Isolation and Identification of Flavonoids from Black Cumin (Nigella sativa) by HPLC-MS and In Silico Molecular Interactions of Their Major Compounds with Fusarium oxysporum Trypsin-like Serine Protease

Author:

El-Beltagi Hossam S.12ORCID,Aziz Seham M. S. Abdel3ORCID,Aboshady A. I.3,Ibrahim Mervat A. R.3ORCID,Ibrahim Mohamed F. M.4ORCID,Alenezi Muneefah Abdullah5ORCID,Darwish Doaa Bahaa Eldin56ORCID,Al-Qahtani Salem Mesfir7ORCID,Al-Harbi Nadi Awad7ORCID,Darwish Hadeer89,Srour Hany A. M.3ORCID

Affiliation:

1. Agricultural Biotechnology Department, College of Agriculture and Food Sciences, King Faisal University, Al-Ahsa 31982, Saudi Arabia

2. Biochemistry Department, Faculty of Agriculture, Cairo University, Giza 12613, Egypt

3. Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo 11566, Egypt

4. Department of Agricultural Botany, Faculty of Agriculture, Ain Shams University, Cairo 11566, Egypt

5. Department of Biology, Faculty of Science, University of Tabuk, Tabuk 71491, Saudi Arabia

6. Botany Department, Faculty of Science, Mansoura University, Mansoura 35511, Egypt

7. Biology Department, University College of Tayma, University of Tabuk, Tabuk 71491, Saudi Arabia

8. Department of Biotechnology, College of Science, Taif University, Taif 21944, Saudi Arabia

9. Department of Medicinal and Aromatic Plants, Horticulture Research Institute, Agricultural Research Center, Giza 12619, Egypt

Abstract

Fusarium oxysporum is one of the most harmful soil-borne pathogens that cause root rot, damping-off, and wilt disease in many plant species. Management of Fusarium oxysporum diseases is often by using many harmful and expensive chemical fungicides which have many harmful effects on the environment and human health. The current study was conducted to identify the chemical constituents of black cumin seeds’ methanolic extract and investigate the ability of the major constituents to inhibit the Fusarium oxysporum trypsin-like serine protease, which play an important role in F. oxysporun pathogenicity. The HPLC-MS analysis of black cumin seeds’ methanolic extract revealed the presence of seven major compounds: amentoflavone, Procyanidin C2, Quercetin3-O-sophoroside-7-O-rhamnoside, 5,7-Dihydroxy-3,4-dimethoxyflavone, Borapetoside A, tetrahydroxy-urs-12-en-28-O-[b-D-glucopyranosyl (1-2)-b-D-glucopyranosyl] ester, and kudzusapongenol A-hexA-pen. The results of molecular docking between these compounds and the active site of Fusarium oxysporium trypsin showed that only four compounds were able to bind to the active site of F. oxysporum trypsin. Amentoflavone, 5,7-Dihydroxy-3,4-dimethoxyflavone, and Quercetin3-O-sophoroside-7-O-rhamnoside have the highest binding energy, −6.4, −6.5, and −6.5 Kcal/mol, respectively. In addition, the results clarify that 5,7-Dihydroxy-3,4-dimethoxyflavone was the only compound to form a hydrogen bond with Asp189 (the residue responsible for substrate specificity). The results of the study strongly indicate that flavonoids of black cumin seeds’ methanolic extract could be used as effective inhibitors for the F. oxysporum trypsin-like serine protease.

Funder

Deanship of Scientific Research, Vice Presidency for Graduate Studies and Scientific Research, King Faisal University, Saudi Arabia

Publisher

MDPI AG

Subject

Filtration and Separation,Analytical Chemistry

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