Isolation, Crystal Structure and Antitussive Activity of 9S,9aS-neotuberostemonine

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摘要

The title compound 9S,9aS-neotuberostemonine (1) was isolated from the 95% ethanol extract of the roots of Stemona tuberosa. The crystal structure of 1, C22H33NO4, was determined by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic system, space group P212121, with a = 9.0115(11), b = 10.612(4), c = 22.074(3) Å, V = 2110.9(8) Å3, Z = 4, Mr = 375.49, Dc = 1.182 g/ cm3, λ= 0.71079 Å, μ = 0.080 cm-1, F(000) = 816, S = 1.019, R = 0.0579 and wR = 0.1358. A total of 3109 unique reflections were collected, of which 2902 were observed (I > 2σ(I)). The absolute configuration of 1 could be assigned by referring to the conserved configuration of the methyl groups at C(13) and C(20). In the solid state, the molecules were linked into a chain along the a-axis through weak hydrogen bond C(11)–H(11A)…O(2). Compound 1 shows significant inhibition of cough by 24%, 44% and 65% at doses of 50, 100 and 150 mg/kg, respectively.

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	吴旖
	叶青美
	刘敬
	徐末
	朱自荣
	江仁望

关键词 ： 9S,9aS-neotuberostemonine, isolation, crystal structure, antitussive

Abstract：The title compound 9S,9aS-neotuberostemonine (1) was isolated from the 95% ethanol extract of the roots of Stemona tuberosa. The crystal structure of 1, C22H33NO4, was determined by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic system, space group P212121, with a = 9.0115(11), b = 10.612(4), c = 22.074(3) Å, V = 2110.9(8) Å3, Z = 4, Mr = 375.49, Dc = 1.182 g/ cm3, λ= 0.71079 Å, μ = 0.080 cm-1, F(000) = 816, S = 1.019, R = 0.0579 and wR = 0.1358. A total of 3109 unique reflections were collected, of which 2902 were observed (I > 2σ(I)). The absolute configuration of 1 could be assigned by referring to the conserved configuration of the methyl groups at C(13) and C(20). In the solid state, the molecules were linked into a chain along the a-axis through weak hydrogen bond C(11)–H(11A)…O(2). Compound 1 shows significant inhibition of cough by 24%, 44% and 65% at doses of 50, 100 and 150 mg/kg, respectively.

Key words： 9S,9aS-neotuberostemonine isolation crystal structure antitussive

收稿日期: 2017-10-11 出版日期: 2018-04-10

基金资助:

This work was supported by Guangdong Key Scientific Project (2013A022100029) and Zhongshan Scientific Scheme (2017B1134)

通讯作者: trwjiang@jnu.edu.com E-mail: trwjiang@jnu.edu.cn

引用本文:

吴旖;叶青美;刘敬;徐末;朱自荣 ;江仁望. Isolation, Crystal Structure and Antitussive Activity of 9S,9aS-neotuberostemonine[J]. 结构化学, 2018, 37(4): 571-576.
WU Yi;YE Qing-Mei;LIU Jing;XU Wei;ZHU Zi-Rong;JIANG Ren-Wang. Isolation, Crystal Structure and Antitussive Activity of 9S,9aS-neotuberostemonine. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37(4): 571-576.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2018/V37/I4/571

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