Structure of an antioxidant from fermented soybeans (tempeh)

In an exhaustive investigation of the antioxidative properties of tempeh constituents, the substance at R _f 0.58 (cyclohexane/ethyl ether, 9:1) was isolated and purified. Until now, only the ultraviolet and fluorescence data of the substance were known, and the presence of an OH group was indicated. In the present paper, the structure of the substance at R _f 0.58 was elucidated by the application of spectroscopic methods and found to be 5-(δ-tocopheroxy)-δ-tocopherol. That previous researchers did not confirm antioxidant activity in tempeh oil has been related to the way the tempeh oil was prepared. Previous suggestions regarding the substance at R _f 0.58 as being one of the main tempeh antioxidants could not be proved. The antioxidative effect of tempeh oil seems to be the result of a synergistic effect of tocopherols (present in the soybeans) and amino acids (liberated during the fermentation process with Rhizopus oligosporus).