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author | Karl Berry <karl@freefriends.org> | 2006-01-09 00:49:07 +0000 |
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committer | Karl Berry <karl@freefriends.org> | 2006-01-09 00:49:07 +0000 |
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tree | 90d17e00e572ecb1e24764b6f29c80e098b08d29 /Master/texmf-dist/doc/latex/chemcono | |
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diff --git a/Master/texmf-dist/doc/latex/chemcono/example.tex b/Master/texmf-dist/doc/latex/chemcono/example.tex new file mode 100644 index 00000000000..a3f311a200c --- /dev/null +++ b/Master/texmf-dist/doc/latex/chemcono/example.tex @@ -0,0 +1,140 @@ +\documentclass[11pt]{article} +\usepackage[tight]{chemcono} +%\usepackage{drftcono} +%\usepackage{showkeysff} +%\renewcommand{\fcite}[1]{\underline{\ffcite{#1}}} + +\newcommand{\grade}{$\,^{\circ}$} +\setlength{\parindent}{0pt} +\setlength{\parskip}{5pt plus 2pt minus 1pt} + +\begin{document} +\begin{center} +\fbox{\textsf{Uncomment packages in the preamble to see different output.}} + +\section*{Composition of the Pheromone System of the male Danaine Butterfly, \emph{Idea +leuconoe}} + +S. Schulz$^{*,a}$, R. Nishida$^{b}$ \\ $^{a}$Institute of Organic Chemistry, TU +Braunschweig, Hagenring 30, D-38106~Braunschweig, Germany, phone +49-531-391 7353, +email:~stefan.schulz@tu-bs.de; +\\$^{b}$Pesticide Research Institute, Kyoto University, Kyoto, 606-01, Japan +\end{center} + +\begin{center} +Keywords: pheromones, Danainae, lipids, \emph{Idea}, lactones +\end{center} +\begin{center} +\textbf{Abstract} +\end{center} + + Male \emph{Idea leuconoe} butterflies release a complex mixture +of volatiles from their pheromone glands (hairpencils) during courtship. The pheromone +components geranyl methyl thioether (\fcite{f2}), viridifloric-$\beta$-lactone +(\fcite{f3}), and 6-hydroxy-4-dodecanolide (\fcite{f8}) have been synthesized for the +first time. Therefore the structural assignment of these new natural products could be +proved. Related 7-hydroxy-5-alkanolides are also present in the extract. The volatiles +are embedded in a lipidic matrix with more than 150 components. This matrix consists of +alkanes, alkenes, 2,5-dialkyltetrahydrofurans, secondary alkanols and alkenols as well as +alkanones and alkenones. Several regioisomers of the oxidized hydrocarbons occur. The +elucidation of double bond positions has been performed by MS using DMDS adducts. + +\begin{center} +\textbf{Introduction} + +\end{center} + Male Danaine butterflies possess striking evertible +pheromone glands, so called hairpencils, which are used during courtship \cite{c1}. +About 30 years ago the first pheromone component of these butterflies, danaidone +(\fcite{f1}), could be identified \cite{c2} and its function as courtship pheromone +proved \cite{c3}. Since then, many danaine species have been investigated and the +chemical composition of their male pheromone glands elucidated \cite{c1,c4,c7}. Despite +the fact that some of the scent bouquets consist of up to 60 components, no pheromonal +function of any other component than \fcite{f1} has been established. + + +Recently we were able to show that male \emph{Idea leuconoe} butterflies emit a complex +mixture of chemicals from their hairpencils. At least three of these components, +danaidone (\fcite{f1}), geranyl methyl thioether (\fcite{f2}), and +(\emph{S,S})-viridifloric-$\beta$-lactone (\fcite{f3}), act as courtship pheromones +\cite{c5}. An artificial mixture of hairpencil compounds containing \fcite{f1}, +\fcite{f2}, and \fcite{f3} as well as phenol, \emph{p}-cresol, benzoic acid, a series of +homologue 6-hydroxy-4-alkanolides ranging from C$_{10}$ to C$_{13}$, +(\emph{E,E})-farnesol, and (\emph{Z})-9-tricosene elicited the same courtship behavior +as a crude hairpencil extract \cite{c5}. In addition, (--)-(\emph{R})-mellein +(8-hydroxy-3-methyl-3,4-dihydroisocoumarin) and another $\beta$-lactone related to +\fcite{f3}, 2-ethyl-2-hydroxy-3-butanolide, could be identified in the hairpencil +extracts. Besides their function as courtship pheromones, other types of interactions, +like a defensive warning odor or intermale recognition (for a discussion, see +\cite{c5}), seem also to be associated with these chemicals. The volatile compounds +identified are embedded into a complex lipidic matrix (see Figure~\ref{f2}). +\marginpar{fig.~\ref{f2} here} In this paper we will report on the synthesis of some +hairpencils constituents, the identification of additional components, and the +composition of the lipid matrix. + +\begin{figure}[h!] + \centering + \caption{Figure}\label{f2} +\end{figure} + +\begin{center} +\textbf{Results} +\end{center} +The structure of the previously unknown geranyl methyl thioether (\fcite{f2}) could be +deduced from its mass spectrum (see Figure~\ref{f3}). \marginpar{fig.~\ref{f3} here}The +presence of sulfur was detected by high-resolution mass spectroscopy, giving a molecular +formula of C$_{11}$H$_{20}$S + (M$^{+}_{obs}$ = 184.1289, M$^{+}_{calc}$ = 184.1286). +Ions at \emph{m/z} = 47 (CH$_{3}$S$^{+}$) and 61 (CH$_{3}$SCH$_{2}^{+}$) and the loss of +48 amu (CH$_{3}$SH) from M$^{+}$ indicated a thiomethyl group in the molecule. Typical +terpenic ions (\emph{m/z} = 41, 69, 81, 93, 123, and 136) suggested that this molecule +could be geranyl methyl thioether (\fcite{f2}). For an unambiguous proof, \fcite{f2} was +synthesized by reaction of geranyl chloride with sodium methanolate in boiling ethanol. +The product showed identical mass spectra and gaschromatographic retention times on +different stationary phases as the natural compound which is therefore +(\emph{E})-2,6-dimethyloctadienyl methyl thioether (\fcite{f2}). The corresponding +(\emph{Z})-isomer exhibited a similar mass spectrum, but a shorter retention time on an +apolar phase. + + +Another pheromone component not reported from nature before is +2-hydroxy-2-(1-methylethyl)-3-butanolide (viridifloric $\beta$-lactone, \fcite{f3}). Its +identification basing on MS-, IR- and NMR-data has been described \cite{c5}. A racemic +mixture of both diastereomers of \fcite{f3} was synthesized for structural assignment +according to Figure 4. + +\begin{thebibliography}{99} +\bibitem{c1}Ackery, P. R.; Vane-Wright, R. I. \emph{Milkweed +Butterflies: Their Cladistics and Biology}; British Museum (Natural +History): London, 1984. +\bibitem{c2}Meinwald, J.; Meinwald, Y. C. +\emph{J. Am. Chem. Soc.} \textbf{1966}, \emph{88}, 1305. +\bibitem{c3}Pliske, T. E.; Eisner, T. \emph{Science} \textbf{1969}, +\emph{164}, 1170. +\bibitem{c4}Schulz, S.; Boppr\'e, M.; Vane-Wright, R. I. +\emph{Phil. Trans. R. Soc. Lond. B} \textbf{1993}, \emph{342}, 161. +\bibitem{c7} +Schulz, S.; Francke, W.; Edgar, J.; Schneider, D. \emph{Z. Naturforsch.} \textbf{1988}, +\emph{43c}, 99; Schulz, S.; Francke, W.; Boppr\'e, M. \emph{Biol.\ Chem.\ Hoppe-Seyler} +\textbf{1988}, \emph{389}, 633; Francke, W.; Bartels, J.; Krohn, S.; Schulz, S.; Baader, +E.; Teng\"o, J.; Schneider, D. \emph{Pure Appl. Chem.} \textbf{1989}, \emph{61}, 539; +Francke, W.; Schulz, S.; Sinnwell, V.; K\"onig, W. A.; Roisin, Y. \emph{Liebigs Ann. +Chem.} \textbf{1989}, 1195. +\bibitem{c5}Nishida, R.; Schulz, S.; Kim, C. H.; Fukami, H.; Kuwahara, +Y.; Honda, K.; Hayashi, N. \emph{J. Chem. Ecol.} \textbf{1995}, submitted. +\end{thebibliography} + +\clearpage +\begin{theffbibliography}{99} +\ffbibitem{f1} danaidone +\ffbibitem{f2} geranyl methyl thioether +\ffbibitem{f3} viridifloric acid lactone +\ffbibitem{f5} ho but sre +\ffbibitem{f6} butensre +\ffbibitem{f7} virid. acid +\ffbibitem{f12} oxobutester +\ffbibitem{f11} hexenolid +\ffbibitem{f9} oxo olid +\ffbibitem{f8} 6-ho-c12-g-lactone +\end{theffbibliography} + \end{document} |