Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel
Using different chromatographic methods, four new compounds were isolated from the aerial parts of Suaeda monoica (Chenopodiaceae) along with 2-hydroxy-1-naphthoic acid (SCM-3). The structures of the new compounds were established as 6′-hydroxy-10′-geranilanyl naphtha-1-oate (SMC-1), 4,4,8β,10β-Tetr...
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doaj-fa0460987c534fffb2e9f07f9392b7fc2020-11-24T21:24:25ZengElsevierSaudi Pharmaceutical Journal1319-01642020-02-01282172186Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. GmelNasir A. Siddiqui0Ramzi A. Mothana1Mansour S. Al-Said2Mohammad K. Parvez3Perwez Alam4M. Tabish Rehman5Mohd. Ali6Mohamed F. Alajmi7Mohammed S. Al-Dosari8Adnan J. Al-Rehaily9Fahd A. Nasr10Jamal M. Khalid11Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia; Corresponding author at: Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. BOX 2457, Riyadh 11451, Saudi Arabia.Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy & Phytochemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, IndiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaMedicinal Aromatic, and Poisonous Plants Research Center, Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi ArabiaDepartment of Botany and Microbiology, College of Science, King Saud University, Riyadh, Saudi ArabiaUsing different chromatographic methods, four new compounds were isolated from the aerial parts of Suaeda monoica (Chenopodiaceae) along with 2-hydroxy-1-naphthoic acid (SCM-3). The structures of the new compounds were established as 6′-hydroxy-10′-geranilanyl naphtha-1-oate (SMC-1), 4,4,8β,10β-Tetramethyl-9β-isobutanyl decalin-13-ol-13-O-β-D-xylopyranoside (SCM-2), 6′-(2-hydroxynaphthalen-3-yl) hexanoic acid (SCM-4) and 1′-(2-Methoxy-3-naphthyl)-4′-(2′'-methylbenzoyl)-n-butane (SMC-5) by IR, EIMS and NMR (1 & 2D) analyses. All compounds (50 μg/mL) were tested for cell proliferative potential on cultured human liver cell HepG2 cells by MTT assay. The results revealed a marked cell proliferative potential of all compounds (1.42–1.48 fold) as compared to untreated control. The results of molecular docking and binding with specific proteins such as PTEN (Phosphatase and Tensin homolog) and p53 also justify the cell proliferative potential of the isolated compounds. Glide program with Schrodinger suit 2018 was used to evaluate the binding between SMC compounds and proteins (PTEN and p53). The binding affinity of all compounds was in order of 104–105 M−1 towards both PTEN and p53. All the SMC compounds have been found to bind at the active site of PTEN, thereby may prevent the binding of phosphatidylinositiol 3,4,5-triphosphate (PI3P). In the locked position, PTEN would not be able to hydrolyze PI3P and hence the PI3P regulated signaling pathway remains active. Similarly, SMC molecules were found to interact with the amino acid residues (Ser99, Thr170, Gly199, and Asp224) which are critically involved in the formation of tetrameric p53. The blockage of p53 to attain its active conformation thus may prevent the recruitment of p53 on DNA and hence may promote cell proliferation. Keywords: Suaeda monoica, Cell-proliferation, Molecular docking, β-Naphthol, Caproic acid, Chenopodiaceae, HepG2 cellshttp://www.sciencedirect.com/science/article/pii/S1319016419301586 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Nasir A. Siddiqui Ramzi A. Mothana Mansour S. Al-Said Mohammad K. Parvez Perwez Alam M. Tabish Rehman Mohd. Ali Mohamed F. Alajmi Mohammed S. Al-Dosari Adnan J. Al-Rehaily Fahd A. Nasr Jamal M. Khalid |
spellingShingle |
Nasir A. Siddiqui Ramzi A. Mothana Mansour S. Al-Said Mohammad K. Parvez Perwez Alam M. Tabish Rehman Mohd. Ali Mohamed F. Alajmi Mohammed S. Al-Dosari Adnan J. Al-Rehaily Fahd A. Nasr Jamal M. Khalid Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel Saudi Pharmaceutical Journal |
author_facet |
Nasir A. Siddiqui Ramzi A. Mothana Mansour S. Al-Said Mohammad K. Parvez Perwez Alam M. Tabish Rehman Mohd. Ali Mohamed F. Alajmi Mohammed S. Al-Dosari Adnan J. Al-Rehaily Fahd A. Nasr Jamal M. Khalid |
author_sort |
Nasir A. Siddiqui |
title |
Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel |
title_short |
Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel |
title_full |
Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel |
title_fullStr |
Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel |
title_full_unstemmed |
Cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of Suaeda monoica Forssk. ex. J.F. Gmel |
title_sort |
cell proliferation activity delineated by molecular docking of four new compounds isolated from the aerial parts of suaeda monoica forssk. ex. j.f. gmel |
publisher |
Elsevier |
series |
Saudi Pharmaceutical Journal |
issn |
1319-0164 |
publishDate |
2020-02-01 |
description |
Using different chromatographic methods, four new compounds were isolated from the aerial parts of Suaeda monoica (Chenopodiaceae) along with 2-hydroxy-1-naphthoic acid (SCM-3). The structures of the new compounds were established as 6′-hydroxy-10′-geranilanyl naphtha-1-oate (SMC-1), 4,4,8β,10β-Tetramethyl-9β-isobutanyl decalin-13-ol-13-O-β-D-xylopyranoside (SCM-2), 6′-(2-hydroxynaphthalen-3-yl) hexanoic acid (SCM-4) and 1′-(2-Methoxy-3-naphthyl)-4′-(2′'-methylbenzoyl)-n-butane (SMC-5) by IR, EIMS and NMR (1 & 2D) analyses. All compounds (50 μg/mL) were tested for cell proliferative potential on cultured human liver cell HepG2 cells by MTT assay. The results revealed a marked cell proliferative potential of all compounds (1.42–1.48 fold) as compared to untreated control. The results of molecular docking and binding with specific proteins such as PTEN (Phosphatase and Tensin homolog) and p53 also justify the cell proliferative potential of the isolated compounds. Glide program with Schrodinger suit 2018 was used to evaluate the binding between SMC compounds and proteins (PTEN and p53). The binding affinity of all compounds was in order of 104–105 M−1 towards both PTEN and p53. All the SMC compounds have been found to bind at the active site of PTEN, thereby may prevent the binding of phosphatidylinositiol 3,4,5-triphosphate (PI3P). In the locked position, PTEN would not be able to hydrolyze PI3P and hence the PI3P regulated signaling pathway remains active. Similarly, SMC molecules were found to interact with the amino acid residues (Ser99, Thr170, Gly199, and Asp224) which are critically involved in the formation of tetrameric p53. The blockage of p53 to attain its active conformation thus may prevent the recruitment of p53 on DNA and hence may promote cell proliferation. Keywords: Suaeda monoica, Cell-proliferation, Molecular docking, β-Naphthol, Caproic acid, Chenopodiaceae, HepG2 cells |
url |
http://www.sciencedirect.com/science/article/pii/S1319016419301586 |
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