Abstract
The extract from Cnidium officinale rhizomes was shown in a prior experiment to markedly recover otic hair cells in zebrafish damaged by neomycin. The current study was brought about to identify the principal metabolite. Column chromatography using octadecyl SiO2 and SiO2 was performed to isolate the major metabolites from the active fraction. The chemical structures were resolved on the basis of spectroscopic data, including NMR, IR, MS, and circular dichroism (CD) data. The isolated phthalide glycosides were assessed for their recovery effect on damaged otic hair cells in neomycin-treated zebrafish. Three new phthalide glycosides were isolated, and their chemical structures, including stereochemical characteristics, were determined. Two glycosides (0.1 μM) showed a recovery effect (p < 0.01) on otic hair cells in zebrafish affected by neomycin ototoxicity. Repeated column chromatography led to the isolation of three new phthalide glycosides, named ligusticosides C (1), D (2), and E (3). Ligusticoside C and ligusticoside E recovered damaged otic hair cells in zebrafish.
Highlights
Cnidium officinale Makino (Apiaceae) is a perennial flowering plant extensively cultivated in East Asian countries [1]
Our advance experiment showed that the n-BuOH fraction from C. officinale rhizome recovered otic hair cells in zebrafish damaged by neomycin treatment
In a subsequent study presented repeated column chromatography (CC) for the n-BuOH fraction yielded three new phthalide glycosides, the chemical structures of which, including stereostructures, were determined without ambiguity based on several spectroscopic data, that is, NMR, IR, MS, and circular dichroism spectroscopy (CD)
Summary
Cnidium officinale Makino (Apiaceae) is a perennial flowering plant extensively cultivated in East Asian countries [1]. Extracts of Cnidium officinale rhizome are reported to have antioxidant [4], anti-inflammatory [5,6], anticancer [5], blood circulation improvement [7], analgesic [6], anticonvulsive [8], and sedative [9] effects. Phthalide derivatives are the most important components and are reported to be key materials participating in several pharmacological activities of C. officinale rhizome [10]. Our advance experiment showed that the n-BuOH fraction from C. officinale rhizome recovered otic hair cells in zebrafish damaged by neomycin treatment. The phthalide glycosides were evaluated for their recovery effect on damaged otic hair cells
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