Arohynapene A Produced by Penicillium steckii JB-NW-2-1 Isolated from Avicennia marina (Forssk.) Vierh and Its Cytotoxic Activities

https://doi.org/10.22146/ijc.83982

Yeni Mulyani(1), Wahyu Syafriansyah(2), Asri Peni Wulandari(3), Azmi Azhari(4), Sari Purbaya(5), Aprilia Permata Sari(6), Galih Bayu Pratama(7), Fajar Fauzi Abdullah(8), Kindi Farabi(9), Unang Supratman(10*), Yoshihito Shiono(11)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Department of Marine Science, Faculty of Fisheries and Marine Science, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(3) Department of Biology, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(7) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(8) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(9) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(10) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Central Laboratory of Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(11) Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan
(*) Corresponding Author

Abstract


Mangrove-associated endophytic fungi are producers of secondary metabolites in unique and diverse structures with interesting biological activities such as antiviral, antifungal, antibacterial, anti-inflammatory, and cytotoxic agents. Endophytes play an important role in the physiological activities of the host plants, influencing the improvement of resistance to stress, insects, nematodes, and diseases. In this study, arohynapene A, a polyketide compound, was successfully isolated from the mangrove-derived fungus Penicillium steckii JB-NW-2-1 obtained from mangrove plant Avicennia marina (Forssk) Vierh. The structure was determined by a spectroscopic method including IR, MS, 1D-, and 2D-NMR techniques. This compound was evaluated for cytotoxic activities using resazurin assay against four cancer cells, HeLa cervical, MCF-7 breast cancer, B16-F10 melanoma, and A549 lung adenocarcinoma. The results showed no significant activities against all cancer cells tested (IC50 > 500 µM).


Keywords


Arohynapene A; Avicennia marina; cytotoxic; endophytic fungi; polyketide



References

[1] Jia, S.L., Chi, Z., Liu, G.L., Hu, Z., and Chi, Z.M., 2020, Fungi in mangrove ecosystems and their potential applications, Crit. Rev. Biotechnol., 40 (6), 852–864.

[2] Lee, N.L.Y., Huang, D., Quek, Z.B.R., Lee, J.N., and Wainwright, B.J., 2019, Mangrove-associated fungal communities are differentiated by geographic location and host structure, Front. Microbiol., 10, 2456.

[3] Bibi, S.N., Gokhan, Z., Rajesh, J., and Mahomoodally, M.F., 2020, Fungal endophytes associated with mangroves – Chemistry and biopharmaceutical potential, S. Afr. J. Bot., 134, 187–212.

[4] Moussa, M., Ebrahim, W., El-Neketi, M., Mándi, A., Kurtán, T., Hartmann, R., Lin, W., Liu, Z., and Proksch, P., 2016, Tetrahydroanthraquinone derivatives from the mangrove-derived endophytic fungus Stemphylium globuliferum, Tetrahedron Lett., 57 (36), 4074–4078.

[5] Cadamuro, R.D., da Silveira Bastos, I.M.A., Silva, I.T., da Cruz, A.C.C., Robl, D., Sandjo, L.P., Alves, S., Lorenzo, J.M., Rodríguez-Lázaro, D., Treichel, H., Steindel, M., and Fongaro, G., 2021, Bioactive compounds from mangrove endophytic fungus and their uses for microorganism control, J. Fungi, 7 (6), 455.

[6] Suzuki, T., Ariefta, N.R., Koseki, T., Furuno, H., Kwon, E., Momma, H., Harneti, D, Maharani, R., Supratman, U., Kimura, K., and Shiono, Y., 2019, New polyketides, paralactonic acids A–E produced by Paraconiothyrium sp. SW-B-1, an endophytic fungus associated with a seaweed, Chondrus ocellatus Holmes, Fitoterapia, 132, 75–81.

[7] Das, G., Gouda, S., Mohanta, Y.K., and Patra, J.K., 2015, Mangrove plants: A potential source for anticancer drugs, Indian J. Geo-Mar. Sci., 44 (5), 666–672.

[8] Liu, J., Xu, M., Zhu, M.Y., and Feng, Y., 2015, Chemoreversal metabolites from the endophytic fungus Penicillium citrinum isolated from a mangrove Avicennia marina, Nat. Prod. Commun., 10 (7), 1203–1205.

[9] Refai, M., El-Yazid, H.A., and Tawakkol, W., 2015, Monograph on the Genus Penicillium: A Guide for Historical, Classification, and Identification of Penicillin, their Industrial Applications and Detrimental Effects, Cairo University, Giza, Egypt.

[10] Nicoletti, R., and Trincone, A., 2016, Bioactive compounds produced by strains of Penicillium and Talaromyces of marine origin, Mar. Drugs, 14 (2), 37.

[11] Abdelwahab, M.F., Fouad, M.A., Kamel, M.S., Özkaya, F.C., Kalscheuer, R., Müller, W.E.G., Lin, W., Liu, Z., Ebrahim, W., Daletos, G., and Proksch, P., 2018, Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp., Fitoterapia, 128, 258–264.

[12] Mady, M.S., and Haggag, E.G., 2020, Review on fungi of genus Penicillium as a producers of biologically active polyketides, J. Adv. Pharm. Res., 4 (2), 33–45.

[13] Zhang, X., Yin, Q., Li, X., Liu, X., Lei, H., and Wu, B., 2022, Structures and bioactivities of secondary metabolites from Penicillium genus since 2010, Fitoterapia, 163, 105349.

[14] Toghueo, R.M.K., and Boyom, F.F., 2020, Endophytic Penicillium species and their agricultural, biotechnological, and pharmaceutical applications, 3 Biotech, 10 (3), 107.

[15] Ma, H.G., Liu, Q., Zhu, G.L., Liu, H.S., and Zhu, W.M., 2016, Marine natural products sourced from marine-derived Penicillium fungi, J. Asian Nat. Prod. Res., 18 (1), 92–115.

[16] ElDohaji, L.M., Hamoda, A.M., Hamdy, R., and Soliman, S.S.M., 2020, Avicennia marina a natural reservoir of phytopharmaceuticals: Curative power and platform of medicines, J. Ethnopharmacol., 263, 113179.

[17] Wen, J., Okyere, S.K., Wang, S., Wang, J., Xie, L., Ran, Y., and Hu, Y., 2022, Endophytic fungi: An effective alternative source of plant-derived bioactive compounds for pharmacological studies, J. Fungi, 8 (2), 205.

[18] Meng, L.H., Li, X.M., Lv, C.T., Huang, C.G., and Wang, B.G., 2014, Brocazines A-F, cytotoxic bisthiodiketopiperazine derivatives from Penicillium brocae MA-231, an endophytic fungus derived from the marine mangrove plant Avicennia marina, J. Nat. Prod., 77 (8), 1921–1927.

[19] Chen, C., Ye, G., Tang, J., Li, J., Liu, W., Wu, L., and Long, Y., 2022, New polyketides from mangrove endophytic fungus Penicillium sp. BJR-P2 and their anti-inflammatory activity, Mar. Drugs, 20 (9), 583.

[20] Masuma, R., Tabata, N., Tomoda, H., Iwai, Y., and Omura, S., 1994, Arohynapenes A and B, new anticoccidial agents produced by Penicillium sp., J. Antibiot., 47 (1), 46–53.

[21] Sandjo, L.P., Thines, E., Opatz, T., and Schüffler, A., 2014, Tanzawaic acids I-L: Four new polyketides from Penicillium sp. IBWF104-06, Beilstein J. Org. Chem., 10, 251–258.

[22] El-Neketi, M., Ebrahim, W., Lin, W., Gedara, S., Badria, F., Saad, H.E.A., Lai, D., and Proksch, P., 2013, Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant ceratonia siliqua, J. Nat. Prod., 76 (6), 1099–1104.

[23] Ebada, S.S., and Ebrahim, W., 2019, A new antioxidant decalin polyketide from freshwater-sediment-derived fungus Penicillium sp. strain S1a1, ChemistrySelect, 4 (33), 9814–9816.



DOI: https://doi.org/10.22146/ijc.83982

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