Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb.
The current study was carried out to reveal the chemical profile and biological screening of Heliotropium dasycarpum Ledeb, as well as the feasibility of its industrial application. Therefore, the methanolic extract (HdM) of H. dasycarpum was divided into n-hexane (HdH), ethyl acetate (HdE) and wate...
| Main Authors: | , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-05-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223001168 |
| _version_ | 1797857723868512256 |
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| author | Mahreen Mukhtar Muhammad Saleem Mamona Nazir Naheed Riaz Nusrat Shafiq Hammad Saleem Saba Tauseef Saima Khan Muhammad Ehsan Mazhar Rasool Bakhsh Tareen Mian Habib ur Rahman Mahmood Muhammad Imran Tousif Suvash Chandra Ojha |
| author_facet | Mahreen Mukhtar Muhammad Saleem Mamona Nazir Naheed Riaz Nusrat Shafiq Hammad Saleem Saba Tauseef Saima Khan Muhammad Ehsan Mazhar Rasool Bakhsh Tareen Mian Habib ur Rahman Mahmood Muhammad Imran Tousif Suvash Chandra Ojha |
| author_sort | Mahreen Mukhtar |
| collection | DOAJ |
| description | The current study was carried out to reveal the chemical profile and biological screening of Heliotropium dasycarpum Ledeb, as well as the feasibility of its industrial application. Therefore, the methanolic extract (HdM) of H. dasycarpum was divided into n-hexane (HdH), ethyl acetate (HdE) and water (HdW) soluble fractions. All the fractions were inactive against acetylcholinesterase (AChE) enzyme, 3T3 and HeLa cell lines, but showed immunomodulatory effect up to 37 %. HdE fraction further displayed significant anti-urease activity with IC50 value of 74.072 ± 0.002, while HdM was found moderate inhibitor (63 %). Thus HdE was subjected to HR-LCMS/MS analysis in positive and negative ionization modes, and a qualitative analytical method with a data mining strategy was utilized. The secondary metabolites were identified by dereplication strategy using molecular networking as a bioinformatics tool, which disclosed the presence of 08 known alkaloids of heliotrine-type (1, 3, 5–10), and 05 (12–16) known flavonoids and flavonoid glycosides along with 03 new (2, 4 and 11) putative pyrrolizidine analogues. DFT simulations of identified compounds were performed using multiple quantum chemical and geometrical descriptors in order to determine their quantitative structure activity relationship. These secondary metabolites were docked against the enzyme urease which substantiated the inhibitory action of pyrrolizidine alkaloids and flavonoid glycosides. Furthermore, ADME analysis provided the base for the use of these compounds for further studies as drug leads and to unveil industrial application of H. dasycarpum in formulating products against gastritis, peptic ulcer and gastric cancer. |
| first_indexed | 2024-04-09T21:01:24Z |
| format | Article |
| id | doaj.art-f92faa58a3cc4a4895ebcb886b731f01 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-09T21:01:24Z |
| publishDate | 2023-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-f92faa58a3cc4a4895ebcb886b731f012023-03-29T09:25:41ZengElsevierArabian Journal of Chemistry1878-53522023-05-01165104655Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb.Mahreen Mukhtar0Muhammad Saleem1Mamona Nazir2Naheed Riaz3Nusrat Shafiq4Hammad Saleem5Saba Tauseef6Saima Khan7Muhammad Ehsan Mazhar8Rasool Bakhsh Tareen9Mian Habib ur Rahman Mahmood10Muhammad Imran Tousif11Suvash Chandra Ojha12Institute of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, 63100 Bahawalpur, PakistanInstitute of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, 63100 Bahawalpur, PakistanDepartment of Chemistry, Government Sadiq College Women University, Bahawalpur, 63100 Bahawalpur, PakistanInstitute of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, 63100 Bahawalpur, PakistanDepartment of Chemistry, Government College Women University, Faisalabad 38000, PakistanInstitute of Pharmaceutical Sciences (IPS), University of Veterinary & Animal Sciences (UVAS), Lahore 54000, PakistanDr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, PakistanInstitute of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, 63100 Bahawalpur, PakistanDepartment of Physics, Bahauddin Zakariya University Multan, PakistanDepartment of Botany, Baluchsitan University Quetta, PakistanDepartment of Chemistry, Division of Science and Technology, University of Education Lahore, PakistanDepartment of Chemistry, Division of Science and Technology, University of Education Lahore, Pakistan; Corresponding authors at: Department of Infectious Diseases, The Affiliated Hospital of Southwest Medical University, Luzhou 646000, China (S.C. Ojha).Department of Infectious Diseases, The Affiliated Hospital of Southwest Medical University, Luzhou 646000, China; Southwest Medical University, Jiangyang District, Luzhou 646000, Sichuan, China; Corresponding authors at: Department of Infectious Diseases, The Affiliated Hospital of Southwest Medical University, Luzhou 646000, China (S.C. Ojha).The current study was carried out to reveal the chemical profile and biological screening of Heliotropium dasycarpum Ledeb, as well as the feasibility of its industrial application. Therefore, the methanolic extract (HdM) of H. dasycarpum was divided into n-hexane (HdH), ethyl acetate (HdE) and water (HdW) soluble fractions. All the fractions were inactive against acetylcholinesterase (AChE) enzyme, 3T3 and HeLa cell lines, but showed immunomodulatory effect up to 37 %. HdE fraction further displayed significant anti-urease activity with IC50 value of 74.072 ± 0.002, while HdM was found moderate inhibitor (63 %). Thus HdE was subjected to HR-LCMS/MS analysis in positive and negative ionization modes, and a qualitative analytical method with a data mining strategy was utilized. The secondary metabolites were identified by dereplication strategy using molecular networking as a bioinformatics tool, which disclosed the presence of 08 known alkaloids of heliotrine-type (1, 3, 5–10), and 05 (12–16) known flavonoids and flavonoid glycosides along with 03 new (2, 4 and 11) putative pyrrolizidine analogues. DFT simulations of identified compounds were performed using multiple quantum chemical and geometrical descriptors in order to determine their quantitative structure activity relationship. These secondary metabolites were docked against the enzyme urease which substantiated the inhibitory action of pyrrolizidine alkaloids and flavonoid glycosides. Furthermore, ADME analysis provided the base for the use of these compounds for further studies as drug leads and to unveil industrial application of H. dasycarpum in formulating products against gastritis, peptic ulcer and gastric cancer.http://www.sciencedirect.com/science/article/pii/S1878535223001168Heliotropium dasycarpumHR-LCMS/MSDFT calculationsBiological screeningMolecular docking studiesADME studies |
| spellingShingle | Mahreen Mukhtar Muhammad Saleem Mamona Nazir Naheed Riaz Nusrat Shafiq Hammad Saleem Saba Tauseef Saima Khan Muhammad Ehsan Mazhar Rasool Bakhsh Tareen Mian Habib ur Rahman Mahmood Muhammad Imran Tousif Suvash Chandra Ojha Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. Arabian Journal of Chemistry Heliotropium dasycarpum HR-LCMS/MS DFT calculations Biological screening Molecular docking studies ADME studies |
| title | Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. |
| title_full | Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. |
| title_fullStr | Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. |
| title_full_unstemmed | Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. |
| title_short | Identification of pyrrolizidine alkaloids and flavonoid glycosides through HR-LCMS/MS analysis, biological screening, DFT and molecular docking studies on Heliotropium dasycarpum Ledeb. |
| title_sort | identification of pyrrolizidine alkaloids and flavonoid glycosides through hr lcms ms analysis biological screening dft and molecular docking studies on heliotropium dasycarpum ledeb |
| topic | Heliotropium dasycarpum HR-LCMS/MS DFT calculations Biological screening Molecular docking studies ADME studies |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223001168 |
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