Sesquiterpenes and diterpenes with cytotoxic activities from the aerial parts of Carpesium humile

Xu, Dongdong; Yuan, Yan; Jiang, Chunxiao; Liang, Jingjing; Li, Hongfang; Wu, Qinghui; Zhu, Yunlong

doi:10.1016/j.fitote.2018.04.015

Cited by 12 publications

(12 citation statements)

References 17 publications

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“…α -Tocopherolquinone was dereplicated with molecular formula (C 29 H 50 O 3 ) and accurate mass 446.3760. This diterpene has reported good cytotoxic activity on HepG2 cells (IC 50 = 6.97 ± 0.5 µg/mL) [ 23 ]. Another terpene dereplicated, phytol (C 20 H 40 O; accurate mass 296.3079) selectively inhibited the growth of the HepG2 cells with an IC 50 value of 78 ± 3.45 μM [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

Metabolomic Profile and Cytotoxic Activity of Cissus incisa Leaves Extracts

Nocedo-Mena

Rios

Ramírez-Cisneros

et al. 2021

Plants

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Cissus incisa leaves have been traditionally used in Mexican traditional medicine to treat certain cancerous illness. This study explored the metabolomic profile of this species using untargeted technique. Likewise, it determined the cytotoxic activity and interpreted all data by computational tools. The metabolomic profile was developed through UHPLC-QTOF-MS/MS for dereplication purposes. MetaboAnalyst database was used in metabolic pathway analysis and the network topological analysis. Hexane, chloroform/methanol, and aqueous extracts were evaluated on HepG2, Hep3B, HeLa, PC3, A549, and MCF7 cancer cell lines and IHH immortalized hepatic cells, using Cell Titer proliferation assay kit. Hexane extract was the most active against Hep3B (IC50 = 27 ± 3 μg/mL), while CHCl3/MeOH extract was the most selective (SI = 2.77) on the same cell line. A Principal Component Analysis (PCA) showed similar profiles between the extracts, while a Venn diagram revealed 80 coincident metabolites between the bioactive extracts. The sesquiterpenoid and triterpenoid biosynthesis pathway was the most significant identified. The Network Pharmacology (NP) approach revealed several targets for presqualene diphosphate, phytol, stearic acid, δ-tocopherol, ursolic acid and γ-linolenic acid, involved in cellular processes such as apoptosis. This work highlights the integration of untargeted metabolomic profile and cytotoxic activity to explore plant extracts, and the NP approach to interpreting the experimental results.

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Section: Resultsmentioning

confidence: 99%

Metabolomic Profile and Cytotoxic Activity of Cissus incisa Leaves Extracts

Nocedo-Mena

Rios

Ramírez-Cisneros

et al. 2021

Plants

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“…Some of these chemical compounds, such as methyl eugenol, a methylated ether previously reported as one the major constituents of the essential oil of red propolis, have been demonstrated to induce anticancer activity [16]. Furthermore, other substances of lower polarity present in samples of red propolis, such as sesquiterpenes, have also exhibited antitumor activity in vitro [17,18].…”

Section: Introductionmentioning

confidence: 99%

Brazilian Red Propolis: Extracts Production, Physicochemical Characterization, and Cytotoxicity Profile for Antitumor Activity

et al. 2020

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Brazilian red propolis has been proposed as a new source of compounds with cytotoxic activity. Red propolis is a resinous material of vegetal origin, synthesized from the bees of the Appis mellifera family, with recognized biological properties. To obtain actives of low polarity and high cytotoxic profile from red propolis, in this work, we proposed a new solvent accelerated extraction method. A complete 23 factorial design was carried out to evaluate the influence of the independent variables or factors (e.g., temperature, number of cycles, and extraction time) on the dependent variable or response (i.e., yield of production). The extracts were analyzed by gas chromatography coupled with mass spectrometry for the identification of chemical compounds. Gas chromatography analysis revealed the presence of hydrocarbons, alcohols, ketones, ethers, and terpenes, such as lupeol, lupenone, and lupeol acetate, in most of the obtained extracts. To evaluate the cytotoxicity profile of the obtained bioactives, the 3-(4,5-dimethyl-2-thiazole)-2,5-diphenyl-2-H-tetrazolium bromide colorimetric assay was performed in different tumor cell lines (HCT116 and PC3). The results show that the extract obtained from 70 °C and one cycle of extraction of 10 min exhibited the highest cytotoxic activity against the tested cell lines. The highest yield, however, did not indicate the highest cytotoxic activity, but the optimal extraction conditions were indeed dependent on the temperature (i.e., 70 °C).

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“…A study of fifteen sesquiterpenes obtained from Parasenecio roborowskii shows that the sesquiterpene eudesmane presented an IC 50 value of 9.2 μg mL −1 , representing a high bioactive compound [48] . Four lactone sesquiterpenes obtained from Carpesium humile showed even higher cytotoxicity against the MDA‐231 cell lines (IC 50 <8 μg mL −1 ) [8] . The monoterpene content could also be partially responsible for the cytotoxic activity observed for M. pubescens EOs.…”

Section: Resultsmentioning

confidence: 99%

“…There are no studies on M. pubescens essential oils (EOs) in the literature, highlighting this component as an interesting research target. Recently, researchers have demonstrated that EOs display cytotoxic activity that could be explored in medicine [6–8] . In recent work, EOs of sixteen different species were assessed in a general screening and showed activity against five different cancer cell lines, namely breast cancer cell lines MCF7, T47D and MDA‐MB‐231, chronic myelogenous erythroleukemia K562 and neuroblastoma cell lines SH‐SY5Y.…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition of Magonia pubescens Essential Oils and Gamma‐Radiation Effects on Its Constituents and Cytotoxic Activity in Leukemia and Breast Cancer Model

Moraes

Camargo

Mercadante-Simões

et al. 2021

Chemistry & Biodiversity

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Magonia pubescens A. St.‐Hil. is a Brazilian species often used in ethnopharmacology for wound and pain healing and seborrhea treatment. For the first time, essential oils (EOs) obtained from M. pubescens inflorescences were studied. The plant materials (Montes Claros, Brazil, 2018) were submitted to different gamma‐radiation doses and their chemical compositions were analyzed by GC/MS and GC‐FID. The cytotoxic activity of the EOs was evaluated against K562 and MDA‐MB‐231 cancer cell lines. A total of 30 components were identified, being 24 compounds detected for the first time in M. pubescens. The main obtained components were hotrienol (35.9 %), cis‐linalool oxide (17.0 %) and trans‐linalool oxide (10.2 %). The chemical composition of the EO was slightly affected by the applied radiation doses. Irradiated and non‐irradiated EOs showed cytotoxic activity against both cell lines and the non‐irradiated EO sample was the most active against the K562 cell lines (IC50=22.10±1.98).

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Sesquiterpenes and diterpenes with cytotoxic activities from the aerial parts of Carpesium humile

Cited by 12 publications

References 17 publications

Metabolomic Profile and Cytotoxic Activity of Cissus incisa Leaves Extracts

Metabolomic Profile and Cytotoxic Activity of Cissus incisa Leaves Extracts

Brazilian Red Propolis: Extracts Production, Physicochemical Characterization, and Cytotoxicity Profile for Antitumor Activity

Chemical Composition of Magonia pubescens Essential Oils and Gamma‐Radiation Effects on Its Constituents and Cytotoxic Activity in Leukemia and Breast Cancer Model

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