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Azerosides A and B: Two new phloroacetophenone glycosides from the roots of Dorema glabrum Fisch. & C.A. Mey

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Abstract

Dorema glabrum (Apiaceae) is a monocarpic plant distributed in southern Caucasus. The gum-resin of this species is traditionally used as diuretic and anti-diarrheal and for the treatment of bronchitis and catarrh. In the present study, free radical-scavenging activity and total phenolic content of the essential oil together with n-hexane, chloroform, ethyl acetate, and methanol extracts of D. glabrum roots were evaluated in DPPH and Folin-Ciocalteu assays, respectively. Methanol extract with the highest free radical-scavenging activity (IC50 = 74.2 ± 6.6 μg ml−1) and total phenolic content (186.7 ± 8.6 mg GAE/g) was subjected to phytochemical investigation using different chromatographic methods on the Si gel (normal and reversed-phase) and Sephadex LH-20 columns. Chemical constituents of the roots oil were also analyzed using GC and GC–MS. Two new phloroacetophenone glycosides, azerosides A (1) and azerosides B (7), along with nine known phenolic compounds, echisoside (2), pleoside (3), hyrcanoside (4), 7,8-dihydroferulic acid-4-O-β-d-glucopyranoside (5), Lavandoside (6), 6,7,8-trihydroxycoumarin (8), chlorogenic acid (9), 4,5-Di-O-caffeoylquinic acid (10), and cynarin (11), were isolated and identified from D. glabrum roots. Among the isolated compounds, 8–11 exhibited potent free radical-scavenging activity (IC50 values of 1.8–2.7 μg ml−1) in comparison with BHT (IC50 = 19.5 ± 0.8 μg ml−1). Twenty-six compounds were also identified in the roots oil, among them myristicin (14.1 %) and elemicin (11.7 %), two bioactive phenylpropanoid derivatives, were main compounds. This study introduces D. glabrum as a source of phloroacetophenone glycosides and caffeoylquinic acid derivatives and suggests it as an appropriate candidate for further pharmacological and toxicological studies.

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Acknowledgments

The authors are grateful to Dr. Hassan Sereshti (Department of Chemistry, Tehran University, Tehran, Iran) for EIMS analyses and to the Central Research Laboratories of Shahid-Beheshti University of Medical Sciences (Tehran, Iran) for Elemental analyses. This research was supported by Tehran University of Medical Sciences and Health Services grant (No. 14101).

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Authors and Affiliations

  1. Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, 14174-14411, Tehran, Iran

    Mohammad-Reza Delnavazi, Abbas Hadjiakhoondi, Yousef Ajani & Narguess Yassa

  2. Drug Applied Research Center, Tabriz University of Medical Sciences, 51664, Tabriz, Iran

    Abbas Delazar

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  1. Mohammad-Reza Delnavazi
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  2. Abbas Hadjiakhoondi
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  3. Abbas Delazar
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Correspondence to Narguess Yassa.

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Delnavazi, MR., Hadjiakhoondi, A., Delazar, A. et al. Azerosides A and B: Two new phloroacetophenone glycosides from the roots of Dorema glabrum Fisch. & C.A. Mey. Med Chem Res 24, 787–796 (2015). https://doi.org/10.1007/s00044-014-1138-2

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