Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: stem bark
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00166-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Laboratorie de Pharmacognosie, Faculté de Pharmacie, Marseille 5, France, ESA 6013 Lab. de Pharmacognosie, Faculté de Pharmacie, Reims, France, ESA 6009, Université d'Aix-Marseille 111, Marseille 20, France
A new triterpenoid saponin named Harpuloside was isolated from the stem bark of Harpullia ramiflora. Its structure was established as 3-O [α-L- rhamno-pyranosyl (1 → 3)-β-D-xylopyranosyl (1 → 2)-β-D-glucurono- pyranosyl]-3β, 16α, 24, 28-tetrahydroxy-21β, 22α-O-diangeloyl-olean-12- ene, using one- and two-dimensional NMR spectral data.
triterpenoid saponin, Sapindaceae, Harpullia ramiflora, Harpuloside, one- and two-dimensional NMR, protoaescigenin
Structure type: oligomer ; 1123 [M-H]-
C
57H
88O
22Location inside paper: p. 1230, Scheme, compound 1, table 1
Trivial name: harpuloside
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_136105,IEDB_140630,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_423153,IEDB_885823
Methods: FAB-MS, extraction, optical rotation measurement, ROESY, TOCSY, CC, melting point determination, HMBC, HMQC, DEPT, COSY, HOHAHA, aci dhydrolysis
NCBI Taxonomy refs (TaxIDs): 151067
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 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,2 bDXylp 104.7 75.1 77.8 71.0 66.9
3,3 aLRhap 103.6 72.2 72.2 73.8 70.8 18.0
3 bDGlcpA 105.0 78.6 86.9 76.9 72.1 172.4
21 lXAng 169.2-169.8 129.2-129.4 138.7-139.5 16.0-16.1 20.8-20.9
22 lXAng 169.2-169.8 129.2-129.4 138.7-139.5 16.0-16.1 20.8-20.9
Subst 39.9 27.0 92.5 44.8 57.5 19.4 34.0 40.9 48.3 37.8 24.9 125.1 143.1 42.4 34.9 69.7 48.5 40.9 47.9 36.9 79.8 74.4 22.7 64.5 16.2 17.2 27.8 63.8 29.7 20.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2 bDXylp 4.52 3.21 3.31 3.56 3.12-3.85
3,3 aLRhap 5.08 4.09 3.69 3.43 3.99 1.26
3 bDGlcpA 4.49 3.61 3.71 3.70 3.45 -
21 lXAng
22 lXAng
Subst
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2 bDXylp 104.7/4.52 75.1/3.21 77.8/3.31 71.0/3.56 66.9/3.12-3.85
3,3 aLRhap 103.6/5.08 72.2/4.09 72.2/3.69 73.8/3.43 70.8/3.99 18.0/1.26
3 bDGlcpA 105.0/4.49 78.6/3.61 86.9/3.71 76.9/3.70 72.1/3.45
21 lXAng NMR TSV error 2: unequal length of 13C and 1H datasets
22 lXAng NMR TSV error 2: unequal length of 13C and 1H datasets
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2 | bDXylp | 4.52 | 3.21 | 3.31 | 3.56 | 3.12
3.85 | |
| 3,3 | aLRhap | 5.08 | 4.09 | 3.69 | 3.43 | 3.99 | 1.26 |
| 3 | bDGlcpA | 4.49 | 3.61 | 3.71 | 3.70 | 3.45 |
|
| 21 | lXAng | |
| 22 | lXAng | |
| | Subst | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,2 | bDXylp | 104.7 | 75.1 | 77.8 | 71.0 | 66.9 | |
| 3,3 | aLRhap | 103.6 | 72.2 | 72.2 | 73.8 | 70.8 | 18.0 | |
| 3 | bDGlcpA | 105.0 | 78.6 | 86.9 | 76.9 | 72.1 | 172.4 | |
| 21 | lXAng | 169.2
169.8 | 129.2
129.4 | 138.7
139.5 | 16.0
16.1 | 20.8
20.9 | |
| 22 | lXAng | 169.2
169.8 | 129.2
129.4 | 138.7
139.5 | 16.0
16.1 | 20.8
20.9 | |
| | Subst | 39.9 | 27.0 | 92.5 | 44.8 | 57.5 | 19.4 | 34.0 | 40.9 | 48.3 | 37.8 | 24.9 | 125.1 | 143.1 | 42.4 | 34.9 | 69.7 | 48.5 | 40.9 | 47.9 | 36.9 | 79.8 | 74.4 | 22.7 | 64.5 | 16.2 | 17.2 | 27.8 | 63.8 | 29.7 | 20.3 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
