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Prenylated Benzophenones from Vismia guianensis Reduced Nematode Growth and Chemotaxis

Carresse Gerald
Carresse Gerald
, 
Rick-Kia Howard
Rick-Kia Howard
, 
Rachael Adesina
Rachael Adesina
, 
Seon Hamer
Seon Hamer
 and 
Omar E. Christian
Omar E. Christian
   | Jan 08, 2023
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Article Category: Research Paper
Published Online: Jan 08, 2023
Page range: -
Received: Apr 06, 2022
DOI: https://doi.org/10.2478/jofnem-2022-0054
Keywords
© 2022 Walter de Gruyter GmbH, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.

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.

Position δC δH (J in Hz)
1 107.5
2 160.3
3 103.8
4 153.1
5 110.4
6 152.9
7a 26.0 2.65 (dd, 17.3, 5.6)
7b 2.90 (dd, 17.3, 5.2)
8 69.0 3.70 (dd, 5.2, 5.6)
9 77.6
10 21.6 1.10 (s)
11 24.2 1.2 (s)
12 116.8 6.50 (d, 9.9)
13 127.4 5.52 (d, 9.9)
14 77.6
15 28.0 1.44 (s)
16 28.1 1.44 (s)
17 193.9
1′ 131.6
2′ 132.1 6.80 (d, 8.8)
3′ 115.2 7.75 (d, 8.8)
4′ 160.3
5′ 115.2 7.75 (d, 8.8)
6′ 132.1 6.80 (d, 8.8)
OCH3 63.4 3.67 (s)
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