Characterization and antibacterial activity of phthalides from the roots of the medicinal herb Levisticum officinale W.D.J. Koch.

Document Type : Research article

Authors

1 Department of Pharmacognosy and Biotechnology, School of Pharmacy, Ardabil University of Medical Sciences, Ardabil, Iran.

2 Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

3 College of Pharmacy, Pusan National University, Busan, South Korea.

4 Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University

5 Molecular Horizons and School of Chemistry & Molecular Bioscience, University of Wollongong, Wollongong, NSW 2500, Australia.

6 Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G.C., Evin, Tehran, Iran.

7 Medicinal Plants and Drugs Res. Inst. Shahid Beheshti University, Velenjak, Tehran

8 Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Tehran, Iran.

Abstract

A new phthalide, namely 7-methoxy-3-propylidenephthalide (1), along with two known compounds (2, 3) were isolated from the roots of the edible herb Levisticum officinale W.D.J. Koch, commonly known as lovage and well known in traditional medicine for its spasmolytic and diuretic effects. The structure of the new compound was established by HRMS and 1D & 2D NMR (1H 1H COSY, HMQC, and HMBC) spectroscopic analysis. All compounds are reported for the first time from L. officinale. Compounds 1-3 were tested against two Gram negative (Escherichia coli, Pseudomonas aeruginosa) and two Gram positive (Staphylococcus aureus and vancomycin-resistant Enterococcus [VRE] faecium) bacteria strains. Compound 3 was active against S. aureus, E. coli and vancomycin-resistant E. faecium with MIC values of 16, 64 and 128 μg/mL, respectively.

Graphical Abstract

Characterization and antibacterial activity of phthalides from the roots of the medicinal herb Levisticum officinale W.D.J. Koch.

Keywords


(1) Lin G, Chan SSK, Chung HS, and Li SL. Studies in Natural Products Chemistry. (2005) 32: 611-669.
(2) Beck JJ, and Chou SC. The structural diversity of phthalides from the Apiaceae.  J Nat Prod. (2007) 70: 891-900.
(3) Pannek J, Gach J, Boratynski F, and Olejniczak T. Antimicrobial activity of extracts and phthalides occurring in Apiaceae plants. Phytother Res. (2018) 1-29.
(4) Nalini VP, and Poonam Y. Synthesis and biological activities of some new Phthalides. Res J Chem Sci. (2012) 57-61.
(5) Miran M, Esfahani HM, Farimani MM, Ahmadi AA, and Ebrahimi SN. Essential oil composition and antibacterial activity of Levisticum officinale Koch at different developmental stages. J Essent Oil Bear Pl. (2018) 21(4): 1051-1055.
(6) Yarnell E. Botanical medicines for the urinary tract. World J Urol. (2002) 20: 285-293.
(7) Guzman JD,  Evangelopoulos D, Gupta A, Prieto JM, Gibbons S, and Bhakta S. Antimycobacterials from lovage root (Ligusticum officinale Koch). Phytother Res. (2013) 27: 993-998.
(8) Duke JA. The green pharmacy. Rodale Press. (1997) 84.
(9) Hagemeier J, Batz O, Schmidt J, Wray V, Hahlbrock K, and Strack D. Accumulation of phthalides in elicitor-treated cell suspension cultures of Petroselinum crispum. Phytochemistry. (1999) 50: 629-635.
(10) Jorgensen JH, and Turnidge JD. Susceptibility test methods: dilution and disk diffution methods. In manual of clinical microbiology, eleventh edition, American Society of Microbiology. (2015).