Dried tempeh is known to be significantly stable to lipid oxidation co
mpared with unfermented soybeans (BS). A new antioxidant was isolated
from the methanol extract of tempeh and identified as 3-hydroxyanthran
ilic acid (HAA) by UV, IR, EI-MS, and H-1-, C-13-, HMQC-, and HMBC-NMR
techniques. HAA was effective in preventing autoxidation of soybean o
il and soybean powder, while 6,7,4'-trihydroxyisoflavone (a well-known
antioxidant) was not. HAA also exhibited strong antioxidative activit
y 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.