TABLE 1.
GC Rts and electron impact mass spectral properties of metabolites formed from pyrene by Mycobacterium sp. strain AP1
| Metabolite | Extracta | Rt (min) | Abundance (%) | m/z of fragment ions (% relative intensity) | Identificationb |
|---|---|---|---|---|---|
| I | A | 22.2 | 100 | 220 (M+, 100), 192 (M+ − CO, 22), 163 (48), 87 (12), 82 (14) | Not identified |
| II | A | 20.9 | 100 | 236 (89), 221 (M+ − CH3, 11), 205 (M+ − OCH3, 97), 177 (M+ − COOCH3, 100), 151 (28), 88 (68) | Phenanthrene 4-carboxylic acid (ME) |
| III | N | 23.7 | 94 | 236 (M+, 44), 218 (M+ − H2O, 100), 189 (78), 176 (16), 94 (33) | cis- and trans-4,5-Pyrene dihydrodiols |
| IV | A | 24.2 | 95 | 302 (M+, 33), 270 (M+ − CH3OH, 31), 243 (M+ − COOCH3, 45), 242 (M+ − COOCH3 − H+, 92), 241 (M+ − COOCH3 − H+ − H+, 45), 226 (M+ − COOCH3 − H+ − H+ − CH3, 100), 210 (M+ − COOCH3 − H+ − CH3OH, 13), 198 (M+ − COOCH3 − H+ − H+ − CH3 − CH3OH, 26), 184 (M+ − COOCH3 − COOCH3, 5), 183 (M+ − COOCH3 − H+ − COOCH3, 9), 182 (M+ − COOCH3 − H+ − H+ − COOCH3, 14), 170 (21), 139 (15) | 6,6′-Dihydroxy-2,2′-biphenyl dicarboxylic acid (diME) |
| VI | A | 23.3 | 100 | 294 (M+, 3), 263 (M+ − OCH3, 2), 235 (M+ − COOCH3, 100), 220 (M+ − COOCH3 − CH3, 57), 204 (6), 192 (16), 176 (M+ − COOCH3 − COOCH3, 12), 163 (15) | Phenanthrene 4,5-dicarboxylic acid (diME) |
| VIII | A | 12.9 | 78 | 194 (M+, 5), 163 (100), 135 (9), 105 (6), 92 (20), 77 (52) | Phthalic acid (diME) |
a
Extract from which the product was purified; A, acidic extract; N, neutral extract.
b
ME, methyl ester; diME, dimethyl ester. Acidic compounds were analyzed as methyl ester derivatives.