NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2022, Vol. 34 ›› Issue (2): 185-193. doi: 10.16333/j.1001-6880.2022.2.002

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Study on the chemical constituents from Achillea alpine

ZHAO Chen-guang1,2,XUE Jin-feng1,2,MA Rui-xiao1,2,LIANG Xu-bo1,2,DU Kun1,2,SI Ying-ying1,2,FENG Wei-sheng1,2*,XUE Gui-min1,2*   

  1. 1 School of Pharmacy,Henan University of Chinese Medicine;2The Engineering and Technology Center for Chinese Medicine Development of Henan Province,Zhengzhou 450046,China
  • Online:2022-02-28 Published:2022-03-07

Abstract:

To study the chemical constituents from the whole plant of Achillea alpine L..Various column chromatography,such as macroporous resin,ODS,Sephadex LH-20 and preparative HPLC were adopted to isolate and purify the compounds,and the structures of compounds 1-16 were identified by NMR,MS and other spectroscopic techniques.Sixteen compounds have been isolated from the 95% ethanol extract of A. alpine,and they were identified as (2E,4E)-N-(2-methylbutyl) deca-2,4-dienamide (1),pellitorine (2),(E,E,Z)-2,4,8-decatrienoicacid isobutylamide-8,9-dehydropellitorine(3),N-2′-methylbutyl-(EE)-2,4-decadienam(4),methyl-(E,E)-2,4,9-oxooctadeca-10,12-dienoate(5),(S)-14-(E,E)-10,12-methyl 14-hydroxy-9-oxo-octadeca-10,12-dienoate(6),(EE)-2,4-undecadiene-8,10-diynamide-N-(2-methylpropyl)(7),(EE)-2,4-decadienoic acid p-hydroxyphenethylamide(8),sinapyl alcohol diisovalerate(9),(S)-13-hydroxyoctadeca-(Z,E)-9,11-dienoic acid(10),(EE)-2,4-decadienamide acid p-methoxyphenethylamide(11),erythro-N-isobutyl-4,5-dihydroxy-2- (E)-decenamide(12,3-O-feruloylquinic acid (13),cinnamic acid (14),chlorogenic acid (15),3-O-caffeoyl-5-O-feruloylquinic acid (16).Compound 1 was a new amide.Compounds 4-6,9,10,12,13,16 were isolated from the Achillea genus for the first time.Compounds 8 and 11 were isolated from this plant for the first time.Cytotoxic effects of compounds 1-11 were screened on four different gastric cancer cell lines,and the results showed that compounds 2,5 and 9 had weak activities on MGC-803 cell line at 50 μM with the inhibitory rates at 38.7%,34.7%,31.5%,respectively.

Key words: Achillea alpine, chemical constituent, amide

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