Secondary Metabolites from Usnea sp. and an Evaluation of Their Cytotoxic and Antibacterial Activities
DOI:
https://doi.org/10.21123/bsj.2024.9440Keywords:
Antibacterial, cytotoxicity, MCF-7 cells, secondary metabolites, Usnea sp.Abstract
The genus Usnea was reported to synthesize the bioactive secondary metabolites, including cytotoxic and antibacterial activities. To continue our study on bioactive compounds from Usnea sp, we studied secondary metabolites and their bioactivities of Usnea sp. The aim of this study was to determine the chemical constituents of lichen Usnea sp. Methanol extract of Usnea sp. was prepared by solid liquid extraction followed by fractionation and purification of the crude extract by several chromatographic techniques using n-hexane and ethyl acetate as solvents to obtain two pure compounds (1 and 2). The structures of both secondary metabolites were analyzed by 1D and 2D (one and two-dimensional) NMR spectroscopy and identified as 2,6-dihydroxy-4-methylbenzoic acid (1) and (-)-placodiolic acid (2). Cytotoxic activity of compounds against MCF-7 cells was evaluated using the MTT assay (IC50 = 554.82 and 5.10 µM, respectively). Both compounds were also assayed for their antibacterial activity using disc diffusion method. Inhibition zones of compound 1 against S. aureus, E. coli, and S. pyogenes were 6.37 ± 0.21, 7.57 ± 0.15, and 5.43 ±0.12 mm, respectively. In addition, compound 2 inhibited the growth of S. aureus, E. coli, and S. pyogenes bacteria (Inhibition zones = 10.43 ± 0.25, 11.63 ± 0.21, and 10.63 ± 0.21). The result of biological activities demonstrated that 2 exhibited stronger cytotoxic activity against MCF-7 cells as well as antibacterial activity than compound 1. Based on the theses results, compound 2 could be a promising candidate of antibiotics in the near future.
Received 13/09/2023
Revised 15/03/2024
Accepted 17/03/2024
Published Online First 20/08/2024
References
Jannah M, Afifah N, Hariri MR, Rahmawati A, Wulansari TYI. Study of Lichen (Usnea spp.) As A Traditional Medicine in Bogor, West Java. Berkala Penelitian Hayati. 2020; 26(1): 32-38. https://doi.org/10.23869/bphjbr.26.1.20206
Sepahvand A, Studzińska-Sroka E, Ramak P, Karimian V. Usnea sp. Antimicrobial potential, bioactive compounds, ethnopharmacological uses and other pharmacological properties; a review article. J Ethnopharmacol. 2021; (268):113656. https://doi.org/10.1016/j.jep.2020.113656
Jannah M, A`yun Q, Afifah N, Prasetya E, Hariri MR. Usnea in West Java: a potential source of bioactive secondary metabolites. Berk Penelit Hayati. 2022; 28: 26–31. https://doi.org/10.23869/bphjbr.28.1.20224
Gerlach A, Clerc P, Lücking R, Moncada B, Nobleza JC, Ohmura Y, et al. The genus Usnea (Parmeliaceae, Ascomycota) in the Southern Philippines: A First Phylogenetic Approach. The Lichenologist. 2023; 55(6): 451-480. https://doi.org/10.1017/S0024282923000579
Popovici V, Matei E, Cozaru GC, Aschie M, Bucur L, Rambu D, et al. Usnic acid and Usnea barbata (L.) F.H. wigg. dry extracts promote apoptosis and DNA damage in human blood cells through enhancing ROS levels. Antioxidants. 2021; 10(8): 1171. https://doi.org/10.3390/antiox10081171
Salgado F, Albornoz L, Cortéz C, Stashenko E, Urrea-Vallejo K, Nagles E, et al. Secondary metabolite profiling of species of the genus Usnea by UHPLC-ESI-OT-MS-MS. Molecules. 2018; 23(1): 54. https://doi.org/10.3390/molecules23010054
Vu TH, Le Lamer AC, Lalli C, Samson JBM, Le Dévéhat FL, Le Seyec J. Depsides: Lichen metabolites active against hepatitis C virus. PLoS One. 2015; 10(3): 1–14. https://doi.org/10.1371/journal.pone.0120405
Dieu A, Mambu L, Champavier Y, Chaleix V, Sol V, Gloaguen V, et al. Antibacterial Activity of the Lichens Usnea Florida and Flavoparmelia caperata. Parmeliaceae. 2020; 34(23): 3358-3362. https://doi.org/10.1080/14786419.2018.1561678
Oh JM, Kim YJ, Gang HS, Han J, Ha HH, Kim H. Antimicrobial activity of divaricatic acid isolated from the lichen Evernia mesomorpha against methicillin-resistant Staphylococcus aureus. Molecules. 2018; 23(12): 1-9. https://doi.org/10.3390/molecules23123068
Yu X, Guo Q, Su G, Yang A, Hu Z, Qu C, et al. Usnic acid derivatives with cytotoxic and antifungal activities from the lichen Usnea longissimi. J Nat Prod. 2016; 79(5): 1373–1380. https://doi.org/10.1021/acs.jnatprod.6b00109
Maulidiyah M, Darmawan A, Ahmad E, Musdalifah A, Wibowo D, Salim LOA, et al. Antioxidant activity-guided isolation of usnic acid and diffractaic acid compounds from lichen genus Usnea sp. J Appl Pharm Sci. 2021; 11(02): 075–083. http://dx.doi.org/10.7324/JAPS.2021.110210
Maulidiyah Sabarwati SH, Harjuliarto R, Watoni AH, Nurdin M. Antibacterial activity of usnic acid from Usnea longissima Ach. Pak. J Pharm Sci. 2020; 33(4): 1631. http://dx.doi.org/10.36721/PJPS.2020.33.4.REG.1631-1639.1
Maulidiyah M, Natsir M, Nazila W, Musdalifah A, Salim OA, Nurdin M. Isolation and antibacterial activity of diffractic acid compound from lichen Usnea blepharea Motyka. J Appl Pharm Sci. 2021; 11(11): 121–130. http://dx.doi.org/10.7324/JAPS.2021.1101116
Maulidiyah M, Azis T, Sabarwati SH, Nurdin M. Isolation and Identification of (-)-usnic acid compound from lichen Usnea sp. and its cytotoxic activity on murine leukemia P388 Cell. Jurnal Ilmu Kefarmasian Indonesia. 2015; 13(1): 40-44. http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/121
Tuong TL, Do LTM, Aree T, Wonganan P, Chavasiri W. Tetrahydroxanthone–chromanone heterodimers from lichen Usnea aciculifera and their cytotoxic activity against human cancer cell lines. Fitoterapia. 2020; 147: 104732. https://doi.org/10.1016/j.fitote.2020.104732
Riga R, Happyana N, Hakim EH. Chemical constituents of Pestalotiopsis microspora HF 12440. J Appl Pharm Sci. 2019; 9(1): 108-124. http://dx.doi.org/10.7324/JAPS.2019.90116
Herlina T, Merlin, Azlan M, Supratman U. Cytotoxic constituents from the bark of Erythrina poeppigiana against the MCF-7 breast cancer cell lines. J Nat Prod. 2019; 10(3): 257–261. http://dx.doi.org/10.2174/2210315509666191115152811
Riga R, Happyana N, Hakim EH. Sesquiterpenes produced by Pestalotiopsis microspora HF 12440 isolated from Artocarpus heterophyllus. Nat Prod Res. 2020; 34(15): 2229-2231. https://doi.org/10.1080/14786419.2019.1578764
Roesman DI, Tjong DH, Hanif MM. Cytotoxic Activities, Determining Toxin, and Molecular Docking of Ovary Pufferfish (Tetraodon leiurus) in Singkarak Lakeas Cancer Chemoprevention Candidate. Baghdad Sci J. 2023; 20(6): 2372-2384. https://doi.org/10.21123/bsj.2023.8785
Suryelita S, Riga R, Etika SB, Ikhsan MH, Febria F, Yolanda M, et al. Phytochemical Screening and Biological Activities of Fungal Phyllosticta capitalensis derived from Andrographis paniculata. Mor J Chem. 2023; 11(2): 553-565. https://doi.org/10.48317/IMIST.PRSM/morjchem-v11i2.33657
Hussein NN, Marzoog TR, Al-Niaame AE. The Antibacterial, Antiheamolytic, and Antioxidant Activities of Laurus nobilis and Alhagi maurorum Native to Iraq. Baghdad Sci J. 2019; 16(3): 707-712. https://doi.org/10.21123/bsj.2019.16.3(Suppl.).0707
Bui VM, Huynh BLC, Pham NKT, Nguyen TAT, Nguyen TTT, Nguyen KPP, et al. Usneaceratins A and B, two new secondary metabolites from the lichen Usnea ceratina. Nat Prod Res. 2022; 36(15): 3945–3950. https://doi.org/10.1080/14786419.2021.1901288
Chae H-J, Kim G-J, Deshar B, Kim H-J, Shin M-J, Kwon H, et al. Anticancer activity of 2-O-caffeoyl alphitolic acid extracted from the lichen, Usnea barbata 2017-kl-10. Molecules. 2021; 26(13): 1–12. https://doi.org/10.3390/molecules26133937
Lee J, Lee J, Kim GJ, Yang I, Wang W, Nam JW, et al. Mycousfurans A and B, antibacterial usnic acid congeners from the fungus Mycosphaerella sp., isolated from marine sediment. Mar Drugs. 2019; 17(7). https://doi.org/10.3390/md17070422
Millot M, Kaouadji M, Champavier Y, Gamond A, Simon A, Chulia AJ. Usnic acid derivatives from Leprocaulon microscopicum. Phytochem Lett. 2013; 6(1): 31–35. https://doi.org/10.1016/j.phytol.2012.10.009
Lee J, Lee J, Kim GJ, Yang I, Wang W, Nam J-W, et al. Mycousfurans A and B, antibacterial usnic acid congeners from the fungus Mycosphaerella sp., isolated from marine sediment. Marine Drugs. 2019; 17(7): 422. https://doi.org/10.3390/md17070422
Bahuguna A, Khan I, Bajpai VK, Kang SC. MTT assay to evaluate the cytotoxic potential of a drug. Bangladesh J Pharmacol. 2017; 12(2): 115–118. http://dx.doi.org/10.3329/bjp.v12i2.30892
Downloads
Issue
Section
License
Copyright (c) 2024 Dewi Meliati Agustini, Riga Riga, Elvira Hermawati, Budi Saputra
This work is licensed under a Creative Commons Attribution 4.0 International License.