In vivo anti-nociceptive potential and cyclooxygenases 1 and 2 selectivity of di-naphthodiospyrols from Diospyros lotus
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In vivo anti-nociceptive potential and cyclooxygenases 1 and 2 selectivity of di-naphthodiospyrols from Diospyros lotus Saud Bawazeer 1 & Abdur Rauf 2 & Saima Naz 3 & Anees Ahmed Khalil 4 & Yahia Nasser Mabkhot 5 & Abdulrhman Asayari 6 & Abdullatif Bin Muhsinah 6 & Hamed Algarni 7,8 & Abdel Rahman Al-Tawaha 9 & Naveed Muhammad 10 & Ashfaq Ur Rehman 11 & Abdul Wadood 11 & Sergey Plygun 12,13,14 & Mohammad Ali Shariati 12 Received: 25 November 2019 / Accepted: 20 January 2020 # Sociedade Brasileira de Farmacognosia 2020
Abstract This paper describes the anti-nociceptive activity of isolated di-naphthodiospyrols from Diospyros lotus L., Ebenaceae. The roots of D. lotus were collected from the surroundings of Razagram, Pakistan. Six dimeric di-naphthodiospyrols were isolated by column chromatography and identified as follows: 5,4-dihydroxy-1-methoxy-6,6-dimethyl-7,3-binaphthyl-1,4,5,8-tetraone (1), 5,8-dihydroxy-5-methoxy-6,6-dimethyl-7,3-binaphthyl-1,4,1,4-tetraone (2), 8,5,8-trihydroxy-6,6-dimethyl-7,3binaphthyl1,4,1,4-tetraone (3), 5′,8′-dihydroxy-6,6′-dimethyl-7,3′-binaphthyl-1,4,1′,4′-tetraone (4), 5′,8′-dihydroxy-5,8dimethoxy-6,6′-dimethyl-7,3′-binaphthyl-1,4,1′,4′-tetraone (5), and 5,8,5-trihydroxy-8-methoxy-6,6-dimethyl-7,3-binaphthyl1,4,1,4-tetraone (6). They were subjected to anti-nociceptive assay by the hot plate test. Results revealed that compounds 3 and 4 significantly increased the latency time and can be considered an evidence for the anti-nociceptive effect of the studied plant material. Molecular docking study was also performed against cyclooxygenase (COX) isomers (type 1 and 2) in order to assess the possible binding mechanism of compounds 3 and 4, which established various significant electrostatic interactions with critical residues in both enzymatic targets. These results suggest that di-naphthodiospyrols are natural products that could be considered to have a good anti-nociceptive potential.
Keywords Naphthoquinones . Anti-nociceptive activities . Anti-inflammatory effects . Molecular modeling . Painkiller
* Abdur Rauf [email protected]
7
Department of Physics, Faculty of Sciences, King Khalid University, Abha, Saudi Arabia
8
Research Center for Advanced Materials Science, King Khalid University, Abha, Saudi Arabia
1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, Mecca, Saudi Arabia
9
2
Department of Chemistry, University of Swabi, Swabi, Khyber Pakhtunkhwa, Pakistan
Department of Biological Sciences, Al-Hussein Bin Talal University, Maan, Jordan
10
3
Department of Biotechnology, Woman University Mardan, Mardan, Khyber Pakhtunkhwa, Pakistan
Department of Pharmacy, Abdul Wali Khan University, Mardan, Khyber Pakhtunkhwa, Pakistan
11
4
Faculty of Allied Health Sciences, University Institute of Diet and Nutritional Sciences, The University of Lahore-Pakistan, Lahore, Pakistan
Department of Chemistry, Abdul Wali Khan University, Mardan, Khyber Pakhtunkhwa, Pakistan
12
Laboratory of Biological Control and Antimic
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