Biological Activities of Sesquiterpene Lactones Isolated from the Genus Centaurea L. (Asteraceae)

Background and Introduction: Sesquiterpene lactones are a class of secondary metabolite that contains sesquiterpenoids and lactone ring as pharmacophore moiety. A large group of bioactive secondary metabolites such as phytopharmaceuticals belong to this category. From the Asteraceae family-based medicinal plants, more than 5,000 sesquiterpene lactones have been reported so far. Sesquiterpene lactone-based pharmacophore moieties hold promise for broad-spectrum biological activities against cancer, inflammation, parasitic, bacterial, fungal, viral infection and other functional disorders. Moreover, these moiety based phytocompounds have been highlighted with a new dimension in the natural drug discovery program worldwide after the 2015 Medicine Nobel Prize achieved by the Artemisinin researchers. Objective: These bitter substances often contain an α, β-unsaturated-γ-lactone as a major structural backbone, which in recent studies has been explored to be associated with anti-tumor, cytotoxic, and anti-inflammatory action. Recently, the use of sesquiterpene lactones as phytomedicine has been increased. This study will review the prospect of sesquiterpene lactones against inflammation and cancer. Methods: Hence, we emphasized on the different features of this moiety by incorporating its structural diversity on biological activities to explore structure-activity relationships (SAR) against inflammation and cancer. Results: How the dual mode of action such as anti-inflammatory and anti-cancer has been exhibitedby these phytopharmaceuticals will be forecasted in this study. Furthermore, the correlation of anti-inflammatory and anti-cancer activity executed by the sesquiterpene lactones for fruitful phytotherapy will also be revealed in the present review in the milieu of pharmacophore activity relation and pharmacodynamics study as well. Conclusion: So, these metabolites are paramount in phytopharmacological aspects. The present discussion on the future prospect of this moiety based on the reported literature could be a guide for anti-inflammatory and anti-cancer drug discovery programs for the upcoming researchers.

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Sesquiterpene Lactones: Promising Natural Compounds to Fight Inflammation

Pharmaceutics ◽

10.3390/pharmaceutics13070991 ◽

2021 ◽

Vol 13 (7) ◽

pp. 991

Author(s):

Melanie S. Matos ◽

José D. Anastácio ◽

Cláudia Nunes dos Santos

Keyword(s):

Biological Activities ◽

Sesquiterpene Lactones ◽

Physiological State ◽

Plant Secondary Metabolites ◽

Inflammatory Pathways ◽

Inflammatory State ◽

Anti Inflammatory ◽

Inflammatory Molecules

Inflammation is a crucial and complex process that reestablishes the physiological state after a noxious stimulus. In pathological conditions the inflammatory state may persist, leading to chronic inflammation and causing tissue damage. Sesquiterpene lactones (SLs) are composed of a large and diverse group of highly bioactive plant secondary metabolites, characterized by a 15-carbon backbone structure. In recent years, the interest in SLs has risen due to their vast array of biological activities beneficial for human health. The anti-inflammatory potential of these compounds results from their ability to target and inhibit various key pro-inflammatory molecules enrolled in diverse inflammatory pathways, and prevent or reduce the inflammatory damage on tissues. Research on the anti-inflammatory mechanisms of SLs has thrived over the last years, and numerous compounds from diverse plants have been studied, using in silico, in vitro, and in vivo assays. Besides their anti-inflammatory potential, their cytotoxicity, structure–activity relationships, and pharmacokinetics have been investigated. This review aims to gather the most relevant results and insights concerning the anti-inflammatory potential of SL-rich extracts and pure SLs, focusing on their effects in different inflammatory pathways and on different molecular players.

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Effect of guaianolides in the meiosis reinitiation of amphibian oocytes

Zygote ◽

10.1017/s0967199416000265 ◽

2016 ◽

Vol 25 (1) ◽

pp. 10-16 ◽

Cited By ~ 2

Author(s):

J. Zapata-Martínez ◽

G. Sánchez-Toranzo ◽

F. Chaín ◽

C.A.N. Catalán ◽

M.I. Bühler

Keyword(s):

Biological Activities ◽

Wide Spectrum ◽

Sesquiterpene Lactones ◽

Inhibitory Effect ◽

Biological Molecules ◽

Plant Metabolites ◽

Major Mechanism ◽

Bufo Arenarum ◽

Asteraceae Family

SummarySesquiterpene lactones (STLs) are a large and structurally diverse group of plant metabolites generally found in the Asteraceae family. STLs exhibit a wide spectrum of biological activities and it is generally accepted that their major mechanism of action is the alkylation of the thiol groups of biological molecules. The guaianolides is one of various groups of STLs. Anti-tumour and anti-migraine effects, an allergenic agent, an inhibitor of smooth muscle cells and of meristematic cell proliferation are only a few of the most commonly reported activities of STLs. In amphibians, fully grown ovarian oocytes are arrested at the beginning of meiosis I. Under stimulus with progesterone, this meiotic arrest is released and meiosis progresses to metaphase II, a process known as oocyte maturation. There are previous records of the inhibitory effect of dehydroleucodin (DhL), a guaianolide lactone, on the progression of meiosis. It has been also shown that DhL and its 11,13-dihydroderivative (2H-DhL; a mixture of epimers at C-11) act as blockers of the resumption of meiosis in fully grown ovarian oocytes from the amphibian Rhinella arenarum (formerly classified as Bufo arenarum). The aim of this study was to analyze the effect of four closely related guaianolides, i.e., DhL, achillin, desacetoxymatricarin and estafietin as possible inhibitors of meiosis in oocytes of amphibians in vitro and discuss some structure–activity relationships. It was found that the inhibitory effect on meiosis resumption is greater when the lactone has two potentially reactive centres, either a α,β–α′,β′-diunsaturated cyclopentanone moiety or an epoxide group plus an exo-methylene-γ-lactone function.

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Erratum: Studies on the Synthesis of Sesquiterpene Lactones, 12. Synthesis of (+)-Colartin, (+)- Arubusclin A, and Their C-4 Epimers and Their Biological Activities

Journal of Natural Products ◽

10.1021/np50082a021 ◽

1992 ◽

Vol 55 (4) ◽

pp. 512-512

Author(s):

Masayoshi Ando ◽

Koji Isogai ◽

Hidenori Azami ◽

Naonori Hirata ◽

Yoshikazu Yanagi

Keyword(s):

Biological Activities ◽

Sesquiterpene Lactones

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Chemical Constituents of Eupatorium japonicum and Anti-Inflammatory, Cytotoxic, and Apoptotic Activities of Eupatoriopicrin on Cancer Stem Cells

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2021/6610347 ◽

2021 ◽

Vol 2021 ◽

pp. 1-12

Author(s):

Minh Giang Phan ◽

Thi Thao Do ◽

Thi Nga Nguyen ◽

Thi Viet Huong Do ◽

Ngoc Phuc Dong ◽

...

Keyword(s):

Anticancer Agents ◽

Human Cancer ◽

Biological Activities ◽

Chemical Constituents ◽

Sesquiterpene Lactones ◽

No Production ◽

Bioactive Constituents ◽

Anti Inflammatory ◽

First Time ◽

Eupatorium Japonicum

Eupatorium japonicum Thunb. of the plant family Asteraceae is a popular traditional herb in Vietnam. However, its chemical constituents as well as bioactive principles have not been investigated yet. We investigated the phytochemistry of E. japonicum in Vietnam and isolated seventeen compounds (1–17) including phytosterols, terpenoids, phenolic acids, flavonoids, fatty alcohols, and fatty acids. They were structurally determined by MS and NMR analysis. Except for compounds 6 and 12, all the other compounds were identified for the first time from E. japonicum. Since many sesquiterpene lactones with α-methylene γ-lactone ring are reported as anti-inflammatory and anticancer agents, eupatoriopicrin (10), 1-hydroxy-8-(4,5-dihydroxytigloyloxy)eudesma-4(15),11(13)-dien-6,12-olide (11) were selected among the isolates for biological assays. Compound 10 was identified as the main bioactive sesquiterpene lactone of E. japonicum showing its potent anti-inflammatory and cytotoxic activity through inhibiting NO production and the growth of HepG2 and MCF-7 human cancer cell lines. For the first time, eupatoriopicrin (10) was demonstrated to strongly inhibit NTERA-2 human cancer stem cell (CSC) line in vitro. It is noticeable that the cytotoxicity of eupatoriopicrin against NTERA-2 cells is mediated by its apoptosis-inducing capability of 10 as demonstrated by the results of Hoechst 33342 staining, flow cytometry apoptosis analysis, and caspase-3 activity assays. The biological activities of the main bioactive constituents 1–7, 10, 12, and 15 supported the reported anti-inflammatory and anticancer properties of extracts from E. japonicum.

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Biological Activities of Natural Sesquiterpene Lactones and the Effect of Synthetic Sesquiterpene Derivatives on Insect Juvenile Hormone Biosynthesis

Journal of Agricultural and Food Chemistry ◽

10.1021/jf9707288 ◽

1998 ◽

Vol 46 (5) ◽

pp. 2030-2035 ◽

Cited By ~ 8

Author(s):

M. Castillo ◽

R. Martínez-Pardo ◽

M. D. Garcerá ◽

F. Couillaud

Keyword(s):

Juvenile Hormone ◽

Biological Activities ◽

Sesquiterpene Lactones ◽

Juvenile Hormone Biosynthesis ◽

Hormone Biosynthesis

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Natural Sesquiterpene Lactones as Potential Trypanocidal Therapeutic Agents: A Review

Natural Product Communications ◽

10.1177/1934578x1601101036 ◽

2016 ◽

Vol 11 (10) ◽

pp. 1934578X1601101 ◽

Cited By ~ 2

Author(s):

Liliana V. Muschietti ◽

Jerónimo L. Ulloa

Keyword(s):

Natural Products ◽

Biological Activities ◽

Wide Spectrum ◽

Sesquiterpene Lactones ◽

Large Body ◽

Therapeutic Agents ◽

New Drugs ◽

Parasitic Diseases ◽

Marginalized Communities ◽

Allergic Contact

Chagas’ disease and Human African Trypanosomiasis are parasitic diseases that remain major health problems, mainly among the poorest and the most marginalized communities from Latin America and Africa. The scarcity of effective chemotherapy, due to the low investment in the research and development (R&D) of new drugs, together with a high incidence of side effects, and the emergence of drug resistance phenomena emphasize the urgent need for new prophylactic and therapeutic agents. Over the ages, humans have employed natural products to treat a wide spectrum of diseases. Recently, the pharmaceutical industry has focused on plant research and a large body of evidence has been collected to demonstrate the immense potential of medicinal plants as a source of bioactive compounds and lead molecules. In the field of parasitic diseases, drug development from plants has been successful for the sesquiterpene lactone (STL) artemisinin, which is employed as an antimalarial agent. STLs are a large group of naturally occurring terpenoids derived from plants that mostly belong to the Asteraceae family which exhibit a variety of skeletal arrangements and are the largest and most diverse category of natural products with an α-methylene-λ-lactone motif. STLs display a broad spectrum of biological activities such as antitumor, cytotoxic, antibacterial, anthelmintic, uterus contracting, antimalarial, neurotoxic, antiprotozoal and allergic (contact dermatitis) activities. In this context, the purpose of the present review is to provide an overview of the trypanocidal activity reported for STLs against Trypanosoma cruzi and T. brucei rhodesiense over the period 1993–2015.

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THE RED BLOOD CELLS CATALASE ACTIVITY IS INFLUENCED BY TARAXACUM OFFICINALE

InterConf ◽

10.51582/interconf.21-22.05.2021.020 ◽

2021 ◽

pp. 167-177

Author(s):

Ala Fulga ◽

Valeriana Pantea ◽

Svetlana Protopop ◽

Olga Tagadiuc ◽

Mihail Todiras ◽

...

Keyword(s):

Antioxidant Activity ◽

Catalase Activity ◽

Biological Activities ◽

Wide Spectrum ◽

Sesquiterpene Lactones ◽

Natural Antioxidants ◽

Taraxacum Officinale ◽

Biologically Active ◽

Ability To Act ◽

Leaves And Roots

Natural antioxidants protect cells against oxidative stress, which is directly involved in ageing processes and in the pathogenesis of cardiovascular, neurodegenerative and neoplastic diseases. Taraxacum officinale (TO) due to its rich content of biologically active ingredients has been commonly used in traditional medicine. It contains a wide spectrum of compounds with antioxidant activity. The content depends of parts of this plant. The roots are rich in phenolic and terpene compounds, sesquiterpene lactones, fructosans and inulin, while leaves are rich in substances belonging to flavonoids, phenolic acids, coumarins and vitamins, especially vitamin A. The literature results prove that antioxidant activity of TO depends on several factors including the plant part, the solvent used, as well as the duration of extraction. The aim of this study was to evaluate and to compare the action of alcoholic extracts of roots and leaves of TO on RBC’s catalase activity. Material and methods. Raw Taraxacum officinale plant material consisted of dried leaves and roots were harvested from a natural site. The extracts for analysis were prepared using 20, 25, 40, 50 and 80% (v/v) ethanol mixtures used as solvents. The catalase activity was established by using RBC of healthy persons. Conclusions. Phytotherapeutic herbs and plants continue to play an important role in the discovery and development of drugs. Leaves and roots of dandelion represent a rich source of bioactive compounds for potential exploitation in nutraceuticals and pharmacological sectors. Taraxacum officinale has a high ability to act as an antioxidant. The highest influence on RBC’s catalase activity was reported in case of roots ethanolic extracts of 25%. These actions are realized due to multiple substances, whose content probably depends of ethanol’s concentration. Additional studies are needed to characterize biological activities of these extracts.

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Traditional Applications, Phytochemistry, and Pharmacological Activities of Eupatorium lindleyanum DC.: A Comprehensive Review

Frontiers in Pharmacology ◽

10.3389/fphar.2020.577124 ◽

2020 ◽

Vol 8 ◽

Author(s):

Xueyi Wang ◽

Shangying Ma ◽

Feifan Lai ◽

Yiqi Wang ◽

Chenghua Lou

Keyword(s):

Biological Activities ◽

Sesquiterpene Lactones ◽

Research Work ◽

Preclinical Research ◽

Pharmacological Activities ◽

Bioactive Substances ◽

Traditional Use ◽

Clinical Safety ◽

Traditional Chinese Herbal Medicine ◽

Underlying Mechanisms

Eupatorium lindleyanum DC. (EL) has a long history of traditional use in China to cure coughs, chronic bronchitis, lobar pneumonia, and hypertension. Because of this extensive use of EL in traditional medicine, this present review gives a systematic overview of the conventional applications, phytochemistry, and pharmacological effects of the herb. Literature was systematically searched using the scientific databases ScienceDirect, SciFinder, CNKI, Wiley, Baidu Scholar, SpringerLink, PubMed, Web of Science, and other professional websites. Information was also gathered from books on traditional Chinese herbal medicine, the Chinese Pharmacopoeia and Chinese Materia Medica. To date, many preparations of EL have been widely used clinically to treat various diseases of the respiratory system. More than 100 compounds have been isolated from the herb, including triterpenes, sesquiterpenes, sesquiterpene lactones, flavonoids, acyclic diterpenoids, sterols, and so on. Among them, terpenoids are considered to be the most important bioactive substances in EL. The pharmacological functions of EL, including anti-asthmatic, anti-tussive, anti-inflammatory, anti-hyperlipidemic, anti-hypertensive, anti-virus, and anti-tumor activities, have been widely investigated. However, most of the studies are preclinical research. Further studies are required to examine the underlying mechanisms of action. Traditionally, EL is used for treating many diseases, especially respiratory diseases. Unfortunately, up to now, modern studies have not yet well elucidated the conventional usage of EL. Most importantly, its biological activities and the corresponding constituents are still unclear. Moreover, studies on the pharmacokinetics and toxicity of EL are few, so data on the clinical safety of EL are lacking. Taken together, research work on EL is quite preliminary. More in-depth studies of phytochemistry, pharmacological activities, pharmacokinetics, and toxicity of the herb are needed. This review aims to provide valuable information on EL to guide future investigations and applications.

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