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Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)

Rahmani, Rizan; Andersson, Fredrik; Andersson, Martin N. LU ; Yuvaraj, Jothi Kumar LU ; Anderbrant, Olle LU and Hedenström, Erik (2019) In Chemoecology 29(3). p.103-110
Abstract


The Carrot psyllid, Trioza apicalis Förster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography–single-sensillum recording (GC–SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC–MS) was used to propose β-sesquiphellandrene and α-cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly... (More)


The Carrot psyllid, Trioza apicalis Förster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography–single-sensillum recording (GC–SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC–MS) was used to propose β-sesquiphellandrene and α-cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly identical with the unknown active compound. But, the retention times differed from the compound in the carrot leaf extract. Thus, to obtain the unidentified compound pure enough and in adequate amounts for nuclear magnetic resonance (NMR) analysis, preparative gas chromatography was applied to separate and concentrate this biologically active compound. Analysis by liquid chromatography quadrupole time of flight mass spectrometry (LC–QTOF) confirmed the unidentified compound to be a compound with the formula of C
15
H
24
and together with GC–MS,
1
H and
13
C NMR analysis sesquisabinene B was identified as the unidentified compound in the extract. GC–SSR was then used to finally confirm the biological activity of sesquisabinene B isolated from the carrot leaf extract via preparative GC.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Analysis, Preparative gas chromatography, Single-sensillum recording, Synthesis, α-cis-Bergamotene, β-Sesquiphellandrene
in
Chemoecology
volume
29
issue
3
pages
103 - 110
publisher
Birkhaüser
external identifiers
  • scopus:85063037685
ISSN
0937-7409
DOI
10.1007/s00049-019-00280-6
language
English
LU publication?
yes
id
5c2ebc10-1a8c-45e9-9137-7ae9aa41b24a
date added to LUP
2019-03-28 14:29:06
date last changed
2019-07-29 15:32:39
@article{5c2ebc10-1a8c-45e9-9137-7ae9aa41b24a,
  abstract     = {<p><br>
                                                         The Carrot psyllid, Trioza apicalis Förster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography–single-sensillum recording (GC–SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC–MS) was used to propose β-sesquiphellandrene and α-cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly identical with the unknown active compound. But, the retention times differed from the compound in the carrot leaf extract. Thus, to obtain the unidentified compound pure enough and in adequate amounts for nuclear magnetic resonance (NMR) analysis, preparative gas chromatography was applied to separate and concentrate this biologically active compound. Analysis by liquid chromatography quadrupole time of flight mass spectrometry (LC–QTOF) confirmed the unidentified compound to be a compound with the formula of C                             <br>
                            <sub>15</sub><br>
                                                         H                             <br>
                            <sub>24</sub><br>
                                                          and together with GC–MS,                              <br>
                            <sup>1</sup><br>
                                                         H and                              <br>
                            <sup>13</sup><br>
                                                         C NMR analysis sesquisabinene B was identified as the unidentified compound in the extract. GC–SSR was then used to finally confirm the biological activity of sesquisabinene B isolated from the carrot leaf extract via preparative GC.                         <br>
                        </p>},
  author       = {Rahmani, Rizan and Andersson, Fredrik and Andersson, Martin N. and Yuvaraj, Jothi Kumar and Anderbrant, Olle and Hedenström, Erik},
  issn         = {0937-7409},
  keyword      = {Analysis,Preparative gas chromatography,Single-sensillum recording,Synthesis,α-cis-Bergamotene,β-Sesquiphellandrene},
  language     = {eng},
  month        = {03},
  number       = {3},
  pages        = {103--110},
  publisher    = {Birkhaüser},
  series       = {Chemoecology},
  title        = {Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)},
  url          = {http://dx.doi.org/10.1007/s00049-019-00280-6},
  volume       = {29},
  year         = {2019},
}