# Chemical Composition and Antimicrobial Properties of Honey Bee Venom
## 2 Results and Discussion
### Chemical Composition of Extractive Compounds
#### 2.2.1 Chemical Composition of Extracts with Diethyl Ether  
In the chromatograms of extracts of dry BV, 90 peaks of C\({}_{2}\)-C\({}_{42}\) organic compounds were registered, while in extracts of fresh venom, 152 compounds were registered with the same range of molecular weights. Table 2 shows the relative content of the nine groups along with the main representatives of each of them. A complete list of substances is given in Table S2 in the Supplementary Materials. \begin{table}
\begin{tabular}{c c c c c} \hline \hline \multirow{2}{*}{**Groups of Compounds**} & \multicolumn{2}{c}{**Dried Venom**} & \multicolumn{2}{c}{**Fresh Venom**} \\ \cline{2-5}  & **Dv-1** & **Dv-2** & **Fv-1** & **Fv-2** \\ \hline Other, including: & 1.42 & 1.85 & - & 2.35 \\ \hline - pyridine & 0.46 & 0.52 & - & 0.71 \\ \hline - 2,3-butanediol & - & - & - & 0.24 \\ \hline - 2-pentylfuran & 0.20 & - & - & - \\ \hline - dimethyl sulfide & - & 0.81 & - & - \\ \hline - acetoin & - & 0.52 & - & trace \\ \hline NN & 0.55 & 1.42 & 6.38 & 7.25 \\ \hline \hline \end{tabular}  
* less than 0.01% TIC, ** component not found.  
\end{table} 
Table 1: _Cont._ \begin{table}
\begin{tabular}{c c c c c} \hline \hline \multirow{2}{*}{**Groups of Compounds**} & \multicolumn{2}{c}{**Dried Venom**} & \multicolumn{2}{c}{**Fresh Venom**} \\ \cline{2-5}  & **Dv-1** & **Dv-2** & **Fv-1** & **Fv-2** \\ \hline Aliphatic Alcohols, Including: & 16.90 (12) * & 13.37 (7) & 18.04 (16) & 19.00 (11) \\ \hline - isopentanol & - ** & - & 0.93 & 0.16 \\ \hline - oleyl alcohol & 0.10 & 0.09 & 0.29 & 0.23 \\ \hline - octadecanol & 0.08 & 0.06 & 0.27 & 0.12 \\ \hline - (9Z)-eicosen-1-ol & 14.75 & 11.71 & 12.40 & 16.16 \\ \hline - 1-docosanol & 0.06 & - & 0.33 & 0.57 \\ \hline - 1-tetracosanol & 0.19 & 0.16 & 0.47 & 0.35 \\ \hline - 1-hexacosanol & 0.23 & 0.17 & 0.37 & 0.33 \\ \hline Aliphatic acids, including: & 3.23 (7) & 4.90 (9) & 27.31 (37) & 31.90 (19) \\ \hline - lactic & 0.05 & 0.05 & 0.48 & trace *** \\ \hline - citric & 1.88 & 3.79 & - & - \\ \hline - palmitic & 0.34 & 0.29 & 2.40 & 4.93 \\ \hline - \(\alpha\)-linoleic & - & - & 2.12 & 1.94 \\ \hline - oleic & 0.80 & 0.65 & 12.15 & 20.14 \\ \hline - stearic & 0.06 & 0.06 & 3.18 & 2.76 \\ \hline \hline \end{tabular}
\end{table} 
Table 2: Group composition (% of TIC) of ether extracts from dried and fresh bee venom. The most numerous group is formed by linear C\({}_{19}\)-C\({}_{33}\) alkanes and C\({}_{21}\)-C\({}_{35}\) alkenes, which account for 32-45% TIC and 25-27% TIC in extracts of dry and fresh bee venom, respectively. The esters of oleic and palmitic acids and aliphatic C\({}_{18}\)-C\({}_{24}\) alcohols form the second largest contribution to the TIC of the chromatogram of the dry BV extract. Aliphatic acids form a large group in extracts of fresh venom, with oleic acid predominating quantitatively. The content of acids in dry BV turned out to be much lower, and the main one was citric acid. A significant share in all four extracts also falls on the share of aliphatic alcohols. In general, ether extracts are characterized by a high content of lipid