Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses

Sherif S. Ebada; Nariman A. Al-Jawabri; Fadia S. Youssef; Dina H. El-Kashef; Tim-Oliver Knedel; Amgad Albohy; Michal Korinek; Tsong-Long Hwang; Bing-Hung Chen; Guan-Hua Lin; Chia-Yi Lin; Sa'ed M. Aldalaien; Ahmad M. Disi; Christoph Janiak; Peter Proksch

doi:10.1039/D0RA04876C

Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses†

Sherif S. Ebada,

*^abc Nariman A. Al-Jawabri,^b Fadia S. Youssef,

^ac Dina H. El-Kashef,^ad Tim-Oliver Knedel,^e Amgad Albohy,^f Michal Korinek,^ghi Tsong-Long Hwang,

^hij Bing-Hung Chen,^gkl Guan-Hua Lin,^m Chia-Yi Lin,^m Sa'ed M. Aldalaien,^b Ahmad M. Disi,ⁿ Christoph Janiak

^e and Peter Proksch*^a

Author affiliations

* Corresponding authors

^a Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, D-40225 Düsseldorf, Germany
E-mail: ss_ebada@mutah.edu.jo, sherif_elsayed@pharma.asu.edu.eg, Peter.Proksch@hhu.de
Fax: +49-211-81-11923
Tel: +49-211-81-14163

^b Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mu'tah University, 61710 Al-Karak, Jordan

^c Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbasia, 11566 Cairo, Egypt

^d Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt

^e Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität, D-40204 Düsseldorf, Germany

^f Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The British University in Egypt (BUE), Cairo-Suez Desert Road, Al-Sherouk City, Egypt

^g Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

^h Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung, Taiwan

ⁱ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan

^j Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, Taiwan

^k Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan

^l Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan

^m The Institute of Biomedical Sciences, National Sun Yat-sen University, Kaohsiung, Taiwan

ⁿ Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Al-Isra University, 11622 Amman, Jordan

Abstract

On Wednesday 11^th March, 2020, the world health organization (WHO) announced novel coronavirus (COVID-19, also called SARS-CoV-2) as a pandemic. Due to time shortage and lack of either a vaccine and/or an effective treatment, many trials focused on testing natural products to find out potential lead candidates. In this field, an edible and folk medicinal Jordanian plant Crepis sancta (Asteraceae) was selected for this study. Phytochemical investigation of its enriched polyphenolic extract afforded four eudesmane sesquiterpenes (1–4) together with (6S,9R)-roseoside (5) and five different methylated flavonols (6–10). Structure elucidation of isolated compounds was unambiguously determined based on HRESIMS, X-ray crystallography, and exhaustive 1D and 2D NMR experiments. All isolated compounds were assessed for their in vitro anti-inflammatory, antiallergic and in silico COVID-19 main protease (M^pro) inhibitory activities. Among the tested compounds, compounds 5–10 revealed potent anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities. Chrysosplenetin (10) is considered as a promising anti-inflammatory and antiallergic lead structure adding to the phytotherapeutic pipeline. Moreover, its inhibitory activity against SARS-CoV-2 M^pro, supported by docking and molecular dynamic studies, strengthens its potential as a lead structure paving the way toward finding out a natural remedy to treat and/or to control the current COVID-19 pandemic.

This article is part of the themed collection: Coronavirus articles - free to access collection

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Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses†

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Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses

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