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Jeong H, Jo SJ, Bae M, Kim YR, Moon K
Actinoflavosides B-D, Flavonoid Type Glycosides from Tidal Mudflat-Derived Actinomyces
Marine Drugs 20(9) (2022)
565
|
R-3HOaiVl-(1-3)-a-D-Sugp-(1-7)-Subst
Sug = 2,3,6-trideoxy-3-amino-D-ribopyranose = SMILES C[C@H]([C@H]({3}[C@H]1N)O)O{1}C(C1)O;
Subst = 7,8-dihydroxy-5-(hydroxymethyl)-2-phenylchroman-4-one = SMILES O=C1CC(C2=CC=CC=C2)OC3=C1{5}C(CO)=C{7}C(O)={8}C3O |
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Streptomyces sp. CNB-689
(Ancestor NCBI TaxID 1883,
species name lookup)
Streptomyces sp. JML48
(Ancestor NCBI TaxID 1883,
species name lookup)
Streptomyces sp. JMS33
(Ancestor NCBI TaxID 1883,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 36135754Publication DOI: 10.3390/md20090565Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Y.R. Kim <kimyr
chonnam.ac.kr>; K. Moon <khmoon
jnu.ac.kr>
Institutions: Research Institute of Pharmaceutical Sciences, College of Pharmacy, Chonnam National University, Gwangju 61186, Korea, College of Pharmacy, Gachon University, Incheon 21936, Korea
Three new secondary metabolites, actinoflavosides B-D (1-3), were discovered in the culture broth of two actinomycete strains (JML48 and JMS33) that were isolated from tidal mudflat sediment in Muan, Republic of Korea. The planar structures of the actinoflavosides were elucidated by MS, UV, and NMR analyses. The stereochemistry of an aminosugar, 2,3,6-trideoxy-3-amino-ribopyranoside in the actinoflavosides was determined by J-based configuration analysis using values obtained from DQF-COSY experiments and modified Mosher's method. Actinoflavosides B-D (1-3) displayed antibacterial activity against Pseudomonas aeruginosa, and actinoflavoside D (3) significantly increased IL-2 production in mouse splenocytes.
structural determination, antibacterial, flavonoid, actinoflavoside, immune modulator, secondary metabolite, tidal mudflat
Structure type: monomer ; 515.2172 [M]+
C
27H
33NO
9Location inside paper: p. 565-1, Fig. 1, table 1, compound 1
Trivial name: actinoflavoside B
Compound class: flavonoid glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, ELISA, FTIR, HPLC, UV, LC-MS, HR-TOF-MS
Comments, role: NMR temperature was not specified
Related record ID(s): 21009
NCBI Taxonomy refs (TaxIDs): 1883
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 C17
7,3 lR3HOaiVl 174.8 47.9 68.3 21.2 14.2
7 aDSugp 94.5 32.9 44.8 70.4 66.4 17.8
Subst - 78.6 44.7 192.3 136.8 106.5 149.1 133.6 151.5 112.9 61.7 139.1 126.7 128.4 128.5 128.4 126.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17
7,3 lR3HOaiVl - 2.28 3.61 1.03 1.06
7 aDSugp 5.80 1.99-2.08 4.34 3.32 3.79 1.09
Subst - 5.61 2.79-3.16 - - 7.17 - - - - 4.87 - 7.59 7.38 7.43 7.38 7.59
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
7,3 lR3HOaiVl 47.9/2.28 68.3/3.61 21.2/1.03 14.2/1.06
7 aDSugp 94.5/5.80 32.9/1.99-2.08 44.8/4.34 70.4/3.32 66.4/3.79 17.8/1.09
Subst 78.6/5.61 44.7/2.79-3.16 106.5/7.17 61.7/4.87 126.7/7.59 128.4/7.38 128.5/7.43 128.4/7.38 126.7/7.59
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 |
|---|
| 7,3 | lR3HOaiVl |
| 2.28 | 3.61 | 1.03 | 1.06 | |
| 7 | aDSugp | 5.80 | 1.99
2.08 | 4.34 | 3.32 | 3.79 | 1.09 | |
| | Subst |
| 5.61 | 2.79
3.16 |
|
| 7.17 |
|
|
|
| 4.87 |
| 7.59 | 7.38 | 7.43 | 7.38 | 7.59 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 |
|---|
| 7,3 | lR3HOaiVl | 174.8 | 47.9 | 68.3 | 21.2 | 14.2 | |
| 7 | aDSugp | 94.5 | 32.9 | 44.8 | 70.4 | 66.4 | 17.8 | |
| | Subst |
| 78.6 | 44.7 | 192.3 | 136.8 | 106.5 | 149.1 | 133.6 | 151.5 | 112.9 | 61.7 | 139.1 | 126.7 | 128.4 | 128.5 | 128.4 | 126.7 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Jeong H, Jo SJ, Bae M, Kim YR, Moon K
Actinoflavosides B-D, Flavonoid Type Glycosides from Tidal Mudflat-Derived Actinomyces
Marine Drugs 20(9) (2022)
565
|
a-D-Sugp3Ac-(1-7)-Subst
Sug = 2,3,6-trideoxy-3-amino-D-ribopyranose = SMILES C[C@H]([C@H]({3}[C@H]1N)O)O{1}C(C1)O;
Subst = 7,8-dihydroxy-5-(hydroxymethyl)-2-phenylchroman-4-one = SMILES O=C1CC(C2=CC=CC=C2)OC3=C1{5}C(CO)=C{7}C(O)={8}C3O |
Show graphically |
Streptomyces sp. CNB-689
(Ancestor NCBI TaxID 1883,
species name lookup)
Streptomyces sp. JML48
(Ancestor NCBI TaxID 1883,
species name lookup)
Streptomyces sp. JMS33
(Ancestor NCBI TaxID 1883,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 36135754Publication DOI: 10.3390/md20090565Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Y.R. Kim <kimyr
chonnam.ac.kr>; K. Moon <khmoon
jnu.ac.kr>
Institutions: Research Institute of Pharmaceutical Sciences, College of Pharmacy, Chonnam National University, Gwangju 61186, Korea, College of Pharmacy, Gachon University, Incheon 21936, Korea
Three new secondary metabolites, actinoflavosides B-D (1-3), were discovered in the culture broth of two actinomycete strains (JML48 and JMS33) that were isolated from tidal mudflat sediment in Muan, Republic of Korea. The planar structures of the actinoflavosides were elucidated by MS, UV, and NMR analyses. The stereochemistry of an aminosugar, 2,3,6-trideoxy-3-amino-ribopyranoside in the actinoflavosides was determined by J-based configuration analysis using values obtained from DQF-COSY experiments and modified Mosher's method. Actinoflavosides B-D (1-3) displayed antibacterial activity against Pseudomonas aeruginosa, and actinoflavoside D (3) significantly increased IL-2 production in mouse splenocytes.
structural determination, antibacterial, flavonoid, actinoflavoside, immune modulator, secondary metabolite, tidal mudflat
Structure type: monomer ; 457.1735 [M]+
C
24H
27NO
8Location inside paper: p. 565-1, Fig. 1, table 1, compound 2
Trivial name: actinoflavoside C
Compound class: flavonoid glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, ELISA, FTIR, HPLC, UV, LC-MS, HR-TOF-MS
Comments, role: NMR temperature was not specified
Related record ID(s): 8479
NCBI Taxonomy refs (TaxIDs): 1883
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 C17
7,3 Ac 169.6 23.2
7 aDSugp 94.3 32.7 45.4 70.6 66.4 17.9
Subst - 78.5 44.6 192.2 136.9 106.3 149.1 133.5 151.6 112.8 61.6 139.2 126.7 128.3 128.4 128.3 126.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17
7,3 Ac - 1.91
7 aDSugp 5.80 1.90-2.03 4.29 3.30 3.76 1.07
Subst - 5.60 2.81-3.15 - - 7.15 - - - - 4.77 - 7.58 7.38 7.44 7.38 7.58
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
7,3 Ac 23.2/1.91
7 aDSugp 94.3/5.80 32.7/1.90-2.03 45.4/4.29 70.6/3.30 66.4/3.76 17.9/1.07
Subst 78.5/5.60 44.6/2.81-3.15 106.3/7.15 61.6/4.77 126.7/7.58 128.3/7.38 128.4/7.44 128.3/7.38 126.7/7.58
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 |
|---|
| 7,3 | Ac |
| 1.91 | |
| 7 | aDSugp | 5.80 | 1.90
2.03 | 4.29 | 3.30 | 3.76 | 1.07 | |
| | Subst |
| 5.60 | 2.81
3.15 |
|
| 7.15 |
|
|
|
| 4.77 |
| 7.58 | 7.38 | 7.44 | 7.38 | 7.58 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 |
|---|
| 7,3 | Ac | 169.6 | 23.2 | |
| 7 | aDSugp | 94.3 | 32.7 | 45.4 | 70.6 | 66.4 | 17.9 | |
| | Subst |
| 78.5 | 44.6 | 192.2 | 136.9 | 106.3 | 149.1 | 133.5 | 151.6 | 112.8 | 61.6 | 139.2 | 126.7 | 128.3 | 128.4 | 128.3 | 126.7 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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