Journal of Multidisciplinary Applied Natural Science
an Open Access Journal
Scopus CiteScore 2025
2.1
Calculated on 05 May, 2025
SJR 2025
0.25
Powered by scimagojr.com
an Open Access Journal
2.1
Calculated on 05 May, 2025
0.25
Powered by scimagojr.com
https://doi.org/10.47352/jmans.2774-3047.462
Fitri Nurvita Sari
Harum Margasari
Leny Nur Fitriani
Novian Ilham Ramadhan
Muhammad Ulul ‘Azmi
Mulyadi Tanjung
Tjitjik Srie Tjahjandarie
Ratih Dewi Saputri
The Calophyllum genus, part of the Calophyllaceae family, produces xanthones as dominant secondary metabolites. Calophyllum biflorum M.R. Hend. & Wyatt-Sm. is an endemic plant of Kalimantan; however, the potential of its xanthone content and biological activity has never been explored. In this study, three known prenylated xanthones: gartanin (1), ananixanthone (2), and α-mangostin (3), were isolated from C. biflorum leaves. Their chemical structures were determined by HRMS and 1D/2D NMR. The antioxidant activities of xanthones 1–3 (via DPPH radical) and their cytotoxicity toward 4T1 breast cancer cells were assessed. Xanthones 1–2 showed strong DPPH activity (IC50: 4.40 and 34.34 µM, respectively). Gartanin (1) also exhibited moderate activity against 4T1 cells (IC50 =16.70 µM). These results indicate the prenylated xanthones from C. biflorum as antioxidant agents.
[1] S. Ferdosh. (2024). "The Extraction of Bioactive Agents from Calophyllum inophyllum L., and Their Pharmacological Properties". Scientia Pharmaceutica. 92 (1): 1-13. 10.3390/scipharm92010006.
DOI: https://doi.org/10.3390/scipharm92010006[2] J. Singh, V. Meshram, and M. Gupta. (2020)."Bioactive Natural Products in Drug Discovery". Springer, Singapore. 10.1007/978-981-15-1394-7.
DOI: https://doi.org/10.1007/978-981-15-1394-7[3] C. Ito, M. Itoigawa, Y. Mishina, V. C. Filho, F. Enjo, H. Tokuda, H. Nishino, and H. Furukawa. (2003). "Chemical Constituents of Calophyllum brasiliense. II. Structure of Three New Coumarins and Chemopreventive Activity of 4-Substituted Coumarins". Journal of Natural Products. 66 (3): 368-371. 10.1021/np0203640.
DOI: https://doi.org/10.1021/np0203640[4] C. H. Ma, B. Chen, H. Y. Qi, B. G. Li, and G. L. Zhang. (2004). "Two Pyranocoumarins from the Seeds of Calophyllum polyanthum". Journal of Natural Products. 67 (9): 1598-1600. 10.1021/np0499158.
DOI: https://doi.org/10.1021/np0499158[5] S. G. Cao, K. Y. Sim, and S. H. Goh. (1997). "Biflavonoids of Calophyllum venulosum". Journal of Natural Products. 60 (12): 1245-1250. 10.1021/np970303f.
DOI: https://doi.org/10.1021/np970303f[6] C. Y. Ragasa, V. Ebajo, M. M. De Los Reyes, E. H. Mandia, R. Brkljača, and S. Urban. (2015). "Triterpenes from Calophyllum inophyllum Linn". International Journal of Pharmacognosy and Phytochemical Research. 7 (4): 718-722.
[7] T. S. Tjahjandarie, W. A. S. Nugroho, H. Palgunadi, R. D. Saputri, and M. Tanjung. (2023). "Two New Chromanone Acids from the Stem Bark of Calophyllum peekelii". Natural Product Research. 37 (19): 3214-3219. 10.1080/14786419.2022.2062754.
DOI: https://doi.org/10.1080/14786419.2022.2062754[8] U. Hasanah, T. S. Tjahjandarie, and M. Tanjung. (2019). "Chromanone Acid Derivatives from the Stem Bark of Calophyllum incrassatum". IOP Conference Series: Earth and Environmental Science. 217 : 012010. 10.1088/1755-1315/217/1/012010
DOI: https://doi.org/10.1088/1755-1315/217/1/012010[9] N. N. Arif, N. Ahmat, R. D. Saputri, T. S. Tjahjandarie, and M. Tanjung. (2025). "Cytotoxic and Anti-Plasmodial Activities of Chromanone Acids from Calophyllum wallichianum Planch. & Triana". Advanced Journal of Chemistry A. 8 (9): 1468-1476. 10.48309/ajca.2025.499062.1764.
[10] R. D. Saputri, Tukiran, Suyatno, F. A. Wati, S. A. Dzulkarnain, M. Zakiyah, T. S. Tjahjandarie, and M. Tanjung. (2024). "Xanthine Oxidase Inhibitory Activity of Xanthones from Calophyllum pseudomole P. F. Stevens". Tropical Journal of Natural Product Research. 8 (1): 5932-5935. 10.26538/tjnpr/v8i1.31.
DOI: https://doi.org/10.26538/tjnpr/v8i1.31[11] T. S. Tjahjandarie, M. Tanjung, D. F. Rahmania, C. I. Rhidoma, and R. D. Saputri. (2021). "Calodioscurins A and B, Two New Isoprenylated Xanthones from the Stem Bark of Calophyllum dioscurii P. F. Stevens". Natural Product Research. 35 (7): 1153-1158. 10.1080/14786419.2019.1643864.
DOI: https://doi.org/10.1080/14786419.2019.1643864[12] M. Tanjung, F. Rachmadiarti, A. Prameswari, U. W. Agyani, R. D. Saputri, T. S. Tjahjandarie, and Y. M. Syah. (2018). "Airlanggins A-B, Two New Isoprenylated Benzofuran-3-Ones from the Stem Bark of Calophyllum soulattri". Natural Product Research. 32 (13): 1493-1498. 10.1080/14786419.2017.1380027.
DOI: https://doi.org/10.1080/14786419.2017.1380027[13] M. Tanjung, T. S. Tjahjandarie, R. D. Saputri, B. D. Kurnia, M. F. Rachman, and Y. M. Syah. (2021). "Calotetrapterins A-C, Three New Pyranoxanthones and Their Cytotoxicity from the Stem Bark of Calophyllum tetrapterum Miq". Natural Product Research. 35 (3): 407-412. 10.1080/14786419.2019.1634714.
DOI: https://doi.org/10.1080/14786419.2019.1634714[14] M. Tanjung, T. S. Tjahjandarie, R. D. Saputri, M. F. Aldin, and H. Purnobasuki. (2022). "Two New Pyranoxanthones from the Stem Bark of Calophyllum pseudomole P. F. Stevens". Natural Product Research. 36 (3): 822-827. 10.1080/14786419.2020.1808638.
DOI: https://doi.org/10.1080/14786419.2020.1808638[15] T. Liu, Z. Q. Zhang, X. Xiao, and X. Q. Li. (2022). "Bioassay-Guided Isolation of Antitumor Polyprenylphloroglucinols from Calophyllum polyanthum and Their Primary Mechanism". Biomedicine & Pharmacotherapy. 151 : 113129. 10.1016/j.biopha.2022.113129.
DOI: https://doi.org/10.1016/j.biopha.2022.113129[16] S. C. Tsai, Y. H. Liang, J. H. Chiang, F. C. Liu, W. H. Lin, S. J. Chang, W. Y. Lin, C. H. Wu, and J. R. Weng. (2012). "Anti-Inflammatory Effects of Calophyllum inophyllum L. in RAW264.7 Cells". Oncology Reports. 28 : 1096-1102. 10.3892/or.2012.1873.
DOI: https://doi.org/10.3892/or.2012.1873[17] C. T. A. Pires, R. B. L. Scondro, M. A. Brenzan, D. A. G. Cortez, V. L. D. G. Lopes, V. L. Siqueira, L. Cardoso-Filho, R. M. Goncalves, K. R. Caleffi-Ferracioli, and R. F. Cardoso. (2016). "Anti-Mycobacterium tuberculosis Activity of Calophyllum brasiliense Extracts Obtained by Supercritical Fluid Extraction and Conventional Techniques". Current Pharmaceutical Biotechnology. 17 (6): 532-539. 10.2174/1389201017666160114094723.
DOI: https://doi.org/10.2174/1389201017666160114094723[18] T. Karunakaran, N. S. Firouz, R. Santhanam, and V. Y. M. Jong. (2022). "Phytochemicals from Calophyllum macrocarpum Hook. f. and Its Cytotoxic Activities". Natural Product Research. 36 (2): 654-659. 10.1080/14786419.2020.1795658.
DOI: https://doi.org/10.1080/14786419.2020.1795658[19] C. Spino, M. Dodier, and S. Satheeswaran. (1998). "Anti-HIV Coumarins from Calophyllum Seed Oil". Bioorganic and Medicinal Chemistry Letters. 8 (24): 3475-3478. 10.1016/S0960-894X(98)00628-3.
DOI: https://doi.org/10.1016/S0960-894X(98)00628-3[20] N. H. Zamakshshari, G. C. L. Ee, I. S. Ismail, Z. Ibrahim, and S. H. Mah. (2019). "Cytotoxic Xanthones Isolated from Calophyllum depressinervosum and Calophyllum buxifolium with Antioxidant and Cytotoxic Activities". Food and Chemical Toxicology. 133 : 110800. 10.1016/j.fct.2019.110800.
DOI: https://doi.org/10.1016/j.fct.2019.110800[21] R. D. Saputri, R. Retnowati, U. Supratman, T. S. Tjahjandarie, and M. Tanjung. (2023). "Three Novel Quinolinone Alkaloids from the Leaves of Melicope denhamii". Natural Product Research. 37 (2): 197-203. 10.1080/14786419.2021.1960524.
DOI: https://doi.org/10.1080/14786419.2021.1960524[22] M. Tanjung, T. S. Tjahjandarie, M. F. Aldin, S. Mardhiyyah, R. D. Saputri, Y. M. Syah, and N. Ahmat. (2025). "Two New Flavonols from Macaranga inermis Pax & K. Hoffm". Natural Product Research. 39 (3): 498-505. 10.1080/14786419.2023.2272783.
DOI: https://doi.org/10.1080/14786419.2023.2272783[23] T. S. Tjahjandarie, M. F. Aldin, R. D. Saputri, and M. Tanjung. (2025). "Dihydrostilbenes from Macaranga javanica Müll. Arg. and Their Antiplasmodial Activity". Natural Product Research. 39 (19): 5437-5443. 10.1080/14786419.2024.2342555.
DOI: https://doi.org/10.1080/14786419.2024.2342555[24] E. Marliana, R. Hairani, T. S. Tjahjandarie, and M. Tanjung. (2018). "Antiplasmodial Activity of Flavonoids from Macaranga tanarius Leaves". IOP Conference Series: Earth and Environmental Science. 144 : 012011. 10.1088/1755-1315/144/1/012011
DOI: https://doi.org/10.1088/1755-1315/144/1/012011[25] M. Tanjung, I. Nurmalasari, A. K. Wilujeng, R. D. Saputri, F. Rachmadiarti, and T. S. Tjahjandarie. (2018). "Acronyculatin P, A New Isoprenylated Acetophenone from the Stem Bark of Acronychia pedunculata". Natural Product Sciences. 24 (4): 284-287. 10.20307/nps.2018.24.4.284.
DOI: https://doi.org/10.20307/nps.2018.24.4.284[26] M. Tanjung, M. F. Aldin, N. N. Arif, R. D. Saputri, N. Ahmat, and T. S. Tjahjandarie. (2025). "4-Propyl- and 4-Phenylcoumarins from Mesua lepidota T. Anderson and Their Cytotoxic Activity". Natural Product Research. 39 (20): 5874-5882. 10.1080/14786419.2024.2358526.
DOI: https://doi.org/10.1080/14786419.2024.2358526[27] R. D. Saputri, T. S. Tjahjandarie, and M. Tanjung. (2021). "Two Novel Coumarins and an Acetophenone Derivative from the Leaves of Melicope quercifolia". Natural Product Research. 35 (8): 1256-1261. 10.1080/14786419.2019.1644634.
DOI: https://doi.org/10.1080/14786419.2019.1644634[28] T. S. Tjahjandarie, M. Tanjung, R. D. Saputri, D. O. Rahayu, A. N. I. Gunawan, and M. F. Aldin. (2021). "Two New 2-Arylbenzofurans from Sesbania grandiflora and Their Cytotoxicity toward Cancer Cells". Natural Product Research. 35 (24): 5637-5642. 10.1080/14786419.2020.1821016.
DOI: https://doi.org/10.1080/14786419.2020.1821016[29] M. Tanjung, R. D. Saputri, and T. S. Tjahjandarie. (2014). "Antioxidant Activity of Two Isomeric Benzoxepins from the Stem Bark of Bauhinia aculeata". Journal of Chemical and Pharmaceutical Research. 6 (1): 705-708.
[30] N. F. N. Azmin, N. Ahmat, A. S. Kamarozaman, N. S. Sulaiman, J. Jalil, and M. Tanjung. (2025). "Flavonoids of Cynometra cauliflora, Their Plausible Biosynthetic Pathway and SAR Study Against DPPH Radicals". Malaysian Journal of Chemistry. 27 (1): 102-109. 10.55373/mjchem.v27i1.102.
DOI: https://doi.org/10.55373/mjchem.v27i1.102[31] T. S. Tjahjandarie, A. R. Setiawan, A. H. Zulfa, R. D. Saputri, N. Ahmat, and M. Tanjung. (2025). "Bioassay-Guided Isolation of Flavonoids from Flemingia macrophylla and Their Cytotoxic and Antioxidant Activities". Advanced Journal of Chemistry A. 8 (10): 1631-1639. 10.48309/ajca.2025.510870.1800.
[32] S. Mardhiyyah, M. Zakiyah, E. D. Renata, T. S. Tjahjandarie, U. Supratman, R. Retnowati, R. D. Saputri, and M. Tanjung. (2023). "Cytotoxic Activity of Xanthones from the Stem Bark of Cratoxylum sumatranum". Tropical Journal of Natural Product Research. 7 (9): 3908-3910. 10.26538/tjnpr/v7i9.9.
DOI: https://doi.org/10.26538/tjnpr/v7i9.9[33] B. T. D. Trinh, T. T. T. Quach, D. N. Bui, D. Staerk, L. D. Nguyen, and A. K. Jäger. (2017). "Xanthones from the Twigs of Garcinia oblongifolia and Their Antidiabetic Activity". Fitoterapia. 118 : 126-131. 10.1016/j.fitote.2017.03.003.
DOI: https://doi.org/10.1016/j.fitote.2017.03.003[34] Q. Xue, Y. Chen, H. Yin, H. Teng, R. Qin, H. Liu, Q. Li, Z. Mei, and G. Yang. (2020). "Prenylated Xanthones and Benzophenones from the Fruits of Garcinia bracteata and Their Potential Antiproliferative and Anti-Inflammatory Activities". Bioorganic Chemistry. 104 : 104339. 10.1016/j.bioorg.2020.104339.
DOI: https://doi.org/10.1016/j.bioorg.2020.104339[35] R. A. Oetari, H. Hasriyani, A. Prayitno, and S. Sahidin. (2019). "Gartanin Compounds from Ethanolic Extract of Garcinia mangostana Pericarp". Open Access Macedonian Journal of Medical Sciences. 7 (22): 3891-3895. 10.3889/oamjms.2019.527.
DOI: https://doi.org/10.3889/oamjms.2019.527[36] F. Kurniadewi, L. M. Fallah, I. R. Kartika, M. Nurjayadi, E. Hermawati, and A. Danova. (2025). "Isolation, Characterization, and Evaluation of Xanthone Derivatives from Garcinia mangostana Twigs as Tyrosine Kinase Inhibitors with Potential EGFR Selectivity". Advanced Journal of Chemistry A. 8 (6): 1024-1042. 10.48309/ajca.2025.481129.1699.
[37] A. H. Zulfa, S. Assyifa, A. R. Setiawan, M. Tanjung, T. S. Tjahjandarie, and R. D. Saputri. (2025). "Xanthones from the Roots of Garcinia rigida Miq. and Their Cytotoxic Activity Against HeLa Cervical Cancer Cell Lines". Tropical Journal of Natural Product Research. 9 (4): 1833-1836. 10.26538/tjnpr/v9i4.57.
DOI: https://doi.org/10.26538/tjnpr/v9i4.57[38] S. Kaennakam, K. Mudsing, K. Rassamee, P. Siripong, and S. Tip-Pyang. (2019). "Two New Xanthones and Cytotoxicity from the Bark of Garcinia schomburgkiana". Journal of Natural Medicines. 73 : 257-261. 10.1007/s11418-018-1240-8.
DOI: https://doi.org/10.1007/s11418-018-1240-8[39] L. C. Klen-Junior, A. Campos, R. Niero, Y. Van der Heyden, and V. C. Filho. (2020). "Xanthones and Cancer: From Natural Resources to Mechanisms of Action". Chemistry & Biodiversity. 17 (2): e1900499. 10.1002/cbdv.201900499.
DOI: https://doi.org/10.1002/cbdv.201900499[40] L. T. T. Nguyen, D. M. Nguyen, and L. H. D. Nguyen. (2013). "A New Xanthone from the Bark of Calophyllum thorelii". Natural Product Research. 27 (6): 563-567. 10.1080/14786419.2012.682992.
DOI: https://doi.org/10.1080/14786419.2012.682992[41] I. Miladiyah, Jumina, S. M. Haryana, and Mustofa. (2018). "Biological Activity, Quantitative Structure-Activity Relationship Analysis, and Molecular Docking of Xanthone Derivatives as Anticancer Drugs". Drug Design, Development and Therapy. 12 : 149-158. 10.2147/DDDT.S149973.
DOI: https://doi.org/10.2147/DDDT.S149973[42] X. Li. (2018). "Comparative Study of 1,1-Diphenyl-2-picryl-hydrazyl Radical (DPPH) Scavenging Capacity of the Antioxidant Xanthone Family". ChemistrySelect. 3 (46): 13081-13086. 10.1002/slct.201803362.
DOI: https://doi.org/10.1002/slct.201803362[43] Y. Chen, H. Fan, G. Z. Yang, Y. Jiang, F. F. Zhong, and W. He. (2010). "Prenylated Xanthones from the Bark of Garcinia xanthochymus and Their 1,1-Diphenyl-2-picrylhydrazyl (DPPH) Radical Scavenging Activities". Molecules. 15 (10): 7438-7449. 10.3390/molecules15107438.
DOI: https://doi.org/10.3390/molecules15107438