Anti-viral and Anti-inflammatory Isoflavonoids from Ukrainian Iris aphylla Rhizomes: Structure-Activity Relationship Coupled with ChemGPS-NP Analysis

Author:

Mykhailenko Olha12,Hsieh Chung-Fan34,El-Shazly Mohamed5,Nikishin Alexander6,Kovalyov Vladimir7,Shynkarenko Pavlo8,Ivanauskas Liudas9,Chen Bing-Hung1011,Horng Jim-Tong312131415,Hwang Tsong-Long14151617,Georgiyants Victoriya1,Korinek Michal101618ORCID

Affiliation:

1. Department of Pharmaceutical Chemistry, National University of Pharmacy of Ministry of Health of Ukraine, Kharkiv, Ukraine

2. Pharmacognosy and Phytotherapy Group, UCL School of Pharmacy, London, United Kingdom

3. Research Center for Emerging Viral Infections, College of Medicine, Chang Gung University, Kweishan, Taoyuan, Taiwan

4. Department of Neurology, Linkou Chang Gung Memorial Hospital, Taoyuan City, Taiwan

5. Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, African Union Organization Street, Abbassia, Cairo, Egypt

6. V. N. Karazin Kharkiv National University, Organic Chemistry Department, Kharkiv, Ukraine

7. Department of Pharmacognosy, National University of Pharmacy of Ministry of Health of Ukraine, Kharkiv, Ukraine

8. Enamine Ltd, Kyiv, Ukraine

9. Lithuanian University of Health Sciences, Department of Analytical and Toxicological Chemistry, Kaunas, Lithuania

10. Department of Biotechnology, College of Life Science, Kaohsiung, Taiwan

11. The Institute of Biomedical Sciences, National Sun Yat-sen University, Kaohsiung, Taiwan

12. Department of Biochemistry and Molecular Biology, College of Medicine, Chang Gung University, Kweishan, Taoyuan, Taiwan

13. Molecular Infectious Disease Research Center, Chang Gung Memorial Hospital, Chang Gung University College of Medicine, Kweishan, Taoyuan, Taiwan

14. Research Center for Chinese Herbal Medicine, Chang Gung University of Science and Technology, Kweishan, Taoyuan, Taiwan

15. Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Kweishan, Taoyuan, Taiwan

16. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Kweishan, Taoyuan, Taiwan

17. Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan

18. Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

Abstract

AbstractDried Iris rhizomes have been used in Chinese and European traditional medicine for the treatment of various diseases such as bacterial infections, cancer, and inflammation, as well as for being astringent, laxative, and diuretic agents. Eighteen phenolic compounds including some rare secondary metabolites, such as irisolidone, kikkalidone, irigenin, irisolone, germanaism B, kaempferol, and xanthone mangiferin, were isolated for the first time from Iris aphylla rhizomes. The hydroethanolic Iris aphylla extract and some of its isolated constituents showed protective effects against influenza H1N1 and enterovirus D68 and anti-inflammatory activity in human neutrophils. The promising anti-influenza effect of apigenin (13, almost 100% inhibition at 50 µM), kaempferol (14, 92%), and quercetin (15, 48%) were further confirmed by neuraminidase inhibitory assay. Irisolidone (1, almost 100% inhibition at 50 µM), kikkalidone (5, 93%), and kaempferol (14, 83%) showed promising anti-enterovirus D68 activity in vitro. The identified compounds were plotted using ChemGPS-NP to correlate the observed activity of the isolated phenolic compounds with the in-house database of anti-influenza and anti-enterovirus agents. Our results indicated that the hydroethanolic Iris aphylla extract and Iris phenolics hold the potential to be developed for the management of seasonal pandemics of influenza and enterovirus infections.

Funder

Chang Gung University of Science and Technology, Taiwan

Chang Gung Memorial Hospital, Linkou

Kaohsiung Medical University

Ministry of Science and Technology, Taiwan

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Complementary and alternative medicine,Drug Discovery,Pharmaceutical Science,Pharmacology,Molecular Medicine,Analytical Chemistry

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