Sesquiterpene Lactones: A Versatile Class of Structurally Diverse Natural Products and Their Semisynthetic Analogs as Potential Anticancer Agents

Chaturvedi, Devdutt; Dwivedi, Parmesh Kumar; Mishra, Meenal

doi:10.1002/9783527684403.ch11

Cited by 7 publications

(3 citation statements)

References 85 publications

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“…A wide variety of biological and pharmacological activities of the SLs have been described [17] , [21] . The potential of many SLs for use in the treatment of cancer and cardiovascular disease have received large interest [18] , [20] , [22] , [23] and anti-cancer activities have been reported [24] . The α-methylene-γ-lactone group found in SLs is correlated with many of their pharmacological actions [20] , [25] .…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic and other bioactivities of a novel and known sesquiterpene lactones isolated from Vernonia leopoldi (Sch. Bip. ex Walp.) Vatke in breast cancer cell lines

Tuasha¹,

Escobar²,

Seifu³

et al. 2022

Toxicology Reports

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Section: Discussionmentioning

confidence: 99%

Cytotoxic and other bioactivities of a novel and known sesquiterpene lactones isolated from Vernonia leopoldi (Sch. Bip. ex Walp.) Vatke in breast cancer cell lines

Tuasha¹,

Escobar²,

Seifu³

et al. 2022

Toxicology Reports

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“…Sesquiterpenes (C 15 H 24 ) are chemically characterized by having 15 carbon atoms, with assembly derived from three isoprenoid units, they are arranged in acyclic or mono, bi, tri or tetracyclic (Figure 3). Currently, a wide variety of complexes have been found that are metabolically derived from only 300 C15 hydrocarbon skeletons, however, the synthesis originates from a single substrate, farnesyl diphosphate (Chaturvedi, 2011;Fu et al, 2019;Moujir et al, 2020;Shu et al, 2021).…”

Section: Figurementioning

confidence: 99%

Exploring the leishmanicidal potential of terpenoids: a comprehensive review on mechanisms of cell death

Rodrigues,

Carloto,

Gonçalves

et al. 2023

Front. Cell. Infect. Microbiol.

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Leishmaniasis is a neglected tropical disease with a wide spectrum of clinical manifestations, ranging from visceral to cutaneous, with millions of new cases and thousands of deaths reported each year. The species of Leishmania and the immune response of the host determine the severity of the disease. Leishmaniasis remains challenging to diagnose and treat, and there is no vaccine available. Several studies have been conducted on the use of herbal medicines for the treatment of leishmaniasis. Natural products can provide an inexhaustible source of chemical diversity with therapeutic potential. Terpenes are a class of natural products derived from a single isoprene unit, a five-carbon compound that forms the basic structure of isoprenoids. This review focuses on the most important and recent advances in the treatment of parasites of the genus Leishmania with different subclasses of terpenes. Several mechanisms have been proposed in the literature, including increased oxidative stress, immunomodulatory role, and induction of different types of parasite cell death. However, this information needs to be brought together to provide an overview of how these compounds can be used as therapeutic tools for drug development and as a successful adjuvant strategy against Leishmania sp.

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“…Micro- and nano-formulation of α,β-unsaturated carbonyls such as prostaglandins and curcumin improve their pharmacological profile. α,β-unsaturated-structure bearing sesquiterpene lactones obtained from feverfew plant have lipophilic character which generally affects their potency [ 212 , 213 ]. For instance, parthenolide ( 8 ) exhibits a significant lipophilicity which may explain its good blood–brain barrier permeability and cytosol penetration for KEAP1-NRF2 signaling pathway activation [ 214 ].…”

Section: Pharmacological Profile Of αβ-Unsaturated Structure-bearing ...mentioning

confidence: 99%

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

Egbujor

Buttari²,

Profumo³

et al. 2022

IJMS

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The surge of scientific interest in the discovery of Nuclear Factor Erythroid 2 (NFE2)-Related Factor 2 (NRF2)-activating molecules underscores the importance of NRF2 as a therapeutic target especially for oxidative stress. The chemical reactivity and biological activities of several bioactive compounds have been linked to the presence of α,β-unsaturated structural systems. The α,β-unsaturated carbonyl, sulfonyl and sulfinyl functional groups are reportedly the major α,β-unsaturated moieties involved in the activation of the NRF2 signaling pathway. The carbonyl, sulfonyl and sulfinyl groups are generally electron-withdrawing groups, and the presence of the α,β-unsaturated structure qualifies them as suitable electrophiles for Michael addition reaction with nucleophilic thiols of cysteine residues within the proximal negative regulator of NRF2, Kelch-like ECH-associated protein 1 (KEAP1). The physicochemical property such as good lipophilicity of these moieties is also an advantage because it ensures solubility and membrane permeability required for the activation of the cytosolic NRF2/KEAP1 system. This review provides an overview of the reaction mechanism of α,β-unsaturated moiety-bearing compounds with the NRF2/KEAP1 complex, their pharmacological properties, structural activity-relationship and their effect on antioxidant and anti-inflammatory responses. As the first of its kind, this review article offers collective and comprehensive information on NRF2-activators containing α,β-unsaturated moiety with the aim of broadening their therapeutic prospects in a wide range of oxidative stress-related diseases.

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Sesquiterpene Lactones: A Versatile Class of Structurally Diverse Natural Products and Their Semisynthetic Analogs as Potential Anticancer Agents

Cited by 7 publications

References 85 publications

Cytotoxic and other bioactivities of a novel and known sesquiterpene lactones isolated from Vernonia leopoldi (Sch. Bip. ex Walp.) Vatke in breast cancer cell lines

Cytotoxic and other bioactivities of a novel and known sesquiterpene lactones isolated from Vernonia leopoldi (Sch. Bip. ex Walp.) Vatke in breast cancer cell lines

Exploring the leishmanicidal potential of terpenoids: a comprehensive review on mechanisms of cell death

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

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