Molecular Docking Simulation of Reported Phytochemical Compounds from Curculigo latifolia Extract on Target Proteins Related to Skin Antiaging
http://www.doi.org/10.26538/tjnpr/v7i11.9
Keywords:
Skin aging, Molecular Docking, Hypoxidaceae, Genus curculigoAbstract
Curculigo latifolia Dryand.Ex W. T. Alton is a plant reported to have antioxidant and anti-aging activities. Studies have shown the interaction of compounds from this plant with target proteins associated with antiaging in silico. This study therefore examines the in silico antiaging activity of selected compounds from Curculigo latifolia using unreported target proteins, including elastase, TNF-alpha, and Tyrosinase. Antiaging activity screening of these compounds was carried out in silico using AutoDock 14.0 software. A total of forty-six (46) compounds were successfully docked with each target protein. The results showed that the test compounds from C. latifolia have good interactions with the target proteins as indicated by their negative binding free energy values. Only a few of the test compounds had the most negative binding free energy values and interacted with the target proteins in a similar fashion as the native ligands. Compounds 4 (mundulone), 11 (orcinol glucoside), 12 (orcinol glucoside B), 14 (curculigoside B), 15 (curculigoside C), 23 (5,2,6-Trihydroxy-7,8 dimethoxyflavone-2-O-β-D-glucoside), 29 (aviprin), 30 (guaiacol), 34 (quercetin), 38 (monobenzone) and 42 (stigmastan-3,6-dione) were shown to have an inhibitory effect on one target protein, while, compounds 2 (pomiferin) and 40 (frangulin B) were predicted to interact with multitarget proteins. Compounds 2 and 40 tend to fulfill the Lipinski rule, pharmacokinetics, and toxicity requirements in silico and therefore could be developed for their potential use as antiaging molecules.
References
Zhang S and Duan E. Fighting against Skin Aging: The Way from Bench to Bedside. Cell Transplant. 2018; 27(5):729-738.
Yousef H, Alhajj M, Sharma S. Anatomy, Skin (Integument), Epidermis. Stat Pearls Publishing. 2020.
Nur S, Angelina AA, Aswad M, Yulianti R, Burhan A, Nursamsiar N. In vitro anti-aging activity of Muntingia calabura L. fruit extract and its fractions. J Pharm Pharmacogn Res. 2021; 9(4):409–421.
Kristianti MT, Goenawan H, Achadiyani A, Sylviana N, Lesmana R. The Potential Role of Vitamin D Administration in The Skin Aging Process Through The Inflammatory Pathway: A Systematic Review. Trop J Nat Prod Res. 2023; 7(4):2675–2681.
Soeratri W, Indrajaya S, Hariyadi DM. Ubiquinone-Nanostructured Lipid Carriers Hydrogel Mask for Antiaging: the Journey so Far. Trop J Nat Prod Res. 2020; 4(11):866–876.
Anggraini NB, Elya B, Iskandarsyah I. Antielastase Activity of Macassar Kernels (Rhus javanica) Stem Extract and Skin Elasticity Evaluation of Its Topical Gel Formulation. Adv Pharmacol Pharm Sci. 2021; 2021:6690029.
Lukitaningsih E, Nur S, Qonithah F, Zulbayu A, Kuswahyuning R, Rumiyati R. In vitro anti-wrinkle and tyrosinase inhibitory activities of grapefruit peel and strawberry extracts. Trad Med J. 2020; 25(3):182–189.
Nur S, Aswad M, Yulianty R, Burhan A, Khairi N, Sami FJ, Nursamsiar. The antioxidant and anti-ageing activity of lyophilisate kersen (Muntingia calabura L) fruit in vitro. Food Res. 2023; 7(2):23-30.
Azwanida ZN, Jonathan OE, Melanie-Jaynes H. Antioxidant, Anti-Collagenase, Anti-Elastase and Anti-Tyrosinase Activities of an Aqueous Cosmos caudatus Kunth (Asteraceae) Leaf Extract. Trop J Nat Prod Res. 2020; 4(12):1124–1130.
Purohit T, He T, Qin Z, Li T, Fisher GJ, Yan Y, Voorhees JJ, Quan T. Smad3-dependent regulation of type I collagen in human dermal fibroblasts: Impact on human skin connective tissue aging. J Dermatol Sci. 2016; 83(1):80-83.
Shin JW, Kwon SH, Choi JY, Na JI, Huh CH, Choi HR, Park KC. Molecular Mechanisms of Dermal Aging and Antiaging Approaches. Int J Mol Sci. 2019; 20(9):2126.
Snezhkina AV, Kudryavtseva AV, Kardymon OL, Savvateeva MV, Melnikova NV, Krasnov GS, Dmitriev AA. ROS Generation and Antioxidant Defense Systems in Normal and Malignant Cells. Oxid Med Cell Longev. 2019; 2019:6175804.
Oh YS, Shin SY, Kim S, Lee KH, Shin JC, Park KM. Comparison of antiaging, anti-melanogenesis effects, and active components of Raspberry (Rubus occidentalis L.) extracts according to maturity. J Food Biochem. 2020; 4(11):e13464.
Rittié L and Fisher GJ. Natural and sun-induced aging of human skin. Cold Spring Harb Perspect Med. 2015; 5(1):a015370.
Kim M and Park HJ. Molecular Mechanisms of Skin Aging and Rejuvenation. In Molecular Mechanisms of the Aging Process and Rejuvenation. Intechopen. 2016.
Kim YH, Chung CB, Kim JG, Ko KI, Park SH, Kim JH, Eom SY, Kim YS, Hwang YI, Kim KH. Anti-wrinkle activity of ziyuglycoside I isolated from a Sanguisorba officinalis root extract and its application as a cosmeceutical ingredient. Biosci Biotechnol Biochem. 2008; 72(2):303-311.
Apak R, Capanoglu E, Shahidi F. Electron transfer-based antioxidant capacity assays and the cupric ion reducing antioxidant capacity (CUPRAC) assay. In: Measurement of Antioxidant Activity & Capacity (eds R. Apak, E. Capanoglu and F. Shahidi). 2017; 57-75p.
Apak R, Güçlü K, Ozyürek M, Bektaşoğlu B, Bener M. Cupric ion reducing antioxidant capacity assay for antioxidants in human serum and for hydroxyl radical scavengers. Methods Mol Biol. 2010; 594:215-239.
Solano F. Photoprotection and Skin Pigmentation: Melanin-Related Molecules and Some Other New Agents Obtained from Natural Sources. Molecules. 2020; 25(7):1537.
Michalak M. Plant-Derived Antioxidants: Significance in Skin Health and the Ageing Process. Int J Mol Sci. 2022; 23(2):585.
Hoang HT, Moon J-Y, Lee Y-C. Natural Antioxidants from Plant Extracts in Skincare Cosmetics: Recent Applications, Challenges and Perspectives. Cosmetics. 2021; 8(4):106.
Petruk G, Del Giudice R, Rigano MM, Monti DM. Antioxidants from Plants Protect against Skin Photoaging. Oxid Med Cell Longev. 2018; 2018:1454936.
Nur S, Setiawan H, Hanafi M, Elya B. In vitro ultra violet ( UV ) protection of Curculigo latifolia extract as a sunscreen candidate. IOP Conf. Series: Earth and Environmental Science. 2022.
Nur S, Hanafi M, Setiawan H, Nursamsiar, Elya B. In silico evaluation of the dermal antiaging activity of Molineria latifolia (Dryand. ex W.T. Aiton) Herb. Ex Kurz compounds. J Pharm Pharmacogn Res. 2023; 11(2):325–345.
Mad Nasir N, Ezam Shah NS, Zainal NZ, Kassim NK, Faudzi SMM, Hasan H. Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia. Plants (Basel). 2021; 10(8):1488.
Wang Y, Li J, Li N. Phytochemistry and Pharmacological Activity of Plants of Genus Curculigo: An Updated Review Since 2013. Molecules. 2021; 26(11):3396.
Zabidi NA, Ishak NA, Hamid M, Ashari SE. Subcritical Water Extraction of Antioxidants from Curculigo latifolia Root. J Chem. 2019; 2019:8047191.
Zabidi NA, Ishak NA, Hamid M, Ashari SE, Latif MAM. Inhibitory evaluation of Curculigo latifolia on α-glucosidase, DPP (IV) and in vitro studies in antidiabetic with molecular docking relevance to type 2 diabetes mellitus. J Enzyme Inhib Med Chem. 2021; 36(1):109-121.
Asnawi A, Nedja M, Febrina E, Purwaniati P. Prediction of a Stable Complex of Compounds in the Ethanol Extract of Celery Leaves (Apium graveolens L.) Function as a VKORC1 Antagonist. Trop J Nat Prod Res. 2023; 7(2):2362–2370.
Nursamsiar, Siregar M, Awaluddin A, Nurnahari N, Nur S, Febrina E, Asnawi A. Molecular docking and molecular dynamic simulation of the aglycone of curculigoside a and its derivatives as alpha glucosidase inhibitors. Rasayan J Chem. 2020; 13(1):690-698.
Nursamsiar, Nur S, Febrina E, Asnawi A, Syafiie S. Synthesis and Inhibitory Activity of Curculigoside A Derivatives as Potential Anti-Diabetic Agents with β-Cell Apoptosis. J Mol Struct. 2022; 1265:133292.
Kontoyianni M, McClellan LM, Sokol GS. Evaluation of docking performance: comparative data on docking algorithms. J Med Chem. 2004; 47(3):558-565.
Muflihunna A and Sukmawati S. In silico study of java wood ( Lannea coromadelica ) as anti- inflammatory in tnf-α and cox-2 mediators. Indon J Pharm Sci Technol. 2023; 1(1):42-50.
Suharti N, Sari MR, Dillasamola D, Putra PP. In Silico and In Vitro Study of The Ethanol Extract of The White Garland Lily (Hedychium coronarium J. Koenig) as a Tyrosinase Inhibitor. Trop J Nat Prod Res. 2023; 7(6):3125–3129.
Adetobi ET, Akinsuyi SO, Ahmed OA, Folajimi EO, Babalola BA. In silico Evaluation of the Inhibitory Potential of Cymbopogonol from Cymbopogon citratus Towards Falcipain-2 (FP2) Cysteine Protease of Plasmodium falciparum. Trop J Nat Prod Res. 2022; 6(10):1687–1684.
Pratami MP, Fendiyanto MH, Satrio RD, Nikmah IA, Awwanah M, Farah N, Sari NIP, Nurhadiyanta. In-silico Genome Editing Identification and Functional Protein Change of Chlamydomonas reinhardtii Acetyl-CoA Carboxylase (CrACCase). Jordan J Biol Sci. 2022; 15(3):431-440.
Savitri AD, Hidayati HB, Veterini L, Widyaswari MS, Muhammad AR, Fairus A, Zulfikar MQB, Astri M, Ramasima NA, Anggraeni DP, Nainatika RSA, Juliana. An In-Silico Study on Allicin Compound in Garlic (Allium Sativum) as A Potential Inhibitor of Human Epidermal Growth Factor Receptor (Her)-2 Positive Breast Cancer. Jordan J Biol Sci. 2023; 16(1):7-12.
Chen D, Oezguen N, Urvil P, Ferguson C, Dann SM, Savidge TC. Regulation of protein-ligand binding affinity by hydrogen bond pairing. Sci Adv. 2016; 2(3):e1501240.
Muslimin L, Zainal TH, Hardianti B, Megawati M, Marwati M. Effect of Solvent Extraction on Antityrosinase and Sun Protection Factor of Mulberry (Morus alba L.) Cultivated in Wajo, Indonesia. Trop J Nat Prod Res. 2023; 7(6):3114–3118.
Tims M. Review of Isolation, Identification and Characterization of Allelochemicals/Natural Products. J Nat Prod. 2017.
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2001; 46(1-3):3-26.
Adianingsih OR, Khasanah U, Anandhy KD, Yurina V. In silico ADME-T and molecular docking study of phytoconstituents from Tithonia diversifolia (Hemsl.) A. Gray on various targets of diabetic nephropathy. J Pharm Pharmacogn Res. 2022; 10(4):571–594.
Riwu AG, Nugraha J, Purwanto DA, Triyono EA. In silico analysis of anti-dengue activity of faloak (Sterculia quadrifida R. Br) stem bark compounds. J Pharm Pharmacogn Res. 2022; 10(6):1006–1014.
Sun L, Yang H, Li J, Wang T, Li W, Liu G, Tang Y. In Silico Prediction of Compounds Binding to Human Plasma Proteins by QSAR Models. Chem Med Chem. 2018; 13(6):572-581.
Yuan Y, Chang S, Zhang Z, Li Z, Li S, Xie P, Yau WP, Lin H, Cai W, Zhang Y, Xiang X. A novel strategy for prediction of human plasma protein binding using machine learning techniques. Chemomet Intell Lab Syst. 2020; 199:103962.
Lynch T and Price A. The effect of cytochrome P450 metabolism on drug response, interactions, and adverse effects. Am Fam Physician. 2007; 76(3):391-396.
Youdim KA, Zayed A, Dickins M, Phipps A, Griffiths M, Darekar A, Hyland R, Fahmi O, Hurst S, Plowchalk DR, Cook J, Guo F, Obach RS. Application of CYP3A4 in vitro data to predict clinical drug-drug interactions; predictions of compounds as objects of interaction. Br J Clin Pharmacol. 2008; 65(5):680-692.
Ooi DJ, Chan KW, Sarega N, Alitheen NB, Ithnin H, Ismail M. Bioprospecting the Curculigoside-Cinnamic Acid-Rich Fraction from Molineria latifolia Rhizome as a Potential Antioxidant Therapeutic Agent. Molecules. 2016; 21(6):682.
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Tropical Journal of Natural Product Research (TJNPR)
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
