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Tetranorsesquiterpenoids as attractants of yucca moths to yucca flowers

Tröger, Armin ; Svensson, Glenn P. LU ; Galbrecht, Hans Martin ; Twele, Robert ; Patt, Joseph M. ; Bartram, Stefan ; Zarbin, Paulo H.G. ; Segraves, Kari A. ; Althoff, David M. and von Reuss, Stephan , et al. (2021) In Journal of Chemical Ecology 47(12). p.1025-1041
Abstract

The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth Tegeticula yuccasella are attracted to the floral scent of the host Yucca filamentosa. Chemical analysis of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from... (More)

The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth Tegeticula yuccasella are attracted to the floral scent of the host Yucca filamentosa. Chemical analysis of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from (E)-4,8-dimethyl-1,3,7-nonatriene. Their structure elucidation was accomplished by NMR analysis of the crude floral scent sample of Yucca treculeana along with GC/MS analysis and confirmed by total synthesis. Since all these volatiles are included in the floral scent of Y. filamentosa, which has been an important model species for understanding the pollination mutualism, we name these compounds filamentolide, filamentol, filamental, and filamentone. Several of these compounds elicited antennal responses in pollinating (Tegeticula) and non-pollinating (Prodoxus) moth species upon stimulation in electrophysiological recordings. In addition, synthetic (Z)-filamentolide attracted significant numbers of both sexes of two associated Prodoxus species in a field trapping experiment. Highly specialized insect-plant interactions, such as obligate pollination mutualisms, are predicted to be maintained through “private channels” dictated by specific compounds. The identification of novel bioactive tetranorsesquiterpenoids is a first step in testing such a hypothesis in the Yucca-yucca moth interaction.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
DMNT-derivatives, Floral scent, Pollinator attraction, Structure elucidation, Tetranorsesquiterpenoids, Total synthesis, Yucca
in
Journal of Chemical Ecology
volume
47
issue
12
pages
17 pages
publisher
Springer
external identifiers
  • pmid:34506004
  • scopus:85114698132
ISSN
0098-0331
DOI
10.1007/s10886-021-01308-4
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2021, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
id
dbe6299d-a4ce-4fd8-be7a-0beb954cd575
date added to LUP
2021-10-12 15:43:12
date last changed
2022-08-19 07:55:18
@article{dbe6299d-a4ce-4fd8-be7a-0beb954cd575,
  abstract     = {{<p>The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth <i>Tegeticula yuccasella</i> are attracted to the floral scent of the host <i>Yucca filamentosa</i>. Chemical analysis of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from (E)-4,8-dimethyl-1,3,7-nonatriene. Their structure elucidation was accomplished by NMR analysis of the crude floral scent sample of Yucca treculeana along with GC/MS analysis and confirmed by total synthesis. Since all these volatiles are included in the floral scent of <i>Y. filamentos</i>a, which has been an important model species for understanding the pollination mutualism, we name these compounds filamentolide, filamentol, filamental, and filamentone. Several of these compounds elicited antennal responses in pollinating (<i>Tegeticula</i>) and non-pollinating (<i>Prodoxus</i>) moth species upon stimulation in electrophysiological recordings. In addition, synthetic (Z)-filamentolide attracted significant numbers of both sexes of two associated Prodoxus species in a field trapping experiment. Highly specialized insect-plant interactions, such as obligate pollination mutualisms, are predicted to be maintained through “private channels” dictated by specific compounds. The identification of novel bioactive tetranorsesquiterpenoids is a first step in testing such a hypothesis in the Yucca-yucca moth interaction.</p>}},
  author       = {{Tröger, Armin and Svensson, Glenn P. and Galbrecht, Hans Martin and Twele, Robert and Patt, Joseph M. and Bartram, Stefan and Zarbin, Paulo H.G. and Segraves, Kari A. and Althoff, David M. and von Reuss, Stephan and Raguso, Robert A. and Francke, Wittko}},
  issn         = {{0098-0331}},
  keywords     = {{DMNT-derivatives; Floral scent; Pollinator attraction; Structure elucidation; Tetranorsesquiterpenoids; Total synthesis; Yucca}},
  language     = {{eng}},
  month        = {{12}},
  number       = {{12}},
  pages        = {{1025--1041}},
  publisher    = {{Springer}},
  series       = {{Journal of Chemical Ecology}},
  title        = {{Tetranorsesquiterpenoids as attractants of yucca moths to yucca flowers}},
  url          = {{http://dx.doi.org/10.1007/s10886-021-01308-4}},
  doi          = {{10.1007/s10886-021-01308-4}},
  volume       = {{47}},
  year         = {{2021}},
}