Antibacterial Activities of Novel Xestospongienol Compounds: Potential Natural Agents Against Vibrio sp.

https://doi.org/10.22146/ijc.101132

Lulu Adilla Latifah(1*), Nunuk Hariani Soekamto(2), Akbar Tahir(3)

(1) Research Center for Marine Aquaculture, National Research and Innovation Agency, KS Kurnaen Sumadiharga, Teluk Kode, Lombok Utara 83352, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan Km. 10, Makassar 90245, Indonesia
(3) Department of Marine Science, Faculty of Marine Science and Fisheries, Hasanuddin University, Jl. Perintis Kemerdekaan Km. 10, Makassar 90245, Indonesia
(*) Corresponding Author

Abstract


The marine sponges, especially Xestospongia, belonging to the class Demospongiae, order Haplosclerida, family Petrosiidae, produce diverse bioactive secondary metabolites, which can be the source of potentially valuable marine natural products. These secondary metabolites could be used as alternative antibiotics to inhibit pathogenic bacteria Vibrio sp. This study aimed to isolate and characterize active compounds from Xestospongia testudinaria collected from Badi Island, South Sulawesi, Indonesia, and to evaluate their antibacterial potential. Research methods were evaporation, fractionation, purification, identification, and characterization of compounds using 1D and 2D NMR. Pure compounds were determined for their antibacterial activities using agar diffusion method against Vibrio harveyi M-120, Vibrio parahaemolyticus T-170, and Vibrio alginolyticus B-425. The fractionation and elucidation results presented two new compounds: xestospongienol, one of the types of brominated polyunsaturated acetylenic fatty acids (BPUFAs). The inhibition zone value of new compounds is 6.33–7.97 mm, where compound 2 showed higher activity than compound 1 against V. harveyi (7.97 mm). This study was the first report on the antibacterial activity of xestospongienol compounds against Vibrio sp., suggesting their potential as natural antibacterial agents.


Keywords


Xestospongia testudinaria; spermonce archipelago; xestospongienol; antibacterial agents; Vibrio sp.

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References

[1] Sarjito, S., Amalia, R., and Sabdaningsih, A., 2022, Screening of sponge-associated bacteria to control vibriosis in vannamei shrimp (Litopenaeus vannamei), Biodiversitas, 23 (10), 5333–5341.

[2] Sarjito, S., and Sabdono, A., 2021, Associated vibrio species in shrimp vibriosis from traditional brackish water pond in the north coastal of Central Java, Indonesia, Genet. Aquat. Org., 5 (2), 45–54.

[3] Béné, C., Arthur, R., Norbury, H., Allison, E.H., Beveridge, M., Bush, S., Campling, L., Leschen, W., Little, D., Squires, D., Thilsted, S.H., Troell, M., and Williams, M., 2016, Contribution of fisheries and aquaculture to food security and poverty reduction: Assessing the current evidence, World Dev., 79, 177–196.

[4] Putra, S.A., Ambo-Rappe, R., Jompa, J., and de Voogd, N.J., 2024, Preliminary study of marine sponges (Porifera) in the littoral of Spermonde Archipelago, Indonesia, ZooKeys, 1208, 275–313.

[5] Khodzori, F.A., Mazlan, N.B., Chong, W.S., Ong, K.H., Palaniveloo, K., and Shah, M.D., 2023, Metabolites and bioactivity of the marine Xestospongia sponges (Porifera, Demospongiae, Haplosclerida) of Southeast Asian waters, Biomolecules, 13 (3), 484.

[6] He, F., Mai, L.H., Longeon, A., Copp, B.R., Loaëc, N., Bescond, A., Meijer, L., Bourguet-Kondracki, M.L., and Al, E., 2015, Novel adociaquinone derivatives from the Indonesian sponge Xestospongia sp., Mar. Drugs, 13 (5), 2617–2628.

[7] Yang, M., Liang, L.F., Wang, T., Wang, H.Y., Liu, H.L., and Guo, Y.W., 2017, Further brominated polyacetylenes with pancreatic lipase inhibitory activity from Chinese marine sponge Xestospongia testudinaria, J. Asian Nat. Prod. Res., 19 (7), 732–737.

[8] Tai, B.H., Hang, D.T.T., Thung, D.C., Trang, D.T., Yen, P.H., Yen, D.T.H., Huong, P.T.T., Dung, D.T., Cuong, N.C., Thao, D.T., Nhiem, N.X., and Van Kiem, P., 2022, Xestospongiene VN1, a new brominated polyunsaturated lipid from marine sponge Xestospongia testudinaria (Lamark, 1815), Vietnam J. Chem., 60 (4), 540–545.

[9] Nguyen, H.M., Ito, T., Win, N.N., Vo, H.Q., Nguyen, H.T., and Morita, H., 2019, A new sterol from the Vietnamese marine sponge Xestospongia testudinaria and its biological activities, Nat. Prod. Res., 33 (8), 1175–1181.

[10] Falsafi, S.R., Sebastian, J., Colussi, R., Ávila do Nascimento, L., Kemerli-Kalbaran, T., Yildirim-Yalcin, M., Adrian Garcia-Galicia, I., Sahin, S., and Delia Alarcon-Rojo, A., 2025, Recent advances in the characterization of food biomacromolecules: Polysaccharide, protein, and lipid, Food Sci. Nutr., 13 (7), e70523.

[11] Bourguet-Kondracki, M.L., Rakotoarisoa, M.T., Martin, M.T., and Guyot, M., 1992, Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria, Tetrahedron Lett., 33 (2), 225–226.

[12] Patil, A.D., Kokke, W.C., Cochran, S., Francis, T.A., Tomszek, T., and Westley, J.W., 1992, Brominated polyacetylenic acids from the marine sponge Xestospongia muta: Inhibitors of HIV protease, J. Nat. Prod., 55 (9), 1170–1177.

[13] Jiang, W., Liu, D., Deng, Z., de Voogd, N.J., Proksch, P., and Lin, W., 2011, Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria, Tetrahedron, 67 (1), 58–68.

[14] Quinn, R.J., and Tucker, D.J., 1985, A brominated bisacetylenic acid from the marine sponge Xestospongia testudinaria, Tetrahedron Lett., 26 (13), 1671–1672.

[15] Brantley, S.E., Molinski, T.F., Preston, C.M., and DeLong, E.F., 1995, Brominated acetylenic fatty acids from Xestospongia sp., a marine sponge-bacteria association, Tetrahedron, 51 (28), 7667–7672.

[16] Alkhilaiwi, F.A., Fadil, S.A., Aljoud, F.A., Yonbawi, A.R., Ashi, A., Hareeri, R.H., Bakhashab, S., Alamri, A.M., Albikairi, A.Y., Shaala, L.A., El-Gamal, A.A., and Youssef, D.T., 2023, Evaluation of cytotoxicity of the methanolic extract of red sea marine sponge Xestospongia testudinaria and its related compounds against MCF-7 human breast cancer cells, Breast Cancer: Targets Ther., 15, 879–890.

[17] Bayona, L.M., van Leeuwen, G., Erol, Ö., Swierts, T., Swierts, T., van der Ent, E., de Voogd, N.J., and Choi, Y.H., 2020, Influence of geographical location on the metabolic production of giant barrel sponges (Xestospongia spp.) revealed by metabolomics tools, ACS Omega, 5 (21), 12398–12408.

[18] El-Gamal, A.A., Al-Massarani, S.M., Shaala, L.A., Alahdald, A.M., Al-Said, M.S., Ashour, A.E., Kumar, A., Abdel-Kader, M.S., Abdel-Mageed, W.M., and Youssef, D.T.A., 2016, Cytotoxic compounds from the Saudi Red Sea Sponge Xestospongia testudinaria, Mar. Drugs, 14 (5), 82.

[19] Ichiba, T., Scheuer, P.J., and Kelly-Borges, M., 1993, Sponge-derived polyunsaturated C16 Di- and tribromocarboxylic acids, Helv. Chim. Acta, 76 (8), 2814–2816.

[20] Choi, J.K., Poudel, S., Yee, N., and Goff, J.L., 2024, Deeply branching Bacillota species exhibit atypical gram-negative staining, Microbiol. Spectrum, 12 (10), e00732-24.

[21] Das, U.N., 2018, Arachidonic acid and other unsaturated fatty acids and some of their metabolites function as endogenous antimicrobial molecules: A review, J. Adv. Res., 11, 57–66.

[22] Ayyad, S.E.N., Katoua, D.F., Alarif, W.M., Sobahi, T.R., Aly, M.M., Shaala, L.A., and Ghandourah, M.A., 2015, Two new polyacetylene derivatives from the Red Sea sponge Xestospongia sp., Z. Naturforsch., C: Biosci., 70 (11–12), 297–303.

[23] Yang, M., Liang, L.F., Yao, L.G., Liu, H.L., and Guo, Y.W., 2019, A new brominated polyacetylene from Chinese marine sponge Xestospongia testudinaria, J. Asian Nat. Prod. Res., 21 (6), 573–578.

[24] Casillas-Vargas, G., Ocasio-Malavé, C., Medina, S., Morales-Guzmán, C., Del Valle, R.G., Carballeira, N.M., and Sanabria-Ríos, D.J., 2021, Antibacterial fatty acids: An update of possible mechanisms of action and implications in the development of the next-generation of antibacterial agents, Prog. Lipid Res., 82, 101093.

[25] Sun, M., Zhou, Z., Dong, J., Zhang, J., Xia, Y., and Shu, R., 2016, Antibacterial and antibiofilm activities of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) against periodontopathic bacteria, Microb. Pathog., 99, 196–203.

[26] Yoon, B.K., Jackman, J.A., Valle-González, E.R., and Cho, N.J., 2018, Antibacterial free fatty acids and monoglycerides: Biological activities, experimental testing, and therapeutic applications, Int. J. Mol. Sci., 19 (4), 1114.

[27] Sanabria-Ríos, D.J., Morales-Guzmán, C., Mooney, J., Medina, S., Pereles-De-León, T., Rivera-Román, A., Ocasio-Malavé, C., Díaz, D., Chorna, N., and Carballeira, N.M., 2020, Antibacterial activity of hexadecynoic acid isomers toward clinical isolates of multidrug-resistant Staphylococcus aureus, Lipids, 55 (2), 101–116.

[28] Latifah, L.A., Soekamto, N.H., and Tahir, A., 2021, New antibacterial activities of brominated C18 and C20 fatty acids isolated from marine sponge Xestospongia testudinaria against shrimp pathogenic bacteria, Rasayan J. Chem., 14 (1), 460–465.

[29] Zhou, T., Song, W.F., Shang, Y., Yao, S.L., and Matalon, S., 2018, Halogen inhalation-induced lung injury and acute respiratory distress syndrome, Chin. Med. J., 131 (10), 1214–1219.

[30] EFSA Scientific Committee, Bennekou, S.H., Allende, A., Bearth, A., Casacuberta, J., Castle, L., Coja, T., Crépet, A., Halldorsson, T., Hoogenboom, L., Knutsen, H., Koutsoumanis, K., Lambré, C., Nielsen, S., Turck, D., Civera, A.V., Villa, R., Zorn, H., Bampidis, V., Castenmiller, J., Chagnon, M.C., Cottrill, B., Darney, K., Gropp, J., Puente, S.L., Rose, M., Vinceti, M., Bastaki, M., Gergelová, P., Greco, L., Innocenti, M.L., Janossy, J., Lanzoni, A., Terron, A., and Benford, D., 2025, Risks to human and animal health from the presence of bromide in food and feed, EFSA J., 23 (1), e9121.



DOI: https://doi.org/10.22146/ijc.101132

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