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Insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes and its constituents against two species of grain storage insects

  • Xiujuan Pan , He Xiao , Xinping Hu and Zhi Long Liu ORCID logo EMAIL logo
Published/Copyright: September 22, 2022
Zeitschrift für Naturforschung C
From the journal Zeitschrift für Naturforschung C Volume 78 Issue 1-2

Abstract

The aim of this research was to evaluate insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes against adults of Liposcelis entomophila and Tribolium castaneum. Gas chromatography-mass spectrometry analyses revealed the presence of 44 compounds with β-eudesmol (19.1%), elemol (8.1%), α-terpineol (8.0%), methyl eugenol (6.5%), and caryophyllene (4.8%) being the major constituents. Bioactivity-directed chromatographic separation of the oil led to the isolation of four constituents, elemol, β-eudesmol, methyl eugenol, and α-terpineol. The essential oil exhibited fumigant toxicity against the adults of L. entomophila and T. castaneum with LC50 values of 0.57 and 4.96 mg/L air while the two isolates, methyl eugenol and α-terpineol possessed fumigant toxicity against the booklice (LC50 = 0.15 and 0.48 mg/L air, respectively) and the beetles (LC50 = 1.81 and 4.96 mg/L air, respectively). The oil also possessed contact toxicity against the booklice and the beetles with LD50 values of 121.56 μg/cm2 and 54.93 μg/adult, respectively, while the two isolates β-eudesmol and elemol showed contact toxicity against L. entomophila (LD50 = 99.21 and 35.19 μg/cm2, respectively) and T. castaneum (LD50 = 35.26 and 8.89 μg/adult, respectively). The results indicate that the oil of R. beesianus rhizomes and its isolates have potential as a source for natural insecticides.

Keywords: contact toxicity; fumigant; Liposcelis entomophila ; Rhynchanthus beesianus essential oil; Tribolium castaneum
Corresponding author: Zhi Long Liu, Department of Entomology and MOA Key Lab of Pest Monitoring and Green Management, College of Plant Protection, China Agricultural University, 2 Yuanmingyuan West Road, Haidian District, Beijing 100193, China, E-mail:

Funding source: Special Fund of Foreign Science and Technology Cooperation of Ningxia Academy of Agriculture and Forestry Sciences

Award Identifier / Grant number: grant no. DWX-2019003

Acknowledgments

We thank Q. R. Liu from the College of Life Sciences, Beijing Normal University, Beijing 100875, for the identification of the investigated plant.

  1. Author contributions: All the authors have accepted respon-sibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This project was supported by Special Fund of Foreign Science and Technology Cooperation of Ningxia Academy of Agriculture and Forestry Sciences (grant no. DWX-2019003).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

Appendix

α-Terpineol (1, Figure 1). Colorless oil, C10H18O. 1H NMR (CDCl3, 500 MHz) δ (ppm): 1.20 (3H, s, H-9), 1.22 (3H, s, H-10), 1.47–1.57 (3H, m, H-4), 1.67 (3H, s, H-7), 1.78–1.88 (2H, m, H-3), 1.89–1.93 (2H, m, H-5), 2.01 (1H, d, J = 5.0 Hz, H-6), 2.11 (1H, d, J = 8.4 Hz, H-3), 5.38–5.44 (1H, m, H-2). 13C NMR (CDCl3, 125 MHz) δ (ppm): 118.45 (C-2), 134.02 (C-1), 45.01 (C-4), 23.98 (C-5), 31.02 (C-6), 23.34 (C-7), 27.46 (C-10), 72.74 (C-8), 26.89 (C-3), 26.29 (C-9). The data matched with previous report and also to a different bioassay used [30].

Methyl eugenol (2, Figure 1). Colorless oil, C11H14O2. 1H NMR (500 MHz, CDCl3) δ (ppm): 3.34 (2H, ddd, J = 6.8, 1.7, 1.4, H-7), 3.86 (3H, s, –OCH3), 3.87 (3H, s, –OCH3), 5.07 (2H, m, H-9), 5.96 (1H, ddt, J = 17.0, 10.4, 6.8, H-8), 6.71 (1H, d, J = 2.0, H-2), 6.74 (1H, dd, J = 8.0, 2.0, H-5), 6.81 (1H, d, J = 8.0, H-6). 13C NMR (125 MHz, CDCl3) δ (ppm): 148.8 (C-4), 147.3 (C-3), 137.7 (C-8), 132.6 (C-6), 120.4 (C-1), 115.6 (C-9), 111.8 (C-2), 111.2 (C-5), 55.9 (–OCH3), 55.7 (–OCH3), 39.8 (C-7). The spectral data matched with previous reports [29, 37].

Elemol (3, Figure 1). Colorless solid, C15H26O. 1H NMR (CDCl3): δ 1.00 (3H, s, 9-CH3), 1.22 (6H, s, 14-CH3, 15-CH3), 1.26–1.50 (5H, m, Ph-H, 13-OH), 1.55–1.70 (3H, m, Ph-H), 1.73 (3H, s, 11-CH3), 1.98 (1H, dd, J = 12.4 Hz, H-5), 4.62 (1H, bs, H-12), 4.83–4.96 (3H, m, H-8, H-12), 5.84 (1H, dd, J = 16, 12 Hz, H-7). 13C NMR: δ 150.2 (C-7), 147.9 (C-9), 112.1 (C-11), 109.9 (C-8), 72.7 (C-12), 52.8 (C-5), 49.4 (C-3), 39.9 (C-1), 39.7 (C-15), 28.5 (C-6), 27.2 (C-4), 27.2 (C-14), 24.8 (C-13), 22.6 (C-10), 16.6 (C-2). The 1H and 13C NMR data were in agreement with the reported data [34, 38].

β-Eudesmol (4, Figure 1), Colorless solid, C15H26O. 1H NMR (CDCl3): δ 0.70 (3H, 15-CH3), 1.20 (6H, 12-CH3, 13-CH3), 4.49–4.73 (2H, 14-CH2). 13C NMR: δ 16.3 (C-15), 22.4 (C-8), 23.5 (C-2), 25.0 (C-6), 27.2 (C-12, C-13), 35.9 (C-10), 36.9 (C-3), 41.1 (C-1), 41.9 (C-9), 49.4 (C-5), 49.8 (C-7), 72.9 (C-11), 105.3 (C-14), 151.1 (C-4). The 1H and 13C NMR data were in agreement with the reported data [34, 39].

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Received: 2022-01-30
Accepted: 2022-08-31
Published Online: 2022-09-22
Published in Print: 2023-01-27

© 2022 Walter de Gruyter GmbH, Berlin/Boston

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  9. Isolation and purification of 12 flavonoid glycosides from Ginkgo biloba extract using sephadex LH-20 and preparative high-performance liquid chromatography
  10. Insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes and its constituents against two species of grain storage insects
https://doi.org/10.1515/znc-2022-0017
Keywords for this article
contact toxicity; fumigant; Liposcelis entomophila; Rhynchanthus beesianus essential oil; Tribolium castaneum

Articles in the same Issue

  1. Frontmatter
  2. Review Articles
  3. Covid-19 vaccines and neurological complications: a systematic review
  4. Santalum Genus: phytochemical constituents, biological activities and health promoting-effects
  5. Sakuranetin and its therapeutic potentials – a comprehensive review
  6. Novel sialidase from non-pathogenic bacterium Oerskovia paurometabola strain O129
  7. Do Colletotrichum gloeosporioides and Rhizopus stolonifer induce alkaloidal and antifungal responses in Annona muricata seedlings?
  8. Sesquiterpenoids from Tithonia diversifolia (Hemsl.) A. Gray induce apoptosis and inhibit the cell cycle progression of acute myeloid leukemia cells
  9. Isolation and purification of 12 flavonoid glycosides from Ginkgo biloba extract using sephadex LH-20 and preparative high-performance liquid chromatography
  10. Insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes and its constituents against two species of grain storage insects
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