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Yadava RN, Reddy KI
A new bio-active flavonol glycoside from the stems of Butea superba Roxb
Journal of Asian Natural Products Research 1(2) (1998)
139-145
|
b-D-Xylp-(1-2)-a-L-Rhap-(1-3)-Subst8Me
Subst = gossypetin = SMILES O=C1{3}C(O)=C(C2=CC={54}C(O){53}C(O)=C2)OC3={8}C(O){7}C(O)=C{5}C(O)=C31 |
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Butea superba
(NCBI TaxID 480422,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: stem
The structure was elucidated in this paperNCBI PubMed ID: 11261215Publication DOI: 10.1080/10286029808039856Journal NLM ID: 100888334Publisher: Harwood Academic Publishers; London: Informa Healthcare
Institutions: Natural Products Laboratory, Departments of Chemistry, Dr. H.S. Gour University, Sagar, India
A new bio-active flavonol glycoside was isolated from the stems of Butea superba Roxb, and its structure was determined by spectral analysis and chemical degradations as 3,5,7,3',4'-pentahydroxy-8-methoxy-flavonol-3-O-beta-D-xylopyranosyl(1-->2) -alpha-L-rhamnopyranoside. The compound 1 showed antimicrobial activity against plant pathogenic fungi Trich viride, Asprgillus fumigatus, A. niger, A. terreus, Penicillium expansum, Helmitnhosporium oryzae, Botxitis cinerea, Rhizopus oligosporus, R. chinensis, Kelbsiella pneumoniae, Fusearium moniliforme and gram-positive bacteria Streplococcus pyogenes, Staphylococcus aureus, Bacillus subtilis gram-negative bacteria Escherichia coli, Proteus vulgaris, Klebsiella pneumoniae, Pseudomonas aeruginosa. The maximum inhibitory effect was shown by H. oryzae, A. niger, B. cinera and gram-positive bacteria.
antimicrobial activity, Leguminosae, Butea superba Roxb, a new bio-active flavonol glycoside
Structure type: oligomer ; 610
C
27H
29O
16Location inside paper: Fig. 1, compound 1, table 1
Compound class: glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823
Methods: 13C NMR, IR, TLC, acid hydrolysis, UV, extraction, permethylation, periodate oxidation, EI-MS, column chromatography, melting point determination, enzymatic treatment, Fehling treatment, QH NMR
Enzymes that release or process the structure: almond emulsin
NCBI Taxonomy refs (TaxIDs): 480422
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
3,2 bDXylp 107.8 75.2 78.0 70.7 67.1
3 aLRhap 103.2 82.4 72.3 73.2 71.9 17.5
8 Me 64.3
Subst 156.8 135.2 178.7 159.5 100.4 161.2 126.3 152.6 105.2 122.7 116.5 145.8 148.3 118.2 122.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
3,2 bDXylp 4.24 ? ? ? ?
3 aLRhap 5.34 ? ? ? ? ?
8 Me 3.86
Subst - - - - - 6.93 - - - 7.80 - - 6.93 7.65
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
3,2 bDXylp 107.8/4.24 75.2/? 78.0/? 70.7/? 67.1/?
3 aLRhap 103.2/5.34 82.4/? 72.3/? 73.2/? 71.9/? 17.5/?
8 Me 64.3/3.86
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 |
|---|
| 3,2 | bDXylp | 4.24 | ? | ? | ? | ? | |
| 3 | aLRhap | 5.34 | ? | ? | ? | ? | ? | |
| 8 | Me | 3.86 | |
| | Subst |
|
|
|
|
| 6.93 |
|
|
| 7.80 |
|
| 6.93 | 7.65 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3,2 | bDXylp | 107.8 | 75.2 | 78.0 | 70.7 | 67.1 | |
| 3 | aLRhap | 103.2 | 82.4 | 72.3 | 73.2 | 71.9 | 17.5 | |
| 8 | Me | 64.3 | |
| | Subst | 156.8 | 135.2 | 178.7 | 159.5 | 100.4 | 161.2 | 126.3 | 152.6 | 105.2 | 122.7 | 116.5 | 145.8 | 148.3 | 118.2 | 122.4 |
|
There is only one chemically distinct structure:
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Hamed A, El-Emary N
Triterpene saponins from Glinus lotoides var. dictamnoides
Phytochemistry 50(3) (1998)
477-480
|
b-L-Arap-(1-3)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-22)-Subst
Subst = 3,16-dihydroxyhopane = SMILES C{22}C(C)(O)[C@@H]1CC[C@@]2(C)C1{16}C(O)C[C@]5(C)C2CCC4[C@@]3(C)CC{3}[C@H](O)[C@](C)(C)C3CC[C@]45C |
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Glinus lotoides var. dictamnoides
(Ancestor NCBI TaxID 169249,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00522-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Science, South Valley University, Aswan, Egypt, Faculty of Pharmacy, Assiut University, Assiut, Egypt
Two 5β-H-hopane triterpenoidal saponins (glinusides D and E) were isolated on reinvestigation of the n-butanol soluble fraction of Glinus lotoides var. dictamnoides, in contrast to the 5α-H, 6-keto-hopane derivatives isolated from the same source. The structures of these saponins were established by extensive spectral analysis as 3-O-β-L-arabinopyranosyl- 22-α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl-5β-H-16β-hydroxyhopane and 3-O-β-L-arabinopyranosyl-22-O-β-D-glucopyranosyl-(1 → 4)-β-D- glucopyranosyl-5β-H-16-β-hydroxyhopane, respectively.
5β-H-hopane, Glinus lotoides var. dictamnoides, glinusides D and E, Molluginaceae, triterpenoidal saponins
Structure type: oligomer ; 944 [M+2Na]+
C
47H
78O
16Location inside paper: p. 478, Scheme, compound 1, table 1, table 2
Trivial name: glinuside D
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, FAB-MS, extraction, HMBC, COSY, NOESY, QH NMR
Related record ID(s): 63569
NCBI Taxonomy refs (TaxIDs): 169249
Show glycosyltransferases
NMR conditions: in C5D5N
[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 bLArap 106.4 74.1 78.6 71.7 66.9
22,4 aLRhap 101.8 72.5 71.5 77.9 69.6 18.4
22 bDGlcp 98.4 79.0 75.3. 66.9 78.6 62.8
Subst 57.5 26.9 88.9 45.4 31.1 39.3 39.2 42.8 48.9 38.8 21.2 23.9 49.7 43.5 44.1 77.9 50.6 40.3 43.7 45.0 67.6 83.1 17.3 17.3 17.1 17.1 18.7 18.4 23.8 24.9
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 bLArap 4.89 4.02 4.00 4.17 3.72-4.16
22,4 aLRhap 6.56 4.87 4.37 4.27 4.23 1.72
22 bDGlcp 5.17 3.99 4.13 4.86 3.70 4.30-4.40
Subst 1.00-1.65 1.93-2.24 3.43 - 2.03 1.07-1.38 1.95 - 1.27 - 1.29-1.53 1.29-1.34 1.53 - 1.15-1.60 4.25 1.89 - 0.90-1.40 1.35-1.60 2.73 - 0.98 1.06 0.71 0.93 1.61 1.55 1.40 1.40
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 bLArap 106.4/4.89 74.1/4.02 78.6/4.00 71.7/4.17 66.9/3.72-4.16
22,4 aLRhap 101.8/6.56 72.5/4.87 71.5/4.37 77.9/4.27 69.6/4.23 18.4/1.72
22 bDGlcp 98.4/5.17 79.0/3.99 75.3./4.13 66.9/4.86 78.6/3.70 62.8/4.30-4.40
Subst 57.5/1.00-1.65 26.9/1.93-2.24 88.9/3.43 31.1/2.03 39.3/1.07-1.38 39.2/1.95 48.9/1.27 21.2/1.29-1.53 23.9/1.29-1.34 49.7/1.53 44.1/1.15-1.60 77.9/4.25 50.6/1.89 43.7/0.90-1.40 45.0/1.35-1.60 67.6/2.73 17.3/0.98 17.3/1.06 17.1/0.71 17.1/0.93 18.7/1.61 18.4/1.55 23.8/1.40 24.9/1.40
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 | bLArap | 4.89 | 4.02 | 4.00 | 4.17 | 3.72
4.16 | |
| 22,4 | aLRhap | 6.56 | 4.87 | 4.37 | 4.27 | 4.23 | 1.72 | |
| 22 | bDGlcp | 5.17 | 3.99 | 4.13 | 4.86 | 3.70 | 4.30
4.40 | |
| | Subst | 1.00
1.65 | 1.93
2.24 | 3.43 |
| 2.03 | 1.07
1.38 | 1.95 |
| 1.27 |
| 1.29
1.53 | 1.29
1.34 | 1.53 |
| 1.15
1.60 | 4.25 | 1.89 |
| 0.90
1.40 | 1.35
1.60 | 2.73 |
| 0.98 | 1.06 | 0.71 | 0.93 | 1.61 | 1.55 | 1.40 | 1.40 |
|
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 | bLArap | 106.4 | 74.1 | 78.6 | 71.7 | 66.9 | |
| 22,4 | aLRhap | 101.8 | 72.5 | 71.5 | 77.9 | 69.6 | 18.4 | |
| 22 | bDGlcp | 98.4 | 79.0 | 75.3. | 66.9 | 78.6 | 62.8 | |
| | Subst | 57.5 | 26.9 | 88.9 | 45.4 | 31.1 | 39.3 | 39.2 | 42.8 | 48.9 | 38.8 | 21.2 | 23.9 | 49.7 | 43.5 | 44.1 | 77.9 | 50.6 | 40.3 | 43.7 | 45.0 | 67.6 | 83.1 | 17.3 | 17.3 | 17.1 | 17.1 | 18.7 | 18.4 | 23.8 | 24.9 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
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Hamed A, El-Emary N
Triterpene saponins from Glinus lotoides var. dictamnoides
Phytochemistry 50(3) (1998)
477-480
|
b-L-Arap-(1-3)-+
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-22)-Subst
Subst = 3,16-dihydroxyhopane = SMILES C{22}C(C)(O)[C@@H]1CC[C@@]2(C)C1{16}C(O)C[C@]5(C)C2CCC4[C@@]3(C)CC{3}[C@H](O)[C@](C)(C)C3CC[C@]45C |
Show graphically |
Glinus lotoides var. dictamnoides
(Ancestor NCBI TaxID 169249,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00522-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Science, South Valley University, Aswan, Egypt, Faculty of Pharmacy, Assiut University, Assiut, Egypt
Two 5β-H-hopane triterpenoidal saponins (glinusides D and E) were isolated on reinvestigation of the n-butanol soluble fraction of Glinus lotoides var. dictamnoides, in contrast to the 5α-H, 6-keto-hopane derivatives isolated from the same source. The structures of these saponins were established by extensive spectral analysis as 3-O-β-L-arabinopyranosyl- 22-α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl-5β-H-16β-hydroxyhopane and 3-O-β-L-arabinopyranosyl-22-O-β-D-glucopyranosyl-(1 → 4)-β-D- glucopyranosyl-5β-H-16-β-hydroxyhopane, respectively.
5β-H-hopane, Glinus lotoides var. dictamnoides, glinusides D and E, Molluginaceae, triterpenoidal saponins
Structure type: oligomer ; 971 [M+K+H2O]+
C
47H
78O
17Location inside paper: p. 478, Scheme, compound 2, table 1, table 2
Trivial name: glinuside E
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, FAB-MS, extraction, HMBC, COSY, NOESY, QH NMR
Related record ID(s): 63403
NCBI Taxonomy refs (TaxIDs): 169249
Show glycosyltransferases
NMR conditions: in C5D5N
[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 bLArap 106.5 74.1 78.4 71.0 66.8
22,4 bDGlcp 107.8 79.5 75.0 66.8 78.4 62.9
22 bDGlcp 98.4 79.0 75.6 66.9 78.6 62.8
Subst 27.2 26.5 88.8 46.0 31.1 39.2 39.2 42.8 48.9 38.8 21.1 23.8 49.7 43.5 44.1 77.8 50.5 40.3 43.7 45.0 67.6 83.0 17.3 17.3 17.1 17.1 18.7 17.4 23.8 25.0
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 bLArap 4.92 4.05 4.01 4.17 3.72-4.16
22,4 bDGlcp 4.99 4.92 4.144.86 3.86 3.80 4.32-4.56
22 bDGlcp 5.16 3.99 4.15 4.92 3.78 4.30-4.40
Subst 1.00-1.65 1.93-2.45 3.54 - 2.03 1.07-1.38 1.95 - 1.18 - 1.29-1.53 1.29-1.34 1.53 - 1.15-1.60 4.25 1.90 - 0.90-1.40 1.40-1.70 2.72 - 1.00 1.17 0.70 0.95 1.58 1.52 1.40 1.40
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 bLArap 106.5/4.92 74.1/4.05 78.4/4.01 71.0/4.17 66.8/3.72-4.16
22,4 bDGlcp 107.8/4.99 79.5/4.92 75.0/4.144.86 66.8/3.86 78.4/3.80 62.9/4.32-4.56
22 bDGlcp 98.4/5.16 79.0/3.99 75.6/4.15 66.9/4.92 78.6/3.78 62.8/4.30-4.40
Subst 27.2/1.00-1.65 26.5/1.93-2.45 88.8/3.54 31.1/2.03 39.2/1.07-1.38 39.2/1.95 48.9/1.18 21.1/1.29-1.53 23.8/1.29-1.34 49.7/1.53 44.1/1.15-1.60 77.8/4.25 50.5/1.90 43.7/0.90-1.40 45.0/1.40-1.70 67.6/2.72 17.3/1.00 17.3/1.17 17.1/0.70 17.1/0.95 18.7/1.58 17.4/1.52 23.8/1.40 25.0/1.40
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 | bLArap | 4.92 | 4.05 | 4.01 | 4.17 | 3.72
4.16 | |
| 22,4 | bDGlcp | 4.99 | 4.92 | 4.144.86 | 3.86 | 3.80 | 4.32
4.56 | |
| 22 | bDGlcp | 5.16 | 3.99 | 4.15 | 4.92 | 3.78 | 4.30
4.40 | |
| | Subst | 1.00
1.65 | 1.93
2.45 | 3.54 |
| 2.03 | 1.07
1.38 | 1.95 |
| 1.18 |
| 1.29
1.53 | 1.29
1.34 | 1.53 |
| 1.15
1.60 | 4.25 | 1.90 |
| 0.90
1.40 | 1.40
1.70 | 2.72 |
| 1.00 | 1.17 | 0.70 | 0.95 | 1.58 | 1.52 | 1.40 | 1.40 |
|
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 | bLArap | 106.5 | 74.1 | 78.4 | 71.0 | 66.8 | |
| 22,4 | bDGlcp | 107.8 | 79.5 | 75.0 | 66.8 | 78.4 | 62.9 | |
| 22 | bDGlcp | 98.4 | 79.0 | 75.6 | 66.9 | 78.6 | 62.8 | |
| | Subst | 27.2 | 26.5 | 88.8 | 46.0 | 31.1 | 39.2 | 39.2 | 42.8 | 48.9 | 38.8 | 21.1 | 23.8 | 49.7 | 43.5 | 44.1 | 77.8 | 50.5 | 40.3 | 43.7 | 45.0 | 67.6 | 83.0 | 17.3 | 17.3 | 17.1 | 17.1 | 18.7 | 17.4 | 23.8 | 25.0 |
|
There is only one chemically distinct structure:
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