Methyl 2-(4’-methoxy-4’-oxobutanamide) benzoate (1) was isolated from Helianthus tuberosus and identified from its spectroscopic data. Compound 1 was previously reported from a dark brown alga, Jolyna laminarioides [1]. In previous biological investigations, compound 1 has been reported to exhibit inhibitory effect on chymotrypsin, and antibacterial and anti-inflammatory activities [2]. The zebrafish model for type 2 diabetes was induced by exposure to excess insulin. Following exposure of excess insulin, the pancreatic islet size and fluorescence intensity were measured [3]. Glucose uptake was evaluated in zebrafish by detecting the uptake of 2-NBDG fluorescence within the pancreatic islets. We evaluated the recovery effect of compound 1 on insulin-induced pancreatic islet damage in zebrafish. Pancreatic islet size of the compound-treated group was significantly increased. Compound 1 treatment led to a great increase in pancreatic islet size at concentrations of 0.05 and 0.1 μM. Glucose uptake of the compound-treated group also was significantly higher compared to the normal group at concentrations of 0.05 and 0.1 μM. In conclusion, compound 1 revealed potent anti-diabetic activity for type 2.
References:
[1] Choudhary MI, Majeed A, Shabbir M, Ghani U, Shameel M. A succinylanthranilic acid ester and other bioactive constituents of Jolyna laminarioides. Phytochemistry 1997; 46: 1215−1218.
[2] Jung YJ, Kim BO, Kwak JH, Pyo S. Inhibitory effect of methyl 2‑(4′-methoxy-4′-oxobutanamide) benzoate from jerusalem artichoke (Helianthus tuberosus) on the inflammatory paracrine loop between macrophages and adipocytes. J Agric Food Chem 2016; 64: 9317-9325
[3] Yang X, Mei S, Gu H, Guo H, Zha L, Cai J, Li X, Liu Z, Cao W. Exposure to excess insulin (glargine) induces type 2 diabetes mellitus in mice fed on a chow diet. J Endocrinol 2014; 221: 469-480