Triterpenes from leaves of <i>Cheiloclinium cognatum</i> and their in vivo antiangiogenic activity

Pereira, Rafael César Gonçalves; Soares, Daniel Crístian Ferreira; Oliveira, Diogo C.P.; Sousa, Grasiely Faria de; Filho, Sidney Augusto Vieira; Mercadante-Simões, Maria Olívia; Lula, Ivana S.; Silva-Cunha, Armando; Duarte, Lucienir Pains

doi:10.1002/mrc.4716

Cited by 4 publications

(6 citation statements)

References 37 publications

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“…The phytochemical study of C. cognatum branches afforded ten TPs ( Figure 1), two presenting ursane skeleton, 3 β ‐acyloxyurs‐12‐ene ( 1 ) and urs‐12‐en‐3 β ‐ol ( α ‐amyrin, 5 ); five of friedelane skeleton, friedelan‐3‐one (friedelin, 2 ), friedelan‐3 β ‐ol ( β ‐friedelinol, 3 ), 28‐hydroxyfriedelan‐3‐one (canophyllol, 8 ), 29‐hydroxyfriedelan‐3‐one ( 9 ) and friedelane‐3 β ,29‐diol ( 10 ); one glutinane, glut‐5‐en‐3 β ‐ol ( 4 ); one oleanane, olean‐12‐en‐3 β ‐ol ( β ‐amyrin, 6 ); and one sterol, β ‐sitosterol ( 7 ). Their chemical structures were confirmed by comparison to previously published 1 H‐ and 13 C‐NMR data ( 1 , [24] 2 , [25] 3 , [26] 4 , [27] 5 , [28] 6 , [29] 7 , [30] 8 , 9 and 10 [21] ) and their spectra are available in the Supporting Information . Previous studies on C. cognatum leaves showed that TPs 9 and 10 represented almost 20 % in weight of the CHCl 3 extract [21] .…”

Section: Resultssupporting

confidence: 64%

“…Their chemical structures were confirmed by comparison to previously published 1 H‐ and 13 C‐NMR data ( 1 , [24] 2 , [25] 3 , [26] 4 , [27] 5 , [28] 6 , [29] 7 , [30] 8 , 9 and 10 [21] ) and their spectra are available in the Supporting Information . Previous studies on C. cognatum leaves showed that TPs 9 and 10 represented almost 20 % in weight of the CHCl 3 extract [21] . TPs 8 and 9 were isolated in great quantities from the branches, providing 1.81 g (2 % of hexane extract and 4.2 % of CHCl 3 extract) and over 2 g (4.9 % of hexane extract and 3.7 % of CHCl 3 extract) of the pure substances, respectively.…”

Section: Resultssupporting

confidence: 64%

“…Previous studies on C. cognatum leaves showed that TPs 9 and 10 represented almost 20 % in weight of the CHCl 3 extract. [21] TPs 8 and 9 were isolated in great quantities from the branches, providing 1.81 g (2 % of hexane extract and 4.2 % of CHCl 3 extract) and over 2 g (4.9 % of hexane extract and 3.7 % of CHCl 3 extract) of the pure substances, respectively. TPs 2, 3, 5, 7 and 8 -10 were assessed for their cytotoxic potentials.…”

Section: Phytochemical Studymentioning

confidence: 99%

“…From its leaves, nine TPs showed about 50 % antiangiogenic activity at in vivo CAM assay. [21] Eleven TPs were identified from root barks. Among them, nine showed considerable antioxidant potential, [22] and two showed trypanocidal activity against Trypanosoma cruzi.…”

Section: Introductionmentioning

confidence: 99%

“…Previous phytochemical studies on C. cognatum leaves and root barks led to the isolation several bioactive TPs. From its leaves, nine TPs showed about 50 % antiangiogenic activity at in vivo CAM assay [21] . Eleven TPs were identified from root barks.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

Pereira

Evangelista

Júnior

et al. 2020

Chemistry & Biodiversity

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Cheiloclinium cognatum (Miers) A.C.Sm. is an endemic species of Brazilian Cerrado that belongs to Celastraceae family. The phytochemical study of C. cognatum branches led to the identification of ten triterpenoids (TPs), 3β-acyloxyurs-12-ene (1), friedelin (2), β-friedelinol (3), glut-5-en-3β-ol (4), α-amyrin (5), βamyrin (6), β-sitosterol (7), canophyllol (8), 29-hydroxyfriedelan-3-one (9) and friedelane-3β,29-diol (10). TPs 4, 5 and 6 are described for the first Cheiloclinium genus and TPs 8 and 9 were isolated in expressive amounts. Their cytotoxic activities were evaluated against THP-1 and K562 leukemia cell lines. TPs 3 and 5 were the most active, exhibiting lower or similar IC 50 against both cell lines when compared to the controls. Their mechanisms of action were investigated suggesting an intrinsic mitochondrial pathway of apoptosis evidenced by up-regulation of BAK mRNA expression. Chemometric studies indicated that their activities may be related to their molecular size and shape as well as electronic interactions of C-3 hydroxy group with molecular targets.

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Section: Resultssupporting

confidence: 64%

Section: Resultssupporting

confidence: 64%

Section: Phytochemical Studymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

Pereira

Evangelista

Júnior

et al. 2020

Chemistry & Biodiversity

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In vitro cultivation of Vismia japurensis: Isolation of the new anthrone 1,8,10-trihydroxy-3,10-dimethyl-9(10H)-anthracenone

LIMA,

SILVA,

SOUZA

et al. 2024

An. Acad. Bras. Ciênc.

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Vismia japurensis Reichardt is a plant of ecological and chemical importance from which a variety of bioactive substances have been isolated. The current study aimed to establish in vitro cultures of this species as a source of secondary metabolites.Appropriate decontamination treatments and germination tests were performed and, after in vitro culture establishment, the propagated plants were multiplied in a sterile environment to increase the biomass of available experimental material. Seeds showed low contamination and a high germination percentage on Woody Plant Medium (WPM) supplemented with gibberellic acid (both at concentrations of 5 and 10 mg/L).V. japurensis nodal segments rapidly regenerated when first grown in WPM and then transplanted to Murashige and Skoog medium (MS). After 60 days in MS medium, the propagated plants were removed, lyophilized, and extracted with hexane and methanol.The hexane extract was fractionated via open column chromatography, and the substance isolated was purified by high performance liquid chromatography. Structural determination of the isolated substance was carried out using one and two-dimensional nuclear magnetic resonance and mass spectrometry. The isolated substance was identified as 1,8,10-trihydroxy-3,10-dimethyl-9(10H)-anthracenone, which, based on the conducted literature search, is reported for the first time.

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Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

et al. 2022

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The Celastraceae family comprises about 96 genera and more than 1.350 species, occurring mainly in tropical and subtropical regions of the world. The species of this family stand out as important plant sources of triterpenes, both in terms of abundance and structural diversity. Triterpenoids found in Celastraceae species display mainly lupane, ursane, oleanane, and friedelane skeletons, exhibiting a wide range of biological activities such as antiviral, antimicrobial, analgesic, anti-inflammatory, and cytotoxic against various tumor cell lines. This review aimed to document all triterpenes isolated from different botanical parts of species of the Celastraceae family covering 2001 to 2021. Furthermore, a compilation of their 13C-NMR data was carried out to help characterize compounds in future investigations. A total of 504 pentacyclic triterpenes were compiled and distinguished as 29 aromatic, 50 dimers, 103 friedelanes, 89 lupanes, 102 oleananes, 22 quinonemethides, 88 ursanes and 21 classified as others.

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Triterpenes from leaves of Cheiloclinium cognatum and their in vivo antiangiogenic activity

Cited by 4 publications

References 37 publications

Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

In vitro cultivation of Vismia japurensis: Isolation of the new anthrone 1,8,10-trihydroxy-3,10-dimethyl-9(10H)-anthracenone

Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

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