Síntese total de α-pironas de ocorrência natural: uma revisão

Marcílio Wagner Fonte Silva; Clécio Souza Ramos; João Rufino de Freitas Filho

doi:10.22481/exon.v14i2.20556

Autores

Marcílio Wagner Fonte Silva Universidade Federal Rural de Pernambuco
Clécio Souza Ramos Universidade Federal Rural de Pernambuco
João Rufino de Freitas Filho Universidade Federal Rural de Pernambuco

DOI:

https://doi.org/10.22481/exon.v14i2.20556

Palavras-chave:

α-Pironas, Compostos bioativos, Síntese total

Resumo

As pironas constituem uma família de compostos cíclicos insaturados de seis membros contendo um átomo de oxigênio. Em vista dos motivos químicos, γ-pirona é a forma vinílica da α-pirona, que possui uma lactona. Como resultado, esses sistemas de anéis compartilham propriedades químicas semelhantes. As α-pironas são encontradas em compostos naturais oriundos de micro-organismos, plantas e animais, apresentando uma diversidade em estruturas e grande potencial biológico. O desenvolvimento de rotas de obtenção destas moléculas pela síntese orgânica, auxilia a elucidação estrutural e ação farmacológica destas moléculas. A presente revisão resume os avanços recentes na síntese total de α-pironas de ocorrência natural.

Downloads

Não há dados estatísticos.

Referências

L. F. Cavalieri, The Chemistry of the Monocyclic α-and γ-Pyrones., Chem. Rev. 41 (1947) 525– 584.

G. P. Ellis, "Pyrans and fused pyrans: (ii) reactivity, in: In Comprehensive Heterocycles Chemistry", Pergamon, Oxford, 1984.

M. Moreno-Mañas, R. Pleixats, "Dehydroacetic Acid, Triacetic Acid Lactone, and Related Pyrones, in: Advances in Heterocyclic Chemistry", Elsevier, Florida, 1992.

G.P. McGlacken, I.J.S. Fairlamb, 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity, Nat. Prod. Rep. 22 (2005) 369.

J. Li, Y. Wang, X. Hao, S. Li, J. Jia, Y. Guan, Z. Peng, H. Bi, C. Xiao, S. Cen, M. Gan, Broad Spectrum Antiviral Natural Products from the Marine-Derived Penicillium sp. IMB17-046, Molecules. 24 (2019) 2821.

P.S. Kothavade, D.M. Nagmoti, V.D. Bulani, A.R. Juvekar, Arzanol, a Potent mPGES-1 Inhibitor: Novel Anti-Inflammatory Agent, The Scientific World Journal. 2013 (2013) 1–9.

G. Appendino, M. Ottino, N. Marquez, F. Bianchi, A. Giana, M. Ballero, O. Sterner, B.L. Fiebich, E. Munoz, Arzanol, an Anti-inflammatory and Anti-HIV-1 Phloroglucinol α-Pyrone from Helichrysum italicum ssp. microphyllum, J. Nat. Prod. 70 (2007) 608–612.

Z. Mao, D. Lai, X. Liu, X. Fu, J. Meng, A. Wang, X. Wang, W. Sun, Z.L. Liu, L. Zhou, Y. Liu, Dibenzo-α-pyrones: a new class of larvicidal metabolites against Aedes aegypti from the endophytic fungus Hyalodendriella sp. Ponipodef12: Dibenzo-α-pyrones, Pest. Manag. Sci. 73 (2017) 1478– 1485.

A. Ligresti, R. Villano, M. Allarà, I. Ujváry, V. Di Marzo, Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand, Pharmacological Research. 66 (2012) 163–169.

T. Grkovic, J.S. Blees, N.H. Colburn, T. Schmid, C.L. Thomas, C.J. Henrich, J.B. McMahon, K.R. Gustafson, Cryptocaryols A–H, α-Pyrone-Containing 1,3-Polyols from Cryptocarya sp. Implicated in Stabilizing the Tumor Suppressor Pdcd4, J. Nat. Prod. 74 (2011) 1015–1020.

T. Sunazuka, S. Ōmura, Total Synthesis of α-Pyrone Meroterpenoids, Novel Bioactive Microbial Metabolites, Chem. Rev. 105 (2005) 4559–4580.

I.-K. Lee, B.-S. Yun, Styrylpyrone-class compounds from medicinal fungi Phellinus and Inonotus spp., and their medicinal importance, J Antibiot. 64 (2011) 349–359.

S. Omura, H. Tomoda, Y.K. Kim, H. Nishida, Pyripyropenes, highly potent inhibitiors of ACYL CoA: cholesterol acyltransferase produced by Aspergillus fumigatus., J. Antibiot. 46 (1993) 1168– 1169.

S. Omura, F. Kuno, K. Otoguro, T. Sunazuka, K. Shiomi, R. Masuma, Y. Iwai, Arisugacin, a Novel and Selective Inhibitor of Acetylcholinesterase from Penicillium sp. FO-4259., J. Antibiot. 48 (1995) 745–746.

H. Shin, H.-S. Lee, J. Lee, J. Shin, M. Lee, H.-S. Lee, Y.-J. Lee, J. Yun, J. Kang, Violapyrones H and I, New Cytotoxic Compounds Isolated from Streptomyces sp. Associated with the Marine Starfish Acanthaster planci, Marine Drugs. 12 (2014) 3283–3291.

E.P. Stout, A.P. Hasemeyer, A.L. Lane, T.M. Davenport, S. Engel, M.E. Hay, C.R. Fairchild, J. Prudhomme, K. Le Roch, W. Aalbersberg, J. Kubanek, Antibacterial Neurymenolides from the Fijian Red Alga Neurymenia fraxinifolia, Org. Lett. 11 (2009) 225–228.

R.E. Charlton, F.X. Webster, A. Zhang, C. Schal, D. Liang, I. Sreng, W.L. Roelofs, Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone., Proceedings of the National Academy of Sciences. 90 (1993) 10202–10205.

J.R. Rocca, J.H. Tumlinson, B.M. Glancey, C.S. Lofgren, The queen recognition pheromone of , preparation of (-6-(1-pentenyl)-2H-pyran-2-one., Tetrahedron Letters. 24 (1983) 1889–1892.

J. Qi, A. Zulfiker, C. Li, D. Good, M. Wei, The Development of Toad Toxins as Potential Therapeutic Agents, Toxins. 10 (2018) 336.

Z.-H. Jiang, Q.-X. Yang, T. Tanaka, I. Kouno, Bicyclic Polyketide Lactones from Chinese Medicinal Ants, Polyrhacis lamellidens, J. Nat. Prod. 71 (2008) 724–727.

H. Irschik, R. Jansen, G. Höfle, K. Gerth, H. Reichenbach, The corallopyronins, new inhibitors of bacterial RNA synthesis from Myxobacteria., J. Antibiot. 38 (1985) 145–152.

H. Irschikk, H. Reichenbach, G. BiotechnologischFeorschung, A. Mikrobiologieand, The myxopyronins, new inhibitors of bacterial rna synthesis from myxococcus fulvus (myxobacterales)t, THE JOURNAL OF ANTIBIOTICS. 8 (1983) 1651-1658.

K. Shima, S. Ledig, N. Loeper, A. Schiefer, K. Pfarr, A. Hoerauf, S. Graspeuntner, J. Rupp, Effective inhibition of rifampicin-resistant Chlamydia trachomatis by the novel DNA-dependent RNA polymerase inhibitor corallopyronin A, International Journal of Antimicrobial Agents. 52 (2018) 523–524.

F. Kock, M. Hauptmann, A. Osterloh, T.F. Schäberle, S. Poppert, H. Frickmann, K.-D. Menzel, G. Peschel, K. Pfarr, A. Schiefer, G.M. König, A. Hoerauf, B. Fleischer, C. Keller, Orientia tsutsugamushi Is Highly Susceptible to the RNA Polymerase Switch Region Inhibitor Corallopyronin A In Vitro and In Vivo, Antimicrobial Agents and Chemotherapy. 62 (2018) 12.

T.I. Moy, A. Daniel, C. Hardy, A. Jackson, O. Rehrauer, Y.S. Hwang, D. Zou, K. Nguyen, J.A. Silverman, Q. Li, C. Murphy, Evaluating the activity of the RNA polymerase inhibitor myxopyronin B against Staphylococcus aureus: Characterization of myxopyronin B in Staphylococcus aureus, FEMS Microbiology Letters. 319 (2011) 176–179.

F. Petersen, H. Zähner, J.W. Metzger, S. Freund, R.-P. Hummel, Germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551., J. Antibiot. 46 (1993) 1126–1138.

Y. Aoki, D. Matsumoto, H. Kawaide, M. Natsume, Physiological role of germicidins in spore germination and hyphal elongation in Streptomyces coelicolor A3(2), J Antibiot. 64 (2011) 607– 611.

Z. Xu, L. Ding, C. Hertweck, A Branched Extender Unit Shared between Two Orthogonal Polyketide Pathways in an Endophyte, Angew. Chem. Int. Ed. 50 (2011) 4667–4670.

M. Ma, M.E. Rateb, D. Yang, J.D. Rudolf, X. Zhu, Y. Huang, L.-X. Zhao, Y. Jiang, Y. Duan, B. Shen, Germicidins H–J from Streptomyces sp. CB00361, J Antibiot. 70 (2017) 200–203.

Y. Du, J. Sun, Q. Gong, Y. Wang, P. Fu, W. Zhu, New α-Pyridones with Quorum-Sensing Inhibitory Activity from Diversity-Enhanced Extracts of a Streptomyces sp. Derived from Marine Algae, J. Agric. Food Chem. 66 (2018) 1807–1812.

J. Zhang, Y. Jiang, Y. Cao, J. Liu, D. Zheng, X. Chen, L. Han, C. Jiang, X. Huang, Violapyrones A–G, α-Pyrone Derivatives from Streptomyces violascens Isolated from Hylobates hoolock Feces, J. Nat. Prod. 76 (2013) 2126–2130.

H.-S. Lee, B.-J. An, H.J. Kim, Y.H. Cho, D.I. Kim, J.Y. Jang, J.H. Kwak, H.-S. Lee, Y.-J. Lee, J.S. Lee, H.J. Shin, Anti-Inflammatory Effect of Violapyrones B and C from a Marine-derived Streptomyces sp., Nat Prod Sci. 21 (2015) 251. https://doi.org/10.20307/nps.2015.21.4.251.

C. Hertweck, The Biosynthetic Logic of Polyketide Diversity, Angew. Chem. Int. Ed. 48 (2009) 4688–4716.

T.F. Schäberle, Biosynthesis of α-pyrones, Beilstein J. Org. Chem. 12 (2016) 571–588. https://doi.org/10.3762/bjoc.12.56.

Y. Matsuda, I. Abe, Biosynthesis of fungal meroterpenoids, Nat. Prod. Rep. 33 (2016) 26–53.

P.M. Dewick, Medicinal natural products: a biosynthetic approach, 2nd ed, Wiley, New York, 2002.

H. Tomoda, N. Tabata, Y. Nakata, H. Nishida, T. Kaneko, R. Obata, T. Sunazuka, S. Ōmura, Biosynthesis of Pyripyropene A, J. Org. Chem. 61 (1996) 882–886.

T. Itoh, K. Tokunaga, Y. Matsuda, I. Fujii, I. Abe, Y. Ebizuka, T. Kushiro, Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases, Nature Chem. 2 (2010) 858–864.

A.A.Q. Al-Khdhairawi, G.A. Cordell, N.F. Thomas, N.B. Shivanagere Nagojappa, J.-F.F. Weber, Natural diterpene pyrones: chemistry and biology, Org. Biomol. Chem. 17 (2019) 8943–8957.

H. Kato, Y. Tsunematsu, T. Yamamoto, T. Namiki, S. Kishimoto, H. Noguchi, K. Watanabe, New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145, J Antibiot. 69 (2016) 561–566.

T. Awakawa, I. Abe, Reconstitution of Polyketide-Derived Meroterpenoid Biosynthetic Pathway in Aspergillus oryzae, JoF. 7 (2021) 486.

H. Sucipto, J.H. Sahner, E. Prusov, S.C. Wenzel, R.W. Hartmann, J. Koehnke, R. Müller, In vitro reconstitution of α-pyrone ring formation in myxopyronin biosynthesis, Chem. Sci. 6 (2015) 5076– 5085.

H. Sucipto, D. Pogorevc, E. Luxenburger, S.C. Wenzel, R. Müller, Heterologous production of myxobacterial α-pyrone antibiotics in Myxococcus xanthus, Metabolic Engineering. 44 (2017) 160–170.

Ö. Erol, T.F. Schäberle, A. Schmitz, S. Rachid, C. Gurgui, M. El Omari, F. Lohr, S. Kehraus, J. Piel, R. Müller, G.M. König, Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A, Chem. Eur. J. of Chem. Bio. 11 (2010) 1253–1265.

J.S. Bauer, M.G.K. Ghequire, M. Nett, M. Josten, H.-G. Sahl, R. De Mot, H. Gross, Biosynthetic Origin of the Antibiotic Pseudopyronines A and B in Pseudomonas putida BW11M1, ChemBioChem. 16 (2015) 2491–2497.