N-acetyldopamine dimers from the edible grasshopper Oxya chinensis sinousa

Recently, research regarding novel food and medicinal materials has focused on insect resources, demonstrating their potential value. Oxya chinensis sinuosa Mistshenko, an edible grasshopper, belongs to the phylum Arthropoda. Traditionally in Korea, it is known as the “famine relief insect” and has been used to treat cough, whooping cough, asthma, bronchitis, paralysis, and seizures. The rice field grasshopper has been registered as a food in the Korean Food Standards Codex, Korea Food & Drug Administration (KFDA). In this study, five N-acetyl dopamine dimers, componds (1) and (2) were identified as new chemicals with chiral center at H-2 and H-3 of the benzo-1,4-dioxane structure, (2R,3S)-2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-1,4-benzodioxane (3), (2R,3S)-2-(3',4'-dihydroxy-phenyl)-3-acetylamino-7-(N-acetyl-2''-aminoethyl)-1,4-benzodioxane (4), (2R,3S)-2-(3',4'-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2''-aminethylene)-1,4-benzodioxane (5) were isolated from Oxya chinensis sinuosa. The structures of compounds 1-5 including absolute configurations were determined by 1D and 2D NMR, HRESIMS, circular dichroism (CD) spectroscopic data analysis.