No abstract

The formation mechanism for the potent antioxidative o-dihydroxyisoflavones, 8-hydroxydaidzein (8-OHD) and 8-hydroxygenistein (8-OHG), was studied by incubating whole soybeans in a solid culture and a soybean extract in a liquid culture with Aspergillus saitoi. Analyses of changes in the isoflavone analogue content, β-glucosidase activity, and isoflavone hydroxylation ability indicated that 8-OHD and 8-OHG were formed from daidzein and genistein, respectively, by microbial hydroxylation, being respectively liberated from daidzin and genistin by β-glucosidase from A. saitoi during incubation. No selective hydroxylation reaction at the 8-position of daidzein and genistein were apparent during the vegetative stage, but were induced at the stage of sporulation.

Dried tempeh is known to be significantly stable to lipid oxidation compared with unfermented soybeans (BS). A new antioxidant was isolated from the methanol extract of tempeh and identified as 3-hydroxyanthranilic acid (HAA) by UV, IR, EI-MS, and 1H-, 13C-, HMQC-, and HMBC-NMR techniques. HAA was effective in preventing autoxidation of soybean oil and soybean powder, while 6,7,4‘-trihydroxyisoflavone (a well-known antioxidant) was not. HAA also exhibited strong antioxidative activity in both water/ethanol and rabbit erythrocyte membrane ghost systems. HAA was not found in BS, but was produced during the incubations with Rhizopus oligosporus IFO 32002 and 32003. The amount of HAA reached a maximum at the stage of 2 days (acceptable), which had the strongest antioxidative activity. Keywords: Tempeh; fermented soybean product; antioxidant; 3-hydroxyanthranilic acid