Bioactivity-guided Isolation and Molecular Modeling of the Anti-inflammatory Constituents from the Leaves of Duranta Erecta Linn

Overview

Journal BMC Complement Med Ther

Publisher Biomed Central

Date 2025 Jan 28

PMID 39875865

Authors

Marina Sobhy

Farid N Kirollos

Sameh F AbouZid

Nasser S M Ismail

Riham A El-Shiekh

Essam Abdel-Sattar

Affiliations

Soon will be listed here.

Abstract

Duranta erecta Linn. belongs to the Verbenaceae family and is primarily found in subtropical, tropical, and temperate climates. The plant has been reported to contain a variety of phytoconstituents, including iridoid glycosides, flavonoids, flavonoid glycosides, alkaloids, phenolics, tannins, terpenoids, steroids, and saponins. In this investigation, a bioactivity-guided isolation was used to isolate cyclooxygenases (COXs) and lipoxygenase (LOX)-inhibiting compounds from the leaves of Duranta erecta Linn. Duranterectoside A (1), lamiide (2), and apigenin 4',7-dimethyl ether (3) were identified employing spectroscopic methods (including ESI-MS, H-NMR, and C-NMR), and by comparing with existing literature data. This is the first report of metabolitrs from D. erecta inhibiting both LOX and COX enzymes. Furthermore, the isolated compounds were analyzed using computerized virtual screening, which enabled the modelling ADME characteristics, molecular docking, and dynamics simulation. The results demonstrated that compound 1 had greater docking scores than the docked lead compounds. Overall, the data reported in this study add to our understanding of the pharmacological properties of the examined plant and Duranterectoside A (1) and pave the way for future research and investigation in inflammation and drug discovery.

References

Ali M, Al-Mokaddem A, Abdel-Sattar E, El-Shiekh R, Farag M, Aljuaydi S . Enhanced wound healing potential of arabincoside B isolated from Caralluma Arabica in rat model; a possible dressing in veterinary practice. BMC Vet Res. 2024; 20(1):282. PMC: 11218188. DOI: 10.1186/s12917-024-04128-2. View

Skrzypczak-Jankun E, Zhou K, Jankun J . Inhibition of lipoxygenase by (-)-epigallocatechin gallate: X-ray analysis at 2.1 A reveals degradation of EGCG and shows soybean LOX-3 complex with EGC instead. Int J Mol Med. 2003; 12(4):415-20. View

Ibrahim R, Abdel-Baki P, Mohamed O, Al-Karmalawy A, Tripathi A, El-Shiekh R . Metabolites profiling, in-vitro and molecular docking studies of five legume seeds for Alzheimer's disease. Sci Rep. 2024; 14(1):19637. PMC: 11344142. DOI: 10.1038/s41598-024-68743-7. View

Gluszko P, Bielinska A . Non-steroidal anti-inflammatory drugs and the risk of cardiovascular diseases: are we going to see the revival of cyclooxygenase-2 selective inhibitors?. Pol Arch Med Wewn. 2009; 119(4):231-5. View

Ali D, El-Shiekh R, El Sawy M, Khalifa A, Elblehi S, Elsokkary N . In vivo anti-gastric ulcer activity of 7-O-methyl aromadendrin and sakuranetin via mitigating inflammatory and oxidative stress trails. J Ethnopharmacol. 2024; 335:118617. DOI: 10.1016/j.jep.2024.118617. View

Delaporte R, Sanchez G, Cuellar A, Giuliani A, de Mello J . Anti-inflammatory activity and lipid peroxidation inhibition of iridoid lamiide isolated from Bouchea fluminensis (Vell.) Mold. (Verbenaceae). J Ethnopharmacol. 2002; 82(2-3):127-30. DOI: 10.1016/s0378-8741(02)00181-2. View

Sobhy M, AbouZid S, Kirollos F, El-Shiekh R, Abdel-Sattar E . Lamiide and Ipolamiide: A Comprehensive Review of Their Bioactive Properties and Therapeutic Potential. Chem Biodivers. 2024; 21(12):e202401069. DOI: 10.1002/cbdv.202401069. View

Rimon G, Sidhu R, Lauver D, Lee J, Sharma N, Yuan C . Coxibs interfere with the action of aspirin by binding tightly to one monomer of cyclooxygenase-1. Proc Natl Acad Sci U S A. 2009; 107(1):28-33. PMC: 2806742. DOI: 10.1073/pnas.0909765106. View

Liavonchanka A, Feussner I . Lipoxygenases: occurrence, functions and catalysis. J Plant Physiol. 2006; 163(3):348-57. DOI: 10.1016/j.jplph.2005.11.006. View

10.

Bunimov N, Laneuville O . Cyclooxygenase inhibitors: instrumental drugs to understand cardiovascular homeostasis and arterial thrombosis. Cardiovasc Hematol Disord Drug Targets. 2008; 8(4):268-77. DOI: 10.2174/187152908786786250. View

11.

Eke I, Okpara G . Anti-hyperglycemic and anti-dyslipidemic activities of methanol ripe fruit extract of L () in normoglycemic and hyperglycemic rats. J Tradit Complement Med. 2021; 11(3):209-216. PMC: 8116715. DOI: 10.1016/j.jtcme.2020.03.007. View

12.

Radi M, El-Shiekh R, Hegab A, Henry S, Avula B, Katragunta K . LC-QToF chemical profiling of Euphorbia grantii Oliv. and its potential to inhibit LPS-induced lung inflammation in rats via the NF-κB, CY450P2E1, and P38 MAPK14 pathways. Inflammopharmacology. 2023; 32(1):461-494. PMC: 10907465. DOI: 10.1007/s10787-023-01298-7. View

13.

Takeda Y, Morimoto Y, Matsumoto T, Ogimi C, Hirata E, Takushi A . Iridoid glucosides from the leaves and stems of Duranta erecta. Phytochemistry. 1995; 39(4):829-33. DOI: 10.1016/0031-9422(95)00024-2. View

14.

Furusawa C, Yasuda S, Tsuji H, Ito S, Miyashita H, Yoshimitsu H . A new triterpenoid glycoside from the leaves and stems of Duranta repens. Nat Prod Res. 2015; 30(2):246-50. DOI: 10.1080/14786419.2015.1046870. View

15.

Li W, Zhu H, Chen Y, Xiao H, Ge Y, Hu H . Bioactivity-guided isolation of anti-inflammatory components from . Food Sci Nutr. 2020; 8(6):2670-2679. PMC: 7300070. DOI: 10.1002/fsn3.1553. View

16.

Kurumbail R, Stevens A, Gierse J, McDonald J, Stegeman R, Pak J . Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 1996; 384(6610):644-8. DOI: 10.1038/384644a0. View

17.

Abdel-Sattar E, Kutkat O, El-Shiekh R, El-Ashrey M, El Kerdawy A . In Silico and In Vitro Screening of Some Pregnane Glycosides Isolated from Certain Caralluma Species as SARS-COV-2 Main Protease Inhibitors. Chem Biodivers. 2024; 21(4):e202301786. DOI: 10.1002/cbdv.202301786. View

18.

Chan K, Mohamad K, Ooi A, Imiyabir Z, Chung L . Bioactivity-guided fractionation of the lipoxygenase and cyclooxygenase inhibiting constituents from Chisocheton polyandrus Merr. Fitoterapia. 2012; 83(5):961-7. DOI: 10.1016/j.fitote.2012.04.018. View

19.

Subsongsang R, Jiraungkoorskul W . An Updated Review on Phytochemical Properties of "Golden Dewdrop" . Pharmacogn Rev. 2017; 10(20):115-117. PMC: 5214555. DOI: 10.4103/0973-7847.194042. View

20.

Ghith A, Youssef K, Ismail N, Abouzid K . Design, synthesis and molecular modeling study of certain VEGFR-2 inhibitors based on thienopyrimidne scaffold as cancer targeting agents. Bioorg Chem. 2018; 83:111-128. DOI: 10.1016/j.bioorg.2018.10.008. View