Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperNCBI PubMed ID: 10606546Publication DOI: 10.1021/jf990608vJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Ho CT <ho
aesop.rutgers.edu>
Institutions: Department of Food Science and Center for Advanced Food Technology, Rutgers University, 65 Dudley Road, New Brunswick, New Jersey 08901-8520, USA, Department of Food and Nutrition, Osaka City University, 3-3-138 Sugimoto Sumiyoshi, Osaka, Japan, Pacific Biomedical Research Center, University of Hawaii, 1993 East-West Road, Honolulu, Hawaii 96822, USA
Two known glycosides and a novel trisaccharide fatty acid ester were isolated from the n-butanolsoluble fraction of the fruits of Morinda citrifolia (Noni). Structure determination was carried out by spectral techniques such as MS, IR, NMR, and 2D-NMR. The novel trisaccharide fatty acid ester was elucidated as 2,6-di-O-(β-D-glucopyranosyl)-1-O-octanoyl-β-D-glucopyranose. The known compounds were identified as rutin and asperulosidic acid.
2, rutin, Noni, Morinda citrifolia, trisaccharide fatty acid ester, 6-di-O-(β-D-glucopyranosyl-1-O-octanoyl-β-D-glucopyranose, asperulosidic acid
Structure type: oligomer ; 609 [M-H]-
C
27H
30O
16Location inside paper: compound 2, fig. 1(2)
Trivial name: rutin
Compound class: glycoside, flavonoid glycoside, flavone 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, FAB-MS, HMBC, HMQC, COSY, NOESY, APCI-MS
Comments, role: NMR temperature was not specified
Related record ID(s): 63269, 63271
NCBI Taxonomy refs (TaxIDs): 43522
Show glycosyltransferases
NMR conditions: in DMSO-d6
[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 aLRhap 101.0 70.6 70.8 70.3 68.5 18.0
3 bDGlcp 101.4 74.3 76.7 72.1 76.1 67.3
xXQuercetin - 156.7 133.5 177.6 161.5 98.9 164.3 93.9 156.9 104.2 121.9 115.5 145.0 148.7 116.5 121.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3,6 aLRhap 4.40 3.00-3.84 3.00-3.84 3.00-3.84 3.00-3.84 1.00
3 bDGlcp 5.35 3.00-3.84 3.00-3.84 3.00-3.84 3.00-3.84 3.00-3.84
xXQuercetin - - - - - 6.22 - 6.41 - - - 7.56 - - 6.86 7.56
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 aLRhap 101.0/4.40 70.6/3.00-3.84 70.8/3.00-3.84 70.3/3.00-3.84 68.5/3.00-3.84 18.0/1.00
3 bDGlcp 101.4/5.35 74.3/3.00-3.84 76.7/3.00-3.84 72.1/3.00-3.84 76.1/3.00-3.84 67.3/3.00-3.84
xXQuercetin 98.9/6.22 93.9/6.41 115.5/7.56 116.5/6.86 121.4/7.56
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3,6 | aLRhap | 4.40 | 3.00
3.84 | 3.00
3.84 | 3.00
3.84 | 3.00
3.84 | 1.00 | |
| 3 | bDGlcp | 5.35 | 3.00
3.84 | 3.00
3.84 | 3.00
3.84 | 3.00
3.84 | 3.00
3.84 | |
| | xXQuercetin |
|
|
|
|
| 6.22 |
| 6.41 |
|
|
| 7.56 |
|
| 6.86 | 7.56 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3,6 | aLRhap | 101.0 | 70.6 | 70.8 | 70.3 | 68.5 | 18.0 | |
| 3 | bDGlcp | 101.4 | 74.3 | 76.7 | 72.1 | 76.1 | 67.3 | |
| | xXQuercetin |
| 156.7 | 133.5 | 177.6 | 161.5 | 98.9 | 164.3 | 93.9 | 156.9 | 104.2 | 121.9 | 115.5 | 145.0 | 148.7 | 116.5 | 121.4 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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