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. 2020 Mar 11;11:350. doi: 10.3389/fmicb.2020.00350

TABLE 1.

Major non-volatile compounds released by Azotobacter chroococcum, Bacillus megaterium, and Pseudomonas fluorescens in pure cultures, and during co-cultivation with Listeria monocytogenes.

Culture TLC spot no. Compound Retention time m/z Chemical formula
A. chroococcum 1 2,4,12-Octadecatrienoic acid isobutylamide 13.94 333.30 C22H39NO
2 1-Chloroethane-1-sulfonyl chloride 0.88 161.93 C2H4Cl2O2S
A. chroococcum + L. monocytogenes 3 Agelasine 16.07 422.33 C26H39N5
CAY10571 8.14 394.11 C21H16FN3O2S
2-(Ethylamino)-4,5-dihydroxybenzamide 1.67 196.08 C9H12N2O3
N-[1-(2-fluorophenyl)ethylideneamino]benzo[1,3]dioxole-5-carboxamide 11.85 300.09 C16H13FN2O3
5-(4,4,5,5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)- 3,6-dihydro-2H-pyran 3.86 211.11 C11H19BO3
4 Piperonyl sulfoxide 8.14 325.18 C18H28O3S
7-Deoxyloganate 11.89 361.15 C16H24O9
B. megaterium 5 2,4,12-Octadecatrienoic acid isobutylamide 13.95 356.29 C22H39NO
6 1-Chloroethane-1-sulfonyl chloride 0.88 161.93 C2H4Cl2O2S
B. megaterium + L. monocytogenes 7 N-[1-(2-fluorophenyl)ethylideneamino]benzo[1,3]dioxole-5-carboxamide 11.85 300.09 C16H13FN2O3
Carbamothioic acid, dimethyl-, S-methyl ester 0.68 119.04 C4H9NOS
8 Amsacrine 8.13 393.11 C21H19N3O3S
P. fluorescens 9 Butanoic acid, 4-(hexadecylamino)-4- oxo-, methyl ester 13.93 355.31 C21H41NO3
10 1-Chloroethane-1-sulfonyl chloride 0.88 161.93 C2H4Cl2O2S
P. fluorescens + L. monocytogenes 11 2-(Ethylamino)-4,5-dihydroxybenzamide 1.67 196.08 C9H12N2O3
3-Azido-2H-1-benzopyran-2-one 1.06 188.04 C9H5N3O2
Carbamothioic acid, dimethyl-, S-methyl ester 0.68 119.04 C4H9NOS
12 7-Deoxyloganate 11.89 361.15 C16H24O9

Compounds in chloroform extracts were identified from UPLC-MS with their retention time, m/z, chemical formula and structure.