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Honma M, Kudo S, Takada N, Tanaka K, Miura T, Hashimoto M
Novel neofusapyrones isolated from Verticillium dahliae as potent antifungal substances
Bioorganic and Medicinal Chemistry Letters 20(2) (2010)
709-712
|
b-D-1,4dxylHexp-(1C-3)-Subst
Subst = deoxyneofusapyrone aglycon = SMILES CCCCCCC(C/C(C)=C\C(/C=C(/C=C/{8}C(O)C(C)(C1=C{4}C(O)={3}CC(O1)=O)C)C)C)C |
Show graphically |
Verticillium dahliae
(NCBI TaxID 27337,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Helianthus annuus
Associated disease: Verticillium wilt
The structure was elucidated in this paperNCBI PubMed ID: 19962895Publication DOI: 10.1016/j.bmcl.2009.11.063Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: Hashimoto M <hmasaru
cc.hirosaki-u.ac.jp>
Institutions: Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan, Graduate School of Health Sciences, Hirosaki University, Hirosaki, Japan
Novel fusapyrone analogs, deoxyneofusapyrone and 7-desmethyldeoxyneofusapyrone were isolated from a pathogenic fungus, Verticillium dahliae, which causes Verticillium wilt disease in Helianthus annuus. Spectral analyses revealed that these are 2-pyrone type analogs of deoxyfusapyrone and its 7-desmethyl derivative, respectively. Biological assay disclosed that 10microg of deoxyneofusapyrone inhibited the growth of MRSA clinical isolate 87-7927.
isolation and structure determination, NMR spectral analysis, 4-hydroxy-2-pyrone, IR spectra, theoretical 13C NMR chemical shift, inhibition of MRSA clinical isolate 87-7927
Structure type: monomer ; 591.3925 [M+H]+
C
34H
54O
8Location inside paper: Fig.1, structure 1, Table 1, 1
Trivial name: deoxyneofusapyrone
Compound class: glycoside
Methods: 13C NMR, 1H NMR, IR, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, HMBC, evaporation, NOESY
Biological activity: Deoxyneofusapyrone inhibited the growth of Cochliobolus miyabeanus in 100 μg/mL concentration and showed no cytotoxicity against HeLa (human cervix carcinoma) and HepG2 (human hepatocellular carcinoma).
Comments, role: NMR temperature was not specified
Related record ID(s): 46015, 46016, 46017
NCBI Taxonomy refs (TaxIDs): 27337
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
3 bD1,4dxylHexp 75.67 73.52 74.07 36.58 78.46 65.70
Subst 167.06 100.30 170.59 100.86 172.15 45.52 78.16 125.97 139.20 131.46 139.56 32.99 131.93 134.01 40.99 32.27 38.31 28.40 30.71 33.07 23.72 14.47 20.39 23.00 13.03 22.17 23.91 20.05
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
3 bD1,4dxylHexp 4.48 3.99 3.63 1.57-1.95 3.60 3.56
Subst - - - 6.08 - - 4.32 5.55 6.23 - 5.31 3.42 5.06 - 1.95 1.59 1.10-1.31 1.30 1.28 1.28 1.28 0.89 1.21 1.15 1.75 0.97 1.63 0.85
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
3 bD1,4dxylHexp 75.67/4.48 73.52/3.99 74.07/3.63 36.58/1.57-1.95 78.46/3.60 65.70/3.56
Subst 100.86/6.08 78.16/4.32 125.97/5.55 139.20/6.23 139.56/5.31 32.99/3.42 131.93/5.06 40.99/1.95 32.27/1.59 38.31/1.10-1.31 28.40/1.30 30.71/1.28 33.07/1.28 23.72/1.28 14.47/0.89 20.39/1.21 23.00/1.15 13.03/1.75 22.17/0.97 23.91/1.63 20.05/0.85
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 |
|---|
| 3 | bD1,4dxylHexp | 4.48 | 3.99 | 3.63 | 1.57
1.95 | 3.60 | 3.56 | |
| | Subst |
|
|
| 6.08 |
|
| 4.32 | 5.55 | 6.23 |
| 5.31 | 3.42 | 5.06 |
| 1.95 | 1.59 | 1.10
1.31 | 1.30 | 1.28 | 1.28 | 1.28 | 0.89 | 1.21 | 1.15 | 1.75 | 0.97 | 1.63 | 0.85 |
|
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 |
|---|
| 3 | bD1,4dxylHexp | 75.67 | 73.52 | 74.07 | 36.58 | 78.46 | 65.70 | |
| | Subst | 167.06 | 100.30 | 170.59 | 100.86 | 172.15 | 45.52 | 78.16 | 125.97 | 139.20 | 131.46 | 139.56 | 32.99 | 131.93 | 134.01 | 40.99 | 32.27 | 38.31 | 28.40 | 30.71 | 33.07 | 23.72 | 14.47 | 20.39 | 23.00 | 13.03 | 22.17 | 23.91 | 20.05 |
|
There is only one chemically distinct structure:
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Honma M, Kudo S, Takada N, Tanaka K, Miura T, Hashimoto M
Novel neofusapyrones isolated from Verticillium dahliae as potent antifungal substances
Bioorganic and Medicinal Chemistry Letters 20(2) (2010)
709-712
|
b-D-1,4dxylHexp-(1C-3)-Subst
Subst = 7-desmethyldeoxyneofusapyrone aglycon = SMILES CCCCCCC(C/C(C)=C\C(/C=C(/C=C/{8}C(O)C(C1=C{4}C(O)={3}CC(O1)=O)C)C)C)C |
Show graphically |
Verticillium dahliae
(NCBI TaxID 27337,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Helianthus annuus
Associated disease: Verticillium wilt
The structure was elucidated in this paperNCBI PubMed ID: 19962895Publication DOI: 10.1016/j.bmcl.2009.11.063Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: Hashimoto M <hmasaru
cc.hirosaki-u.ac.jp>
Institutions: Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan, Graduate School of Health Sciences, Hirosaki University, Hirosaki, Japan
Novel fusapyrone analogs, deoxyneofusapyrone and 7-desmethyldeoxyneofusapyrone were isolated from a pathogenic fungus, Verticillium dahliae, which causes Verticillium wilt disease in Helianthus annuus. Spectral analyses revealed that these are 2-pyrone type analogs of deoxyfusapyrone and its 7-desmethyl derivative, respectively. Biological assay disclosed that 10microg of deoxyneofusapyrone inhibited the growth of MRSA clinical isolate 87-7927.
isolation and structure determination, NMR spectral analysis, 4-hydroxy-2-pyrone, IR spectra, theoretical 13C NMR chemical shift, inhibition of MRSA clinical isolate 87-7927
Structure type: monomer ; 577.3750 [M+H]+
C
33H
52O
8Location inside paper: Fig.1, structure 2, Table 1, 2
Trivial name: 7-desmethyldeoxyneofusapyrone
Compound class: glycoside
Methods: 13C NMR, 1H NMR, IR, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, HMBC, evaporation, NOESY
Biological activity: 7-desmethyldeoxyneofusapyrone inhibited the growth of Cochliobolus miyabeanus in 100 μg/mL concentration and showed no cytotoxicity against HeLa (human cervix carcinoma) and HepG2 (human hepatocellular carcinoma).
Comments, role: NMR temperature was not specified
Related record ID(s): 46014, 46016, 46017
NCBI Taxonomy refs (TaxIDs): 27337
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
3 bD1,4dxylHexp 75.70 73.44 74.06 36.54 78.44 65.66
Subst 167.21 100.48 168.85 102.27 170.84 46.56 75.88 127.66 139.04 131.87 139.75 32.99 131.38 134.08 40.98 32.28 38.33 28.39 30.71 33.06 23.72 14.47 15.32 13.01 22.15 23.92 20.04
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
3 bD1,4dxylHexp 4.48 4.00 3.60 1.58-1.95 3.60 3.56
Subst - - - 6.05 - 2.61 4.21 5.51 6.23 - 5.34 3.42 5.06 - 1.91 1.59 1.13-1.34 1.28 1.28 1.28 1.28 0.89 1.13 1.77 0.98 1.63 0.85
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
3 bD1,4dxylHexp 75.70/4.48 73.44/4.00 74.06/3.60 36.54/1.58-1.95 78.44/3.60 65.66/3.56
Subst 102.27/6.05 46.56/2.61 75.88/4.21 127.66/5.51 139.04/6.23 139.75/5.34 32.99/3.42 131.38/5.06 40.98/1.91 32.28/1.59 38.33/1.13-1.34 28.39/1.28 30.71/1.28 33.06/1.28 23.72/1.28 14.47/0.89 15.32/1.13 13.01/1.77 22.15/0.98 23.92/1.63 20.04/0.85
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 |
|---|
| 3 | bD1,4dxylHexp | 4.48 | 4.00 | 3.60 | 1.58
1.95 | 3.60 | 3.56 | |
| | Subst |
|
|
| 6.05 |
| 2.61 | 4.21 | 5.51 | 6.23 |
| 5.34 | 3.42 | 5.06 |
| 1.91 | 1.59 | 1.13
1.34 | 1.28 | 1.28 | 1.28 | 1.28 | 0.89 | 1.13 | 1.77 | 0.98 | 1.63 | 0.85 |
|
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 |
|---|
| 3 | bD1,4dxylHexp | 75.70 | 73.44 | 74.06 | 36.54 | 78.44 | 65.66 | |
| | Subst | 167.21 | 100.48 | 168.85 | 102.27 | 170.84 | 46.56 | 75.88 | 127.66 | 139.04 | 131.87 | 139.75 | 32.99 | 131.38 | 134.08 | 40.98 | 32.28 | 38.33 | 28.39 | 30.71 | 33.06 | 23.72 | 14.47 | 15.32 | 13.01 | 22.15 | 23.92 | 20.04 |
|
There is only one chemically distinct structure:
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Honma M, Kudo S, Takada N, Tanaka K, Miura T, Hashimoto M
Novel neofusapyrones isolated from Verticillium dahliae as potent antifungal substances
Bioorganic and Medicinal Chemistry Letters 20(2) (2010)
709-712
|
b-D-1,4dxylHexp-(1C-3)-Subst
Subst = neofusapyrone aglycon = SMILES CCCCCCC(C/C(C)=C\C(/C=C(/C=C/{8}C(O)C(C)(C1=C{4}C(O)={3}CC(O1)=O)C)C){27}CO)C |
Show graphically |
Verticillium dahliae
(NCBI TaxID 27337,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Helianthus annuus
Associated disease: Verticillium wilt
NCBI PubMed ID: 19962895Publication DOI: 10.1016/j.bmcl.2009.11.063Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: Hashimoto M <hmasaru
cc.hirosaki-u.ac.jp>
Institutions: Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan, Graduate School of Health Sciences, Hirosaki University, Hirosaki, Japan
Novel fusapyrone analogs, deoxyneofusapyrone and 7-desmethyldeoxyneofusapyrone were isolated from a pathogenic fungus, Verticillium dahliae, which causes Verticillium wilt disease in Helianthus annuus. Spectral analyses revealed that these are 2-pyrone type analogs of deoxyfusapyrone and its 7-desmethyl derivative, respectively. Biological assay disclosed that 10microg of deoxyneofusapyrone inhibited the growth of MRSA clinical isolate 87-7927.
isolation and structure determination, NMR spectral analysis, 4-hydroxy-2-pyrone, IR spectra, theoretical 13C NMR chemical shift, inhibition of MRSA clinical isolate 87-7927
Structure type: monomer
Location inside paper: Fig.1, structure 3
Trivial name: fusapyrone, neofusapyrone
Compound class: glycoside
Methods: 13C NMR, 1H NMR, IR, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, HMBC, evaporation, NOESY
Related record ID(s): 46010, 46014, 46015, 46017
NCBI Taxonomy refs (TaxIDs): 27337
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Honma M, Kudo S, Takada N, Tanaka K, Miura T, Hashimoto M
Novel neofusapyrones isolated from Verticillium dahliae as potent antifungal substances
Bioorganic and Medicinal Chemistry Letters 20(2) (2010)
709-712
|
b-D-1,4dxylHexp-(1C-3)-Subst
Subst = deoxyfusapyrone aglycon = SMILES CCCCCCC(C/C(C)=C\C(/C=C(/C=C/{8}C(O)C(C)(C1=CC({3}C={2}C(O)O1)=O)C)C)C)C |
Show graphically |
Verticillium dahliae
(NCBI TaxID 27337,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Helianthus annuus
Associated disease: Verticillium wilt
NCBI PubMed ID: 19962895Publication DOI: 10.1016/j.bmcl.2009.11.063Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: Hashimoto M <hmasaru
cc.hirosaki-u.ac.jp>
Institutions: Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan, Graduate School of Health Sciences, Hirosaki University, Hirosaki, Japan
Novel fusapyrone analogs, deoxyneofusapyrone and 7-desmethyldeoxyneofusapyrone were isolated from a pathogenic fungus, Verticillium dahliae, which causes Verticillium wilt disease in Helianthus annuus. Spectral analyses revealed that these are 2-pyrone type analogs of deoxyfusapyrone and its 7-desmethyl derivative, respectively. Biological assay disclosed that 10microg of deoxyneofusapyrone inhibited the growth of MRSA clinical isolate 87-7927.
isolation and structure determination, NMR spectral analysis, 4-hydroxy-2-pyrone, IR spectra, theoretical 13C NMR chemical shift, inhibition of MRSA clinical isolate 87-7927
Structure type: monomer
Location inside paper: Fig.1, structure 4
Trivial name: deoxyfusapyrone
Compound class: glycoside
Methods: 13C NMR, 1H NMR, IR, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, HMBC, evaporation, NOESY
Related record ID(s): 46012, 46014, 46015, 46016, 46021
NCBI Taxonomy refs (TaxIDs): 27337
Show glycosyltransferases
There is only one chemically distinct structure:
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