# Chemical Composition and Antimicrobial Properties of Honey Bee Venom
## 2 Results and Discussion
### Chemical Composition of Extractive Compounds
#### 2.2.2 Chemical Composition of Methanol Extracts  
In the chromatograms of methanol extracts of dry BV, 137 peaks with a relative content of at least 0.01% TIC were recorded, while in the case of fresh venom there were 161 peaks. In total, 201 compounds were registered in all four samples. The group composition of the extracts is given in Table 3, and the full composition is given in Table S3 in the Supplementary Materials. \begin{table}
\begin{tabular}{l c c c c} \hline \hline \multirow{2}{*}{**Groups of Compouns**} & \multicolumn{2}{c}{**Dry Venom**} & \multicolumn{2}{c}{**Fresh Venom**} \\ \cline{2-5}  & **Dv-1** & **Dv-2** & **Fv-1** & **Fv-2** \\ \hline \multicolumn{5}{c}{Aliphatic Alcohols, Including:} & 3.56 (2) * & 2.15 (3) & 5.51 (12) & 5.58 (2) \\ \hline - glycerol & 0.42 & 0.15 & 2.25 & 2.24 \\ \hline - (9\(Z\))-eicosen-1-ol & 3.14 & 0.97 & 1.82 & 3.34 \\ \hline - oleyl alcohol & - ** & 0.04 & - & - \\ \hline \multicolumn{5}{c}{Aliphatic acids, including:} & 33.60 (18) & 28.62 (18) & 17.17 (26) & 12.61 (17) \\ \hline - lactic & 0.49 & 0.22 & 4.00 & 0.38 \\ \hline - glycolic & 0.11 & 0.05 & - & 0.10 \\ \hline - glyceric & 0.62 & 0.04 & - & - \\ \hline - succinic & 0.67 & 0.16 & 1.04 & 0.52 \\ \hline - malic & 0.34 & 0.23 & 0.14 & 0.24 \\ \hline - citric & 29.51 & 27.60 & 0.09 & - \\ \hline \multicolumn{5}{c}{Aminoacids, including:} & 3.97 (10) & 1.13 (14) & 22.81 (21) & 19.10 (24) \\ \hline - glycine & 0.14 & 0.08 & 1.12 & 0.76 \\ \hline - alanine & 0.91 & 0.07 & 3.52 & 2.80 \\ \hline - proline & 2.05 & 0.45 & 4.30 & 4.98 \\ \hline - 5-oxoproline & 0.77 & 0.09 & 0.10 & 1.28 \\ \hline - \(\beta\)-alanine & 0.10 & 0.15 & 1.59 & 0.73 \\ \hline - glutamine & trace & 0.10 & 0.74 & 1.65 \\ \hline - lysine & trace & 0.02 & 0.49 & 1.05 \\ \hline - hydroxyproline & - & - & 0.09 & 0.92 \\ \hline - \(\gamma\)-aminobenz (GABA) & - & 0.01 & Trace *** & 0.27 \\ \hline \multicolumn{5}{c}{Other N-containing compounds, including:} & 12.10 (15) & 23.71 (21) & 7.63 (13) & 7.36 (16) \\ \hline - 2-aminoethanol & 0.12 & 0.10 & 0.40 & trace \\ \hline - putrescine & 0.72 & 0.63 & 1.54 & 1.49 \\ \hline - cadaverine & 0.33 & 0.56 & trace & trace \\ \hline - histamine & 5.74 & 18.25 & 1.81 & 0.35 \\ \hline - uridine & 0.99 & 0.32 & - & - \\ \hline - uracil & - & - & 0.40 & 0.43 \\ \hline - adenine & - & - & trace & 0.29 \\ \hline - serotonin & 1.91 & 0.80 & - & 0.56 \\ \hline - inosine & 1.91 & 0.80 & - & 0.56 \\ \hline \hline \end{tabular}
\end{table} 
Table 3: Group composition (% of TIC) of methanol extracts from dry and fresh honey bee venom. These extracts were characterized by the largest number of unidentified compounds (most of them were minor components). In all four extracts, the largest number of identified compounds belong to the group of carbohydrates and related compounds (sugar alcohols and acids). The predominant carbohydrates in them were monosaccharides and disaccharide trehalose, while sucrose and trisaccharides (1-kestose, erlose, and melzitose) were found only in dry BV extracts. The second largest group is formed by aliphatic acids, predominantly polar hydroxy acids, the main one of which was citric acid, but only in dry BV extract. Interestingly, in these methanol BV extracts, citric acid was the main individual compound, accounting for 29.5% and 27.6% of TIC. It was previously found by the authors in dried BV obtained by electrical stimulation [5]. The number of amino acids identified in the analyzed samples differed: in fresh venom samples there were more than 20 amino acids, and their composition almost overlapped with that published by the authors [5]. However, we identified 14 amino acids in dry BV. Their list includes both proteinogenic and non-proteinogenic amino acids such as sarcosine, \(\beta\)-alanine, hydroxyproline, and GABA. Quantitatively, the predominant components were proline and alanine, which is consistent with the data of [5]. All analyzed samples also contained a large number of other nitrogen-containing compounds, the main one of which was histamine.