Recent patents on sesquiterpene lactones with therapeutic application

Sülsen, Valeria P.; Elso, Orlando G.; Borgo, Jimena; Laurella, Laura C.; Catalán, César A.N.

doi:10.1016/b978-0-12-819487-4.00017-3

Cited by 8 publications

(6 citation statements)

References 38 publications

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“…For instance, sesquiterpene lactones were detected solely in C. lipii ( Figure 3 ) belonging to the germacranolides, guaianolides, cadinanolides, elemanolides, and eudesmanolides. Diverse biological activities were reported for sesquiterpene lactones, including anti-inflammatory, antiparasitic, antiviral, cytotoxic, and others [ 18 ]. Moreover, sesquiterpene lactones were recognized as potential candidates for cancer treatment owing to their selective inhibition of tumor and cancer stem cells [ 18 ].…”

Section: Discussionmentioning

confidence: 99%

“…Diverse biological activities were reported for sesquiterpene lactones, including anti-inflammatory, antiparasitic, antiviral, cytotoxic, and others [ 18 ]. Moreover, sesquiterpene lactones were recognized as potential candidates for cancer treatment owing to their selective inhibition of tumor and cancer stem cells [ 18 ]. Indeed, former investigations have highlighted that the biological activity of sesquiterpene lactones is attributed to the inhibition of enzymes, transcription factors, and/or functional proteins [ 18 ].…”

Section: Discussionmentioning

confidence: 99%

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Feature-Based Molecular Networking for the Exploration of the Metabolome Diversity of Common Egyptian Centaurea Species in Relation to Their Cytotoxic Activity

et al. 2023

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Centaurea is a genus compromising over 250 herbaceous flowering species and is used traditionally to treat several ailments. Among the Egyptian Centaurea species, C. lipii was reported to be cytotoxic against multidrug-resistant cancer cells. In this context, we aimed to explore the metabolome of C. lipii and compare it to other members of the genus in pursuance of identifying its bioactive principles. An LC-MS/MS analysis approach synchronized with feature-based molecular networks was adopted to offer a holistic overview of the metabolome diversity of the Egyptian Centaurea species. The studied plants included C. alexandrina, C. calcitrapa, C. eryngioides, C. glomerata, C. lipii, C. pallescens, C. pumilio, and C. scoparia. Their constitutive metabolome showed diverse chemical classes such as cinnamic acids, sesquiterpene lactones, flavonoids, and lignans. Linking the recorded metabolome to the previously reported cytotoxicity identified sesquiterpene lactones as the major contributors to this activity. To confirm our findings, bioassay-guided fractionation of C. lipii was adopted and led to the isolation of the sesquiterpene lactone cynaropicrin with an IC50 of 1.817 µM against the CCRF-CEM leukemia cell line. The adopted methodology highlighted the uniqueness of the constitutive metabolome of C. lipii and determined the sesquiterpene lactones to be the responsible cytotoxic metabolites.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Feature-Based Molecular Networking for the Exploration of the Metabolome Diversity of Common Egyptian Centaurea Species in Relation to Their Cytotoxic Activity

et al. 2023

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“…However, a high number of the studies have been conducted with artemisinin and its derivatives, which are classified as cadinanolides, and are currently in use as antimalarials. In this sense, the STLs artemisinin and its derivatives, alantolactone, isoalantolactone, alloalantolactone and thapsigargin, which have been included in patents related to pancreatic cancer, deserve to be highlighted [ 128 ]. These compounds have shown specific modes of action that could lead to the development of more effective and selective drugs to treat pancreatic cancer.…”

Section: Discussionmentioning

confidence: 99%

Sesquiterpene Lactones as Promising Candidates for Cancer Therapy: Focus on Pancreatic Cancer

et al. 2022

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Pancreatic ductal adenocarcinoma (PDAC) is a highly aggressive disease which confers to patients a poor prognosis at short term. PDAC is the fourth leading cause of death among cancers in the Western world. The rate of new cases of pancreatic cancer (incidence) is 10 per 100,000 but present a 5-year survival of less than 10%, highlighting the poor prognosis of this pathology. Furthermore, 90% of advanced PDAC tumor present KRAS mutations impacting in several oncogenic signaling pathways, many of them associated with cell proliferation and tumor progression. Different combinations of chemotherapeutic agents have been tested over the years without an improvement of significance in its treatment. PDAC remains as one the more challenging biomedical topics thus far. The lack of a proper early diagnosis, the notable mortality statistics and the poor outcome with the available therapies urge the entire scientific community to find novel approaches against PDAC with real improvements in patients’ survival and life quality. Natural compounds have played an important role in the process of discovery and development of new drugs. Among them, terpenoids, such as sesquiterpene lactones, stand out due to their biological activities and pharmacological potential as antitumor agents. In this review, we will describe the sesquiterpene lactones with in vitro and in vivo activity against pancreatic tumor cells. We will also discuss the mechanism of action of the compounds as well as the signaling pathways associated with their activity.

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“…It was demonstrated that the biological activity of these compounds is related to the existence of the α-meth- ylene-γ-lactone group in their structure. [56] α-methylene-γlactone groups have shown promising cytotoxic and anti-tumor activities, which is the result of an irreversible reaction between this moiety and biological nucleophiles. [57] In a previous study by Luca et al, a series of sesquiterpene lactones were isolated from Ferula penninervis root extract.…”

Section: Cytotoxicity Activitymentioning

confidence: 99%

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

Mehrabani,

Iranshahi,

Mehrabani

et al. 2023

ChemistrySelect

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Ferula species have been recognized as crucial medicinal plants that are known for producing a variety of sesquiterpenes, such as sesquiterpene lactones and sesquiterpene coumarins. However, guaianolide sesquiterpenes, which are sesquiterpene lactones that contain an alpha‐methylene‐gamma‐lactone moiety, are rare in Ferula spp. Ferula hindukushensis, an endemic species found in Afghanistan, Pakistan, and Iran, belongs to the Ferula genus. In this study, the normal column chromatography technique was employed to fractionate the dichloromethane extract of F. hindukushensis. The structures of two guaianolide sesquiterpenes were identified using various nuclear magnetic resonance (NMR) spectra, such as 13C NMR, 1H NMR, and heteronuclear multiple bond correlation (HMBC), and were compared with the literature interpretation to confirm their structural characteristics. Moreover, the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay was employed to examine the cytotoxicity of guaianolide compounds on various cell lines, including MCF‐7, 3T3, HT‐29, MCF‐10, PC12, and A549. The antioxidant effects of these compounds were evaluated using ferric reducing antioxidant power (FRAP) and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) assays. The findings indicated that the antioxidant activity of the compounds was lower than that of vitamin C at the same concentration. The cytotoxic effects of the compounds varied depending on the cell types. Nevertheless, except for HT‐29, a concentration lower than 125 μg/mL was found to be non‐toxic for all cell lines.

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Recent patents on sesquiterpene lactones with therapeutic application

Cited by 8 publications

References 38 publications

Feature-Based Molecular Networking for the Exploration of the Metabolome Diversity of Common Egyptian Centaurea Species in Relation to Their Cytotoxic Activity

Feature-Based Molecular Networking for the Exploration of the Metabolome Diversity of Common Egyptian Centaurea Species in Relation to Their Cytotoxic Activity

Sesquiterpene Lactones as Promising Candidates for Cancer Therapy: Focus on Pancreatic Cancer

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

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