Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum

Ten new iridoid glycosides (1-10) and two new monoterpenoids (11 and 12), together with nine known compounds (13-21), were isolated from the n-butanol extract of the aerial parts of Anarrhinum pedatum. The structural characterization of all compounds was performed by spectroscopic analysis, including 1D and 2D NMR, and HRESIMS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, using zebrafish embryos and chicken chorioallantoic membranes (CAMs). The results showed that among the new compounds, 6'-O-menthiafoloylmussaenosidic acid-11-(5-O-β-D-fructopyranosyl) ester (9), exhibited the most potent antiangiogenic activity in both the zebrafish embryos and CAM assays, reducing the growth of blood vessels. Antiangiogenic effects were also observed for the known compounds, 6-O-nerol-8-oyl-antirrinoside (13), antirrinoside (14), 6-O-trans and cis-p-coumaroyl antirrinoside (15), and (6S)-2E-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid β-glucopyranosyl ester (18).