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Molecules 2020-May

New Methyl Threonolactones and Pyroglutamates of Spilanthes acmella (L.) L. and Their Bone Formation Activities

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Retno Widyowati
Melanny Sulistyowaty
Nguyen Uyen
Sachiko Sugimoto
Yoshi Yamano
Hideaki Otsuka
Katsuyoshi Matsunami

Keywords

Abstract

In our continuing research for bioactive constituents from natural resources, a new methyl threonolactone glucopyranoside (1), a new methyl threonolactone fructofuranoside (2), 2 new pyroglutamates (3 and 4), and 10 known compounds (5-14) were isolated from the whole plant of Spilanthes acmella (L.) L. The structures of these compounds were determined based on various spectroscopic and chemical analyses. All of the isolated compounds were evaluated on bone formation parameters, such as ALP (alkaline phosphatase) and mineralization stimulatory activities of MC3T3-E1 cell lines. The results showed that the new compound, 1,3-butanediol 3-pyroglutamate (4), 2-deoxy-D-ribono-1,4-lactone (6), methyl pyroglutamate (7), ampelopsisionoside (10), icariside B1 (11), and benzyl α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (12) stimulated both ALP and mineralization activities.

Keywords: Spilanthes acmella; alkaline phosphatase; methyl threonolactone; mineralization; pyroglutamate.

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