Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i>
Grammicin, a polyketide metabolite produced by the endolichenic fungus <i>Xylaria grammica</i> KCTC 13121BP, shows strong nematicidal activity against <i>Meloidogyne incognita.</i> This study was performed to elucidate the grammicin biosynthesis pathway of <i>X. grammic...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/15/4675 |
| _version_ | 1797525258589175808 |
|---|---|
| author | Yoon Jee Kim Kalaiselvi Duraisamy Min-Hye Jeong Sook-Young Park Soonok Kim Yookyung Lee Van Thi Nguyen Nan Hee Yu Ae Ran Park Jin-Cheol Kim |
| author_facet | Yoon Jee Kim Kalaiselvi Duraisamy Min-Hye Jeong Sook-Young Park Soonok Kim Yookyung Lee Van Thi Nguyen Nan Hee Yu Ae Ran Park Jin-Cheol Kim |
| author_sort | Yoon Jee Kim |
| collection | DOAJ |
| description | Grammicin, a polyketide metabolite produced by the endolichenic fungus <i>Xylaria grammica</i> KCTC 13121BP, shows strong nematicidal activity against <i>Meloidogyne incognita.</i> This study was performed to elucidate the grammicin biosynthesis pathway of <i>X. grammica</i> KCTC 13121BP and to examine the nematicidal activity of the biosynthesis intermediates and derivatives against <i>M. incognita</i>. Two grammicin biosynthesis intermediates were isolated from a T-DNA insertion transformant (strain TR-74) of <i>X. grammica</i> KCTC 13121BP and identified as 2-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione (compound <b>1</b>) and 2,5-dihydroxybenzaldehyde (compound <b>2</b>), which were also reported to be intermediates in the biosynthesis pathway of patulin, an isomer of grammicin. This indicates that the grammicin biosynthesis pathway overlaps almost with that of patulin, except for the last few steps. Among 13 grammicin biosynthesis intermediates and their derivatives (except grammicin), toluquinol caused the highest <i>M. incognita</i> J2 mortality, with an LC<sub>50/72 h</sub> value of 11.13 µg/mL, which is similar to grammicin with an LC<sub>50/72 h</sub> value of 15.95 µg/mL. In tomato pot experiments, the wettable powder type formulations (WP) of toluquinol (17.78 µg/mL) and grammicin (17.78 µg/mL) also effectively reduced gall formation on the roots of tomato plants with control values of 72.22% and 77.76%, respectively, which are much higher than abamectin (16.67%), but lower than fosthiazate (100%). The results suggest that toluquinol can be used directly as a biochemical nematicide or as a lead molecule for the development of new synthetic nematicides for the control of root-knot nematode diseases. |
| first_indexed | 2024-03-10T09:11:13Z |
| format | Article |
| id | doaj.art-85df8125609e42cd9bf1514e0aed1dac |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T09:11:13Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-85df8125609e42cd9bf1514e0aed1dac2023-11-22T06:01:38ZengMDPI AGMolecules1420-30492021-08-012615467510.3390/molecules26154675Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i>Yoon Jee Kim0Kalaiselvi Duraisamy1Min-Hye Jeong2Sook-Young Park3Soonok Kim4Yookyung Lee5Van Thi Nguyen6Nan Hee Yu7Ae Ran Park8Jin-Cheol Kim9Department of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Plant Medicine, Sunchon National University, Suncheon 57922, KoreaDepartment of Plant Medicine, Sunchon National University, Suncheon 57922, KoreaBiological and Genetic Resources Assessment Division, National Institute of Biological Resources, 42 Hwangyeong-ro, Incheon 22689, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaDepartment of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Science, Chonnam National University, Gwangju 61186, KoreaGrammicin, a polyketide metabolite produced by the endolichenic fungus <i>Xylaria grammica</i> KCTC 13121BP, shows strong nematicidal activity against <i>Meloidogyne incognita.</i> This study was performed to elucidate the grammicin biosynthesis pathway of <i>X. grammica</i> KCTC 13121BP and to examine the nematicidal activity of the biosynthesis intermediates and derivatives against <i>M. incognita</i>. Two grammicin biosynthesis intermediates were isolated from a T-DNA insertion transformant (strain TR-74) of <i>X. grammica</i> KCTC 13121BP and identified as 2-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione (compound <b>1</b>) and 2,5-dihydroxybenzaldehyde (compound <b>2</b>), which were also reported to be intermediates in the biosynthesis pathway of patulin, an isomer of grammicin. This indicates that the grammicin biosynthesis pathway overlaps almost with that of patulin, except for the last few steps. Among 13 grammicin biosynthesis intermediates and their derivatives (except grammicin), toluquinol caused the highest <i>M. incognita</i> J2 mortality, with an LC<sub>50/72 h</sub> value of 11.13 µg/mL, which is similar to grammicin with an LC<sub>50/72 h</sub> value of 15.95 µg/mL. In tomato pot experiments, the wettable powder type formulations (WP) of toluquinol (17.78 µg/mL) and grammicin (17.78 µg/mL) also effectively reduced gall formation on the roots of tomato plants with control values of 72.22% and 77.76%, respectively, which are much higher than abamectin (16.67%), but lower than fosthiazate (100%). The results suggest that toluquinol can be used directly as a biochemical nematicide or as a lead molecule for the development of new synthetic nematicides for the control of root-knot nematode diseases.https://www.mdpi.com/1420-3049/26/15/4675biosynthesis intermediatesgrammicin<i>Meloidogyne incognita</i>nematicidal activity<i>Xylaria grammica</i> |
| spellingShingle | Yoon Jee Kim Kalaiselvi Duraisamy Min-Hye Jeong Sook-Young Park Soonok Kim Yookyung Lee Van Thi Nguyen Nan Hee Yu Ae Ran Park Jin-Cheol Kim Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> Molecules biosynthesis intermediates grammicin <i>Meloidogyne incognita</i> nematicidal activity <i>Xylaria grammica</i> |
| title | Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> |
| title_full | Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> |
| title_fullStr | Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> |
| title_full_unstemmed | Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> |
| title_short | Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in <i>Xylaria grammica</i> KCTC 13121BP against <i>Meloidogyne incognita</i> |
| title_sort | nematicidal activity of grammicin biosynthesis pathway intermediates in i xylaria grammica i kctc 13121bp against i meloidogyne incognita i |
| topic | biosynthesis intermediates grammicin <i>Meloidogyne incognita</i> nematicidal activity <i>Xylaria grammica</i> |
| url | https://www.mdpi.com/1420-3049/26/15/4675 |
| work_keys_str_mv | AT yoonjeekim nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT kalaiselviduraisamy nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT minhyejeong nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT sookyoungpark nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT soonokkim nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT yookyunglee nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT vanthinguyen nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT nanheeyu nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT aeranpark nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai AT jincheolkim nematicidalactivityofgrammicinbiosynthesispathwayintermediatesinixylariagrammicaikctc13121bpagainstimeloidogyneincognitai |