Characterization and antimutagenic activity of soybean saponins.
An extract was prepared from a commercial soybean-processing by-product (soybean molasses) and was fractionated into purified chemical components. In previous work, this extract (phytochemical concentrate, PCC) repressed induced genomic DNA damage, whole cell clastogenicity and point mutation in cultured mammalian cells. In the current study, a chemical fraction was isolated from PCC using preparative high-performance liquid chromatography (HPLC). This fraction, PCC100, repressed 2-acetoxyacetylaminofluorene (2AAAF)-induced DNA damage in Chinese hamster ovary (CHO) cells as measured by single cell gel electrophoresis (alkaline Comet assay). Using liquid chromatography-electrospray ionization-mass spectroscopy and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, PCC100 was shown to consist of a mixture of group B soyasaponins and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) soyasaponins. These include soyasaponins I, II, III, IV, V, Be, betag, betaa, gammag and gammaa. Purified soyasapogenol B aglycone prepared from fraction PCC100 demonstrated significant antigenotoxic activity against 2AAAF. To our knowledge, these data demonstrate for the first time the antimutagenic activity of soybean saponins in mammalian cells.
Berhow
M A
MA
United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL 61604, USA.
Wagner
E D
ED
Vaughn
S F
SF
Plewa
M J
MJ
D000818:Animals; D016587:Antimutagenic Agents / Q000494:pharmacology*; D016466:CHO Cells / Q000187:drug effects; D002273:Carcinogens / Q000633:toxicity; D005591:Chemical Fractionation; D006224:Cricetinae; D005449:Fluorenes / Q000633:toxicity; D008965:Molasses; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D011753:Pyrones / Q000737:chemistry / Q000494:pharmacology; D011804:Quinolines / Q000633:toxicity; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology*; D013025:Glycine max / Q000737:chemistry*
C110646:2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one; C091862:7-acetyl-N-acetoxy-2-aminofluorene; D016587:Antimutagenic Agents; D002273:Carcinogens; D005449:Fluorenes; D009153:Mutagens; D010936:Plant Extracts; D011753:Pyrones; D011804:Quinolines; D012503:Saponins; C407096:soyasapogenol B; C029216:2-amino-3-methylimidazo(4,5-f)quinoline; D009828:Oleanolic Acid