Inhibitory effects of phenylpropionamides from the hemp seed husk on tyrosinase

• Published in: International journal of biological macromolecules 2024-12, Vol.282 (Pt 2), p.136939, Article 136939
• Main Authors: Kim, Jang Hoon, Han, Kyung-Sook, Lee, Eun-Song, Kim, Yong-Goo, Kim, Yong-Il, Cheon, Jae-Young, Jung, Hyun-Ju, Kim, Ki Mo, Lee, Ik Soo
• Format: Article
• Language: English
• Subjects: Amides - chemistry; Amides - pharmacology; Animals; Cannabis - chemistry; Cell Line, Tumor; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Hemp seed husk; Melanins - antagonists & inhibitors; Melanins - biosynthesis; Melanoma, Experimental; Mice; Molecular Docking Simulation; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; Phenylpropionamides; Plant Extracts - chemistry; Plant Extracts - pharmacology; Seeds - chemistry; Tyrosinase
• ISSN: 0141-8130; 1879-0003; 1879-0003
• DOI: 10.1016/j.ijbiomac.2024.136939

Tyrosinase is an enzyme involved in melanin production. To identify inhibitors of this enzyme in natural products, extracts and fractions of hemp seed husk were screened for tyrosinase inhibition. Phenylpropionamides 1–9, which were isolated from the ethyl acetate fraction, had inhibitory effects; compounds 3 and 4 had the greatest inhibitory effects. Cannabisin A (3) was a non-competitive and cannabisin B (4) was a competitive inhibitor. The binding sites and interactions of each inhibitor on tyrosinase were calculated by computational chemistry. Potential inhibitor 3 decreased the melanin content and tyrosinase activity in B16F10 melanoma cells. Therefore, cannabisin A (3) has potential as a tyrosinase inhibitor.