DEREPLICATION OF ISOQUINOLINE ALKALOIDS FROM Duguetia Quitarensis (benth.) AND EVALUATION OF PHYTOTOXIC ACTIVITY

Authors

  • Márcia Bay Federal Institute of Education, Science and Technology of Rondônia, Campus Calama, Porto Velho, Rondônia, Brazil
  • Vitória C. da-Silva-Nery Federal Institute of Education, Science and Technology of Rondônia, Campus Calama, Porto Velho, Rondônia, Brazil
  • Hugo Rodrigues-da-Silva Federal Institute of Education, Science and Technology of Rondônia, Campus Calama, Porto Velho, Rondônia, Brazil
  • Anderson Rogério-dos-Santos Federal Institute of Education, Science and Technology of Rondônia, Campus Calama, Porto Velho, Rondônia, Brazil

Keywords:

Duguetia quitarensis, Annonaceae, alkaloids, dereplication, phytotoxic activity.

Abstract

Duguetia quitarensis (Benth.) is a species distributed across the Amazon region, from Venezuela to Bolivia. This study aimed to characterize the chemical profile of the methanolic extract of D. quitarensis through dereplication by direct infusion and to evaluate its phytotoxic potential against Allium cepa L. and Lactuca sativa L. Ten isoquinoline alkaloids were annotated, including aporphine-, benzyl-tetrahydroisoquinoline-, 7-hydroxyaporphine-, and oxoaporphine-type compounds. The methanolic extract exhibited phytotoxic effects of varying intensity, as indicated by seedling growth inhibition and germination assays. Root elongation was more sensitive than hypocotyl growth, particularly in A. cepa. The presence of multiple isoquinoline alkaloids suggests their contribution to the observed phytotoxicity, possibly through interference in cellular processes such as respiration and DNA synthesis. These findings expand the chemical knowledge of D.quitarensis and indicate its potential as a natural source of allelopathic or bioherbicidal compounds.

References

PIRES, N. M.; OLIVEIRA, V. R. “Alelopatia”. Em: OLIVEIRA, R. S et al. (eds.). Biologia e Manejo de Plantas Daninhas. Omnipax, Curitiba, 2011, Cap.5. pp 95-124. Alelopatia. ISBN 978-85-64619-02-9. Disponível: https://www.alice.cnptia.embrapa.br/alice/handle/doc/910833

DE SOUZA, C. S. M. et al. “Alelopatia do extrato aquoso de folhas de aroeira na germinação de sementes de alface”. Rev. Verde Agroecologia e Desenvolv. Sustent. 2007, 2, 96-100. https://doi.org/10.1590/1983-084X/14_160

BALBINOT JUNIOR, A. A.. Manejo das plantas daninhas pela alelopatia. Agropecuária Catarinense, 2011. 17(1), 61-64. Recuperado de https://publicacoes.epagri.sc.gov.br/rac/article/view/994. ISSN: 2525-6076.

DE OLIVEIRA, A. K. M.; MATIAS, R.; PINA, J.C.; DA SILVA, L. T. “Alelopatia e seu potencial na formulação de bioherbicidas”. Em: GUIDOLIN, D. G. F.; BARBOSA-FERREIRA, M.; PEREIRA, S. H. (Eds.). Produção e gestão agroindustrial. Editora Científica, Londrina, 2017, pp 90-104. ISBN: 978-65-00-11649-6. Disponível em: https://repositorio.pgsscogna.com.br/bitstream/123456789/29667/1/Coletana%20-

%20Produ%C3%A7%C3%A3o%20e%20Gest%C3%A3o%202017.pdf . Acesso em: 21 Set. 2025.

DA SILVA, M. A. D. et al. “Alelopatia de espécies da Caatinga”. Research Society and Development. 2021, 10, e57610414328 e57610414328. DOI: https://doi.org/10.33448/rsd-v10i4.14328. ISSN:2525-3409.

CASCAES, M. M. et al. “Essential Oils fromAnnonaceae Species from Brazil: A Systematic Review of Their Phytochemistry, and Biological

Activities”. International Journal of Molecular Sciences. 2021, 22(22), 12140. DOI: https://doi.org/10.3390/ijms222212140. ISSN: 1422-0067.

BAY, M. et al. “Atividades antioxidante e antibacteriana in vitro de extratos vegetais da família Annonaceae”. South American Journal of Basic Education Techinical. and Technological. 2020, 7, 128-144. ISSN: 2446-4821. https://teste-periodicos.ufac.br/index.php/SAJEBTT/article/download/3661/2488

MOGHADAMTOUSI, S. Z. et al. “Annona muricata (Annonaceae): A review of its traditional uses, isolated acetogenins and biological activities”. International Journal of Molecular Sciences. 2015,16, 15625-15658. DOI: https://doi.org/10.3390/ijms160715625

CARNEVALE NETO, F. Elaboração de métodos analíticos de derreplicação para o estudo metabolômico de especies de Quela (Vochysiaceae): detecção e elucidação in situ de micromoléculas com potencial antioxidante e antimalárico Dissertação de Mestrado em Química, Instituto de Química, Universidade Estadual Paulista, UNESP, Araraquara, 2020, 104 pp. http://hdl.handle.net/11449/97891

MACÍAS, F. A.; CASTELLANO, D.; MOLINILLO, J. M. G. “Search for a standard phytotoxic bioassay for allelochemicals. Selection of

standard target species”. Journal of Agricultural and Food Chemistry. 2000, 48, 2512-2521. DOI: https://doi.org/10.1021/jf9903051

PINTO, G. F. S.; ROMA, L. P.; KOLB, R. M. “Phytotoxicity of organic extracts of five medicinal plants of the Neotropical savanna”. Brazilian Journal of Biology. 2023, 83, e270122. DOI: https://doi.org/10.1590/1519-6984.270122

OLIVEIRA, S. C. C. et al. “Estudo fitoquímico de Solanum lycocarpum A. St.-Hil (Solanaceae) e sua aplicação na alelopatia”. Acta Botanica Brasilica. 2012, 26, 607-618. DOI: https://doi.org/10.1590/S0102-33062012000300010

BARBOSA, W. L. R. et al. “Manual para análise fitoquímica e cromatográfica de extratos vegetais”. Revista Científica da UFPA, 2004, 4, 1-19. ISSN:2179-7536.

DOS SANTOS, A. R.; VAZ, N. P. “Isoquinoline alkaloids and chemotaxonomy”. In: Ramawat, K. (Eds.). Biodiversity and Chemotaxonomy. Sustainable Development and Biodiversity, Springer Cham., Switzerland. 2019, pp 167-193.

DOI: https://doi.org/10.1007/978-3-030-30746-2_8

SHIM, H. J. et al. “General fragmentations of alkaloids in electrospray ionization tandem mass spectrometry”. Mass Spectrometry Letters. 2013, 4,79-82. DOI: https://doi.org/10.5478/MSL.2013.4.4.79

DE LIMA, B. R. et al. “Integrative approach based on leaf spray mass spectrometry, HPLC-DAD-MS/MS, and NMR for comprehensive

characterization of isoquinoline-derived alkaloids in leaves of Onychopetalum amazonicum R.E.Fr”. Journal of the Brazilian Chemical Society. 2020, 31, 79-89. DOI: http://dx.doi.org/10.21577/0103-5053.20190125

WANG, Z. et al. “Lotus (Nelumbo nucifera Gaertn.) leaf: A narrative review of its phytoconstituents, health benefits and food industry

applications”. Trends in Food Science & Technology. 2021, 112, 631-650. DOI: https://doi.org/10.1016/j.tifs.2021.04.033

CONCEIÇÃO, R. S. et al. “Rapid structural characterization of benzylisoquinoline and aporphine alkaloids from Ocotea spixiana acaricide extract by HPTLC-DESI-MSn”. Phytochemical Analysis. 2020,31, 711-721. DOI: https://doi.org/10.1002/pca.2935

MARQUES, J. V. et al. “A multi-omics strategy resolves the elusive nature of alkaloids in Podophyllum species”. Molecular BioSystems. 2013,10, 2838-2849. DOI: https://doi.org/10.1039/C4MB00403E

YAN, R. et al. “Studies on the alkaloids of the bark of Magnolia officinalis: Isolation and on-line analysis HPLC-ESI-MSn”. Molecules. 2013, 18, 7739-7750. DOI: https://doi.org/10.3390/molecules18077739

BARAKAT, S. A.; FERAS, Q. A.; AL HAMMOURI, M. A. “Dereplication study on Glaucium aleppicum Boiss. In Jordan”. Oriental Journal of Chemistry. 2016, 32, 1815-1822. DOI:http://dx.doi.org/10.13005/ojc/320409

SCHMIDT, J. et al. “Analysis of benzylisoquinoline-type alkaloids by electrospray tamdem mass spectrometry and atmospheric pressure photoionization”. European Journal of Mass Spectrometry. 2005, 11, 325-333. DOI: https://doi.org/10.1255/ejms.745

DE SOUZA, C. A. S. et al. “Asarone-derived phenylpropanoids and isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities”. Quimica. Nova. 2020, 43, 1397-1403. DOI: http://dx.doi.org/10.21577/0100-4042.20170617

DA SILVA, F. M. A. et al. “Positive electrospray ionization ion trap mass spectrometry and ab initio computational studies of the

multi-pathway fragmentation of oxoaporphine alkaloids”. International Journal of Mass Spectrometry. 2017,

, 30-36. DOI: https://doi.org/10.1016/j.ijms.2016.12.004

FERREIRA, A. G.; AQUILA, M. E. A. “Alelopatia: uma área emergente da ecofisiologia”. Revista Brasileira de Fisiologia Vegetal. 2000, 12,

-204. v12 (Especial) p175.PDF. ISSN: 0103-3131

HAIG, T. “Allelochemicals in Plants”. In: Zeng, R.S., Mallik, A.U., Luo, S.M. (eds.). Allelopathy in Sustainable Agriculture and Forestry. Springer, New York, NY. 2008. DOI: https://doi.org/10.1007/978-0-387-77337-7_4

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Published

2026-03-04

How to Cite

Bay, M., da-Silva-Nery, V. C., Rodrigues-da-Silva, H., & Rogério-dos-Santos, A. (2026). DEREPLICATION OF ISOQUINOLINE ALKALOIDS FROM Duguetia Quitarensis (benth.) AND EVALUATION OF PHYTOTOXIC ACTIVITY. Revista Cubana De Química, 37. Retrieved from https://cubanaquimica.uo.edu.cu/index.php/cq/article/view/5455

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Vol. 37 (2025)

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