Abstract
Most of the natural products containing tetramic acid have trans configuration of the decalin moiety. Undana A (1), a new cis decalin-bearing tetramic acid metabolite was isolated from endophytic fungi Nigrospora oryzae associated with Avicennia marina. The structure was determined based on the mass and NMR spectral data together with the comparison of the literature. This is the first report of cis decalin-tetramic acid metabolite from the mangrove endophytic fungus. Compound 1 was tested for cytotoxic against L5178Y mouse cancer cells and antibacterial activity against several gram-positive including MRSA and gram-negative bacteria but was found inactive.
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References
Mo X, Li Q, Ju J. Naturally occurring tetramic acid products: isolation, structure elucidation and biological activity. RSC Adv. 2014;4:50566–93.
Li G, Kusari S, Spiteller M. Natural products containing ‘decalin’ motif in microorganisms. Nat Prod Rep. 2014;31:1175–201.
Watanabe K, Sato M, Osada H. Recent advances in the chemo-biological characterization of decalin natural products and unraveling of the workings of Diels–Alderases. Fungal Biol Biotechnol. 2022;9:9.
Si XG, Zhang ZM, Zheng CG, Li ZT, Cai Q. Enantioselective synthesis of cis-decalin derivatives by the inverse-electron-demand diels–alder reaction of 2-pyrones. Angew Chem Int Ed. 2020;59:18412–7.
Wheeler MH, Stipanovic RD, Puckhaber LS. Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum. Mycol Res. 1999;103:967–73.
Phillips NJ, Goodwin JT, Fraiman A, Cole RJ, Lynn DG. Characterization of the fusarium toxin: the use of phenylboronates in structure assignment. J Am Chem Soc. 1989;111:8223–31.
Hellwig V, Grothe T, Mayer-Bartschmid A, Endermann R, Geschke FU, Henkel T, et al. Altersetin, a new antibiotic from cultures of endophytic Alternaria spp. Taxonomy, fermentation, isolation, structure elucidation and biological activities. J Antibiot. 2002;55:881–92.
Herath K, Jayasuriya H, Zink DL, Sigmund J, Vicente F, de la Cruz M, et al. Isolation, structure elucidation, and antibacterial activity of methiosetin, a tetramic acid from a tropical sooty mold (Capnodium sp.). J Nat Products. 2012;75:420–4.
Li JY, Strobel G, Harper J, Lobkovsky E, Clardy J. Cryptocin, a potent tetramic acid antimycotic from the endophytic fungus cryptosporiopsis cf. quercina. Org Lett. 2000;2:767–70.
Marfori EC, Kajiyama SI, Fukusaki E-I, Kobayashi A. Trichosetin, a novel tetramic acid antibiotic produced in dual culture of Trichoderma harzianum and Catharanthus roseus callus. Z für Naturforsch C. 2002;57:465–70.
Koyama N, Nagahiro T, Yamaguchi Y, Ohshiro T, Masuma R, Tomoda H, et al. Spylidone, a novel inhibitor of lipid droplet accumulation in mouse macrophages produced by phoma sp. FKI-1840. J Antibiot. 2005;58:338–45.
Nogawa T, Kawatani M, Uramoto M, Okano A, Aono H, Futamura Y, et al. Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus. J Antibiotics. 2013;66:621–3.
Boros C, Dix A, Katz B, Vasina Y, Pearce C. Isolation and identification of cissetin-a setin-like antibiotic with a novel cis-octalin ring fusion. J Antibiot. 2003;56:862–5.
Ola ARB, Lapailaka T, Wogo HE, Henuk JBD, Simamora A, Mukkun L, et al. Bioactive secondary metabolites from the mangrove endophytic fungi Nigrospora oryzae. Indones J Chem. 2021;21:1016–22.
Ola ARB, Soa CAP, Sugi Y, Da Cunha T, Belli HLL, Lalel HJD. Antimicrobial metabolite from the endophytic fungi Aspergillus flavus isolated from Sonneratia Alba, a mangrove plant of Timor-Indonesia. Rasayan J Chem. 2020;13:377–81.
Ola ARB, Debbab A, Kurtán T, Brötz-Oesterhelt H, Aly AH, Proksch P. Dihydroanthracenone metabolites from the endophytic fungus Diaporthe melonis isolated from Annona squamosa. Tetrahedron Lett. 2014;55:3147–50.
Lin ZJ, Lu ZY, Zhu TJ, Fang YC, Gu QQ, Zhu WM. Penicillenols from penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum. Chem Pharm Bull. 2008;56:217–21.
Aoki S, Higuchi K, Ye Y, Satari R, Kobayashi M. Melophlins A and B, novel tetramic acids reversing the phenotype of ras-transformed cells, from the marine sponge melophlus sarassinorum. Tetrahedron. 2000;56:1833–6.
Jadulco RC, Koch M, Kakule TB, Schmidt EW, Orendt A, He H, et al. Isolation of pyrrolocins A–C: cis- and trans-decalin tetramic acid antibiotics from an endophytic fungal-derived pathway. J Nat Products. 2014;77:2537–44.
Singh SB, Zink DL, Heimbach B, Genilloud O, Teran A, Silverman KC, et al. Structure, stereochemistry, and biological activity of integramycin, a novel hexacyclic natural product produced by actinoplanes sp. that Inhibits HIV-1 integrase. Org Lett. 2002;4:1123–6.
Winterer M, Kempf K, Schobert R. Synthesis of an isomer of the decalinoyltetramic acid methiosetin by a stereocontrolled IMDA reaction of a metal-chelated 3-trienoyltetramate. J Org Chem. 2016;81:7336–41.
Ashour M, Edrada R, Ebel R, Wray V, Wätjen W, Padmakumar K, Proksch P. Kahalalide derivatives from the Indian sacoglossan Mollusk Elysia grandifolia. J Nat Products. 2006;69:1547–53. https://doi.org/10.1021/np060172v.
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Ola, A.R.B. Cis -decalin tetramic acid metabolite from a mangrove derived endophytic fungus Nigrospora oryzae. J Antibiot (2024). https://doi.org/10.1038/s41429-024-00764-w
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DOI: https://doi.org/10.1038/s41429-024-00764-w