New Methyl Threonolactones and Pyroglutamates of <i>Spilanthes acmella</i> (L.) L. and Their Bone Formation Activities
Retno Widyowati,
Melanny Ika Sulistyowaty,
Nguyen Hoang Uyen,
Sachiko Sugimoto,
Yoshi Yamano,
Hideaki Otsuka,
Katsuyoshi Matsunami
Affiliations
Retno Widyowati
Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Airlangga University, Gedung Nanizar Zaman Joenoes, Kampus C Unair, Surabaya 60115, Indonesia
Melanny Ika Sulistyowaty
Graduate School of Biomedical & Health Sciences, Hiroshima University; 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
Nguyen Hoang Uyen
Graduate School of Biomedical & Health Sciences, Hiroshima University; 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
Sachiko Sugimoto
Graduate School of Biomedical & Health Sciences, Hiroshima University; 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
Yoshi Yamano
Graduate School of Biomedical & Health Sciences, Hiroshima University; 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
Hideaki Otsuka
Graduate School of Pharmacy, Yasuda Women’s University, Hiroshima 734-8551, Japan
Katsuyoshi Matsunami
Graduate School of Biomedical & Health Sciences, Hiroshima University; 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan
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.
