Rosmarinic acid and its ester derivatives for enhancing antibacterial, α‐glucosidase inhibitory, and lipid accumulation suppression activities. Issue 2 (11th November 2018)

• Record Type: Journal Article
• Authors: Zhu, Fengxian; Wang, Jue; Takano, Hayato; Xu, Zhongming; Nishiwaki, Hisashi; Yonekura, Lina; Yang, Ronghua; Tamura, Hirotoshi
• Is Part Of: Journal of food biochemistry. Volume 43:Issue 2(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2018-11-11
• Subjects: 3T3‐L1 cell -- α‐glucosidase inhibitory activity -- antibacterial activity -- lipid accumulation suppression -- molecular docking -- rosmarinic acid; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; Biochemistry -- Periodicals; 664.024
• DOI: 10.1111/jfbc.12719
• Languages: English
• ISSNs: 0145-8884

Abstract

Abstract: Rosmarinic acid (RA), commonly found in Nepetoidae subfamily of Lamiaceae family, possesses various biological activities. To expand its application, RA was modified by esterification with methyl (me), propyl (pro), and hexyl (hex) alcohols and then tested antibacterial, α‐glucosidase inhibitory, and lipid accumulation suppression activities. Consequently, RA derivatives enhanced antibacterial activity, especially the RA‐pro and RA‐hex, which effectively inhibited the growth of Bacillus cereus rather than tannic acid, a natural antibacterial agent. RA‐hex also inhibited α‐glucosidase inhibitory activity greater than luteolin. By computational molecular docking, dihydroxyphenyl group and hexyl group were selected as essential groups for interaction with the active site of α‐glucosidase through hydrogen bonding and hydrophobic interaction, contributing to the great inhibitory activity. Furthermore, RA‐pro and RA‐hex effectively suppressed lipid accumulation of 3T3‐L1 cells, superior to EGCG, a well‐known anti‐obesity phytochemical. These biological effects of RA derivatives commonly attributed to hydrophobicity, hydrogen bonding, and steric bulkiness of the side chain. Practical applications: Rosmarinic acid (RA), a fundamental compound in the family Lamiaceae, is one of powerful naturally occurring antioxidants as well as other biological activities. Furthermore, its abundance in nature was also high in amount in the plant kingdom. So, natural RA can be one of possible natural resources for creating potent natural drugs and biologically useful substances after chemical modification. Studies on various biological activities may intensively expand usage and application of RA. In this study, RA was derivatized to corresponding ester such as methyl, propyl, and hexyl alcohols with higher hydrophobicity, and found great antibacterial, α‐glucosidase inhibitory, and lipid accumulation suppression activities. RA‐pro and RA‐hex significantly suppressed lipid accumulation and cell differentiation. Therefore, RA derivatives with multiple biological activities have the potential to be applied in the food and pharmaceutical industries as food ingredients and supplements. Abstract : Rosmarinic acid and its derivatives showed antibacterial activity, α‐glucosidase inhibitory activity, and lipid accumulation suppression of 3T3‐L1 cell. Molecular docking approach suggested that these biological effects were related to the physical properties of RA and its derivatives such as hydrophobicity, hydrogen bonding, and other forces of the phenolic hydroxyl group and bulkiness of the side chain of the RA derivatives synthesized and isolated from natural Perilla leaf.