5.9(Q2)
CiteScore
31
h-index

Structural Features of Xanthone from Leaves of Garcinia nigrolineata Planch. ex T. Anderson against 4T1 Breast Cancer Cells and DPPH Radicals

Document Type : Original Research Article

Authors

1 Department of Chemistry, Faculty of Mathematics and Science, Universitas Negeri Surabaya, Surabaya, Indonesia

2 Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Surabaya, Indonesia

10.48309/ajca.2026.562739.1985
Abstract
Xanthones are the most dominant phenolic compounds found in the genus Garcinia. Structurally, xanthones possess antioxidant potential, scavenging harmful free radicals. Xanthones also show cytotoxic potential against various cancer cells. To reveal the cytotoxic and antioxidant potential of xanthone derivatives from Garcinia nigrolineata Planch. ex. T. Anderson leaves against DPPH radicals is the aim of this study. Phytochemical investigations on G. nigrolineata yielded two xanthone derivatives, namely 5-O-methylmacluraxanthone and macluraxanthone. The structures of the xanthone were determined using 1D and 2D NMR spectroscopy and high-resolution MS data. Variations in oxygenation patterns, particularly the presence of a hydroxyl group, have been demonstrated to have a considerable impact on radical scavenging and cytotoxic activity. Macluraxanthone showed antioxidant potential against DPPH radicals with an IC50 value of 6.32 µg/mL, while 5-O-methylmacluraxanthone was inactive. Macluraxanthone also showed moderate activity against breast cancer (4T1 cells) with an IC50 value of 32.58 µM. These findings highlight that minor structural modifications can critically alter their biological performance.

Graphical Abstract

Structural Features of Xanthone from Leaves of Garcinia nigrolineata Planch. ex T. Anderson against 4T1 Breast Cancer Cells and DPPH Radicals

Keywords

Subjects


OPEN ACCESS

©2026 The author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit: http://creativecommons.org/licenses/by/4.0/

PUBLISHER NOTE

Sami Publishing Company remains neutral concerning jurisdictional claims in published maps and institutional affiliations.

CURRENT PUBLISHER

Sami Publishing Company

[1] Assyifa, S., Zulfa, A.H., Setiawan, A.R., Tanjung, M., Tjahjandarie, T.S., Saputri, R.D. Cytotoxic Activity of Xanthones from Garcinia parvifolia Miq. Advanced Journal of Chemistry, Section A, 2025, 8(8), 1309-1316.
[2] Kurniadewi, F., Palah, L.M., Kartika, I.R., Nurjayadi, M., Hermawati, E., Danova, A. Isolation, Characterization, and Evaluation of Xanthone Derivatives from Garcinia Mangostana Twigs as Tyrosine Kinase Inhibitors with Potential EGFR Selectivity. Advanced Journal of Chemistry, Section A, 2025, 8(6), 1027-1042.
[3] Zulfa, A.H., Assyifa, S., Setiawan, A.R., Tanjung, M., Tjahjandrie, T.S., Saputri, R.D. Xanthones from the Roots of Garcinia rigida Miq. and Their Cytotoxic Activity against HeLa Cervical Cancer Lines. Tropical Journal of Natural Product Research, 2025, 9(4), 1833-1836.
[4] Kaennakam, S., Mudsing, K., Rassamee, K., Siripong, P., Tip-Pyang, S. Two new xanthones and cytotoxicity from the bark of Garcinia schomburgkiana. Journal of Natural Medicines, 2019, 73(1), 257-261.
[5] Xue, Q., Chen, Y., Yin, H., Teng, H., Qin, R., Liu, H., Yang, G. Prenylated xanthones and benzophenones from the fruits of Garcinia bracteata and their potential antiproliferative and anti-inflammatory activities. Bioorganic Chemistry, 2020, 104, 104339.
[6] Dzoyem, J.P., Lannang, A.M., Fouotsa, H., Mbazoa, C.D., Nkengfack, A.E., Sewald, N., Eloff, J.N. Anti-inflammatory activity of benzophenone and xanthone derivatives isolated from Garcinia (Clusiaceae) species. Phytochemistry Letters, 2015, 14, 153-158.
[7] Rifaldi, Sukandar, E.R., Fadlan, A., Fatmawati, S., Purnomo, A.S., Wairata, J., Ersam, T. A new biphenyl from the stem bark of Garcinia macrantha AC Sm. Natural Product Research, 2024, 38(15), 2697-2702.
[8] Cheng, L.Y., Tsai, Y.C., Fu, S.L., Cheng, M.J., Sung, P.J., Chung, M.I., Chen, J.J. Acylphloroglucinol derivatives from Garcinia multiflora with anti-inflammatory effect in LPS-induced RAW264. 7 macrophages. Molecules, 2018, 23(10), 2587.
[9] Hassan, N.K.N.C., Taher, M., Susanti, D. Phytochemical constituents and pharmacological properties of Garcinia xanthochymus-a review. Biomedicine & Pharmacotherapy, 2018, 106, 1378-1389.
[10] Ibrahim, S.R., Abdallah, H.M., El-Halawany, A.M., Radwan, M.F., Shehata, I.A., Al-Harshany, E.M., Mohamed, G.A. Garcixanthones B and C, new xanthones from the pericarps of Garcinia mangostana and their cytotoxic activity. Phytochemistry Letters, 2018, 25, 12-16.
[11] Espirito Santo, B.L.S.D., Santana, L.F., Kato Junior, W.H., de Araújo, F.D.O., Bogo, D., Freitas, K.D.C., Filiú, W.F.D.O. Medicinal potential of Garcinia species and their compounds. Molecules, 2020, 25(19), 4513.
[12] Mariano, L.N.B., Vendramini-Costa, D.B., Ruiz, A.L.T.G., de Carvalho, J.E., Corrêa, R., Cechinel Filho, V., Niero, R. In vitro antiproliferative activity of uncommon xanthones from branches of Garcinia achachairu. Pharmaceutical Biology, 2016, 54(9), 1697-1704.
[13] Auranwiwat, C., Laphookhieo, S., Rattanajak, R., Kamchonwongpaisan, S., Pyne, S.G., Ritthiwigrom, T. Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana. Tetrahedron, 2016, 72(43), 6837-6842.
[14] Xue, Q., Chen, Y., Yin, H., Teng, H., Qin, R., Liu, H., Yang, G. Prenylated xanthones and benzophenones from the fruits of Garcinia bracteata and their potential antiproliferative and anti-inflammatory activities. Bioorganic Chemistry, 2020, 104, 104339.
[15] Tauchen, J., Frankova, A., Manourova, A., Valterova, I., Lojka, B., Leuner, O. Garcinia kola: A critical review on chemistry and pharmacology of an important West African medicinal plant. Phytochemistry Reviews, 2023, 22(5), 1305-1351.
[16] Phukhatmuen, P., Raksat, A., Laphookhieo, S., Charoensup, R., Duangyod, T., Maneerat, W. Bioassay-guided isolation and identification of antidiabetic compounds from Garcinia cowa leaf extract. Heliyon, 2020, 6(4).
[17] Trinh, B.T., Quach, T.T., Bui, D.N., Staerk, D., Nguyen, L.H.D., Jäger, A.K. Xanthones from the twigs of Garcinia oblongifolia and their antidiabetic activity. Fitoterapia, 2017, 118, 126-131.
[19] Chen, Y., Fan, H., Yang, G.Z., Jiang, Y., Zhong, F.F., He, H.W. Prenylated xanthones from the bark of Garcinia xanthochymus and their 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities. Molecules, 2010, 15(10), 7438-7449.
[20] da Veiga, A.A.S., de Jesus Chaves Neto, A.M., da Silva, A.B.F., Herculano, A.M., Oliveira, K.R.M., dos Santos Borges, R. Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin. Medicinal Chemistry Research, 2018, 27(4), 1276-1282.
[21] Tjahjandarie, T.S., Setiawan, A.R., Zulfa, A.H., Saputri, R.D., Ahmat, N., Tanjung, M. Bioassay-Guided Isolation of Flavonoids from Flemingia macrophylla and Their Cytotoxic and Antioxidant Activities. Advanced Journal of Chemistry, Section A, 2025, 8(10), 1631-1639.
[22] Arif, N.N., Ahmat, N., Saputri, R.D., Tjahjandarie, T.S., Tanjung, M. Cytotoxic and Anti-Plasmodial Activities of Chromanone Acids from Calophyllum wallichianum Plach. and Triana. Advanced Journal of Chemistry, Section A, 2025, 8(9), 1468-1476.
[23] Marliana, E., Hairani, R., Tjahjandarie, T., Tanjung, M. Antiplasmodial activity of flavonoids from Macaranga tanarius leaves. In IOP Conference Series: Earth and Environmental Science, 2018,  144(1)  012011.
[24] Saputri, R.D., Retnowati, R., Supratman, U., Tjahjandarie, T.S., Tanjung, M. Three novel quinolinone alkaloids from the leaves of Melicope denhamii. Natural Product Research, 2023, 37(2), 197-203.
[25] Tanjung, M., Mujahidin, D., Hakim, E.H., Darmawan, A., Syah, Y.M. Geranylated flavonols from Macaranga rhizinoides. Natural Product Communications, 2010, 5(8), 1209-1211.
[26] Tjahjandarie, T.S., Tanjung, M., Saputri, R.D., Rahayu, D.O., Gunawan, A.N.I., Aldin, M.F. Two new 2-arylbenzofurans from Sesbania grandiflora L. and their cytotoxicity towards cancer cell. Natural Product Research, 2021, 35(24), 5637-5642.
[27] Aminah, N.S., Kristanti, A.N., Tanjung, M. Antioxidant activity of flavonoid compounds from the leaves of Macaranga gigantea. Journal of Chemical and Pharmaceutical Research, 2014, 6(6), 688-692.
[28] Tanjung, M., Saputri, R.D., Fitriati, F.F., Tjahjandarie, T.S. Antimalarial and antioxidant activities of isoprenylated coumarins from the stem bark of Mesua borneensis L. Journal of Biologically Active Products from Nature, 2016, 6(2), 95-100.
[29] Tanjung, M., Saputri, R.D., Tjahjandarie, T.S. Antioxidant activity of two isomeric benzoxepin derivatives from the stem bark of Bauhinia aculeata L. Journal of Chemical and Pharmaceutical Research, 2014, 6, 705-708.
[30] Azmin, N.F.N., Ahmat, N., Kamarozaman, A.S., Sulaiman, N.S., Jalil, J., Tanjung, M. Flavonoids of Cynometra cauliflora, their Plausible Biosynthetic Pathway and SAR Study against DPPH Radicals. Malaysian Journal of Chemistry, 2025, 27(1), 102-109.
[31] Tanjung, M., Aldin, M.F., Arif, N.N., Saputri, R.D., Ahmat, N., Tjahjandarie, T.S. 4-Propyl-and 4-phenylcoumarins from mesua lepidota T. Anderson and their cytotoxic activity. Natural Product Research, 2025, 39(20), 5874-5882.
[32] Tjahjandarie, T.S., Tanjung, M., Saputri, R.D., Aldin, M.F., Susanti, R.A., Pertiwi, N.P., Halizah, I.N. Cytotoxicity evaluation of two new chalcones from the leaves of Flemingia macrophylla (Willd.) Merr. Phytochemistry Letters, 2021, 44(78-81.
[33] Saputri, R.D., Tjahjandarie, T.S., Tanjung, M. Meliglabrin, a new flavonol derivative from the leaves of Melicope glabra (Blume) TG Hartley. Natural Product Sciences, 2018, 24(3), 155-158.
[34] Kookrae, C., Jung-Hee, K., Jong-Wuk, S., Eunjoo, K. Numerical learning of deep features from drug-exposed cell images to calculate IC50 without staining. Scientific Reports, 2022, 12, 1-11.
[35] Iinuma, M., Tosa, H., Tanaka, T., Yonemori, S. Two xanthones from root bark of Calophyllum inophyllum. Phytochemistry, 1994, 35(2), 527-532.
[36] Mardhiyyah, S., Zakiyah, M., Renata, E.D., Tjahjandarie, T.S., Supratman, U., Retnowati, R., Tanjung, M. Cytotoxic Activity of Xanthones from the Stem Bark of Cratoxylum sumatranum. Tropical Journal of Natural Product Research, 2023, 7(9), 3908-3910.
[37] Almukram, A.M.A., Al-hussaniy, H.A., Jabarah, M.A., Al-Abdeen, S.H.Z. MDM2 antagonists and p53-targeting therapies in cancer: Clinical applications, adverse effects, and resistance mechanismsMedical and Pharmaceutical Journal2025, 4(1), 47-63.
[38] Kancheva, V.D., Dettori, M.A., Fabbri, D., Alov, P., Angelova, S.E., Slavova-Kazakova, A.K., Carta, P., Menshov, V.A., Yablonskaya, O.I., Trofimov, A.V., Tsakovska, I. Natural chain-breaking antioxidants and their synthetic analogs as modulators of oxidative stressAntioxidants2021, 10(4), 624.
[39] Tanjung, M., Tjahjandarie, T.S., Saputri, R.D., Kurnia, B.D., Rachman, M.F., Syah, Y.M. Calotetrapterins AC, three new pyranoxanthones and their cytotoxicity from the stem bark of Calophyllum tetrapterum MiqNatural Product Research2021, 35(3), 407-412.
[40] Tjahjandarie, T.S., Nugroho, W.A.S., Palgunadi, H., Saputri, R.D., Tanjung, M. Two new chromanone acids from the stem bark of Calophyllum peekelii LauterbNatural Product Research2023, 37(19), 3214-3219.
[41] Tanjung, M., Nurmalasari, I., Wilujeng, A.K., Saputri, R.D., Rachmadiarti, F., Tjahjandarie, T.S. Acronyculatin P, a new isoprenylated acetophenone from the stem bark of Acronychia pedunculata. Natural Product Sciences, 2018, 24(4), 284-287. 
[42] Kuete, V., Efferth, T. African flora has the potential to fight multidrug resistance of cancer. BioMed Research International, 2015, 2015(1), 914813.

Articles in Press, Accepted Manuscript
Available Online from 26 February 2026

  • Receive Date 29 November 2025
  • Revise Date 05 January 2026
  • Accept Date 20 February 2026