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Isoindolines and phthalides from the rhizomes of Ligusticum chuanxiong and their relaxant effects on the uterine smooth muscle.

Authors :
Liu J
Feng R
Dai O
Ni H
Liu LS
Shu HZ
Lu Y
Peng C
Xiong L
Source :
Phytochemistry [Phytochemistry] 2022 Jun; Vol. 198, pp. 113159. Date of Electronic Publication: 2022 Mar 10.
Publication Year :
2022

Abstract

Three undescribed isoindoline alkaloids, (+)-(R)-3-butyl-3-ethoxyisoindolin-1-one, (+)-(3S,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, and (-)-(3R,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, along with nine known phthalides were isolated from a water decoction of the rhizomes of Ligusticum chuanxiong using chromatographic methods. Their structures and absolute configurations were determined by extensive spectroscopic analyses and ECD data calculations. The relaxant effects of the isolated compounds on uterine contractions induced by oxytocin were investigated using a rat uterine smooth muscle contraction model. Furthermore, the effects of riligustilide on extracellular Ca <superscript>2+</superscript> influx and intracellular Ca <superscript>2+</superscript> release were assessed using high-KCl solution-induced and oxytocin-induced uterine smooth muscle contraction in a Ca <superscript>2+</superscript> -free balanced salt solution. The results showed that all the tested phthalides had inhibitory effects on oxytocin-induced uterine smooth muscle contraction. Riligustilide, a phthalide dimer, was the most active. Further examinations indicated that riligustilide reduced uterine smooth muscle contraction by inhibiting extracellular Ca <superscript>2+</superscript> influx and intracellular Ca <superscript>2+</superscript> release.<br /> (Copyright © 2022 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1873-3700
Volume :
198
Database :
MEDLINE
Journal :
Phytochemistry
Publication Type :
Academic Journal
Accession number :
35283167
Full Text :
https://doi.org/10.1016/j.phytochem.2022.113159