Phenolic compounds of Iris adriatica and their antimycobacterial effects

Ochensberger, Sandra; Alperth, Fabian; Mitić, Božena; Kunert, Olaf; Mayer, Stefanie; Mourão, Maria Ferreira; Turek, Ivana; Luca, Simon Vlad; Skalicka-Woźniak, Krystyna; Maleš, Željan; Hruševar, Dario; Duka, Ivan; Bucar, Franz

doi:10.2478/acph-2019-0037

Abstract

Little is known about the pharmacological activities of Iris adriatica (Iridaceae), a plant endemic to Dalmatia (Croatia). We therefore performed a bioassay-guided fractionation including high-performance counter current chromatography (HPCCC) and antibacterial tests using Mycobacterium smegmatis mc² 155. One obtained fraction was found to be antimycobacterially active with a MIC of 64 mg L⁻¹. Furthermore, fractions were tested for resistance modulatory effects using ethidium bromide as substrate. We were able to identify the pure isoflavonic compounds irigenin and irilone and a fraction containing mainly benzophenone 2,4,6-trihydroxy-4-methoxy-benzophenone, responsible for the resistance-modulatory activity of this plant.

References

1. B. Mitić, Iris adriatica (Iridaceae), a new species from Dalmatia (Croatia), Phyton42 (2002) 305–314.
Search in Google Scholar Back to article
2. The Plant List. Version 1.1 (2013); http://www.theplantlist.org; last access date January 23, 2019
Search in Google Scholar Back to article
3. E. Wollenweber, J. F. Stevens, K. Klimo, J. Knauft, N. Frank and C. Gerhauser, Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica, Planta Med.69 (2003) 15–20; https://doi.org/10.1055/s-2003-3703010.1055/s-2003-3703012567273
Search in Google Scholar Back to article
4. G.-Y. Xie, Y. Zhu, P. Shu, X.-Y. Qin, G. Wu, Q. Wang and M.-J. Qin, Phenolic metabolite profiles and antioxidants assay of three Iridaceae medicinal plants for traditional Chinese medicine “She-gan” by on-line HPLC–DAD coupled with chemiluminescence (CL) and ESI-Q-TOF-MS/MS, J. Pharmaceut. Biomed.98 (2014) 40–51. https://doi.org/10.1016/j.jpba.2014.05.00810.1016/j.jpba.2014.05.00825106824
Search in Google Scholar Back to article
5. S. H. Wani, B. A. Padder, T. Mokhdomi, J. I. Mir, H. A. Bhat, Q. P. Hassan and R. A. Qadri, Antiproliferative activity of methanolic extracts of different Iris plant species against A549 and Caco-2 cell lines, J. Pharmacogn. Phytochem.6 (2017) 1034–1037.
Search in Google Scholar Back to article
6. F. Conforti, D. Rigano, F. Menichini, M. R. Loizzo and F. Senatore, Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents, Fitoterapia80 (2009) 62–67; https://doi.org/10.1016/j.fitote.2008.10.00510.1016/j.fitote.2008.10.00519000749
Search in Google Scholar Back to article
7. D. G. Spoerke Jr. and S. C. Smolinske, Toxicity of Houseplants, 1^st ed., CRC Press, Boca Raton 1990.
Search in Google Scholar Back to article
8. F. Alperth, B. Mitić, S. Mayer, Ž. Maleš, O. Kunert, D. Hruševar and F. Bucar, Metabolic profiling of rhizomes of native populations of the strictly endemic Croatian species Iris adriatica, Plant Biosyst.153 (2019) 317–324; https://doi.org/10.1080/11263504.2018.147890610.1080/11263504.2018.1478906
Search in Google Scholar Back to article
9. D. Bukvički, M. Novaković, N. Ab Ghani, P. D. Marin and Y. Asakawa, Secondary metabolites from endemic species Iris adriatica Trinajstić ex Mitić (Iridaceae), Nat. Prod. Res.32 (2018) 1849–1852; https://doi.org/10.1080/14786419.2017.140230910.1080/14786419.2017.140230929126369
Search in Google Scholar Back to article
10. S. R. M. Ibrahim, G. A. Mohamed, M. F. Zayed and S. A. Ross, 8-Hydroxyirilone 5-methyl ether and 8-hydroxyirilone, new antioxidant and α-amylase inhibitors isoflavonoids from Iris germanica rhizomes, Bioorg. Chem.70 (2017) 192–198; https://doi.org/10.1016/j.bioorg.2016.12.01010.1016/j.bioorg.2016.12.01028069265
Search in Google Scholar Back to article
11. S. Lutter, K. Schmalbach, H. L. Esch and L. Lehmann, The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover, Arch. Toxicol.88 (2014) 309–321; https://doi.org/10.1007/s00204-013-1114-510.1007/s00204-013-1114-523982890
Search in Google Scholar Back to article
12. Jyotshna, P. Khare and K. Shanker, Mangiferin: A review of sources and interventions for biological activities, BioFactors,42 (2016) 504–514; https://doi.org/10.1002/biof.130810.1002/biof.130827658353
Search in Google Scholar Back to article
13. C. Cao, M. Su and F. Zhou, Mangiferin inhibits hippocampal NLRP3 inflammasome and exerts antidepressant effects in a chronic mild stress mice model, Behav. Pharmacol.28 (2017) 356–364; https://doi.org/10.1097/FBP.000000000000030510.1097/FBP.000000000000030528410265
Search in Google Scholar Back to article
14. World Health Organization, Editor, Global Tuberculosis Report 2018, ISBN: 978-92-4-156564-6.
Search in Google Scholar Back to article
15. L. Fernandez and R. E. W. Hancock, Adaptive and mutational resistance: Role of porins and efflux pumps in drug resistance, Clin. Microbiol. Rev.25 (2012) 661–681; https://doi.org/10.1128/CMR.00043-1210.1128/CMR.00043-12348574923034325
Search in Google Scholar Back to article
16. D. J. Newman and G. M. Cragg, Natural products as sources of new drugs from 1981 to 2014, J. Nat. Prod.79 (2016) 629–661; https://doi.org/10.1021/acs.jnatprod.5b0105510.1021/acs.jnatprod.5b0105526852623
Search in Google Scholar Back to article
17. S. H. Wani, A. Amin, M. A. Rather, J. A. Parray, Q. Parvaiz and R. A. Qadri, Antibacterial and phyto-chemical screening of different extracts of five Iris species growing in Kashmir, J. Pharm. Res.5 (2012) 3376–3378.
Search in Google Scholar Back to article
18. F.-C. Czygan, D. Frohne, K. Hiller, C. Holtzel and A. Nagell, Herbal drugs and phytopharmaceuticals - A Handbook for Pratice on a Scientific Basis (Eds. M. Wichtl), 3^rd ed., Medpharm - Scientific Publishers, Stuttgart 2004, pp. 312–314.
Search in Google Scholar Back to article
19. F. Alperth, Phytochemische und mikrobiologische Untersuchungen an Iris adriatica, Diploma thesis, Faculty of Natural Sciences, University of Graz, 2017.
Search in Google Scholar Back to article
20. D. Lechner, S. Gibbons and F. Bucar, Plant phenolic compounds as ethidium bromide efflux inhibitors in Mycobacterium smegmatis, J. Antimirob. Chemoth.62 (2008) 345–348; https://doi.org/10.1093/jac/dkn17810.1093/jac/dkn17818430720
Search in Google Scholar Back to article
21. S. H. Wani, S. A. Lone, M. F. Mustafa, J. I. Mir, R. A. Qadri and Q. P. Hassan, Evaluation of prominent isoflavonoids of iris plant as futuristic cancer drug components, Int. J. Botany Stud. 2 (2017) 129–134.
Search in Google Scholar Back to article
22. G-Y. Xie, X-Y. Qin, R. Lui, Q. Wang, B-B. Lin, G-K. Wang, G-K. Xu, R. Wen and M-J. Qin, New isoflavones with cytotoxic activity from the rhizomes of Iris germanica L., Nat. Prod. Res. 27 (2013) 2173–2177; https://doi.org/10.1080/14786419.2013.79646810.1080/14786419.2013.79646823662687
Search in Google Scholar Back to article

Phenolic compounds of Iris adriatica and their antimycobacterial effects

Abstract

Paradigm

My account