Complex compound with transitional metal of Akway Bark (Drimys piperita Hook f.) as low molecular weight scavenging antioxidant: a computational study

Hostalige Hutasoit, Dionysius Joseph Djoko, Sutiman B Sumitro, Simon Bambang Widjanarko

Abstract


Akway (Drimys piperita Hook f.) was known as an endogenous plant of Indonesia. This plant was investigated as free radical scavenger based on paramagnetic properties. This study aimed to identify the bioactive compound and the role of Fe metals ions to enhance the free radical scavenger capacity as Low molecular weight antioxidant (LWMA) of akway. This study was designed by ultra-performance liquid chromatography (UPLC) coupled with ultra-high-resolution time of flight-mass spectrometry detector (TOF-MS), docking (Pyrex and Discovery Studio 2016 Client) and pharmacokinetic properties prediction (SwissADME). UPLC-TOF-MS analysis showed that herbal akway bark has five molecular formula (C4H3N10O21-, C14H19N4O91-, C4H7N6O51-, C15H28NO31+, and C23H32NO71+). The docking was illustrated the complex binding akway formula with Fe and its role as a metal donor and metal acceptor. It also confirmed on pharmacokinetics properties prediction which molecular compounds of akway have aqueous solubility. It meant the herbal akway bark complexed to Fe could be a low molecular weight antioxidant and it could be escalated free radical scavenger capacity.


Keywords


akway, antioxidant, endogenous plant, herbal medicine, metal donor, metal acceptor, molecular formula

Full Text:

PDF

References


Santos-Sánchez NF, Salas-Coronado R, Villanueva-Cañongo C, Hernández-Carlos B (2019) Antioxidant Compounds and Their Antioxidant Mechanism. Intech Open. 1-28. doi: 10.5772/intechopen.85270.

Grammenandi K, Kyriazi M, Katsarou-Katsari A, Papadopoulos O, Anastassopoulou I, Papaioannou GT, Sagriotis A, Rallis M, Maibach HI (2016) Low-Molecular-Weight Hydrophilic and Lipophilic Antioxidants in Nonmelanoma Skin Carcinomas and Adjacent Normal-Looking Skin. Skin Pharmacol Physiol 2016 (29): 324-331. doi :10.1159/000453456.

Saljoughian M (2008) An Overview of Antioxidants. US Pharm. 33( 10):HS-22-HS-28.

Shahidi F, Ambigaipalan P (2015) Phenolics and polyphenolics in foods, beverages and spices: Antioxidant activity and health effects – A review, Journal of Functional Foods, 18 ( Part B) : 820-897. doi :10.1016/j.jff.2015.06.018.

Cepeda GN, Lisangan MM, Silamba I (2019) Aktivitas Antibakteri Minyak Atsiri Kulit Kayu Akway (Drimys piperita Hook. f.) pada Beberapa Tingkat Konsentrasi, Keasaman (pH) dan Kandungan Garam. Jurnal Aplikasi Teknologi Pangan 149-154. doi : 10.17728/jatp.4692

Hutasoit H, Santjojo DJDH, Sumitro S B, Widjanarko S B (2019) Investigation of Paramagnetic Character in the Complex of Akway Bark (Drimys piperita Hook f.) as a Radical Scavenger. In Proceedings of the 2nd International Conference on Biosciences and Medical Engineering (ICBME2019) AIP Conf. Proc. 2155, 020052-1–020052-7. https://doi.org/10.1063/1.5125556.

Parubak AS (2013) Senyawa flavonoid yang bersifat antibakteri dari akway (Drimys becariana. Gibbs) Chem. Prog. 6 (1) : 34-37.

Ma F, Cui Q, Bai G (2019) Combining UPLC/Q-TOF-MS/MS With Biological Evaluation for NF-κB Inhibitors in Uyghur Medicine Althaea rosea Flowers. Frontiers in Plant Science 1975 (9) doi: 10.3389/fpls.2018.01975.

Xu M, Shao Q, Ye S, Li S, Wu M, Ding M (2017) Simultaneous extraction and identification of phenolic compounds in Anoectochilus roxburghii using microwave-assisted extraction combined with UPLC-Q-TOF-MS/MS and their antioxidant activities. Front. Plant Sci. 8:(1474) doi :10.3389/fpls.2017.01474.

Ye T, Hao YH, Yu L, Shi H, Reiter RJ, Feng YQ (2017) A simple, rapid method for determination of melatonin in plant tissues by UPLC Coupled with high resolution orbitrap mass spectrometry. Front. Plant Sci. 8:(64) doi :10.3389/fpls.2017.00064.

Widyarti S, Kamaruddin M, Aristyani S, Elvina M, Subagjo S, Rahayu T, Sumitro, SB (2019) Bioinorganic Chemistry and Computational Study of Herbal Medicine to Treatment of Tuberculosis. Intech Open. 1-20. doi: 10.5772/intechopen.90155.

Sumitro SB, Sukmaningsih AASA. Herbal medicine, radical scavenger and metal detoxification: Bioinorganic, complexity and nano science perspectives (2018) IOP Conference Series: Earth and Environmental Science 130:012003 doi: 10.1088/1755-1315/130/1/012003.

Sukmaningsih AASA, Permana S, Santjojo DJDH, Wardoyo AYP, Sumitro SB (2018) Investigating natural transition metal coordination anthocyanin complex in java plum (Syzygium cumini) fruit as free radical scavenging Rasayan Journal of Chemistry 11(3):1193-1203. doi : 10.31788/RJC.2018.1133047

Engwa GA. Free radicals and the role of plant phytochemicals as antioxidants against oxidative stress-related diseases (2018) In: Phytochemicals - Source of Antioxidants and Role in Disease Prevention doi: 10.5772/intechopen.76719.

Zielinska D, Zielinski H. (2009) Low molecular weight antioxiants and other biologically active components of buckwheat seeds. The European Journal of Plant Science and Biotechnology 3(1):29-38.

Deng S, West BJ, Jensen CJ (2013) UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit Journal of analytical methods in chemistry 710972. doi: 10.1155/2013/710972.

Pérez S, Tvaroška I (2014). Carbohydrate-protein interactions: molecular modeling insights. Advances in carbohydrate chemistry and biochemistry, (71): 9-136. doi: 10.1016/B978-0-12-800128-8.00001-7.

Jayanti GE, Widyarti S, Sabarudin A, Sumitro, SB (2018) Egg White Albumin Form Complex With Aspirin And Caffeine And Its Role As Free Radical Scavenger. Asian Journal of Pharmaceutical and Clinical Research, 11(7) : 340-344. doi : 10.22159/ajpcr.2018.v11i7.25440.

Wibowo S, Widyarti S, Sabarudin A, Soeatmadji DW, Sumitro SB (2019). The role of astaxanthin compared with metformin in preventing glycated human serum albumin from possible unfolding: a molecular dynamic study. Asian Journal of Pharmaceutical and Clinical Research 12(9): 276-282. doi: 10.22159/ajpcr.2019.v12i9.34617.

Feinstein WP, Brylinski M (2015) Calculating an optimal box size for ligand docking and virtual screening against experimental and predicted binding pockets. Journal of Cheminformatics, 7 (18) doi : 10.1186/s13321-015-0067-5.

Daina A, Michielin O, Zoete V (2017) SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep 7 (42717) doi: 10.1038/srep42717

Gondokesumo ME, Pardjianto B, Sumitro S B, Widowati W, Handono K (2019) Xanthones Analysis and Antioxidant Activity Analysis (Applying ESR) of Six Different Maturity Levels of Mangosteen Rind Extract (Garcinia mangostana Linn.) Pharmacognosy Journal 11(1): 369-373 doi : 10.5530/pj.2019.11.56

Wang L, Cui Q, Hou Y, Bai F, Sun J, Cao X, (2013) An integrated strategy of ultra-high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry and virtual screening for the identification of α-glucosidase inhibitors in acarviostatin-containing complex J. Chromatogr. A (1319) : 88–96 doi : 10.1016/j.chroma.2013.10.035

Jabeen E, Janjua N K, Ahmed S, Murtaza I, Ali T, Hameed S (2017) Radical scavenging propensity of Cu 2+, Fe 3+ complexes of flavonoids and in-vivo radical scavenging by Fe3+-primuletin. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 171 : 432–438. doi : 10.1016/j.saa.2016.08.035

Bren KL, EisenbergR, Gray H B (2015) Discovery of the magnetic behavior of hemoglobin: A beginning of bioinorganic chemistry. Proceedings of the National Academy of Sciences 112(43): doi:13123. 10.1073/pnas.

Bencini A, Faili P, Valtancoli, B, Bani, D (2010) Low Molecular Weight Compounds with Transition Metals as Free Radical Scavengers and Novel Therapeutic Agents. Cardiovascular & Hematological Agents in Medicinal Chemistry. 8(3): 128-146. doi: 10.2174/187152510791698389

Gupta SP (2018) Roles of metals in human health MOJ Bioorganic & Organic Chemistry. 2(5): 221-224. doi: 10.15406/mojboc.2018.02.00085

Abbaspour N, Hurrell R, Kelishadi R (2014) Review on iron and its importance for human health. Journal of research in medical sciences: the official journal of Isfahan University of Medical Sciences 19(2) : 164–174.

Cepeda G N, Santoso B B, Lisangan M M, Silamba I (2011) Komposisi kimia minyak atsiri kulit kayu akway (Drimys piperita Hook. F). Bionatura – Jurnal Ilmu-Ilmu Hayati dan Fisik 13(2): 117-123.




DOI: http://dx.doi.org/10.11594/jtls.11.03.02

Copyright (c) 2021 Journal of Tropical Life Science