Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 9883595Publication DOI: 10.1016/s0031-9422(98)00413-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Laboratory for Ecological Chemistry, University of Stellenbosch, Stellenbosch, South Africa, Department of Pharmacology, Medical School, University of Stellenbosch, Tygerberg, South Africa, Varian NMR Applications Laboratory, Darmstadt, Germany
Two new triterpenoid saponins, beciumecine 1 and 2, were isolated from the root bark of Becium grandiflorum var. obovatum and their structures established as 3-O-(beta-D-glucopyranosyl) terminolic acid 28-O-beta-D-apiofuranosyl(1-3)-[alpha-L-rhamnopy-anosyl (1-3)-beta-D-xylopyranosyl(1-4)]-alpha-L-rhamnopyranosyl (1-2)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl) 24-hydroxyterminolic acid 28-O-alpha-L-rhamnopyranosyl(1-3)-beta-D-xylopyranosyl(1-4)-alpha-L- rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside, respectively.
triterpenoid saponins, Lamiaceae, Becium grandiflorum var. obovatum
Structure type: oligomer ; 1381.2 [M+Na]+
Location inside paper: p. 2088, Scheme, compound 1, table 1, table 2
Trivial name: beciumecine 1
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GC-MS, optical rotation measurement, TOCSY, column chromatography, HMBC, DEPT, LC, COSY, NOESY, HSQC, extraciton, HSQC-TOCSY, TOF-MALDI
Related record ID(s): 61587
NCBI Taxonomy refs (TaxIDs): 39173
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[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 bDGlcp 103.7 73.8 76.8 70.0 76.5 61.0
28,2,3 bDApif 110.2 75.9 78.4 73.2 62.5
28,2,4,3 aLRhap 100.6 70.5 70.5 72.0 68.0 17.7
28,2,4 bDXylp 102.9 74.3 81.1 68.2 65.8
28,2 aLRhap 99.4 70.0 79.8 75.9 67.1 17.5
28 aLArap 90.9 74.3 67.1 63.5 59.9
Subst 45.7 69.2 80.7 42.3 46.9 65.6 39.7 38.1 47.7 35.4 23.0 122.3 142.6 41.8 26.9 223.1 46.3 40.7 45.3 30.3 33.2 31.8 63.4 15.6 17.9 17.4 25.6 175.5 32.7 23.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29
3 bDGlcp 4.29 3.05 3.13 3.07 3.07 3.41-3.62
28,2,3 bDApif 5.11 3.90 - 3.58-3.98 3.33-3.37
28,2,4,3 aLRhap 4.93 3.67 3.48 3.18 3.91 1.08
28,2,4 bDXylp 4.54 3.06 3.33 3.34 3.05-3.72
28,2 aLRhap 4.70 3.77 3.70 3.58 3.53 1.11
28 aLArap 5.68 3.61 3.81 3.70 3.32-3.79
Subst 0.98-1.82 4.14 3.45 1.17 4.32 1.32-1.57 - 1.45 - 1.87-1.97 5.27 - - 0.96-1.65 1.60-1.92 - 2.87 1.06-1.64 - 1.16-1.32 1.42-1.68 3.19-3.55 1.19 1.52 0.93 1.05 - 0.88 0.90
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 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29
3 bDGlcp 103.7/4.29 73.8/3.05 76.8/3.13 70.0/3.07 76.5/3.07 61.0/3.41-3.62
28,2,3 bDApif 110.2/5.11 75.9/3.90 73.2/3.58-3.98 62.5/3.33-3.37
28,2,4,3 aLRhap 100.6/4.93 70.5/3.67 70.5/3.48 72.0/3.18 68.0/3.91 17.7/1.08
28,2,4 bDXylp 102.9/4.54 74.3/3.06 81.1/3.33 68.2/3.34 65.8/3.05-3.72
28,2 aLRhap 99.4/4.70 70.0/3.77 79.8/3.70 75.9/3.58 67.1/3.53 17.5/1.11
28 aLArap 90.9/5.68 74.3/3.61 67.1/3.81 63.5/3.70 59.9/3.32-3.79
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 |
|---|
| 3 | bDGlcp | 4.29 | 3.05 | 3.13 | 3.07 | 3.07 | 3.41
3.62 | |
| 28,2,3 | bDApif | 5.11 | 3.90 |
| 3.58
3.98 | 3.33
3.37 | |
| 28,2,4,3 | aLRhap | 4.93 | 3.67 | 3.48 | 3.18 | 3.91 | 1.08 | |
| 28,2,4 | bDXylp | 4.54 | 3.06 | 3.33 | 3.34 | 3.05
3.72 | |
| 28,2 | aLRhap | 4.70 | 3.77 | 3.70 | 3.58 | 3.53 | 1.11 | |
| 28 | aLArap | 5.68 | 3.61 | 3.81 | 3.70 | 3.32
3.79 | |
| | Subst | 0.98
1.82 | 4.14 | 3.45 | 1.17 | 4.32 | 1.32
1.57 |
| 1.45 |
| 1.87
1.97 | 5.27 |
|
| 0.96
1.65 | 1.60
1.92 |
| 2.87 | 1.06
1.64 |
| 1.16
1.32 | 1.42
1.68 | 3.19
3.55 | 1.19 | 1.52 | 0.93 | 1.05 |
| 0.88 | 0.90 |
|
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 | bDGlcp | 103.7 | 73.8 | 76.8 | 70.0 | 76.5 | 61.0 | |
| 28,2,3 | bDApif | 110.2 | 75.9 | 78.4 | 73.2 | 62.5 | |
| 28,2,4,3 | aLRhap | 100.6 | 70.5 | 70.5 | 72.0 | 68.0 | 17.7 | |
| 28,2,4 | bDXylp | 102.9 | 74.3 | 81.1 | 68.2 | 65.8 | |
| 28,2 | aLRhap | 99.4 | 70.0 | 79.8 | 75.9 | 67.1 | 17.5 | |
| 28 | aLArap | 90.9 | 74.3 | 67.1 | 63.5 | 59.9 | |
| | Subst | 45.7 | 69.2 | 80.7 | 42.3 | 46.9 | 65.6 | 39.7 | 38.1 | 47.7 | 35.4 | 23.0 | 122.3 | 142.6 | 41.8 | 26.9 | 223.1 | 46.3 | 40.7 | 45.3 | 30.3 | 33.2 | 31.8 | 63.4 | 15.6 | 17.9 | 17.4 | 25.6 | 175.5 | 32.7 | 23.3 |
|
There is only one chemically distinct structure:
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 9883595Publication DOI: 10.1016/s0031-9422(98)00413-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Laboratory for Ecological Chemistry, University of Stellenbosch, Stellenbosch, South Africa, Department of Pharmacology, Medical School, University of Stellenbosch, Tygerberg, South Africa, Varian NMR Applications Laboratory, Darmstadt, Germany
Two new triterpenoid saponins, beciumecine 1 and 2, were isolated from the root bark of Becium grandiflorum var. obovatum and their structures established as 3-O-(beta-D-glucopyranosyl) terminolic acid 28-O-beta-D-apiofuranosyl(1-3)-[alpha-L-rhamnopy-anosyl (1-3)-beta-D-xylopyranosyl(1-4)]-alpha-L-rhamnopyranosyl (1-2)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl) 24-hydroxyterminolic acid 28-O-alpha-L-rhamnopyranosyl(1-3)-beta-D-xylopyranosyl(1-4)-alpha-L- rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside, respectively.
triterpenoid saponins, Lamiaceae, Becium grandiflorum var. obovatum
Structure type: oligomer ; 1262.4 [M+Na]+
Location inside paper: p. 2088, Scheme, compound 1, table 1, table 2
Trivial name: beciumecine 2
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GC-MS, optical rotation measurement, TOCSY, column chromatography, HMBC, DEPT, LC, COSY, NOESY, HSQC, extraciton, HSQC-TOCSY, TOF-MALDI
Related record ID(s): 61586
NCBI Taxonomy refs (TaxIDs): 39173
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 333 K
[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 bDGlcp 103.9 73.7 76.7 70.0 76.5 61.0
28,2,4,3 aLRhap 100.2 70.4 70.4 71.9 67.9 17.8
28,2,4 bDXylp 104.5 74.8 80.8 67.8 65.9
28,2 aLRhap 99.4 70.2 70.4 80.5 67.1 17.4
28 aLArap 91.1 73.9 67.5 63.9 60.5
Subst 46.1 69.1 80.8 48.2 47.8 64.7 37.7 38.0 48.0 35.4 23.0 122.1 142.6 41.8 27.0 ? 46.2 40.7 45.2 30.3 33.1 ? 59.4 60.7 ? 17.5 25.5 175.0 32.7 23.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3 bDGlcp 4.29 3.04 3.13 3.04 3.05 3.42-3.62
28,2,4,3 aLRhap 5.01 3.68 3.49 3.18 3.88 1.09
28,2,4 bDXylp 4.44 3.11 3.32 3.33 3.09-3.71
28,2 aLRhap 4.77 3.65 3.66 3.45 3.50 1.14
28 aLArap 5.64 3.62 3.79 3.68 3.32-3.76
Subst 1.03-1.78 4.09 3.57 - 1.36 4.26 1.47-1.59 - 1.48 - 1.88-1.96 5.27 - - 0.98-1.65 1.58-1.92 - 2.86 1.06-1.65 - 1.14-1.33 1.44-1.66 3.69-3.78 3.55-4.48 1.53 0.93 1.06 - 0.88 0.89
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 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3 bDGlcp 103.9/4.29 73.7/3.04 76.7/3.13 70.0/3.04 76.5/3.05 61.0/3.42-3.62
28,2,4,3 aLRhap 100.2/5.01 70.4/3.68 70.4/3.49 71.9/3.18 67.9/3.88 17.8/1.09
28,2,4 bDXylp 104.5/4.44 74.8/3.11 80.8/3.32 67.8/3.33 65.9/3.09-3.71
28,2 aLRhap 99.4/4.77 70.2/3.65 70.4/3.66 80.5/3.45 67.1/3.50 17.4/1.14
28 aLArap 91.1/5.64 73.9/3.62 67.5/3.79 63.9/3.68 60.5/3.32-3.76
Subst 46.1/1.03-1.78 69.1/4.09 80.8/3.57 47.8/1.36 64.7/4.26 37.7/1.47-1.59 48.0/1.48 23.0/1.88-1.96 122.1/5.27 27.0/0.98-1.65 ?/1.58-1.92 40.7/2.86 45.2/1.06-1.65 33.1/1.14-1.33 ?/1.44-1.66 59.4/3.69-3.78 60.7/3.55-4.48 ?/1.53 17.5/0.93 25.5/1.06 32.7/0.88 23.3/0.89
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3 | bDGlcp | 4.29 | 3.04 | 3.13 | 3.04 | 3.05 | 3.42
3.62 | |
| 28,2,4,3 | aLRhap | 5.01 | 3.68 | 3.49 | 3.18 | 3.88 | 1.09 | |
| 28,2,4 | bDXylp | 4.44 | 3.11 | 3.32 | 3.33 | 3.09
3.71 | |
| 28,2 | aLRhap | 4.77 | 3.65 | 3.66 | 3.45 | 3.50 | 1.14 | |
| 28 | aLArap | 5.64 | 3.62 | 3.79 | 3.68 | 3.32
3.76 | |
| | Subst | 1.03
1.78 | 4.09 | 3.57 |
| 1.36 | 4.26 | 1.47
1.59 |
| 1.48 |
| 1.88
1.96 | 5.27 |
|
| 0.98
1.65 | 1.58
1.92 |
| 2.86 | 1.06
1.65 |
| 1.14
1.33 | 1.44
1.66 | 3.69
3.78 | 3.55
4.48 | 1.53 | 0.93 | 1.06 |
| 0.88 | 0.89 |
|
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 | bDGlcp | 103.9 | 73.7 | 76.7 | 70.0 | 76.5 | 61.0 | |
| 28,2,4,3 | aLRhap | 100.2 | 70.4 | 70.4 | 71.9 | 67.9 | 17.8 | |
| 28,2,4 | bDXylp | 104.5 | 74.8 | 80.8 | 67.8 | 65.9 | |
| 28,2 | aLRhap | 99.4 | 70.2 | 70.4 | 80.5 | 67.1 | 17.4 | |
| 28 | aLArap | 91.1 | 73.9 | 67.5 | 63.9 | 60.5 | |
| | Subst | 46.1 | 69.1 | 80.8 | 48.2 | 47.8 | 64.7 | 37.7 | 38.0 | 48.0 | 35.4 | 23.0 | 122.1 | 142.6 | 41.8 | 27.0 | ? | 46.2 | 40.7 | 45.2 | 30.3 | 33.1 | ? | 59.4 | 60.7 | ? | 17.5 | 25.5 | 175.0 | 32.7 | 23.3 |
|
The spectrum also has 3 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 2 records.
Displayed records from 1 to 2
(later renamed to: Ocimum grandiforum var. obovatum)