Synthesis and Conformational Analysis of Leptocarpin Derivatives: Influence of Modification of the Oxirane Ringon Leptocarpin's Cytotoxic Activity

Martínez, Rolando; Kesternich, Víctor; Carracso, Héctor; Álvarez-Contreras, Carolina; Montenegro, Carolina; Ugarte, Ricardo; Gutierrez, Elena; Moreno, José Ma; García, Carlos Ramírez; Werner, Enrique; Cárcamo, Juan G.

doi:10.4067/s0717-97072006000400003

Cited by 9 publications

(4 citation statements)

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“…Jasminka et al [ 30 ] found that IGF-1R was overexpressed in endometrial carcinoma. According to Martinez et al [ 14 ], LTC had no effect on DNA or RNA synthesis but produced marked effects on the protein biosynthesis in cancerous cell lines, which showed the biological activity of LTC, as an anti-neoplastic agent of natural origin.…”

Section: Discussionmentioning

confidence: 99%

“…Asteraceae, which produces many bioactive compounds such as polyacetylenes, diterpenes, and sesquiterpene lactones [ 8 ], expresses various clinical activities, including anti-tumor, anti-ulcer, anti-inflammatory, neurocytotoxic, and cardiotonic activities [ 9 , 10 ], as well as the ability to influence critical biological processes such as cell signaling, cell proliferation, apoptosis, and mitochondrial metabolism [ 11 ]. Leptocarpin (LTC) is the one of the major components of Leptocarpha rivularis , which belongs to the Asteraceae family and was been widely used as a folk remedy [ 12 – 14 ]. In our study, LTC was used as an anti-tumor drug to treat MG63 cells.…”

Section: Introductionmentioning

confidence: 99%

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Leptocarpin Suppresses Proliferation, Migration, and Invasion of Human Osteosarcoma by Targeting Type-1 Insulin-Like Growth Factor Receptor (IGF-1R)

Zheng¹,

Wan

Miao³

et al. 2017

Med Sci Monit

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BackgroundLeptocarpin (LTC) has drawn much attention for suppressing tumor growth or reducing inflammation. However, the effect of LTC on osteosarcoma has rarely been reported. Our object was to determine whether LTC suppresses MG63 cell proliferation, migration, and invasion, and whether type-1 insulin-like growth factor receptor (IGF-1R) is one of the targets in LTC suppressing osteosarcoma.Material/MethodsCytotoxicity of LTC was performed by use of a cell-counting kit-8 (CCK-8). RNA interference (RNAi) or pEABE-bleo IGF-1R plasmid were used for silencing or overexpressing IGF-1R, Western blot (WB) analysis was used for IGF-1R expression, CCK-8 for proliferation, and transwell assay for migration and invasion.ResultsLTC (23.533 μM) treatment for 48 h was taken as the 50% inhibiting concentration (IC50), which significantly (P<0.05) suppressed MG63 cells proliferation, migration, and invasion. LTC (IC50) obviously inhibited IGF-1R expression in MG63 cells, with similar effect to small interfering RNA (siRNA), while pEABE-bleo IGF-1R transfection overexpressed IGF-1R. siRNA silencing IGF-1R suppressed MG63 cells proliferation, migration, and invasion, while pEABE-bleo IGF-1R transfection was significantly (P<0.05) promoted. With or without siRNA or pEABE-bleo IGF-1R transfection, LTC (IC50) suppressed MG63 cells proliferation, migration, and invasion. The effect of LTC (IC50) combined with siRNA on suppressing MG63 cells proliferation, migration, and invasion was more obvious, while the effect of LTC (IC50) combined with pEABE-bleo IGF-1R transfection was less significant (P<0.05).ConclusionsLTC suppressed osteosarcoma proliferation, migration, and invasion by inhibiting IGF-1R expression. IGF-1R is one of the targets in LTC suppressing osteosarcoma.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Leptocarpin Suppresses Proliferation, Migration, and Invasion of Human Osteosarcoma by Targeting Type-1 Insulin-Like Growth Factor Receptor (IGF-1R)

Zheng¹,

Wan

Miao³

et al. 2017

Med Sci Monit

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“…Previous phytochemical studies of L. rivularis have shown that extracts obtained from leaves, bark, and flowers exhibit antioxidant, hypoglycemic, and anticancer effects [3][4][5][6][7]. These biological activities have been attributed to the presence of sesquiterpene lactones, i.e., leptocarpine (LTC) as the major component and small amounts of rivularin and the 17,18-dihydroleptocarpin derivative [8][9][10][11]. It has also been described that LTC presents important cytotoxic effects on several cancer cell lines by inducing apoptosis [10], and inhibitory activity on specific growth factors in osteosarcoma [11].…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Profiling and Assessment of Anticancer Activity of Leptocarpha rivularis Extracts Obtained from In Vitro Cultures

Rubio

Arias

Robles-Kelly

et al. 2022

Plants

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Plant cell culture is a source of plant material from which bioactive metabolites can be extracted. In this work, the in vitro propagation of Leptocarpha rivularis, an endemic Chilean shrub with anticancer activity, is described. Different media were tested and optimized for the introduction, propagation, and rooting steps of the micropropagation process. At the end of this process, 83% of plants were successfully acclimatized under greenhouse conditions. Callus induction from the internodal stem segment was performed using various combinations of phytohormones. Green-colored, friable, and non-organogenic callus was generated with a callus induction index higher than 90%. The chemical composition of extracts and callus, obtained from clonal plants, was assessed and the results indicate that the phytochemical profiles of extracts from micropropagated plants are like those found for plants collected from natural habitats, leptocarpine (LTC) being the major component. However, no LTC was detected in callus extract. HeLa and CoN cells, treated with LTC or extract of micropropagated plants, exhibit important diminution on cell viability and a drastic decrease in gene expression of IL-6 and mmp2, genes associated with carcinogenic activity. These effects are more important in cancer cells than in normal cells. Thus, micropropagated L. rivularis could be developed as a potential source of efficient antiproliferative agents.

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“…The secondary metabolite characteristic of this family includes acetylenics, sesquiterpenes, and sesquiterpene lactones. L. rivularis also contains essentials oils, flavonoids, and triterpenes [ 4 ]. Despite the great interest in Leptocarpha rivularis DC due to the wide variety of secondary metabolites with biological activity that it produces—as in all plant extracts containing antineoplastic activity profusely studied in recent decades—descriptions of flower extracts, composition, antioxidant capacity, or cytotoxic effect against cancer cell lines are still incomplete.…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition, Antioxidant and Anticancer Activities of Leptocarpha rivularis DC Flower Extracts

et al. 2020

Self Cite

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An evaluation of antioxidant and anticancer activity was screened in Leptocarpha rivularis DC flower extracts using four solvents (n-hexane (Hex), dichloromethane (DCM), ethyl acetate (AcOEt), and ethanol (EtOH)). Extracts were compared for total extract flavonoids and phenol contents, antioxidant activity (2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), ferric reducing antioxidant potential (FRAP), total reactive antioxidant properties (TRAP) and oxygen radical absorbance capacity (ORAC)) across a determined value of reduced/oxidized glutathione (GSH/GSSG), and cell viability (the sulforhodamine B (SRB) assay). The most active extracts were analyzed by chromatographic analysis (GC/MS) and tested for apoptotic pathways. Extracts from Hex, DCM and AcOEt reduced cell viability, caused changes in cell morphology, affected mitochondrial membrane permeability, and induced caspase activation in tumor cell lines HT-29, PC-3, and MCF-7. These effects were generally less pronounced in the HEK-293 cell line (nontumor cells), indicating clear selectivity towards tumor cell lines. We attribute likely extract activity to the presence of sesquiterpene lactones, in combination with other components like steroids and flavonoids.

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Synthesis and Conformational Analysis of Leptocarpin Derivatives: Influence of Modification of the Oxirane Ringon Leptocarpin's Cytotoxic Activity

Cited by 9 publications

References 3 publications

Leptocarpin Suppresses Proliferation, Migration, and Invasion of Human Osteosarcoma by Targeting Type-1 Insulin-Like Growth Factor Receptor (IGF-1R)

Leptocarpin Suppresses Proliferation, Migration, and Invasion of Human Osteosarcoma by Targeting Type-1 Insulin-Like Growth Factor Receptor (IGF-1R)

Phytochemical Profiling and Assessment of Anticancer Activity of Leptocarpha rivularis Extracts Obtained from In Vitro Cultures

Chemical Composition, Antioxidant and Anticancer Activities of Leptocarpha rivularis DC Flower Extracts

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