Alkene lactones from Persea fulva (Lauraceae): Evaluation of their effects on tumor cell growth in vitro and molecular docking studies

Reis, Isabella Mary Alves; Conceição, Rodrigo Souza; Ferreira, Rafael Short; Santos, Cleonice Creusa dos; Silva, Girliane Regina da; Oliveira, Larissa de Mattos; Cassiano, Dayse Santos Almeida; Santos, Manoelito Coelho dos; Botura, Mariana Borges; Silva, Víctor Diógenes Amaral da; Costa, Sílvia Lima; Silva, Tânia Maria Sarmento da; Vieira, Ivo José Curcino; Braz-Filho, Raimundo; Branco, Alexsandro

doi:10.1016/j.bioorg.2019.02.023

Cited by 8 publications

(11 citation statements)

References 38 publications

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“…With respect to the correlated structures 4 – 6 , compound 6 was the most active (EC 50 of 3.6 μM) followed by derivatives 5 and 4 (EC 50 of 29.9 and 45.2 μM, respectively). Based on structural aspects, the data herein suggest that side chain extension plays an important role in the anti‐ T. cruzi potential, similarly to what was previously described for the antiproliferative activity [21] …”

Section: Resultssupporting

confidence: 84%

“…NMR and ESI‐HR‐MS data of 1 – 5 were identical to those reported in the literature [8,21] for majoranolide B, majorenolide, majorynolide, lincomolide D, and isolinderanolide E, respectively ( Figure 1). However, the configuration of C‐5 was not previously determined for compounds 1 – 3 .…”

Section: Resultssupporting

confidence: 78%

“…Details concerning the collection of P. fulva were previously reported [21] . Roots of P. americana were collected in São Paulo, SP, Brazil (−23.489090 and −46.673826) in February 2006 (SISGEN number A4123E4).…”

Section: Methodsmentioning

confidence: 99%

“…Details concerning the isolation of 1 – 3 from P. fulva leaves were previously reported [21] . Dried roots (350 g) from P. americana were grounded and extracted with hexane at room temperature to afford 3.6 g of crude extract.…”

Section: Methodsmentioning

confidence: 99%

“…Additionally, γ‐lactones isolated from Lauraceae species have been shown to possess diverse biological activities, such as antimycobacterial, [9] anti‐inflammatory [10] and cytotoxic activities [8,11,13,19,20] . In a previous study, [21] four alkene‐γ‐lactones isolated from leaves of Persea fulva showed antiproliferative activity against tumor cells in vitro .…”

Section: Introductionmentioning

confidence: 98%

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γ‐Lactones from Persea americana and Persea fulva – in Vitro and in Silico Evaluation of Trypanosoma cruzi Activity

Reis

Umehara

Conceição

et al. 2021

Chemistry & Biodiversity

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In the present study, five known γ‐lactones (majoranolide B – 1, majorenolide – 2, majorynolide – 3, lincomolide D – 4, and isolinderanolide E – 5), as well as a new one (perseanolide – 6), were isolated from Persea fulva and P. americana. All isolated compounds exhibited potential activity against trypomastigote forms of Trypanosoma cruzi, whereas compounds 2 (EC50 of 4.8 μM) and 6 (EC50 of 3.6 μM) displayed superior activity than the positive control benznidazole (EC50 of 16.4 μM), with selectivity index (SI) values of 17.8 and >55.6, respectively (benznidazole, SI>12.2). Molecular docking studies were performed for 1–6 against six T. cruzi molecular targets. Using this approach, we observed that, even though perseanolide (6) showed favorable docking to several studied targets, the results were especially promising for hypoxanthine phosphoribosyl transferase (PDB 1TC1). As PDB 1TC1 is associated to the transference of a monophosphorylated ribose from phosphoribosylpyrophosphate (PRPP) in the ribonucleotide synthesis pathway, this interaction may affect the survival of T. cruzi in mammalian cells. The data herein also indicate that possible intermolecular interactions between 6 and PDB 1TC1 derive from (i) hydrogen bonds in the α,β‐unsaturated‐γ‐lactone unity and (ii) hydrophobic interactions in the long‐chain alkyl group. Based on our results, perseanolide (6), reported for the first time in this work, can auspiciously contribute to future works regarding new trypanocidal agents.

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Section: Resultssupporting

confidence: 84%

Section: Resultssupporting

confidence: 78%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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γ‐Lactones from Persea americana and Persea fulva – in Vitro and in Silico Evaluation of Trypanosoma cruzi Activity

Reis

Umehara

Conceição

et al. 2021

Chemistry & Biodiversity

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Chemistry and Bioactivity of the Genus Persea ‐ A Review

Totini,

Umehara,

Reis

et al. 2023

Chemistry & Biodiversity

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This review provides the first comprehensive appraisal of bioactive compounds and their biological activities in Persea species from 1950 to 2023. Relevant articles from reputable databases, including PubMed, Web of Science, Science Direct and Google Scholar were collected, leading to the isolation of about 141 metabolite compounds, mainly flavonoids, terpenoids, fatty alcohols, lignoids, and γ‐lactone derivatives. These compounds exhibit diverse biological activities, including insecticidal, antifeedant, nematicidal, antibacterial, antifungal, antiviral, cytotoxic, anti‐inflammatory, and antioxidant properties. The review emphasizes the significant chemical and pharmacological potential of different Persea species, encouraging further research in various fields and medicine. Valuable insights into potential applications of Persea plants are provided.

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A review of natural products and small‐molecule therapeutics acting on central nervous system malignancies: Approaches for drug development, targeting pathways, clinical trials, and challenges

Pasdaran,

Grice,

Hamedi

2024

Drug Development Research

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In 2021, the World Health Organization released the fifth edition of the central nervous system (CNS) tumor classification. This classification uses histopathology and molecular pathogenesis to group tumors into more biologically and molecularly defined entities. The prognosis of brain cancer, particularly malignant tumors, has remained poor worldwide, approximately 308,102 new cases of brain and other CNS tumors were diagnosed in the year 2020, with an estimated 251,329 deaths. The cost and time‐consuming nature of studies to find new anticancer agents makes it necessary to have well‐designed studies. In the present study, the pathways that can be targeted for drug development are discussed in detail. Some of the important cellular origins, signaling, and pathways involved in the efficacy of bioactive molecules against CNS tumorigenesis or progression, as well as prognosis and common approaches for treatment of different types of brain tumors, are reviewed. Moreover, different study tools, including cell lines, in vitro, in vivo, and clinical trial challenges, are discussed. In addition, in this article, natural products as one of the most important sources for finding new chemotherapeutics were reviewed and over 700 reported molecules with efficacy against CNS cancer cells are gathered and classified according to their structure. Based on the clinical trials that have been registered, very few of these natural or semi‐synthetic derivatives have been studied in humans. The review can help researchers understand the involved mechanisms and design new goal‐oriented studies for drug development against CNS malignancies.

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Alkene lactones from Persea fulva (Lauraceae): Evaluation of their effects on tumor cell growth in vitro and molecular docking studies

Cited by 8 publications

References 38 publications

γ‐Lactones from Persea americana and Persea fulva – in Vitro and in Silico Evaluation of Trypanosoma cruzi Activity

γ‐Lactones from Persea americana and Persea fulva – in Vitro and in Silico Evaluation of Trypanosoma cruzi Activity

Chemistry and Bioactivity of the Genus Persea ‐ A Review

A review of natural products and small‐molecule therapeutics acting on central nervous system malignancies: Approaches for drug development, targeting pathways, clinical trials, and challenges

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