TABLE 1.
Ring cleavage products produced during the biotransformation of hydroxylated biphenyls by T. mucoides SBUG 801 as revealed by GC-MS analyses
| Compoundsa | Identification | Characteristic mass ions (m/z) (relative abundance [%]) |
|---|---|---|
| I | (5-Oxo-3-phenyl-2,5-dihydrofuran-2-yl)acetic acid | 218 [M+] (32), 172 [M]-HCOOH (56), 131 [M]-CH2COOH-CO (56), 103 [M]-CH2COOH-2CO (100), 77 C6H5 (32) |
| II | 3-Phenyl-2-pyrone-6-carboxylic acid | 230 [M+] (20), 202 [M]-CO (6), 171 [M]-COOCH3 (100), 115 [M]-COOCH3-2CO (95) |
| III | 2-Hydroxy-4-phenylmuconic acid | 276 [M+] (2), 261 [M]-CH3 (2), 245 [M]-OCH3 (5), 217 [M]-COOCH3 (100), 202 [M]-CH3-COOCH3 (5), 185 [M]-COOCH3-CH3OH (12), 115 [M]-COOCH3-2CO (28), 59 (COOCH3+) (8) |
| IV | 4-Phenyl-2-pyrone-6-carboxylic acid | 230 [M+] (30), 202 [M]-CO (4), 171 [M]-COOCH3 (72), 115 [M]-COOCH3-2CO (100) |
| V | 2-Hydroxy-5-phenylmuconic acid | 276 [M+] (4), 245 [M]-OCH3 (6), 217 [M]-COOCH3 (100), 202 [M]-CH3-COOCH3 (14), 185 [M]-COOCH3-CH3OH (4), 115 [M]-COOCH3-2CO (52), 59 [COOCH3+] (18) |
| VI | [5-Oxo-3-(4′-hydroxyphenyl)-2,5-dihydrofuran- 2-yl]acetic acid | 262 [M+] (30), 234 [M]-CO (35), 189 [M]-CH2COOCH3 (20), 161 [M]-CH2COOCH3-CO (45), 133 [M]-CH2COOCH3-2CO (100), 132 [C9H8O+] (75) |
| VII | 4-(4′-Hydroxyphenyl)-2-pyrone-6-carboxylic acid | 260 [M+] (22), 232 [M]-CO (5), 201 [M]-COOCH3 (80), 145 [M]-COOCH3-2CO (100), 102 (45) |
| VIII | 3-(4′-Hydroxyphenyl)-2-pyrone-6-carboxylic acid | 260 [M+] (35), 232 [M]-CO (10), 201 [M]-COOCH3 (100), 145 [M]-COOCH3-2CO (70), 102 (32) |
a
Compounds II to VIII were completely methylated