Artículos de Revisión
Published 2020-12-30
Keywords
- Acetogenins,
- Secondary metabolism,
- Annonaceae
How to Cite
León Méndez, G., Pájaro Castro, N. ., & Granados Conde, C. . (2020). Annonaceae squamosa a source of acetogenins today. Ciencia Y Salud Virtual, 12(2), 88–101. https://doi.org/10.22519/21455333.1289
Abstract
Chemical studies on plants of the Annonaceae family have intensified in recent decades due to the discovery of molecules with medicinal potential. Moreover, until 2004, 593 acetogenins (ACG), 51 species in 13 genera were identified. This suggests that plants of this family allocate significant resources for the biosynthesis of these compounds. Despite the diversity of these molecules, their biological functions, including their physiological and ecological functions are not well understood. This paper presents a review of their knowledge, in particular on the biosynthetic pathway and biogenetic acetogenins, which will improve our understanding of secondary metabolism of these pharmacologically important molecules.
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References
1. Kelly, LM. Annonaceae Juss. Flora del Valle de Tehuacán-Cuicatlán. 2000; 31: 1–5.
2. Chih-Chuang, L., Fang-Rong, C., Shu-Li, C., Chin-Chung, W., Kuo-Hsiung, L., Yang-Chang, W. Novel cytotoxic monotetrahydrofuranic Annonaceous acetogenins from Annona Montana. Bioorganic & Medicinal Chemistry. 2005; 13: 4767–4776.
3. De la Cruz-Chacón, I., Castro-Moreno, M., Luna-Cázares, L., González-Esquinca, A., La familia Annonaceae Juss. En México. ACANDONIA. 2016; 10(2): 71-82.
4. Xicohténcatl-Lara, L., Figueroa-Castro, D., Andrés-Hernández, A., Campos-Villanueva, A. Aspects of the reproductive biology of Stenanona flagelliflora (Annonaceae). Pak. J. Bot. 2016; 48(1): 211-221.
5. Baldwins S., Matto L., Allisho A., Khand, W., McLean, S. Mono-Tetrahidrofuran Annonaceaus from Annona montana. Nat. Prod. Rep. 2000; 63: 1235-1238.
6. Guerrero E., Fischer G. Integrated management of sugar apple (Annona squamosa L.) Revista Colombiana De Ciencias Hortícolas. 2007; 2(1): 154-169.
7. Ramos J. Síntesis quimioenzimática de anillos THF presentes en acetogeninas. Universidad de la Republica, Montevideo, Uruguay. 2014. Recuperado de http://riquim.fq.edu.uy/archive/files/9384a6b70193861f279358368242a693.pdf
8. Kladi, M., Vagias, C., Papazafiri, P., Brogi, S., Tafi, A., Roussis, V. Tetrahydrofuran acetogenins from Laurencia glandulifera. J. Nat. Prod. 2009; 72: 190–193.
9. Moreno, N., Miranda, D., Martínez, F. Germination of sugar apple (Annona squamosa L.) seeds submitted to estratification. Revista Colombiana de Ciencias Hortícolas. 2013; 7(1): 20-30.
10. Morton, J. Sugar apple (Annona squamosa). 1987; 69-72. Recuperado de http://www.tradewindsfruit.com/content/sugar-apple.htm
11. Alali, F., Laughlin, J. Annonaceus acetogenins: Recent progress. J Nat Prod. 1999; 62(3): 504- 540.
12. Cave, A. Acetogenin from annonaceae. Progress in the chemistry of organic Natural products. 1997: 81-287.
13. Schlie-Guzmán, M., González-Esquinca, A., Luna-Cazáres, L. Las acetogeninas de Annonaceae: efecto antiproliferativo en líneas celulares neoplásicas. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas. 2009; 8(4): 245-257.
14. Ye, Q., Zhao, G., McLaughlin, J. Loncigin and Goniothalamicinone, bioactivite Mono-tetrahidrofuran Acetogenins from Asimicina longifola. Nat. Prod. Rep. 1996; 85.
15. Rieser, M., Gu, Z., Colmillo, X., Zeng, L., McLaughlin J. Five Novel Mono-tetrahydrofuran Ring Acetogenins from the Seeds of Annona muricata. Nat. Prod. Rep. 1996; 59: 100-108.
16. Zeng, L., McLaughlin, J., Johnson, H. Muricoreacin and murihexocin, MTF acetogenin from the leaves of Annona muricata. Nat. Prod. Rep. 1998; 14: 275-306.
17. Ávalos-García, A., Pérez-Urria, E. Metabolismo secundario de plantas. Reduca (Biología). Serie Fisiología Vegetal. 2009; 2(3): 119-145.
18. Gu, Z., Fang, X., Zeng, L., McLaughlin, J. Goniocin from Goniothalamus giganteus: the first tri-THF acetogeonin. Tetrahedron Lett. 1994; 35: 5367-5368.
19. Fang, X. Annonaceaes Acetogenins. An Updated Review. Phytochemical Analysis. 1993; 28(4): 35-44.
20. Shahzad-Aslam, M., Syarhabil-Ahmad, M., Soh-Mamat, A., Ahmad, M. Goniothalamus: Phytochemical and Ethnobotanical Review. Recent Advances in Biology and Medicine. 2016; 2: 34-47.
21. Chuzeville-Munguía C. Identificación de la modulación de la proteína tau en el tratamiento in vitro con acetogeninas de guanábana (Annona muricata). Universidad Veracruzana, Veracruz, México. 2015. Recuperado de https://cdigital.uv.mx/bitstream/handle/123456789/42611/ChuzevilleMunguiaCarolee.pdf;jsessionid=B3A460AE01A876C6841DF057097F9BE6?sequence=2
22. Kuwabara, K. Desing syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics. Eur. J. Biochem. 2000; 207: 2538-2546.
23. Chahboune, N. Guanaconetins, new antitumoral acetogenins, mitochondrial complex I and tumor cell growth inhibitors. Bioorg Med Chem. 2006; 14(4): 1089-94.
24. Figadère, B. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat. Prod. Rep. 2005; 22: 269–303.
2. Chih-Chuang, L., Fang-Rong, C., Shu-Li, C., Chin-Chung, W., Kuo-Hsiung, L., Yang-Chang, W. Novel cytotoxic monotetrahydrofuranic Annonaceous acetogenins from Annona Montana. Bioorganic & Medicinal Chemistry. 2005; 13: 4767–4776.
3. De la Cruz-Chacón, I., Castro-Moreno, M., Luna-Cázares, L., González-Esquinca, A., La familia Annonaceae Juss. En México. ACANDONIA. 2016; 10(2): 71-82.
4. Xicohténcatl-Lara, L., Figueroa-Castro, D., Andrés-Hernández, A., Campos-Villanueva, A. Aspects of the reproductive biology of Stenanona flagelliflora (Annonaceae). Pak. J. Bot. 2016; 48(1): 211-221.
5. Baldwins S., Matto L., Allisho A., Khand, W., McLean, S. Mono-Tetrahidrofuran Annonaceaus from Annona montana. Nat. Prod. Rep. 2000; 63: 1235-1238.
6. Guerrero E., Fischer G. Integrated management of sugar apple (Annona squamosa L.) Revista Colombiana De Ciencias Hortícolas. 2007; 2(1): 154-169.
7. Ramos J. Síntesis quimioenzimática de anillos THF presentes en acetogeninas. Universidad de la Republica, Montevideo, Uruguay. 2014. Recuperado de http://riquim.fq.edu.uy/archive/files/9384a6b70193861f279358368242a693.pdf
8. Kladi, M., Vagias, C., Papazafiri, P., Brogi, S., Tafi, A., Roussis, V. Tetrahydrofuran acetogenins from Laurencia glandulifera. J. Nat. Prod. 2009; 72: 190–193.
9. Moreno, N., Miranda, D., Martínez, F. Germination of sugar apple (Annona squamosa L.) seeds submitted to estratification. Revista Colombiana de Ciencias Hortícolas. 2013; 7(1): 20-30.
10. Morton, J. Sugar apple (Annona squamosa). 1987; 69-72. Recuperado de http://www.tradewindsfruit.com/content/sugar-apple.htm
11. Alali, F., Laughlin, J. Annonaceus acetogenins: Recent progress. J Nat Prod. 1999; 62(3): 504- 540.
12. Cave, A. Acetogenin from annonaceae. Progress in the chemistry of organic Natural products. 1997: 81-287.
13. Schlie-Guzmán, M., González-Esquinca, A., Luna-Cazáres, L. Las acetogeninas de Annonaceae: efecto antiproliferativo en líneas celulares neoplásicas. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas. 2009; 8(4): 245-257.
14. Ye, Q., Zhao, G., McLaughlin, J. Loncigin and Goniothalamicinone, bioactivite Mono-tetrahidrofuran Acetogenins from Asimicina longifola. Nat. Prod. Rep. 1996; 85.
15. Rieser, M., Gu, Z., Colmillo, X., Zeng, L., McLaughlin J. Five Novel Mono-tetrahydrofuran Ring Acetogenins from the Seeds of Annona muricata. Nat. Prod. Rep. 1996; 59: 100-108.
16. Zeng, L., McLaughlin, J., Johnson, H. Muricoreacin and murihexocin, MTF acetogenin from the leaves of Annona muricata. Nat. Prod. Rep. 1998; 14: 275-306.
17. Ávalos-García, A., Pérez-Urria, E. Metabolismo secundario de plantas. Reduca (Biología). Serie Fisiología Vegetal. 2009; 2(3): 119-145.
18. Gu, Z., Fang, X., Zeng, L., McLaughlin, J. Goniocin from Goniothalamus giganteus: the first tri-THF acetogeonin. Tetrahedron Lett. 1994; 35: 5367-5368.
19. Fang, X. Annonaceaes Acetogenins. An Updated Review. Phytochemical Analysis. 1993; 28(4): 35-44.
20. Shahzad-Aslam, M., Syarhabil-Ahmad, M., Soh-Mamat, A., Ahmad, M. Goniothalamus: Phytochemical and Ethnobotanical Review. Recent Advances in Biology and Medicine. 2016; 2: 34-47.
21. Chuzeville-Munguía C. Identificación de la modulación de la proteína tau en el tratamiento in vitro con acetogeninas de guanábana (Annona muricata). Universidad Veracruzana, Veracruz, México. 2015. Recuperado de https://cdigital.uv.mx/bitstream/handle/123456789/42611/ChuzevilleMunguiaCarolee.pdf;jsessionid=B3A460AE01A876C6841DF057097F9BE6?sequence=2
22. Kuwabara, K. Desing syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics. Eur. J. Biochem. 2000; 207: 2538-2546.
23. Chahboune, N. Guanaconetins, new antitumoral acetogenins, mitochondrial complex I and tumor cell growth inhibitors. Bioorg Med Chem. 2006; 14(4): 1089-94.
24. Figadère, B. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat. Prod. Rep. 2005; 22: 269–303.