A Novel Green Extraction and Molecular Docking Study: Effect of Native Cyclodextrins and Derivatives on the Extraction of Andrographolide from Andrographis paniculata (Burm.f.) Nees http://www.doi.org/10.26538/tjnpr/v7i10.21
Article Sidebar
Main Article Content
Abstract
Andrographolide (AP) is a sparingly water solubility bioactive compound from Andrographis paniculata. It exhibits several pharmacological activities. With respect to its hydrophobicity, the high-yield extract of AP is primarily obtained from organic solvents, which are considered as environmentally harmful substances. Therefore, the green extraction using an alternative solvent is eventually performed to obtain the highest AP extract. The objectives of this study are to investigate the extraction efficiency of AP using different types of cyclodextrins (CDs) in aqueous media and in silico molecular docking study of AP with the corresponding CDs. The cyclodextrin-assisted extraction of AP using alpha cyclodextrin (αCD), beta cyclodextrin (βCD), gamma cyclodextrin (γCD), methyl beta cyclodextrin (MβCD), trimethyl beta cyclodextrin (triMβCD) and hydroxypropyl beta cyclodextrin (HPβCD) at a concentration of 1 mM was investigated in aqueous media comparing with water and methanol by ultrasonication. The amount of AP in each extract was determined by an HPLC method. In screening process, HPβCD exhibited the highest extraction yield of AP compared with the other CDs. However, it was significantly lower than that in the methanolic extract (P < 0.05). Subsequently, the extraction of AP was performed as a function of HPβCD concentration. Increasing the concentration of HPβCD resulted to obtain the better extraction yield of AP comparing with a positive control of methanol (P < 0.05). In conclusion, the green extraction using HPβCD could be an alternative method to achieve a higher AP in the extract than that in the methanolic extract.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Hossain S, Urbi Z, Karuniawati H, Mohiuddin RB, Moh Qrimida A, Allzrag AMM, Ming LC, Pagano E, Capasso R. Andrographis paniculata (Burm. f.) Wall. ex Nees: An Updated Review of Phytochemistry, Antimicrobial Pharmacology, and Clinical Safety and Efficacy. Life (Basel). 2021; 11(4): 348.
Zhao J, Yang G, Liu H, Wang D, Song X, Chen Y. Determination of andrographolide, deoxyandrographolide and neoandrographolide in the Chinese herb Andrographis paniculata by micellar electrokinetic capillary chromatography. Phytochem. Anal. 2002; 13: 222–227.
Pramanick S, Banerjee S, Achari B, Das B, Sen Sr AK, Mukhopadhyay S, Neuman A, Prang´e T. Andropanolide and isoandrographolide, minor diterpenoids from Andrographis paniculata: structure and X-ray crystallographic analysis. J Nat Prod. 2006; 69: 403–405.
Dai Y, Chen SR, Chai L, Zhao J, Wang Y, Wang Y. Overview of Pharmacological Activities of Andrographis paniculata and its Major Compound Andrographolide. Crit Rev Food Sci Nutr. 2019; 59(Sup1): S17-29.
Jayakumar T, Hsieh CY, Lee JJ, Sheu JR. Experimental and Clinical Pharmacology of Andrographis paniculata and Its Major Bioactive Phytoconstituent Andrographolide. Evid Based Complement Altern Med. 2013; 2013: 846740.
Chua LS. Review on liver inflammation and antiinflammatory activity of Andrographis paniculata for hepatoprotection. Phytother Res. 2014; 28(11): 1589-1598.
Chemat F, Abert-Vian M, Fabiano-Tixier AS, Strube J, Uhlenbrock L, Gunjevic V, Cravotto G. Green extraction of natural products. Origins, current status, and future challenges, TrAC, Trends Anal Chem. 2019; 118: 248-263.
Kultys E, Kurek MA. Green Extraction of Carotenoids from Fruit and Vegetable Byproducts: A Review. Molecules. 2022; 27(2): 518.
Sixt M, Strube J. Systematic and Model-Assisted Evaluation of Solvent Based- or Pressurized Hot Water Extraction for the Extraction of Artemisinin from Artemisia annua L. Processes. 2017; 5(4): 86.
Kazlauskaite JA, Ivanauskas L, Bernatoniene J. Cyclodextrin-Assisted Extraction Method as a Green Alternative to Increase the Isoflavone Yield from Trifolium pratensis L. Extract. Pharmaceutics. 2021; 13(5): 620.
Terekhova IV, Hammitzsch-Wiedemann M, Shi Y, Sungthong B, Scriba GK. Investigation of the pH-dependent complex formation between beta-cyclodextrin and dipeptide enantiomers by capillary electrophoresis and calorimetry. J Sep Sci. 2010; 33(16): 2499-505.
Lee JU, Lee SS, Lee S, Oh HB. Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host-Guest Interactions in the Gas Phase and Condensed Phase. Molecules. 2020; 25(18): 4048.
Gidwani B, Vyas A. A Comprehensive Review on Cyclodextrin-Based Carriers for Delivery of Chemotherapeutic Cytotoxic Anticancer Drugs. Biomed Res Int. 2015; 2015: 198268.
Jansook P, Ogawa N, Loftsson T. Cyclodextrins: Structure, physicochemical properties and pharmaceutical applications. Int J Pharm. 2018; 535(1-2): 272-284.
Zhu QY, Zhang QY, Cao J, Cao W, Xu JJ, Peng LQ. Cyclodextrin-assisted liquid-solid extraction for determination of the composition of jujube fruit using ultrahigh performance liquid chromatography with electrochemical detection and quadrupole time-of-flight tandem mass spectrometry. Food Chem. 2016; 213: 485-493.
Xie J, Xu Y, Shishir MR, Zheng X, Chen W. Green extraction of mulberry anthocyanin with improved stability using β-cyclodextrin. J Sci Food Agric. 2019; 99(5): 2494-2503.
Mura P. Analytical techniques for characterization of cyclodextrin complexes in the solid state: A review. J Pharm Biomed Anal. 2015; 113: 226-238.
Rui C, Yuan Y, Cui L, Wang Z, Yue T. Cyclodextrin-assisted extraction of phenolic compounds: Current research and future prospects. Trends Food Sci Technol. 2018; 79: 19-27.
Boonma T, Nutho B, Sungthong B, Sripadung P, Rungrotmongkol T, Nunthaboot N. Molecular insights into complex formation between scandenin and various types of β-cyclodextrin. J Mol Liq. 2021; 344: 117774.
Department of Medical Sciences, Ministry of Public Health. Thai Herbal Pharmacopoeia 2016. Nonthaburi: The Agricultural Co-operative Federation of Thailand; 2016. 103-108 p.
Wongpituk P, Nutho B, Panman W, Kungwan N, Wolschann P, Rungrotmongkol T, Nunthaboot N. Structural dynamics and binding free energy of neral-cyclodextrins inclusion complexes: Molecular dynamics simulation, Mol. Simul. 2017; 43(13-16): 1356–1363.
Frisch A, Nielsen AB, Holder AJ. Gauss View Molecular Visualization Program. User Manual, Gaussian Inc., Pittsburg. 2001.
Ulkarni AS, Dias RJ, Ghorpade VS, Mali KK. Freeze-Dried Multicomponent Inclusion Complexes of Curcumin for Enhancement of Solubility and Anti-Inflammatory Activity. Trop J Nat Prod Res. 2020; 4(11): 887–894
.
Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem. 2009; (30): 2785–2791.
Weiner SJ, Kollman PA, Nguyen T, Case DA. An all atom force field for simulations of proteins and nucleic acids. J Comput Chem. 1986; 7(2): 230–252,
Gasteiger J, Marsili M. Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron. 1980; 36(22): 3219–3228.
Pettersen EF, Goddard TD, Huang CC, Meng EC, Couch GS, Croll TI, Morris JH, Ferrin TE. UCSF ChimeraX: Structure visualization for researchers, educators, and developers. Protein Sci. 2021; 30(1): 70-82.
PubChem [Internet]. Bethesda (MD): National Library of Medicine (US), National Center for Biotechnology Information; 2004-. PubChem Compound Summary for CID 5318517, Andrographolide; [Updated 2023 Aug. 18]. Available from: https://pubchem.ncbi.nlm.nih.gov/compound/Andrographolide
Saokham P, Muankaew C, Jansook P, Loftsson T. Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes. Molecules. 2018; 123(5): 1161.
Terekhova IV, Scriba GK. Study on complex formation of biologically active pyridine derivatives with cyclodextrins by capillary electrophoresis. J Pharm Biomed Anal. 2007; 45(4): 688-693.
Zhang Y, Sang J, Chen Ff, Sang J, Li CQ. β-Cyclodextrin-assisted extraction and green chromatographic analysis of Hibiscus sabdariffa L. anthocyanins and the effects of gallic/ferulic/caffeic acids on their stability in beverages. J Food Meas Charact. 2018; 12: 2475–2483.
Parmar I., Sharma S, Rupasinghe HPV. Optimization of β-cyclodextrin-based flavonol extraction from apple pomace using response surface methodology. J Food Sci Technol. 2015; 52: 2202–2210.
Del Valle EMM. Cyclodextrins and their uses: a review. Process Biochem. 2004; 39(9): 1033-1046.
Majumdar M, Misra TK, Roy DN. In vitro anti-biofilm activity of 14-deoxy-11,12-didehydroandrographolide from Andrographis paniculata against Pseudomonas aeruginosa. Braz J Microbiol. 2020; 51: 15–27.
Li Z, Li K, Teng M, Li M, Sui X, Liu B, Tian B, Fu Q. Functionality-related characteristics of hydroxypropyl-β-cyclodextrin for the complexation. J Mol Liq. 2022; 365:120105.