Antibacterial, Antioxidant, and Cytotoxic Flavonoid Compound from Sterculia Quadrifida Leaves
doi.org/10.26538/tjnpr/v5i11.15
Keywords:
Sterculia quadrifida, aurone, antibacterial, antioxidant, cytotoxicAbstract
Sterculia quadrifida is empirically used as a medicinal plant. The leaves of the plant are reported to have anti-infective, antioxidant, and anti-cancer activities. This study aims to identify active compounds from the plant leaves by bioassay-guided isolation. S. quadrifida leaves were extracted with 80% methanol, then partitioned with n-hexane, chloroform, ethyl acetate, n-butanol, and insoluble n-butanol fractions by liquid-liquid partition. Purification of compoundswas done using preparative HPLC, identification and structure elucidation were by comprehensive spectroscopic analyses. The in vitro antioxidant assay of the isolated compound was investigated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), nitric oxide (NO), and hydrogen peroxide (H2O2) radical scavenging methods. The in vitro antibacterial assay was done using the microdilution method. The in vitro cytotoxic effect of the compound was investigated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The isolation results from the n-butanol fraction found a new aurone compound named (2E)‐2‐[(3,4-dihydroxy phenyl)(hydroxy)methylidene]‐4,6‐dihydroxy‐2,3‐dihydro‐1-benzofuran‐3‐one. The antioxidant assay results showed IC50 values of 46.36, 38.41, 37.85, and 20.50 μg/mL in the DPPH, ABTS, NO, and H2O2 assays, respectively. The antibacterial assay results showed IC50 values of 23.38, 26.22, 58.45, 100.92, 103.14, and 193.98 μg/mL against P. aureginosa, H. pylori, S. bovis, S. aureus, S. thypi, E. coli, respectively. The cytotoxicity assay showed IC50 values of 4.05, 12.53, 15.38, and 25.91 μg/mL against breast cancer cell lines (4T1, MCF7, MDA-MB-435, and T47D). The aurone compound could be developed as a potential antibacterial, antioxidant, and cytotoxic agent.
References
El-Sherei MM, Ragheb AY, Kassem MES, Marzouk MM, Mosharrafa SA, Saleh NAM. Phytochemistry, biological activities and economical uses of the genus Sterculia and the related genera: A reveiw. Asian Pac J Trop Dis. 2016; 6(6):492-501.
Pandit P, Teli MD, Singha K, Maiti S, Maity S. Extraction and characterization of novel Sterculia foetida fruit shell fibre for composite applications. Clean Eng Technol. 2021; 4 (2):10-15.
Rollando R. Hedyotis corymbosa L. and Sterculia quadrifida R.Br ethanolic extract enhances cisplatin’s cytotoxicity on t47d breast cancer cells through cell cycle modulation. J Pure Appl Chem Res. 2018; 7(2):159-171.
Rollando R, Engracia M, Monica E, Siswadi S. Immunomodulatory activity test of syrup dosage form of combination Phyllantus niruri linn. and Sterculia quadrifida R.br. extract. Int J Res Pharm Sci. 2020; 11(1):191-199.
Rollando R, Sitepu R, Eva M. Cytotoxic activity of 2-iminoethyl 2-(2-(1-hydroxypentan-2-yl) phenyl) acetate from Sterculia quadrifida R. Br
ethyl acetate fraction. J Glob Pharm Technol. 2018; 10(6):204-212.
Rollando R and Alfanaar R. Isolation of naphtoquinone derivatives from faloak bark (Sterculia quadrifida r.br) and assay of anticancer
activity on T47D breast cancer cells. CAKRA Kim Indones E-J Appl Chem. 2017; 5(1):12-17.
Siswadi S and Saragih GS. Acute tocixity of Sterculia quadrifida R.br bark ethanol extract on sprague-dawley rats. Maj Obat Tradis. 2018;
(2):127-134.
Rollando R. Determination of total phenolic content and antioxidant activity test of water fraction methanol extract of faloak bark (Sterculia
quadrifida r.br). Sci J Farm dan Kesehat. 2018; 8(1):30-36.
Astuti P, Rollando R, Wahyuono S, Nurrochmad A. Antimicrobial activities of isoprene compounds produced by an endophytic fungus
isolated from the leaves of Coleus amboinicus Lour. J Pharm Pharmacogn Res. 2020; 8(4):280-289.
Dzoyem JP, Tchamgoue J, Tchouankeu JC, Kouam SF, Choudhary MI, Bakowsky U. Antibacterial activity and cytotoxicity of
flavonoids compounds isolated from Pseudarthria hookeri Wight & Arn. (Fabaceae). South Afr J Bot. 2018; 2 (114): 100-103.
Cain R, Narramore S, McPhillie M, Simmons K, Fishwick CWG. Applications of structure-based design to antibacterial drug discovery. Bio Chem. 2014; 55(2):69–76.
Fidrianny I, Harnovi M, Insanu M. Evaluation of antioxidant activities from various extracts of sweet orange peels using dpph, frap assays and correlation with phenolic, flavonoid, carotenoid content. Asian J Pharm Clin Res. 2014; 16 (4):186–190.
Kosakowska O, Bączek K, Przybył JL, PióroJabrucka E, Czupa W, Synowiec A, Węglarz Z. Antioxidant and antibacterial activity of roseroot (Rhodiola rosea L.) dry extracts. Molecules. 2018; 23(7):18-23.
Wojdyło A, Samoticha J, Chmielewska J. Effect of different pre-treatment maceration techniques on the content of phenolic compounds and color of Dornfelder wines elaborated in cold climate. Food Chem. 2021; 339 (3): 127-132.
Zuriarrain-Ocio A, Zuriarrain J, Vidal M, Dueñas MT, Berregi I. Antioxidant activity and phenolic profiles of ciders from the Basque Country. Food Bio. 2021; 41(3): 10-18.
Segun PA, Ogbole OO, Ismail FMD, Nahar L, Evans AR, Ajaiyeoba EO, Sarker SD. Bioassayguided isolation and structure elucidation of
cytotoxic stilbenes and flavonols from the leaves of Macaranga barteri. Fitoter. 2019; 134(2):151–157.
Mai NTT, Hai NX, Phu DH, Trong PNH, Nhan NT. Three new geranyl aurones from the leaves of Artocarpus altilis. Phytochem Lett. 2012;
(3):647-650.
Yahiaoui S, Peuchmaur M, Boumendjel A. A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class
of natural products into another. Tetrahedron. 2011; 67(40):7703-7707.
Huang H-Q, Li H-L, Tang J, Lv Y-F, Zhang W-D. A new aurone and other phenolic constituents from Veratrum schindleri Loes. f. Biochem Syst Ecol. 2008; 36(7):590-592.
Miller A and Solomon PH. Writing Reaction Mechanisms in Organic Chemistry. Elsevier; 2012;2(1):34-93.
Deng M, Jia X, Dong L. Structural elucidation of flavonoids from Shatianyu (Citrus grandis L. Osbeck) pulp and screening of key antioxidant
components. Food Chem. 2022; 36 (6):13-19.
Owen RW, Haubner R, Mier W. Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. Food Chem Toxicol. 2003; 41(5):703-717.
Oppong MB, Zhang B-Y, Fang S-M, Qiu F. Secondary metabolites from Sterculia lychnophora Hance (Pangdahai). Biochem Syst
Ecol. 2020; 92 (1):14-19.
Chen M, Su S, Zhou Q. Antibacterial and antiviral activities and action mechanism of flavonoid derivatives with a benzimidazole moiety. J Saudi Chem Soc. 2021; 25(2):10-17.
Ferreira EO, Salvador MJ, Pral EMF, Alfieri SC, Ito IY, Dias DA. A new heptasubstituted (E)-aurone glucoside and other aromatic compounds
of Gomphrena agrestis with biological activity. Z Naturforschung C J Biosci. 2004; 59(7-8):499-505.
Wu D, Kong Y, Han C. d-Alanine:d-alanine ligase as a new target for the flavonoids quercetin and apigenin. Int J Antimicrob Agents. 2008;
(5):421-426.
Al Muqarrabun LMR and Ahmat N. Medicinal uses, phytochemistry and pharmacology of family Sterculiaceae: A review. Eur J Med Chem. 2015; 92 (2):514-530.
Kumar S, Lathwal E, Kumar G. Synthesis of pyrazole based novel aurone analogs and their cytotoxic activity against MCF-7 cell line. Chem
Data Collect. 2020; 30 (4):15-19.
Huang L, Wall ME, Wani MC. New compounds with DNA strand-scission activity from the combined leaf and stem of Uvaria hamiltonii. J
Nat Prod. 1998; 61(4):446-450.
Suzuki K, Yahara S, Maehata K, Uyeda M. Isoaurostatin, a novel topoisomerase inhibitor produced by Thermomonospora alba. J Nat Prod.
; 64(2): 204-207.
Hassan GS, Georgey HH, George RF, Mohamed ER. Aurones and furoaurones: Biological activities and synthesis. Bull Fac Pharm Cairo
Univ. 2018; 56(2):121-127.
Alsayari A, Muhsinah AB, Hassan MZ, Ahsan MJ, Alshehri JA, Begum N. Aurone: A biologically attractive scaffold as anticancer
agent. Eur J Med Chem. 2019; 166 (2):417-431.
Huang W, Liu M-Z, Li Y, Tan Y, Yang G-F. Design, syntheses, and antitumor activity of novel chromone and aurone derivatives. Bioorg Med
Chem. 2007; 15(15):5191-5197.
Kafle A, Bhattarai S, Handy ST. The first synthesis of peracetyl glycosyl aurone derivatives and aurone glucosides. Tetrahedron. 2020;
(43):13-18.
Published
How to Cite
Issue
Section
License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
