and spectral studies. CS-3 is 7-O-(6-O-galloyl-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp)-(+)-catechin-(4α-8)-(−)-epigallocatechin-(4β-8)-(+)-catechin-(4α-8)-(−)-epigaLLocatechin-(4β-8)-(−)-epigallocatechin-(4β-8)-(−)-epigallocatechin, and CS-4 is 3-O-galloyl-7-O-[6-O-galloyl-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp-(+)-gallocatechin-(4α-8)-[(+)-catechin-(4α-8)-(3-O-galloyl-(−)-epigallocatechin]2-(4β-8)-(−)-epicatechin.
proanthocyanidin glycoside, epicatechin, catehin, Clementsia semenovii
Structure type: oligomer ; 2754
C
127H
128O
69Location inside paper: table 1, CS-3, p. 41 (fig.)
Compound class: tannin
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, IR, TLC, enzymatic hydrolysis, MS, alkaline hydrolysis, UV, optical rotation measurement, methylation analysis, reduction, PC, HCl hydrolysis, sulfuric acid hydrolysis, thiolylic cleavage
Comments, role: NMR temperature was not specified
Related record ID(s): 62879, 62880, 62882
NCBI Taxonomy refs (TaxIDs): 666566
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13
8,8,8,8,7,6,6,6,6,6 xXGallic 122.5 111.1 147.0 140.3 147.0 111.1 168.0
8,8,8,8,7,6,6,6,6 bDGlcp 101.3 74.1 78.3 70.2 77.5 63.7
8,8,8,8,7,6,6,6 bDGlcp 103.8 73.0 78.3 70.2 77.5 65.3
8,8,8,8,7,6,6 bDGlcp 103.8 73.0 78.3 70.2 77.5 65.3
8,8,8,8,7,6 bDGlcp 103.8 73.0 78.3 70.2 77.5 65.3
8,8,8,8,7 bDGlcp 103.8 73.0 78.3 70.2 77.5 65.3
8,8,8,8 Subst1 78.3 66.6 30.5 98.0 107.7 103.8 157.5 131.6 111.1 147.0 134.3 147.0 111.
8,8,8 Subst2 77.5 72.6 35.8 98.0 107.7 101.3 157.5 131.6 111.1 147.0 134.3 147.0 111.1
8,8 Subst1 85.5 73.0 38.1 98.0 107.7 103.8 155.1 131.6 117.0 147.0 147.0 117.0 120.0
8 Subst2 77.5 72.6 35.6 98.0 107.7 101.3 157.5 131.6 111.1 147.0 134.1 147.0 111.1
Subst3 84.0 72.6 38.1 98.0 97.6 100.0 155.1 131.6 117.0 147.0 147.0 117.0 120.0
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 |
|---|
| 8,8,8,8,7,6,6,6,6,6 | xXGallic | 122.5 | 111.1 | 147.0 | 140.3 | 147.0 | 111.1 | 168.0 | |
| 8,8,8,8,7,6,6,6,6 | bDGlcp | 101.3 | 74.1 | 78.3 | 70.2 | 77.5 | 63.7 | |
| 8,8,8,8,7,6,6,6 | bDGlcp | 103.8 | 73.0 | 78.3 | 70.2 | 77.5 | 65.3 | |
| 8,8,8,8,7,6,6 | bDGlcp | 103.8 | 73.0 | 78.3 | 70.2 | 77.5 | 65.3 | |
| 8,8,8,8,7,6 | bDGlcp | 103.8 | 73.0 | 78.3 | 70.2 | 77.5 | 65.3 | |
| 8,8,8,8,7 | bDGlcp | 103.8 | 73.0 | 78.3 | 70.2 | 77.5 | 65.3 | |
| 8,8,8,8 | Subst1 | 78.3 | 66.6 | 30.5 | 98.0 | 107.7 | 103.8 | 157.5 | 131.6 | 111.1 | 147.0 | 134.3 | 147.0 | 111. |
| 8,8,8 | Subst2 | 77.5 | 72.6 | 35.8 | 98.0 | 107.7 | 101.3 | 157.5 | 131.6 | 111.1 | 147.0 | 134.3 | 147.0 | 111.1 |
| 8,8 | Subst1 | 85.5 | 73.0 | 38.1 | 98.0 | 107.7 | 103.8 | 155.1 | 131.6 | 117.0 | 147.0 | 147.0 | 117.0 | 120.0 |
| 8 | Subst2 | 77.5 | 72.6 | 35.6 | 98.0 | 107.7 | 101.3 | 157.5 | 131.6 | 111.1 | 147.0 | 134.1 | 147.0 | 111.1 |
| | Subst3 | 84.0 | 72.6 | 38.1 | 98.0 | 97.6 | 100.0 | 155.1 | 131.6 | 117.0 | 147.0 | 147.0 | 117.0 | 120.0 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Matamarova KN, Kuliev ZA, Vdovin AD, Abdullaev ND, Murzubraimov MB
Oligomeric proanthocyanidin glycosides of Clementsia semenovii. II
Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(1) (1999)
39-45
|
Gallic-(7-3)-+
|
Gallic-(7-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-7)-Subst1-(4C-8)-Subst2-(4C-8)-Subst3-(4C-8)-Subst4
Subst1 = (2R,3S,4R)-2-(3,4,5-trihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2c{55}c(O){54}c(O){53}c(O)c2){3}[C@@H](O){4}[C@@H]3O;
Subst2 = (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2cc{54}c(O){53}c(O)c2){3}[C@@H](O){4}[C@@H]3O;
Subst3 = (2R,3R,4S)-2-(3,4,5-trihydroxyphenyl)-3,4,5,7-chromanetetrol = SMILES O{7}c1c{5}c(O)c3c({8}c1)O[C@H](c2c{55}c(O){54}c(O){53}c(O)c2){3}[C@H](O){4}[C@H]3O;
Subst4 = (-)-epicatechin = SMILES O{7}C1=C{5}C(O)=C2C{3}[C@H]([C@H](OC2={8}C1)C3=C{53}C(O)={54}C(O)C=C3)O |
Show graphically |
Clementsia semenovii
(previously named: Sedum semenovii; later renamed to: Rhodiola semenovii)
(NCBI TaxID 666566,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperPublication DOI: 10.1007/BF02238207Journal NLM ID: 0151571Publisher: Tashkent: Izdatelstvo Fan
Institutions: Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan, Osh State University, Osh, USSR
The structures of proanthocyanidins CS-3 and CS-4, isolated from the roots of Clementsia semenovii have been established on the basis of chemical and spectral studies. CS-3 is 7-O-(6-O-galloyl-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp)-(+)-catechin-(4α-8)-(−)-epigallocatechin-(4β-8)-(+)-catechin-(4α-8)-(−)-epigaLLocatechin-(4β-8)-(−)-epigallocatechin-(4β-8)-(−)-epigallocatechin, and CS-4 is 3-O-galloyl-7-O-[6-O-galloyl-β-D-Glcp→6O-β-D-Glcp→6O-β-D-Glcp-(+)-gallocatechin-(4α-8)-[(+)-catechin-(4α-8)-(3-O-galloyl-(−)-epigallocatechin]2-(4β-8)-(−)-epicatechin.
proanthocyanidin glycoside, epicatechin, catehin, Clementsia semenovii
Structure type: oligomer ; 2568
C
122H
112O
62Location inside paper: table 2, CS-4, p. 43 (fig.)
Compound class: tannin
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, IR, TLC, enzymatic hydrolysis, MS, alkaline hydrolysis, UV, optical rotation measurement, methylation analysis, reduction, PC, HCl hydrolysis, sulfuric acid hydrolysis, thiolylic cleavage
Comments, role: NMR temperature was not specified
Related record ID(s): 62879, 62880, 62881
NCBI Taxonomy refs (TaxIDs): 666566
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
8,3 xXGallic 121.8 111.5 147.1 140.7 147.1 111.5 169.2
8,8,8,7,6,6,6 xXGallic 121.8 111.5 147.1 140.7 147.1 111.5 169.2
8,8,8,7,6,6 bDGlcp 101.0 75.9 78.9 70.1 77.8 67.8
8,8,8,7,6 bDGlcp 104.1 74.1 78.9 70.1 77.8 63.7
8,8,8,7 bDGlcp 104.1 74.1 78.9 70.1 77.8 63.7
8,8,8 Subst1 80.5 74.1 36.5 153.8-158.8 97.8 153.8-158.8 97.8 153.8-158.8 101.0 132.3 111.5 147.1 134.4 147.1 111.5
8,8 Subst2 83.2 72.2 38.5 153.8-158.8 97.0 153.8-158.8 107.7 153.8-158.8 104.1 132.3 116.2 147.1 147.1 117.7 120.6
8 Subst3 77.8 72.2 36.5 153.8-158.8 97.8 153.8-158.8 107.1 153.8-158.8 101.0 132.3 111.5 147.1 134.4 147.1 111.5
Subst4 78.9 67.8 30.8 153.8-158.8 97.8 153.8-158.8 107.7 153.8-158.8 104.1 132.3 116.2 147.1 147.1 117.7 120.6
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 8,3 | xXGallic | 121.8 | 111.5 | 147.1 | 140.7 | 147.1 | 111.5 | 169.2 | |
| 8,8,8,7,6,6,6 | xXGallic | 121.8 | 111.5 | 147.1 | 140.7 | 147.1 | 111.5 | 169.2 | |
| 8,8,8,7,6,6 | bDGlcp | 101.0 | 75.9 | 78.9 | 70.1 | 77.8 | 67.8 | |
| 8,8,8,7,6 | bDGlcp | 104.1 | 74.1 | 78.9 | 70.1 | 77.8 | 63.7 | |
| 8,8,8,7 | bDGlcp | 104.1 | 74.1 | 78.9 | 70.1 | 77.8 | 63.7 | |
| 8,8,8 | Subst1 | 80.5 | 74.1 | 36.5 | 153.8
158.8 | 97.8 | 153.8
158.8 | 97.8 | 153.8
158.8 | 101.0 | 132.3 | 111.5 | 147.1 | 134.4 | 147.1 | 111.5 |
| 8,8 | Subst2 | 83.2 | 72.2 | 38.5 | 153.8
158.8 | 97.0 | 153.8
158.8 | 107.7 | 153.8
158.8 | 104.1 | 132.3 | 116.2 | 147.1 | 147.1 | 117.7 | 120.6 |
| 8 | Subst3 | 77.8 | 72.2 | 36.5 | 153.8
158.8 | 97.8 | 153.8
158.8 | 107.1 | 153.8
158.8 | 101.0 | 132.3 | 111.5 | 147.1 | 134.4 | 147.1 | 111.5 |
| | Subst4 | 78.9 | 67.8 | 30.8 | 153.8
158.8 | 97.8 | 153.8
158.8 | 107.7 | 153.8
158.8 | 104.1 | 132.3 | 116.2 | 147.1 | 147.1 | 117.7 | 120.6 |
|
There is only one chemically distinct structure:
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