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Prenylated Benzophenones from Vismia guianensis Reduced Nematode Growth and Chemotaxis Cover

Prenylated Benzophenones from Vismia guianensis Reduced Nematode Growth and Chemotaxis

Journal of Nematology
Volume 54 (2022): Issue 1 (February 2022)
By: Carresse Gerald,  Rick-Kia Howard,  Rachael Adesina,  Seon Hamer and  Omar E. Christian  
Open Access
|Jan 2023

Figures & Tables

Figure 1

Ring assay plate.
Ring assay plate.

Figure 2

Compound isolated from Vismia guianensis. 8,9-epoxyvismiaphenone F (1).
Compound isolated from Vismia guianensis. 8,9-epoxyvismiaphenone F (1).

Figure 3

Clusiaphenone B (2) and benzophenone (3).
Clusiaphenone B (2) and benzophenone (3).

Figure 4

Effects of 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) on nematode chemotaxis and growth. (A) Nematodes in the bacterial ring. (B) Nematodes in the compound. (C) Nematode growth on day 3. Chemotaxis and growth decreased with 3-d exposure to 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3). Nematodes were placed in the middle of nutrient growth agar plates in compounds (1, 2, 3) for 3 d. Nematodes in the bacterial ring and middle of ring assay plates were counted on day 3. Clusiaphenone B (3) decreased the number of nematodes in the bacterial ring compared to control on day 3 when conducting a one-way ANOVA (P-value <0.05). 8,9-Expoxyvismiaphenone F (1) and 2,4,6-trihydroxybenzophenone (3) did not significantly decrease nematodes in the bacterial ring on day 3 when compared to control (P-value >0.05). 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) decreased nematodes in the middle of ring assay plate when compared to control on day 3, and the corresponding P-values are 0.0005 (***), <0.0001 (****), and 0.0026 (**), respectively. On day 3, all live nematodes on ring assay plates were counted and the number demonstrates growth. 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) decreased nematode growth when compared to control on day 3, and the corresponding P-values are 0.0314 (*), 0.0028 (**), and 0.012 (*), respectively. Significance was determined under a one-way ANOVA and Tukey’s post-hoc test. Data are presented as the mean ± SEM for A–C for three independent replicates, each containing three ring assay plates per treatment group, n = 9.
Effects of 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) on nematode chemotaxis and growth. (A) Nematodes in the bacterial ring. (B) Nematodes in the compound. (C) Nematode growth on day 3. Chemotaxis and growth decreased with 3-d exposure to 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3). Nematodes were placed in the middle of nutrient growth agar plates in compounds (1, 2, 3) for 3 d. Nematodes in the bacterial ring and middle of ring assay plates were counted on day 3. Clusiaphenone B (3) decreased the number of nematodes in the bacterial ring compared to control on day 3 when conducting a one-way ANOVA (P-value <0.05). 8,9-Expoxyvismiaphenone F (1) and 2,4,6-trihydroxybenzophenone (3) did not significantly decrease nematodes in the bacterial ring on day 3 when compared to control (P-value >0.05). 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) decreased nematodes in the middle of ring assay plate when compared to control on day 3, and the corresponding P-values are 0.0005 (***), <0.0001 (****), and 0.0026 (**), respectively. On day 3, all live nematodes on ring assay plates were counted and the number demonstrates growth. 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) decreased nematode growth when compared to control on day 3, and the corresponding P-values are 0.0314 (*), 0.0028 (**), and 0.012 (*), respectively. Significance was determined under a one-way ANOVA and Tukey’s post-hoc test. Data are presented as the mean ± SEM for A–C for three independent replicates, each containing three ring assay plates per treatment group, n = 9.

Figure 5

Effects of 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) on acetylcholinesterase activity. 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) had no effect on nematode acetylcholinesterase activity. C. elegans were exposed to compounds for 3 d. All nematodes were preserved and subjected to acetylcholinesterase activity assay. No significant difference was found when test compounds were compared to the control one-way ANOVA and a Tukey’s post-hoc test (P > 0.05). Data are presented as the mean ± SEM for A–C for three independent replicates, each containing three ring assay plates per treatment group, n = 9.
Effects of 8,9-epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) on acetylcholinesterase activity. 8,9-Epoxyvismiaphenone F (1), clusiaphenone B (2), and 2,4,6-trihydroxybenzophenone (3) had no effect on nematode acetylcholinesterase activity. C. elegans were exposed to compounds for 3 d. All nematodes were preserved and subjected to acetylcholinesterase activity assay. No significant difference was found when test compounds were compared to the control one-way ANOVA and a Tukey’s post-hoc test (P > 0.05). Data are presented as the mean ± SEM for A–C for three independent replicates, each containing three ring assay plates per treatment group, n = 9.

1H and 13C NMR data for 8,9-epoxyvismiaphenone F (1) in CDCl3_

PositionδCδH (J in Hz)
1107.5
2160.3
3103.8
4153.1
5110.4
6152.9
7a26.02.65 (dd, 17.3, 5.6)
7b 2.90 (dd, 17.3, 5.2)
869.03.70 (dd, 5.2, 5.6)
977.6
1021.61.10 (s)
1124.21.2 (s)
12116.86.50 (d, 9.9)
13127.45.52 (d, 9.9)
1477.6
1528.01.44 (s)
1628.11.44 (s)
17193.9
1′131.6
2′132.16.80 (d, 8.8)
3′115.27.75 (d, 8.8)
4′160.3
5′115.27.75 (d, 8.8)
6′132.16.80 (d, 8.8)
OCH363.43.67 (s)
DOI: https://doi.org/10.2478/jofnem-2022-0054 | Journal eISSN: 2640-396X | Journal ISSN: 0022-300X
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Language: English
Submitted on: Apr 6, 2022
Published on: Jan 8, 2023
Published by: Society of Nematologists, Inc.
In partnership with: Paradigm Publishing Services
Publication frequency: 1 issue per year
Keywords:
anthelminthic,
behavior,
biopesticides,
interaction,
Vismia guianensis
Related subjects:
Life sciences,
Life sciences, other

© 2023 Carresse Gerald, Rick-Kia Howard, Rachael Adesina, Seon Hamer, Omar E. Christian, published by Society of Nematologists, Inc.
This work is licensed under the Creative Commons Attribution 4.0 License.

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