EN PRENSA. Purificación de fomacta-1(15),4,8-trieno: precursor de fomactinas, antagonistas del factor activador de plaquetas. EN PRENSA
PDF

Palabras clave

Fomacta-1(15),4,8-trieno
Purificación
Nitrato de plata
Relevancia biológica

Métricas de PLUMX 

Resumen

La purificación de fomacta-1(15),4,8-trieno es un proceso esencial debido a su rol como precursor de las fomactinas, compuestos diterpénicos con propiedades biológicas significativas, como antagonistas del factor activador de plaquetas (PAF). Este trieno actúa como intermediario clave en las rutas biosintéticas de estos compuestos, que han demostrado potencial terapéutico, particularmente en estudios farmacológicos. Sin embargo, su purificación presenta retos debido a la complejidad de las mezclas obtenidas durante su síntesis. Este trabajo presenta un enfoque innovador mediante el uso de gel de sílice impregnado con nitrato de plata, una estrategia que mejora la separación del fomacta-1(15),4,8-trieno y optimiza la calidad del espectro de resonancia magnética nuclear (RMN). El método propuesto facilita una purificación más eficiente, lo que permite una caracterización más precisa del compuesto. Estos resultados subrayan la importancia de técnicas de purificación avanzadas en la investigación de metabolitos con aplicaciones farmacológicas de alto potencial.

https://doi.org/10.15741/revbio.12.e1868
PDF

Citas

Chow, S. Y., Williams, H. J., Pennington, J. D., Nanda, S., Reibenspies, J. H., & Scott, A. I. (2007). Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene. Tetrahedron, 63(27), 6204-6209. https://doi.org/10.1016/j.tet.2007.03.029

Damyanova, B., Momtchilova, S., Bakalova, S., Zuilhof, H., Christie, W. W., & Kaneti, J. (2002). Computational probes into the conceptual basis of silver ion chromatography: I. Silver(I) ion complexes of unsaturated fatty acids and esters. Journal of Molecular Structure: THEOCHEM, 589–590, 239–249. https://doi.org/10.1016/S0166-1280(02)00281-6

Daramwar, P. P., Srivastava, P. L., Priyadarshini, B., & Thulasiram, H. V. (2012). Preparative separation of α- and β-santalenes and (Z)-α- and (Z)-β-santalols using silver nitrate-impregnated silica gel medium pressure liquid chromatography and analysis of sandalwood oil. Analyst, 137(19), 4564–4570. https://doi.org/10.1039/C2AN35575B

Del Río-Chávez, Á. A., García-Gutiérrez, H. A., Román-Marín, L. U., Beiza-Granados, L., Cerda-García-Rojas, C. M., Joseph-Nathan, P., & Hernández-Hernández, J. D. (2019). Absolute configuration of phomactatriene diterpenoids obtained by Wagner–Meerwein rearrangement of epimeric verticillols. Chirality, 31(12), 1–13. https://doi.org/10.1002/chir.23061

Drugkar, K., Rathod, W., Sharma, T., Sharma, A., Joshi, J., Pareek, V. K., Ledwani, L., & Diwekar, U. (2021). Advanced separation strategies for up-gradation of bio-oil into value-added chemicals: A comprehensive review. Separation and Purification Technology, 283, 120149.

https://doi.org/10.1016/j.seppur.2021.120149

Goldring, W. P. D., & Pattenden, G. (2006). The Phomactins. A Novel Group of Terpenoid Platelet Activating Factor Antagonists Related Biogenetically to the Taxanes. Accounts Of Chemical Research, 39(5), 354-361. https://doi.org/10.1021/ar050186c

Hammerschick, T., & Vetter, W. (2023). Silver ion chromatography enables the separation of 2‑methylalkylresorcinols from alkylresorcinols. Journal of Separation Science, 46(20), e2300243. https://doi.org/10.1002/jssc.202300243

Hernández-Hernández, J. D., Román-Marín, L. U., Cerda-García-Rojas, C. M., & Joseph-Nathan, P. (2005). Verticillane Derivatives from Bursera suntui and Bursera kerberi. Journal Of Natural Products, 68(11), 1598-1602. https://doi.org/10.1021/np050323e

Kuroda, Y., Nicacio, K. J., Da Silva-Jr, I. A., Leger, P. R., Chang, S., Gubiani, J. R., Deflon, V. M., Nagashima, N., Rode, A., Blackford, K., Ferreira, A. G., Sette, L. D., Williams, D. E., Andersen, R. J., Jancar, S., Berlinck, R. G. S., & Sarpong, R. (2018). Isolation, synthesis and bioactivity studies of phomactin terpenoids. Nature Chemistry, 10(9), 938-945. https://doi.org/10.1038/s41557-018-0084-x

Li, T.-S., Li, J.-T., & Li, H.-Z. (1995). Modified and convenient preparation of silica impregnated with silver nitrate and its application to the separation of steroids and triterpenes. Journal of Chromatography A, 715, 372–375. https://doi.org/10.1016/0021-9673(95)00619-X

Liao, S., Dillon, J. T., Huang, C., Santos, E., & Huang, Y. (2021). Silver (I)-dimercaptotriazine functionalized silica: A highly selective liquid chromatography stationary phase targeting unsaturated molecules. Journal of Chromatography A, 1645, 462122. https://doi.org/10.1016/j.chroma.2021.462122

Morita, M., Mihashi, S., Itokawa, H., & Hara, S. (1983). Silver nitrate impregnation of preparative silica gel columns for liquid chromatography. Analytical Chemistry, 55(2), 412–414. https://doi.org/10.1021/ac00253a065

Niu, T., Yu, J., Wang, Z., Wang, C., Guo, Y., Li, J., & Wang, X. (2024). Purification of triterpenoid saponins and 25R/25S‐inokosterone from Achyranthes bidentata Bl. by high‐speed countercurrent chromatography coupled silver nitrate coordination. Journal Of Separation Science, 47(7). https://doi.org/10.1002/jssc.202300901

Palframan, M. J., & Pattenden, G. (2019). The verticillenes: Pivotal intermediates in the biosynthesis of the taxanes and the phomactins. Natural Product Reports, 36(1), 108–121. https://doi.org/10.1039/c8np00034d

Roth, G. A., Mensah, G. A., & Fuster, V. (2020). The global burden of cardiovascular diseases and risks: A compass for global action. Journal of the American College of Cardiology, 76(25), 2980–2981. https://doi.org/10.1016/j.jacc.2020.11.010

Tokiwano, T., Fukushi, E., Endo, T., & Oikawa, H. (2004). Biosynthesis of phomactins: common intermediate phomactatriene and taxadieneElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for labelled and unlabelled 1.See http://www.rsc.org/suppdata/cc/b4/b401377h/. Chemical Communications, 11, 1324. https://doi.org/10.1039/b401377h

Tryon‑Tasson, N., Ryoo, D., Eor, P., & Anderson, J. L. (2023). Silver‑mediated separations: A comprehensive review on advancements of argentation chromatography, facilitated transport membranes, and solid‑phase extraction techniques and their applications. Journal of Chromatography A, 1705, 464133. https://doi.org/10.1016/j.chroma.2023.464133

Tsujikawa, K., Okada, Y., Segawa, H., Yamamuro, T., Kuwayama, K., Kanamori, T., & Iwata, Y. T. (2022). Thin-layer chromatography on silver nitrate-impregnated silica gel for analysis of homemade tetrahydrocannabinol mixtures. Forensic Toxicology, 40(1), 125–131. https://doi.org/10.1007/s11419-021-00592-9

Williams, C. M., & Mander, L. N. (2001). Chromatography with silver nitrate. Tetrahedron, 57(3), 425-447. https://doi.org/10.1016/s0040-4020(00)00927-3

Yin, Z., & Dickschat, J. S. (2023). Engineering fungal terpene biosynthesis. Natural Product Reports, 40(1), 28–45. https://doi.org/10.1039/D2NP00020B

Zhang, L., Zhang, B., Zhu, A., Liu, S. H., Wu, R., Zhang, X., Xu, Z., Tan, R. X., & Ge, H. M. (2023). Biosynthesis of Phomactin platelet activating factor antagonist requires a two-enzyme cascade. Angewandte Chemie International Edition, 62(47), e202312996. https://doi.org/10.1002/anie.202312996

Zhang, Q., Lin, L., & Ye, W. (2018). Techniques for extraction and isolation of natural products: a comprehensive review. Chinese Medicine, 13(1). https://doi.org/10.1186/s13020-018-0177-x

Zhang, W.-M., Zhai, Y.-C., Yang, H.-J., Zhang, R.-G., Hao, J., Han, J.-Q., & Zhang, Y.-L. (2015). Silver nitrate–silica gel column chromatography purification linolenic acid in walnut oil. Science and Technology of Food Industry, 36(10), 229–232. https://doi.org/10.13386/j.issn1002-0306.2015.10.039

Licencia Creative Commons
Revista Bio Ciencias por Universidad Autónoma de Nayarit se encuentra bajo una Licencia Creative Commons Atribución-NoComercial-SinDerivadas 4.0 Unported.
Basada en una obra en http://biociencias.uan.edu.mx/.
Permisos que vayan más allá de lo cubierto por esta licencia pueden encontrarse en http://editorial.uan.edu.mx/index.php/BIOCIENCIAS.licencia de Creative Commons Reconocimiento-NoComercial-SinObraDerivada 4.0 Internacional