Amine Derivative from the Aerial Part of Spilanthes acmella Murr. and their Alkaline Phosphatase Activity

Background: Spilanthes acmella Murr. is included in Asteraceae family which is used as a traditional remedy for tooth-aches, and originated from Africa, America, Borneo, India, Sri Lanka, Bangladesh, China, Japan, Thailand, and Indonesia. The present research aims to isolate the amine derivative from the ethyl acetate layer of this plant and to evaluate the isolated compounds of alkaline phosphatase activity as a sign of bone formation. Methods: The air-dried plants of Spilanthes acmella Murr. were extracted with methanol, then partitioned with n-hexane and ethyl acetate successively by using liquid-liquid extraction, and then the chromatographic techniques were repeated, such as silica gel, octadecyl silylated silica gel, and HPLC. The isolated compounds were determined by spectrometric analysis using ultraviolet, infrared, high-resolution electrospray ionization mass spectrometry, 1D and 2D NMR. Results: Benzenepropanoic acid, 4 hydroxy-2-oxo-3 piperidinyl ester (1), was isolated from the ethyl acetate layer of the whole plants of Spilanthes acmella Murr. together with dendranthemoside A (2), uridine (3), icariside B2 (4), chicoriin (5), dendranthemoside B (6), and ampelopsisionoside (7) from their butanol layer. Conclusion: An amine derivative, a benzenepropanoic acid that determined as 4 hydroxy-2-oxo-3 piperidinyl ester (1) was isolated and reported for the first time from the ethyl acetate layer of Spilanthes acmella naturally. All the isolated compounds from this plant stimulated alkaline phosphatase activity as a mark of bone formation up to 128%.