Pederins, mycalamides, onnamides and theopederins: Distinctive polyketide families with intriguing therapeutic potentialities

Albarano, 2020, Genome Mining as New Challenge in Natural Products Discovery, Mar. Drugs, 18, 199, 10.3390/md18040199 Almaliti, 2023, Methods in marine natural product drug discovery: what’s new?, Expert Opin Drug Discov., 687, 10.1080/17460441.2023.2214360 Atanasov, 2021, Natural products in drug discovery: advances and opportunities, Nat. Rev. Drug Discov, 20, 200, 10.1038/s41573-020-00114-z Bauman, 2021, Genome mining methods to discover bioactive natural products, Nat. Prod. Rep., 38, 2100, 10.1039/D1NP00032B Boswell, 2023, In-Silico Approaches for the Screening and Discovery of Broad-Spectrum Marine Natural Product Antiviral Agents Against Coronaviruses, Infect Drug Resist, 2321, 10.2147/IDR.S395203 Brega, 1968, Studies on the mechanism of action of pederine, J. Cell Biol., 36, 485, 10.1083/jcb.36.3.485 Burres, 1989, Antitumor activity and mechanism of action of the novel marine natural products mycalamide-A and-B and onnamide, Cancer Res., 49, 2935 Buskes, 2023, Accelerating Drug Discovery: Synthesis of Complex Chemotypes via Multicomponent Reactions, ACS Med. Chem. Lett., 14, 376, 10.1021/acsmedchemlett.3c00012 Cardani, 1965, The structure of Pederin, Tetrahedron Lett., 6, 2537, 10.1016/S0040-4039(01)84020-X Carroll, 2023, Marine natural products, Nat. Prod. Rep., 40, 275, 10.1039/D2NP00083K Chu, 2020, Genome mining as a biotechnological tool for the discovery of novel marine natural products, Crit. Rev. Biotechnol., 40, 571, 10.1080/07388551.2020.1751056 Cichewicz, 2004, Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family, Org. Lett., 6, 1951, 10.1021/ol049503q Costantini, 2020, Genome Mining and Synthetic Biology in Marine Natural Product Discovery, Mar. Drugs, 18, 10.3390/md18120615 Cragg, 1997, Natural products in drug discovery and development, J. Nat. Prod., 60, 52, 10.1021/np9604893 D'Agostino, 2023 Dias, 2012, A historical overview of natural products in drug discovery, Metabolites, 2, 303, 10.3390/metabo2020303 El-Demerdash, 2018, Chemical diversity and biological activities of Phaeosphaeria fungi genus: A systematic review, J. Fungi, 4, 130, 10.3390/jof4040130 El-Demerdash, 2018, Batzella, Crambe and Monanchora: highly prolific marine sponge genera yielding compounds with potential applications for cancer and other therapeutic areas, Nutrients, 10, 33, 10.3390/nu10010033 El-Demerdash, 2018, Chemistry and biological activities of the marine sponges of the genera Mycale (Arenochalina), Biemna and Clathria. Mar. Drugs, 16, 214, 10.3390/md16060214 El-Demerdash, 2019, Chemical diversity and biological activities of marine sponges of the genus Suberea: A systematic review, Mar. Drugs, 17, 115, 10.3390/md17020115 El-Demerdash, 2020, Short-Cut Bio-Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids, Eur. J. Org. Chem., 2020, 5677, 10.1002/ejoc.202000744 El-Demerdash, 2021, Investigating the structure–activity relationship of marine natural polyketides as promising SARS-CoV-2 main protease inhibitors, RSC Adv., 11, 31339, 10.1039/D1RA05817G Elgohary, 2022, Investigating the structure-activity relationship of marine polycyclic batzelladine alkaloids as promising inhibitors for SARS-CoV-2 main protease (Mpro), Comput. Biol. Med., 147 Feng, 2012, Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs, J. Am. Chem. Soc., 134, 17083, 10.1021/ja3057612 Floreancig, 2014, Structure inspires a new method that delivers the synthesis of natural products and analogs in the pederin family, Strategies and Tactics in Organic Synthesis, Elsevier, 183 Fusetani, 1992, Bioactive marine metabolites. 41. Theopederins AE, potent antitumor metabolites from a marine sponge, Theonella sp., J. Org. Chem., 57, 3828, 10.1021/jo00040a021 Ghareeb, 2020, Insights about clinically approved and Preclinically investigated marine natural products, Curr. Res. Biotechnol., 2, 88, 10.1016/j.crbiot.2020.09.001 Harvey, 2008, Natural products in drug discovery, Drug Discovery Today, 13, 894, 10.1016/j.drudis.2008.07.004 Harvey, 2015, The re-emergence of natural products for drug discovery in the genomics era, Nat. Rev. Drug Discov, 14, 111, 10.1038/nrd4510 Hirano, 2015, Irciniastatin A, a pederin-type translation inhibitor, promotes ectodomain shedding of cell-surface tumor necrosis factor receptor 1, J. Antibiotics, 68, 417, 10.1038/ja.2015.3 Hood, 2001, Induction of apoptosis by the marine sponge (Mycale) metabolites, mycalamide A and pateamine, Apoptosis, 6, 207, 10.1023/A:1011340827558 Huang, 2022, Teaching an old dog new tricks: Drug discovery by repositioning natural products and their derivatives, Drug Discovery Today., 10.1016/j.drudis.2022.02.007 Jewett, 2007, Total synthesis of pederin, Angew. Chem., 119, 6622, 10.1002/ange.200701677 Kačar, 2022, In vivo production of pederin by labrenzin pathway expansion, Metabolic Eng. Commun., 14, e00198, 10.1016/j.mec.2022.e00198 Kampa, 2013, Metagenomic natural product discovery in lichen provides evidence for a family of biosynthetic pathways in diverse symbioses, Proc. Nat. Acad. Sci., 110, E3129, 10.1073/pnas.1305867110 Kellar, 2006 Kobayashi, J.i., Itagaki, F., Shigemori, H., Sasaki, T., 1993. Three new onnamide congeners from the Okinawan marine sponge Theonella sp. J. Nat. Prod. 56, 976-981. Kocienski, 2000, Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin, J. Chem. Soc. Perkin Trans., 1, 2357, 10.1039/a909898d Koparde, 2019 Kumar, G., 2023. Natural products and their analogues acting against Mycobacterium tuberculosis: A recent update. Drug Dev. Res. Kust, 2018, Discovery of a pederin family compound in a nonsymbiotic bloom-forming Cyanobacterium, ACS Chem. Biol., 13, 1123, 10.1021/acschembio.7b01048 Lyu, 2021, CMNPD: a comprehensive marine natural products database towards facilitating drug discovery from the ocean, Nucleic Acids Res., 49, D509, 10.1093/nar/gkaa763 Matsumoto, 1968, A revised structure of pederin, Tetrahedron Lett., 9, 6297, 10.1016/S0040-4039(00)75458-X Matsunaga, 1992, Eight new cytotoxic metabolites closely related to onnamide A from two marine sponges of the genus Theonella, Tetrahedron, 48, 8369, 10.1016/S0040-4020(01)86585-6 Mayer, 2010, The odyssey of marine pharmaceuticals: a current pipeline perspective, Trends Pharmacol. Sci., 31, 255, 10.1016/j.tips.2010.02.005 Meoded, 2018, A Polyketide Synthase Component for Oxygen Insertion into Polyketide Backbones, Angew. Chem. Int. Ed., 57, 11644, 10.1002/anie.201805363 Montaser, 2011, Marine natural products: a new wave of drugs?, Future Med. Chem., 3, 1475, 10.4155/fmc.11.118 Montuori, 2023, Marine Natural Products with Activities against Prostate Cancer: Recent Discoveries, Int. J. Mol. Sci., 24, 1435, 10.3390/ijms24021435 Moriou, 2021, Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge Suberea clavata (Pulitzer-Finali, 1982), Mar. Drugs, 19, 143, 10.3390/md19030143 Mosey, 2012, Isolation, biological activity, synthesis, and medicinal chemistry of the pederin/mycalamide family of natural products, Nat. Prod. Rep., 29, 980, 10.1039/c2np20052j Nakabachi, 2019, Diaphorin, a polyketide produced by a bacterial symbiont of the Asian citrus psyllid, kills various human cancer cells, PLOS ONE, 14, e0218190, 10.1371/journal.pone.0218190 Nakamura, 2023, Two Onnamide Analogs from the Marine Sponge Theonella conica: Evaluation of Geometric Effects in the Polyene Systems on Biological Activity, Molecules, 28, 2524, 10.3390/molecules28062524 Narquizian, R., Kocienski, P., 2000a. The pederin family of antitumor agents: structures, synthesis and biological activity. The role of natural products in drug discovery, 25-56. Narquizian, 2000, The Pederin Family of Antitumor Agents: Structures, Synthesis and Biological Activity, 25 Newman, 2023, Drug Discovery from Natural Sources, Curr. Pharmacol. Rep., 9, 67, 10.1007/s40495-023-00313-3 Ogawara, 1991, Change of ras-transformed NRK-cells back to normal morphology by mycalamides A and B, antitumor agents from a marine sponge, Chem. Pharm. Bull., 39, 2152, 10.1248/cpb.39.2152 Paul, 2002, Theopederins K and L. Highly potent cytotoxic metabolites from a marine sponge Discodermia species, J. Nat. Prod., 65, 59, 10.1021/np0103766 Pereira, 2023, Investigating the antiviral therapeutic potentialities of marine polycyclic lamellarin pyrrole alkaloids as promising inhibitors for SARS-CoV-2 and Zika main proteases (Mpro), J. Biomol. Struct. Dyn., 1, 10.1080/07391102.2023.2217513 Perry, 1988, Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale, J. Am. Chem. Soc., 110, 4850, 10.1021/ja00222a067 Perry, 1990, Antiviral and antitumor agents from a New Zealand sponge, Mycale sp. 2. Structures and solution conformations of mycalamides A and B, J. Org. Chem., 55, 223, 10.1021/jo00288a037 Pettit, 2004, Antineoplastic Agents. 520. Isolation and Structure of Irciniastatins A and B from the Indo-Pacific Marine Sponge Ircinia ramosa, J. Med. Chem., 47, 1149, 10.1021/jm030207d Piel, J., Hui, D., Wen, G., Butzke, D., Platzer, M., Fusetani, N., Matsunaga, S., 2004a. Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei. Proceedings of the National Academy of Sciences 101, 16222-16227. Piel, 2004, Unprecedented diversity of catalytic domains in the first four modules of the putative pederin polyketide synthase, ChemBioChem, 5, 93, 10.1002/cbic.200300782 Piel, 2005, Exploring the Chemistry of Uncultivated Bacterial Symbionts: Antitumor Polyketides of the Pederin Family, J. Nat. Prod., 68, 472, 10.1021/np049612d Piel, J.r., Höfer, I., Hui, D., 2004c. Evidence for a symbiosis island involved in horizontal acquisition of pederin biosynthetic capabilities by the bacterial symbiont of Paederus fuscipes beetles. J. Bacteriol. 186, 1280-1286. Piel, J., 2002. A polyketide synthase-peptide synthetase gene cluster from an uncultured bacterial symbiont of Paederus beetles. Proceedings of the National Academy of Sciences 99, 14002-14007. Ramsey, 2015, Metabolic interplay between the Asian citrus psyllid and its Profftella symbiont: an Achilles’ heel of the citrus greening insect vector, PLoS One, 10, e0140826, 10.1371/journal.pone.0140826 Rust, M., Helfrich, E.J.N., Freeman, M.F., Nanudorn, P., Field, C.M., Rückert, C., Kündig, T., Page, M.J., Webb, V.L., Kalinowski, J., Sunagawa, S., Piel, J., 2020. A multiproducer microbiome generates chemical diversity in the marine sponge Mycale hentscheli. Proceedings of the National Academy of Sciences 117, 9508-9518. Sakemi, 1988, Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp, J. Am. Chem. Soc., 110, 4851, 10.1021/ja00222a068 Schleissner, 2017, Bacterial Production of a Pederin Analogue by a Free-Living Marine Alphaproteobacterium, J. Nat. Prod., 80, 2170, 10.1021/acs.jnatprod.7b00408 Shinde, P., Banerjee, P., Mandhare, A., 2019. Marine natural products as source of new drugs: A patent review (2015–2018). Expert opinion on therapeutic patents 29, 283-309. Simpson, 2000, Mycalamides C and D, cytotoxic compounds from the marine sponge Stylinos n. species, J. Nat. Prod., 63, 704, 10.1021/np990431z Singh, S., Chib, S., Akhtar, M.J., Kumar, B., Chawla, P.A., Bhatia, R., 2023. Paradigms and Success Stories of Natural Products in Drug Discovery against. Current Neuropharmacology. Soldati, 1966, Cytotoxicity of pederin and some of its derivatives on cultured mammalian cells, Experientia, 22, 176, 10.1007/BF01897720 Thomford, 2018, Natural products for drug discovery in the 21st century: innovations for novel drug discovery, Int. J. Mol. Sci., 19, 1578, 10.3390/ijms19061578 Tsukamoto, 1999, Theopederins FJ: Five new antifungal and cytotoxic metabolites from the marine sponge, Theonella swinhoei, Tetrahedron, 55, 13697, 10.1016/S0040-4020(99)00841-8 Ul Haq, 2023, Chapter 18 - Polyketides and SARS-CoV-2, 423 Venturi, 2012, The protein synthesis inhibitors mycalamides A and E have limited susceptibility toward the drug efflux network, J. Biochem. Mol. Toxicol., 26, 94, 10.1002/jbt.20414 Vuong, 2001, Onnamide F: A New Nematocide from a Southern Australian Marine Sponge, Trachycladus laevispirulifer, J. Nat. Prod., 64, 640, 10.1021/np000474b Wakimoto, 2023, Biosynthesis of Bioactive Natural Products Derived from Theonellidae Family Marine Sponges, Chem. Pharm. Bull., 71, 1, 10.1248/cpb.c22-00715 West, 2000, Mycalamide D, a new cytotoxic amide from the New Zealand marine sponge Mycale species, J. Nat. Prod., 63, 707, 10.1021/np9904511 Wu, F., Green, M.E., Floreancig, P.E., 2011. Total Synthesis of Pederin and Analogs. Angewandte Chemie (International ed. in English) 50, 1131. Yamada, 2019, Diaphorin, a polyketide synthesized by an intracellular symbiont of the Asian citrus psyllid, is potentially harmful for biological control agents, PLoS One, 14, e0216319, 10.1371/journal.pone.0216319 Yang, 2020, Exploration and genome mining of natural products from marine Streptomyces, Appl. Microbiol. Biotechnol., 104, 67, 10.1007/s00253-019-10227-0 Yeung, A.W.K., El-Demerdash, A., Berindan-Neagoe, I., Atanasov, A.G., Ho, Y.-S., 2018. Molecular responses of cancers by natural products: modifications of autophagy revealed by literature analysis. Crit. Rev. Oncog 23. Zimmermann, K., Engeser, M., Blunt, J.W., Munro, M.H., Piel, J.r., 2009. Pederin-type pathways of uncultivated bacterial symbionts: analysis of O-methyltransferases and generation of a biosynthetic hybrid. Journal of the American Chemical Society 131, 2780-2781.