Cytotoxic Clerodane Diterpenes from <i>Casearia rupestris</i>

Vieira, Gerardo Magela; Dutra, Luiz Antônio; Ferreira, Paulo Michel Pinheiro; Moraes, Manoel Odoríco de; Costa-Lotufo, Letı́cia V.; Pessoa, Cláudia; Torres, Roseli Buzanelli; Boralle, Nivaldo; Bolzani, Vanderlan da Silva; Cavalheiro, Alberto José

doi:10.1021/np100840w

Cited by 46 publications

(37 citation statements)

References 35 publications

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“…Caseaobliquin A was purified by preparative HPLC‐PDA (C18 column, 250 mm × 21.2 mm, 10 μm) using methanol/water as the mobile phase 34 . Casearupestrins A, B and C were purified by column chromatography (silica C18, 78.0 × 3.0 cm, 40 μm) using a step gradient of water/methanol followed by silica gel column chromatography (21.8 × 2 cm, 230–400, 40–63 μm) eluted with hexane/ethyl acetate 35 . These standards were identified using spectrometric data (NMR, UV, FT‐IR and HRMS) and by comparison with spectral information available in the literature.…”

Section: Methodsmentioning

confidence: 99%

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Danuello

Castro

Pilon

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Clerodane‐type diterpenes from Casearia species show important pharmacological activites such as antitumor, antimicrobial and anti‐inflamatory. There are several mass spectrometry (MS)‐based methods for identification of diterpenes; however, there is still a lack of MS procedures capable of providing characteristic fragmentation pathways for a rapid and unambiguous elucidation of casearin‐like compounds. Methods Casearin‐like compounds were investigated by electrospray ionization tandem mass spectrometry (ESI‐MS/MS). The fragmentation studies were carried out by tandem mass spectrometry in space (quadrupole time‐of‐flight (QTOF)) using different collision energies and also by tandem mass spectrometry in time (QIT) by selective isolation of product ions. Results Casearin‐like compounds presented a predominance of sodium‐ and potassium‐cationized precursor ions. Both QIT and QTOF techniques provided sequential neutral losses of esters related to the R1 to R5 substituents linked to the nucleus of the clerodane diterpenes. The fragmentation pathway is initiated with a cleavage of the ester moieties R2 followed by the elimination of the ester groups R3, both losing neutral carboxylic acids. Using QIT, it was also possible to observe the cleavage of the ester groups R1 or R5 by MS4 experiments. Conclusions Through a rational analysis of the fragmentation mechanisms of Casearia diterpenes it was possible to suggest an annotation strategy based on the sequential cleavages of the ester groups related to the R2, R3 and R5 substituents. These results will assist studies of the dereplication and metabolomics involving casearin‐like compounds present in complex extracts of Casearia species.

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Section: Methodsmentioning

confidence: 99%

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Danuello

Castro

Pilon

et al. 2020

Rapid Comm Mass Spectrometry

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“…17 Intrapetacins A ( 38 ) and B ( 39 ) displayed moderate cytotoxicity against KB cells, with IC 50 values of 2.0 and 0.8 μg mL ±1 . 21 In addition, compound 39 caused a significant (21 mm) zone of inhibition of fungal growth.…”

Section: Biological Activitiesmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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“…Casearia species are known by the phytotherapeutic potential used in folk medicine once C. elliptica has been described for the treating of malaria and fever, C. esculenta for the treating of diabetes mellitus and C. sylvetris for the treatment of a variety of diseases . Regarding the phytochemical aspects, the Casearia genus has been described to produce casearins, a clerodane‐type diterpene derivative which displayed in vitro cytotoxic effects, including the apoptosis induction of tumor cells and antiproliferative activity . Previous works reported the isolation of cytotoxic clerodane diterpenes, casearborins A–E from C. arborea, which exhibited activity against LOX and SF539 tumor cell lines …”

Section: Introductionmentioning

confidence: 99%

Antileishmanial Activity and Immunomodulatory Effects of Tricin Isolated from Leaves of Casearia arborea (Salicaceae)

Santos

Yamamoto

Passero

et al. 2017

Chemistry & Biodiversity

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Bioactivity-guided fractionation of antileishmanial active extract from leaves of Casearia arborea led to isolation of three metabolites: tricin (1), 1',6'-di-O-β-d-vanilloyl glucopyranoside (2) and vanillic acid (3). Compound 1 demonstrated the highest activity against the intracellular amastigotes of Leishmania infantum, with an IC value of 56 μm. Tricin (1) demonstrated selectivity in mammalian cells (SI > 7) and elicited immunomodulatory effect on host cells. The present work suggests that tricin modulated the respiratory burst of macrophages to a leishmanicidal state, contributing to the parasite elimination. Therefore, the natural compound tricin could be further explored in drug design studies for leishmaniasis treatment.

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Cytotoxic Clerodane Diterpenes from Casearia rupestris

Cited by 46 publications

References 35 publications

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time‐of‐flight and ion trap)

Clerodane diterpenes: sources, structures, and biological activities

Antileishmanial Activity and Immunomodulatory Effects of Tricin Isolated from Leaves of Casearia arborea (Salicaceae)

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