Details
| Original language | English |
|---|---|
| Pages (from-to) | 81-86 |
| Number of pages | 6 |
| Journal | Phytochemistry letters |
| Volume | 22 |
| Early online date | 6 Oct 2017 |
| Publication status | Published - Dec 2017 |
Abstract
Crude methanol extract of the leaves of Caesalpinia welwitschiana was found to possess moderate larvicidal activity against second-instar larvae of Tuta absoluta Meyrick. Bioassay-guided fractionation of this extract led to the isolation of two oxygenated cyclohexene derivatives, welwitschianalol A (1, (1α,2β)-2-acetoxy-1-hydroxy-1- benzoyloxymethylcyclohex-5-ene) and B (2, (1α,2β)-2- benzoyloxy −1-cinnamoyloxymethyl-1-hydroxycyclohex-5-ene), together with eight known compounds, comprising bonducellin, dipteryxic acid, 3′-hydroxygenkwarin, afzelin, quercitrin, myricitrin, methyl gallate and gallic acid. The structures of the unknown compounds as well as those of the known ones were elucidated based on their MS, 1D and 2D NMR spectra, and in the case of known compounds, by comparison with the reported data. Each of welwitschianalol A and B, bonducellin, dipteryxic acid, afzelin, quercitrin and myricitrin showed more than 50% mortality of T. absoluta larvae at 5 ppm, which was comparable to that of azadirachtin (the most bioactive constituent of Azadirachta indica). The most potent constituent of C. welwitschiana was welwitschianalol B with LD50 of 3.8 ppm, which was higher than that of azadirachtin (LD50 of 7.8 ppm).
Keywords
- Caesalpinia welwitschiana, Fabaceae, Larvicidal activity, Welwitschianalol
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Agricultural and Biological Sciences(all)
- Agronomy and Crop Science
- Agricultural and Biological Sciences(all)
- Plant Science
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Phytochemistry letters, Vol. 22, 12.2017, p. 81-86.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Welwitschianalol A and B, two cyclohexene derivatives and other insecticidal constituents of Caesalpinia welwitschiana (Oliv.) Brenan
AU - Essoung, Flaure Rosette Ehawa
AU - Mba'ning, Brice Mittérant
AU - Lwande, Wilber
AU - Ngouela, Silvère Augustin
AU - Tsamo, Etienne
AU - Chhabra, Sumesh Chander
AU - Hassanali, Ahmed
AU - Cox, Russell John
N1 - Funding information: This work was supported by ANSTI-DAAD from German Research Foundation (DFG) grant to F.R.E. Essoung ( A/14/93802 ). They authors acknowledge the DFG for funding for LCMS instrumentation to R.J. Cox (INST 187/621-1 ). We are also grateful to Organic Chemistry Institute (OCI) of Leibniz University, Germany, for help with spectroscopic data.
PY - 2017/12
Y1 - 2017/12
N2 - Crude methanol extract of the leaves of Caesalpinia welwitschiana was found to possess moderate larvicidal activity against second-instar larvae of Tuta absoluta Meyrick. Bioassay-guided fractionation of this extract led to the isolation of two oxygenated cyclohexene derivatives, welwitschianalol A (1, (1α,2β)-2-acetoxy-1-hydroxy-1- benzoyloxymethylcyclohex-5-ene) and B (2, (1α,2β)-2- benzoyloxy −1-cinnamoyloxymethyl-1-hydroxycyclohex-5-ene), together with eight known compounds, comprising bonducellin, dipteryxic acid, 3′-hydroxygenkwarin, afzelin, quercitrin, myricitrin, methyl gallate and gallic acid. The structures of the unknown compounds as well as those of the known ones were elucidated based on their MS, 1D and 2D NMR spectra, and in the case of known compounds, by comparison with the reported data. Each of welwitschianalol A and B, bonducellin, dipteryxic acid, afzelin, quercitrin and myricitrin showed more than 50% mortality of T. absoluta larvae at 5 ppm, which was comparable to that of azadirachtin (the most bioactive constituent of Azadirachta indica). The most potent constituent of C. welwitschiana was welwitschianalol B with LD50 of 3.8 ppm, which was higher than that of azadirachtin (LD50 of 7.8 ppm).
AB - Crude methanol extract of the leaves of Caesalpinia welwitschiana was found to possess moderate larvicidal activity against second-instar larvae of Tuta absoluta Meyrick. Bioassay-guided fractionation of this extract led to the isolation of two oxygenated cyclohexene derivatives, welwitschianalol A (1, (1α,2β)-2-acetoxy-1-hydroxy-1- benzoyloxymethylcyclohex-5-ene) and B (2, (1α,2β)-2- benzoyloxy −1-cinnamoyloxymethyl-1-hydroxycyclohex-5-ene), together with eight known compounds, comprising bonducellin, dipteryxic acid, 3′-hydroxygenkwarin, afzelin, quercitrin, myricitrin, methyl gallate and gallic acid. The structures of the unknown compounds as well as those of the known ones were elucidated based on their MS, 1D and 2D NMR spectra, and in the case of known compounds, by comparison with the reported data. Each of welwitschianalol A and B, bonducellin, dipteryxic acid, afzelin, quercitrin and myricitrin showed more than 50% mortality of T. absoluta larvae at 5 ppm, which was comparable to that of azadirachtin (the most bioactive constituent of Azadirachta indica). The most potent constituent of C. welwitschiana was welwitschianalol B with LD50 of 3.8 ppm, which was higher than that of azadirachtin (LD50 of 7.8 ppm).
KW - Caesalpinia welwitschiana
KW - Fabaceae
KW - Larvicidal activity
KW - Welwitschianalol
UR - http://www.scopus.com/inward/record.url?scp=85029939538&partnerID=8YFLogxK
U2 - 10.1016/j.phytol.2017.09.010
DO - 10.1016/j.phytol.2017.09.010
M3 - Article
AN - SCOPUS:85029939538
VL - 22
SP - 81
EP - 86
JO - Phytochemistry letters
JF - Phytochemistry letters
SN - 1874-3900
ER -