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Characterization of four new antifungal yanuthones from Aspergillus niger
Four new yanuthone analogs ( 1–4 ) were isolated from the filamentous fungus Aspergillus niger . The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with 13 C 8 -6-methylsalicylic acid iden...
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| Published in: | Journal of antibiotics 2015-03, Vol.68 (3), p.201-205 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c509t-7bd6f8eb531d0084184689a6dd5749200653a60fa041fb5ad016657260f06a463 |
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| cites | cdi_FETCH-LOGICAL-c509t-7bd6f8eb531d0084184689a6dd5749200653a60fa041fb5ad016657260f06a463 |
| container_end_page | 205 |
| container_issue | 3 |
| container_start_page | 201 |
| container_title | Journal of antibiotics |
| container_volume | 68 |
| creator | Petersen, Lene M Holm, Dorte K Knudsen, Peter B Nielsen, Kristian F Gotfredsen, Charlotte H Mortensen, Uffe H Larsen, Thomas O |
| description | Four new yanuthone analogs (
1–4
) were isolated from the filamentous fungus
Aspergillus niger
. The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with
13
C
8
-6-methylsalicylic acid identified three class I yanuthones originating from the polyketide 6-methylsalicylic acid (yanuthone K, L and M (
1–3
)) and a class II yanuthone, which was named yanuthone X
2
(
4
). The four new compounds were tested toward the pathogenic yeast
Candida albicans
and all displayed antifungal activity. Yanuthone X
2
represents the first example of a bioactive class II yanuthone, demonstrating the pharmaceutical potential of this class. |
| doi_str_mv | 10.1038/ja.2014.130 |
| format | article |
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1–4
) were isolated from the filamentous fungus
Aspergillus niger
. The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with
13
C
8
-6-methylsalicylic acid identified three class I yanuthones originating from the polyketide 6-methylsalicylic acid (yanuthone K, L and M (
1–3
)) and a class II yanuthone, which was named yanuthone X
2
(
4
). The four new compounds were tested toward the pathogenic yeast
Candida albicans
and all displayed antifungal activity. Yanuthone X
2
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1–4
) were isolated from the filamentous fungus
Aspergillus niger
. The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with
13
C
8
-6-methylsalicylic acid identified three class I yanuthones originating from the polyketide 6-methylsalicylic acid (yanuthone K, L and M (
1–3
)) and a class II yanuthone, which was named yanuthone X
2
(
4
). The four new compounds were tested toward the pathogenic yeast
Candida albicans
and all displayed antifungal activity. Yanuthone X
2
represents the first example of a bioactive class II yanuthone, demonstrating the pharmaceutical potential of this class.</description><subject>631/1647/2258</subject><subject>631/326/22/1292</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - isolation & purification</subject><subject>Antifungal Agents - pharmacology</subject><subject>Aspergillus niger - metabolism</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Candida albicans - drug effects</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Microbiology</subject><subject>Organic Chemistry</subject><subject>original-article</subject><subject>Yeasts</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kd1LwzAUxYMoOqdPvkvBF0E7b5o2SR_H8GMw8EWfQ9omW0ubzKRF5l9vxqaIiBC4kPvj3HvPQegCwwQD4XeNnCSA0wkmcIBGmHMc45Tmh2gEkOCY8wRO0Kn3DQBhhPFjdJJkSU5yxkdoPltJJ8teufpD9rU1kdWRtoOLjHqPpOlrPZilbKONNEO_skb5SDvbRVO_Vm5Zt-3gI1MvlTtDR1q2Xp3v6xi9Pty_zJ7ixfPjfDZdxGUGeR-zoqKaqyIjuALgKeYp5bmkVZWxNE8AaEYkBS0hxbrIZAWY0owl4QuoTCkZo-ud7trZt0H5XnS1L1XbSqPs4EXAGUlJ0A3o1S-0CZeZsJ1ICME0vP8pzDgN_m3dGqObHVU6671TWqxd3Um3ERjENgfRSLHNQYQcAn251xyKTlXf7JfxAbjdAT60TLDvx9A_9D4Bq6KOxg</recordid><startdate>20150301</startdate><enddate>20150301</enddate><creator>Petersen, Lene M</creator><creator>Holm, Dorte K</creator><creator>Knudsen, Peter B</creator><creator>Nielsen, Kristian F</creator><creator>Gotfredsen, Charlotte H</creator><creator>Mortensen, Uffe H</creator><creator>Larsen, Thomas O</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QL</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>PRINS</scope><scope>7X8</scope></search><sort><creationdate>20150301</creationdate><title>Characterization of four new antifungal yanuthones from Aspergillus niger</title><author>Petersen, Lene M ; 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1–4
) were isolated from the filamentous fungus
Aspergillus niger
. The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with
13
C
8
-6-methylsalicylic acid identified three class I yanuthones originating from the polyketide 6-methylsalicylic acid (yanuthone K, L and M (
1–3
)) and a class II yanuthone, which was named yanuthone X
2
(
4
). The four new compounds were tested toward the pathogenic yeast
Candida albicans
and all displayed antifungal activity. Yanuthone X
2
represents the first example of a bioactive class II yanuthone, demonstrating the pharmaceutical potential of this class.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>25293978</pmid><doi>10.1038/ja.2014.130</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | Journal of antibiotics, 2015-03, Vol.68 (3), p.201-205 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1667343184 |
| source | Springer Nature |
| subjects | 631/1647/2258 631/326/22/1292 Antifungal agents Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Aspergillus niger - metabolism Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Candida albicans - drug effects Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Microbiology Organic Chemistry original-article Yeasts |
| title | Characterization of four new antifungal yanuthones from Aspergillus niger |
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