Abstract
Bacopa gratioloides (Cham.) Chodat & Hassl., Plantaginaceae, is an aquatic species underexplored and found in the hostile biome Chaco, Brazil. In this work, a new sesquiterpene was obtained, which is accumulated in high levels in B. gratioloides volatile oil when extracted via an improved and eco-friendly hydrodistillation method (16 h—4 h/day). Bacopa gratioloides volatile oil was purified by recrystallization using methanol and deionized water (7:3, v/v) to isolate the new sesquiterpene, which was structurally characterized by MS, NMR, and 13C and 1H chemical shift simulations. The applied procedures improved the yield of B. gratioloides volatile oil (0.15%) by about 3.5 times and facilitated the isolation of the new sesquiterpene di-7,10-epi-dihydroartemisinic acid, since the most volatile compounds were reduced in the volatile oil. This sesquiterpene is a derivative of antimalarial artemisinin and it was isolated with a high yield (73%). The sesquiterpene di-7,10-dihydroartemisinic acid showed potential against B16F10-Nex2 melanoma cancer cells with a marked inhibition of cell migration and antiparasitic activity against Trypanosoma cruzi. These are the first phytochemical and biological studies of B. gratioloides, which is a promising source of di-7,10-epi-dihydroartemisinic acid on a large scale and through sustainable processes.
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Acknowledgements
The authors are thankful to UFMS (Universidade Federal de Mato Grosso do Sul), INAU (Instituto Nacional de Áreas Úmidas), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico, process number 313047/2020-0), FUNDECT (Fundação de Apoio ao Desenvolvimento do Ensino, Ciência e Tecnologia do Estado de Mato Grosso do Sul – process number 71/000.491/2021), and CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior).
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NSC: conceptualization, methodology, investigation, writing—original draft, visualization. LBS: investigation. JMA: investigation, formal analysis, writing of the original draft. CFRO: investigation, writing of the original draft, and formal analysis. LHM, KPS, EJPG, and TT: Investigation and formal analysis. JCPM: conceptualization. RCOA, HFVT, CLH, and RCS: investigation. AJM: Formal analysis, resources. FMSJ: formal analysis. DBS: conceptualization, methodology, writing, review and editing of manuscript, resources, and supervision. All authors read and approved the final version of the submitted manuscript.
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Cassemiro, N.S., Sanches, L.B., de Almeida, J.M. et al. A Novel Artemisinin-Derived Sesquiterpene from Bacopa gratioloides Volatile Oil by Sustainable and Enhanced Procedures. Rev. Bras. Farmacogn. (2024). https://doi.org/10.1007/s43450-024-00537-4
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DOI: https://doi.org/10.1007/s43450-024-00537-4