Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test
Miyazawa, M; Hisama, M
| HERO ID | 1166553 |
|---|---|
| In Press | No |
| Year | 2001 |
| Title | Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test |
| Authors | Miyazawa, M; Hisama, M |
| Journal | Journal of Agricultural and Food Chemistry |
| Volume | 49 |
| Issue | 8 |
| Page Numbers | 4019-4025 |
| Abstract | A methanol extract from clove (Syzygium aromaticum) showed a suppressive effect of the SOS-inducing activity on the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide) in the Salmonella typhimurium TA1535/pSK1002 umu test. The methanol extract was re-extracted with hexane, dichloromethane, ethyl acetate, butanol, and water. The hexane fraction showed a suppressive effect. Suppressive compounds in the hexane fraction were isolated by silica gel column chromatography and identified as trans-isoeugenol (1) and eugenol (2) by GC, GC-MS, IR, and (1)H and (13)C NMR spectroscopy. Compounds 1 and 2 suppressed the furylfuramide-induced SOS response in the umu test. Compounds 1 and 2 suppressed 42.3 and 29.9% of the SOS-inducing activity at a concentration of 0.60 micromol/mL. These compounds were assayed with other mutagens, 4-nitroquinolin 1-oxide (4NQO) and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). In addition, compounds 1 and 2 were assayed with aflatoxin B(1) (AfB(1)) and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), which require liver metabolizing enzymes. These compounds showed suppressive effects of the SOS-inducing activity against furylfuramide, 4NQO, AfB(1), and Trp-P-1. To research the structure-activity relationship, methyl esters of 1 and 2 (1Me and 2Me) and o-eugenol (3), as compounds similar to 2, were also assayed with all mutagens. Compounds 1Me, 2Me, and 3 showed weak suppressive effects of the SOS-inducing activity against furylfuramide. |
| Doi | 10.1021/jf0103469 |
| Pmid | 11513704 |
| Wosid | WOS:000170598600085 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Source: Web of Science 000170598600085Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034838634&doi=10.1021%2fjf0103469&partnerID=40&md5=a3c5caefa777830243cb2d496b578dec |
| Is Public | Yes |
| Language Text | English |
| Keyword | clove; Syzygium aromaticum; trans-isoeugenol; eugenol; SOS response; umu test; Salmonella typhimurium TA1535/pSK1002 |
| Is Qa | No |