Chemical Constituents of the Artemisia ciniformis Aerial Parts Grown in the Northeast of Iran and Their Chemotaxonomic Significance

Abstract

Background: The Artemisia genus is one of the largest genera of the Asteraceae family, with various traditional and modern reported uses. Within this group, Artemisia ciniformis (Dermane Talaei) is an endemic plant of Iran with antioxidant, antimalarial, anticancer, cytoprotective, and neuroprotective properties. Due to these potential benefits, further phytochemical research needs to be conducted to understand its chemotaxonomic and pharmaceutical effects. Objectives: The main purpose of this study is to investigate the dichloromethane fraction of A. ciniformis from Iran for phytochemical and chemotaxonomic aspects. Methods: Artemisia ciniformis aerial parts were collected, dried, and extracted by the maceration method using dichloromethane after defatting. The prepared extract was subjected to chromatographic techniques, including column chromatography, vacuum liquid chromatography, and HPLC, to isolate purified compounds, which were identified using spectroscopic analyses such as NMR and EI-MS. Results: Two tetrahydrofuran-type sesquiterpenoids: (1) Hydroxydavanone and (2) arteincultone; two acetophenone derivatives: (3) Xanthoxylin and (4) 2,4-dihydroxy-6-methoxy acetophenone; and a flavonoid, (5) jaceosidin, were isolated. Additionally, a polymethoxylated flavone was obtained in small amounts, and its structure was tentatively assigned as (6) 5,6-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one (Ciniformon). Conclusions: Artemisia ciniformis is a rich source of phytochemicals from various categories, such as sesquiterpenes and phenolic compounds, that can be used in systematic studies and medicinal research to treat human disorders by discovering new biologically active as well as lead compounds.