Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: flower
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(97)01051-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Industrial Research Ltd, Lower Hutt, New Zealand
Flowers of the red/mauve carnation cultivars "Kortina Chanel" and "Purple Torres" contain a unique macrocyclic anthocyanin pigment, a malylated cyanidin 3,5-diglucoside in which the malyl group is linked to both sugars. The native anthocyanin readily undergoes ring opening to yield cyanidin 3-O-(6-O-malyl glucoside)-5-O-glucoside. This lability was found to be due to the inherent instability of the malyl interglycosidic bridge. In this paper we report the structure elucidation of the native anthocyanin, and the ring opened product.
Caryophyllaceae, carnation, Dianthus caryophyllus, malylated cyanidin 3, 5-diglucoside
Structure type: cyclic polymer repeating unit ; 710
Location inside paper: p. 225, Scheme, compound 1, table 1
Trivial name: cyanidin 3,5-di-O-glucoside(6'', 6'''-malyl diester)
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, MS, HPLC, extraction, ROESY, TOCSY, alkaline hydrloysis, TOCSY< MS
Comments, role: published NMR singal order in 2HOSuc was inverted by CSDB staff
Related record ID(s): 61749
NCBI Taxonomy refs (TaxIDs): 3570
Show glycosyltransferases
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16
1,1,5 bDGlcp 100.5 74.6 78.0 69.5 76.1 62.0
1,1 xXCyanidin - 164.0 145.4 132.05 156.6 104.4 169.2 97.2 156.5 112.6 120.8 118.3 147.5 156.0 117.6 128.8
1 bDGlcp 101.2 74.5 77.9 71.4 76.1 65.6
x?2HOSuc 171.5 69.8 40.0 174.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
1,1,5 bDGlcp 5.59 ? ? ? ? 5.03
1,1 xXCyanidin - - - 8.80 - 6.93 - 7.05 - - - 8.02 - - 7.03 8.26
1 bDGlcp 5.36 ? ? ? ? 4.18-4.30
x?2HOSuc - 4.40 2.80 -
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 C14/H14 C15/H15 C16/H16
1,1,5 bDGlcp 100.5/5.59 74.6/? 78.0/? 69.5/? 76.1/? 62.0/5.03
1,1 xXCyanidin 132.05/8.80 104.4/6.93 97.2/7.05 118.3/8.02 117.6/7.03 128.8/8.26
1 bDGlcp 101.2/5.36 74.5/? 77.9/? 71.4/? 76.1/? 65.6/4.18-4.30
x?2HOSuc 69.8/4.40 40.0/2.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 1,1,5 | bDGlcp | 5.59 | ? | ? | ? | ? | 5.03 | |
| 1,1 | xXCyanidin |
|
|
| 8.80 |
| 6.93 |
| 7.05 |
|
|
| 8.02 |
|
| 7.03 | 8.26 |
| 1 | bDGlcp | 5.36 | ? | ? | ? | ? | 4.18
4.30 | |
| | x?2HOSuc |
| 4.40 | 2.80 |
| |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 1,1,5 | bDGlcp | 100.5 | 74.6 | 78.0 | 69.5 | 76.1 | 62.0 | |
| 1,1 | xXCyanidin |
| 164.0 | 145.4 | 132.05 | 156.6 | 104.4 | 169.2 | 97.2 | 156.5 | 112.6 | 120.8 | 118.3 | 147.5 | 156.0 | 117.6 | 128.8 |
| 1 | bDGlcp | 101.2 | 74.5 | 77.9 | 71.4 | 76.1 | 65.6 | |
| | x?2HOSuc | 171.5 | 69.8 | 40.0 | 174.4 | |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: flower
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(97)01051-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Industrial Research Ltd, Lower Hutt, New Zealand
Flowers of the red/mauve carnation cultivars "Kortina Chanel" and "Purple Torres" contain a unique macrocyclic anthocyanin pigment, a malylated cyanidin 3,5-diglucoside in which the malyl group is linked to both sugars. The native anthocyanin readily undergoes ring opening to yield cyanidin 3-O-(6-O-malyl glucoside)-5-O-glucoside. This lability was found to be due to the inherent instability of the malyl interglycosidic bridge. In this paper we report the structure elucidation of the native anthocyanin, and the ring opened product.
Caryophyllaceae, carnation, Dianthus caryophyllus, malylated cyanidin 3, 5-diglucoside
Structure type: oligomer ; 728
Location inside paper: p. 225, Scheme, compound 2, table 1
Trivial name: cyanidin 3-O-(6-O-malyl glucoside)-5-O-glucoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, MS, HPLC, extraction, ROESY, TOCSY, alkaline hydrloysis, TOCSY< MS
Comments, role: published NMR singal order in 2HOSuc was inverted by CSDB staff
Related record ID(s): 61748
NCBI Taxonomy refs (TaxIDs): 3570
Show glycosyltransferases
NMR conditions: in CD3OD / TFA
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16
3,6 x?2HOSuc 172.2 68.2 39.9 176.3
3 bDGlcp 102.8 74.4 78.1 71.5 75.7 65.0
5 bDGlcp 102.5 74.8 78.0 71.1 78.8 62.4
xXCyanidin - 164.7 146.0 134.9 157.1 105.5 169.7 97.5 156.7 113.1 121.0 118.6 147.6 156.6 117.6 129.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3,6 x?2HOSuc - 4.37 2.70 -
3 bDGlcp 5.41 ? ? ? ? 4.30-4.60
5 bDGlcp 5.18 ? ? ? ? 3.95
xXCyanidin - - - 8.92 - 7.01 - 7.06 - - - 8.03 - - 7.03 8.28
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 C14/H14 C15/H15 C16/H16
3,6 x?2HOSuc 68.2/4.37 39.9/2.70
3 bDGlcp 102.8/5.41 74.4/? 78.1/? 71.5/? 75.7/? 65.0/4.30-4.60
5 bDGlcp 102.5/5.18 74.8/? 78.0/? 71.1/? 78.8/? 62.4/3.95
xXCyanidin 134.9/8.92 105.5/7.01 97.5/7.06 118.6/8.03 117.6/7.03 129.0/8.28
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3,6 | x?2HOSuc |
| 4.37 | 2.70 |
| |
| 3 | bDGlcp | 5.41 | ? | ? | ? | ? | 4.30
4.60 | |
| 5 | bDGlcp | 5.18 | ? | ? | ? | ? | 3.95 | |
| | xXCyanidin |
|
|
| 8.92 |
| 7.01 |
| 7.06 |
|
|
| 8.03 |
|
| 7.03 | 8.28 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3,6 | x?2HOSuc | 172.2 | 68.2 | 39.9 | 176.3 | |
| 3 | bDGlcp | 102.8 | 74.4 | 78.1 | 71.5 | 75.7 | 65.0 | |
| 5 | bDGlcp | 102.5 | 74.8 | 78.0 | 71.1 | 78.8 | 62.4 | |
| | xXCyanidin |
| 164.7 | 146.0 | 134.9 | 157.1 | 105.5 | 169.7 | 97.5 | 156.7 | 113.1 | 121.0 | 118.6 | 147.6 | 156.6 | 117.6 | 129.0 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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