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Piperine analogs in a hydrophobic fraction from Piper ribersoides (Piperaceae) and its insect antifeedant activity

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Abstract

Piper ribersoides Wall. (Piperaceae), which is called “Khua Sa khan” in the local language, is mainly grown in Laos. This plant is used as a food in Laos, but no report on its metabolites exists. Crushed stems were immersed in methanol. The ethyl acetate fraction showed potential insect antifeedant activity for Spodoptera litura (Fabricius) (Lepidoptera: Noctuidae), and some of the active compounds were piperine analogs. Piperine and its geometrical isomer independently showed potent antifeedant activities, and piperine was presumably the main active compound in the methanol extract. Interestingly, we discovered that the antifeedant activity was reduced when they were mixed (50:50).

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Acknowledgments

The authors express sincere gratitude to Professor Emeritus Seiji Sawada, Kyoto University of Education, for supporting our research. This research was partially supported by the Ministry of Education, Science, Sports and Culture, Grant-in-Aid for Scientific Research (B), 17406003, 2005.

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Authors and Affiliations

  1. Department of Advanced Bioscience, Graduate School of Agriculture, Kinki University, Nara, 631-8505, Japan

    Takashi Kitayama, Kanako Yasuda & Takeharu Kihara

  2. Department of Pharmacognosy, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto, 606-8501, Japan

    Michiho Ito

  3. Department of Applied Biological Chemistry, Graduate School of Agriculture, Kinki University, Nara, 631-8505, Japan

    Hiromi Fukumoto & Masanori Morimoto

Authors
  1. Takashi Kitayama
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  2. Kanako Yasuda
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  3. Takeharu Kihara
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  4. Michiho Ito
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  5. Hiromi Fukumoto
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  6. Masanori Morimoto
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Corresponding author

Correspondence to Takashi Kitayama.

Appendix

Appendix

1; 1H NMR (CDCl3): δ 1.62 (m, 4H), 1.65 (m, 2H), 3.58 (brm, 4H), 5.97 (s, 2H), 6.43 (d, 1H, J = 14.6 Hz), 6.73 (m, 1H), 6.74 (m, 1H), 6.78 (d, 1H, J = 8.1 Hz), 6.89 (dd, 1H, J = 1.4 and 8.1 Hz), 6.98 (d, 1H, J = 1.4 Hz), 7.31 (m, 1H).

2; 1H NMR (CDCl3): δ 1.60 (m, 4H), 1.65 (m, 2H), 3.56 (brm, 4H), 5.97 (s, 2H), 5.98 (d, 1H, J = 11.5 Hz), 6.50 (m, 1H), 6.62 (m, 1H), 6.76 (d, 1H, J = 8.1), 6.90 (dd, 1H, J = 1.7 and 8.1 Hz), 7.04 (d, 1H, J = 1.7 Hz), 7.43 (m, 1H).

3; 1H NMR (CDCl3): 1.62 (m, 4H), 1.65 (m, 2H), 2.66 (t, 2H, J = 7.5 Hz), 3.56 (brm, 4H), 6.05 (dt, 1H, J = 6.9 and 15.0 Hz), 6.19 (dd, 1H, J = 10.2 and 15.0 Hz), 6.26 (d, 1H, J = 15.0 Hz), 6.61 (dd, 1H, J = 1.8 and 7.8 Hz), 6.66 (d, 1H, J = 1.8 Hz), 6.72 (d, 1H, J = 7.8 Hz), 7.21 (dd, 1H, J = 10.2 and 15.0 Hz).

4; 1H NMR (CDCl3): δ 1.52 (m, 4H), 1.58 (m, 4H), 1.67 (m, 2H), 2.21 (m, 2H), 2.25 (m, 2H), 3.56 (brm, 4H), 5.95 (s, 2H), 6.08 (m, 1H), 6.27 (d, 1H, J = 15.0 Hz), 6.30 (d, 1H, J = 15.0 Hz), 6.75 (d, 1H, J = 8.0), 6.78 (dd, 1H, J = 1.6 and 8.0 Hz), 6.84 (m, 1H), 6.90 (d, 1H, J = 1.6 Hz).

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Kitayama, T., Yasuda, K., Kihara, T. et al. Piperine analogs in a hydrophobic fraction from Piper ribersoides (Piperaceae) and its insect antifeedant activity. Appl Entomol Zool 48, 455–459 (2013). https://doi.org/10.1007/s13355-013-0204-4

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  • DOI: https://doi.org/10.1007/s13355-013-0204-4

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