Sesquiterpene lactones represent a group of compounds responsible for the medicinal characteristics of centaurea species. Structural diversity and their biological activities devdutt chaturvedi natural products chemistry division, northeast institute of science and technology csir jorhat785006, assam, india abstract. Review article sesquiterpene lactones from artemisia genus. Isolation and oxidative modifications of sesquiterpene lactones. Biological activities and methods of analysis biancaivanescu, 1 ancamiron, 2 andandreiacorciova 3 department of pharmaceutical botany, faculty of pharmacy, university of medicine and pharmacy grigore t. Biological activities of sesquiterpene lactones from.
A little or no sesquiterpene lactone had been detected in other species. Biosynthesis of sesquiterpene lactones in plants and metabolic engineering for their. Comprehensive in its coverage, this book also provides readers with a brief description of the. Biological activities of sesquiterpene lactones antitumor activity. All experimental evidence about the biological activities of sesquiterpene lactones seems to indicate that the. Centaurea, sesquiterpene lactones, antibacterial, antifungal, biological activities, plant metabolites. Sesquiterpene lactones represent a group of compounds responsible for the. Sesquiterpene lactones in sunflowers, helianthus spp. Since results obtained in vivo pointed to disruptions on juvenile hormone jhregulated physiology, we tested the sesquiterpene lactones and a family of synthetic sesquiterpene derivatives for their ability to disturb the. Sesquiterpene lactones exhibit a wide range of biological activities, such as antitumor, antiinflammatory. Sesquiterpene lactones sqls are an important group of bioactive compounds that are usually found in the asteraceae family, where they seem to be some of the most important constituents for defense against microorganisms. The present chapter will be highlighted on the recent developments on the sls and their diverse biological activities. Antibacterial, antimicrobial and antiviral activity antimicrobial activity was recorded in tanacetopsis mucronata s. Hologram qsar studies of antiprotozoal activities of sesquiterpene lactones gustavo h.
In recent years, many researchers over the world have reported that sesquiterpene lactones possess potential anticancer activity. The j b c 2000 by the american society for biochemistry and. Pdf biological activities of sesquiterpene lactones. Sesquiterpene lactones structural diversity and their. Sesquiterpenes lactones sls have been isolated from numerous genera of the family asteraceae compositae and can. In several chromatographic steps, three flavonoids and three sesquiterpene lactones stls were isolated and identified from the most active fractions of the ethanol extract. They are described as the active constituents of a variety of medicinal plants used in traditional medicine for the treatment of inflammatory diseases. Artemisia species are popular plants which are used for the treatment of diseases such as hepatitis, cancer, inflammation and infections by fungi, bacteria. Sesquiterpene lactone mix mx18 your patch testing results indicate that you have a contact allergy to sesquiterpene lactone mix. This book addresses chemical and biological aspects related to sesquiterpene lactones stls. In order to study the reactivity of sesquiterpene lactones in biological systems, we describe herein the asymmetric synthesis of a simple model, the methylene. Within this family, genus artemisia is very well represented, having approximately 500 species characterized by the presence of eudesmanolides and guaianolides, especially highly oxygenated. They are known to possess wide variety of biological and pharmacological activities. Sesquiterpene lactones stls present a wide range of biological activities, mostly based on their alkylating capabilities, which underlie their therapeutic potential.
Compositae is an alternative name for the official term, asteraceae. Theantimalarialdrugartemisinin and its derivatives are very potent anticancer compounds. It is important that you familiarize yourself with this chemical and take steps to avoid coming in contact with it. Isolation and purification of sesquiterpene lactones from. Inhibition of phosphofructokinase by molluscicidal. Among them, centaurea species are well known to be used in. Four new sesquiterpene lactones, cichoriolide a and cichoriosides a, b and c, have been isolated from cichorium endivia l. Sesquiterpene lactones, a vast range of terpenoids isolated from asteraceae species, exhibit a broad spectrum of biological effects and several of. Structurehepatoprotective activity relationship study of sesquiterpene lactones. Investigations of chemical analyses and biological potential exhibited that flavonoids and sesquiterpene lactones, in particular germacranolides, eudesmanolides, elemanolides. They are known to poison livestock, to act as insect feeding deterrents and to cause allergic contact dermatitis in humans. Sesquiterpene lactones from the aerial parts of anthemis. Examples edit artemisinin, a new, highlyeffective anti malarial compound, is a sesquiterpene lactone found in artemisia annua. Sesquiterpene lactones are a large group of natural compounds, found primarily in plants of asteraceae family, with over 5000 structures reported to date.
Because sesquiterpene lactones are responsible for the toxicity of several livestock poisons it is useful to focus on their effects on mammals such as cattle, sheep and horses. Sesquiterpene lactones can be divided into several main classes including germacranolides, heliangolides, guaianolides, pseudoguaianolides, hypocretenolides, and eudesmanolides. Free cyclodextrins did not show significant activity and therefore the enhancement in activity was due to complexation. Sesquiterpene lactones from plants of the family asteraceae in the kazakhstan flora and their biological activity. These compounds have an antibiotic effect on gramnegative and grampositive bacteria as well as on some fungi. These compounds are the active constituents of a variety of plants, frequently used as herbal remedies. They exert a broad range of activities, including antiinflammatory, antibacterial and anticancer properties. It is generally believed that they might present certain biological. Biological activities and methods of analysis biancaivanescu,1 ancamiron,2 andandreiacorciova3. Metabolite profiling of sesquiterpene lactones from lactuca. Sesquiterpene lactones and their toxicity to livestock the objective of this web page is to describe the different classes of naturallyoccurring sesquiterpene lactones. Sesquiterpene lactones are natural stereochemically pure compounds, which show a number of biological activities. Among the compositae, over 500 different members of the sl family have been described including not only constitutively produced secondary metabolites but also phytoalexins, which are only synthesized following microbial challenge 2, 4, 5.
In vitro leishmanicidal activities of sesquiterpene. Within this family, genus artemisia is very well represented, having approximately 500 species characterized by the presence of eudesmanolides and guaianolides, especially highly oxygenated ones, and rarely of germacranolides. Sesquiterpene definition of sesquiterpene by medical dictionary. Biological activity of flavonoids and rare sesquiterpene lactones. Biological activities of sesquiterpene lactones sciencedirect. Further reproduction prohibited without permission. Five new sesquiterpene lactones, racemosalactones ae 15, along with 19 known sesquiterpene latones 624, were isolated from the. As sesquiterpenoids exhibit a wide range of bioactivities which include toxicity of certain cancer cell lines and induction of detoxifying enzymes, the sesquiterpene content of salads and. The promising nature is shown of the search for biologically active sesquiterpene. Sesquiterpene lactones, secondary metabolites of plants, present in a large number of species mostly from the asteracea family, are used in the traditional medicine of many countries for the treatment of various pathological conditions. Biological activity of flavonoids and rare sesquiterpene. One of the naturally occurring sesquiterpene lactones is costunolide, which has been extensively investigated for a wide range of biological activities. These secondary metabolites have a skeleton of 15 carbon atoms and are derived from farnesyl diphosphate.
Introduction sesquiterpene lactones sls constitute a large and diverse group of. Various activities of sesquiterpene lactones suggest their evolu tionary significance in plants as deterrents against herbivores and antiofungal, antibacterial allelopathic agents. Costunolide 1, an important compound of this class, is an active component from the crude extract of the root of. The activities on etiolated wheat coleoptiles, standard target species and parasitic weeds were improved. Pdf pharmacological activity of sesquiterpene lactones. Sesquiterpene lactone composition of wild and cultivated. Sesquiterpene lactones structural diversity and their biological activities free download as pdf file. Research in this area considering antimicrobial, antioxidant, cytotoxic, antiinflammatory, and other properties, is currently expanding, reporting various species to possess such biological effects. Multiple lines of preclinical studies have reported that the compound possesses antioxidative, antiinflammatory, antiallergic, bone. While there are numerous books on heterocycles and natural products, this text fills the need for an uptodate summary focusing on recently developed and improved synthetic methods for the preparation of the most important classes of lactones and lactams all in one volume.
Helenalin a sesquiterpene lactone with multidirectional. Experts in different fields have been invited to contribute on this class of compounds chemistry, isolation and identification, biological activities antibacterial, antifungal, antiviral, antitrypanosomal, antileishmanial,antiplasmodial, antiproliferative and antiinflammatory, synthesis. Structural investigation and biological activity of sesquiterpene. Conclusion many of tested khorasanian artemisia species contained. Experts in different fields have been invited to contribute on this class of compounds chemistry, isolation and identification, biological activities antibacterial, antifungal, antiviral, antitrypanosomal, antileishmanial,antiplasmodial, antiproliferative and antiinflammatory. Two stls, one for which we created the trivial name ragusinin, and hemistepsin a are here reported for the first time as constituents of the genus centaurea. Costunolidea bioactive sesquiterpene lactone with diverse. Chemical constituents and biological activities of. Novel sesquiterpene lactone hatem ghouila and sesquiterpene. Investigation of structure activity relationships of all data helps the understanding of the. Recent developments in the assessment of biological activities and structure relationships. Hologram qsar studies of antiprotozoal activities of. Experts in different fields have been invited to contribute on this class of compounds chemistry, isolati. Biological activity of flavonoids and rare sesquiterpene lactones isolated from centaurea ragusina l.
What is sesquiterpene lactone mix and where is it found. The structures of the new compounds were established on the basis of chemical and spectral data. The antimicrobial and cytotoxic activities of chloroform extracts from the weeds centaurea tweediei and c. Screening of several biological activities induced by. Three natural sesquiterpene lactones have been assayed for their biological activity on locust locusta migratoria nymphs. Synergistic antimycobacterial activities of sesquiterpene. Sep 15, 2016 esterified drimanetype sesquiterpene lactones such as astellolides display various biological activities and are widely produced by plants and fungi. Fourteen new compounds of this series belonging to the germacranolides, eudesmanolides, guaianolides, and pseudogermanolides have. Grienke u, radic brkanac s, vujcic v, urban e, ivankovic s, stojkovic r, rollinger jm, kralj j, brozovic a and radic stojkovic m 2018 biological activity of flavonoids and rare sesquiterpene lactones isolated from centaurea ragusina l. Sesquiterpene lactone mix chemotechnique diagnostics.
Sesquiterpenes lactones sls have been isolated from numerous genera of the family asteraceae compositae and can also be found in other angiosperm families. Different types of sesquiterpene lactones have been reported from this genus, eudesmanolides, guaianolides and pseudoguaianolides being the most common 2. Within this family, genus artemisia is very well represented, having approximately 500 species characterized by the presence of eudesmanolides and guaianolides, especially highly oxygenated ones, and rarely of. Oct 01, 2015 the present paper proposes an overview of biological activities and of methods used for the identification and quantification of sesquiterpene lactones found in artemisia genus. The aim of this study was to determine the antimycobacterial potential of laurel oil, its fractions and its two sesquiterpene lactones against several mycobacterial strains and clinical isolates, and to establish the possibility of occurrence of some synergistic effects between those lactones using a modification of the fluorometric alamar blue microassay fmaba.
Compositae allergy refers to contact allergic reactions caused by a group of plants commonly known as compositae. Sesquiterpene lactones from dimerostemma species asteraceae and in vitro potential antiinflammatory activities ricardo stefania,b, karin schorra,b, juliana maria turetab, walter vichnewskib, irmgard merfortc, and fernando b. The activity is connected to presence of, unsaturated lacton ring 7. Cyclodextrins preserved or enhanced the activity of the three sesquiterpene lactones. The potential for drug development from artemisia species continues to grow, particularly in the area of parasitic diseases and cancer treatment. The sesquiterpene lactones are highly irritating to the nose, eyes, and gastrointestinal tract. Sheep and goats are the main livestock species affected, primarily because the plants are unpalatable and rarely consumed in toxic quantities by cattle and horses.
Sneezeweed poisoning is often referred to as spewing sickness because of the. Fourteen new compounds of this series belonging to the germacranolides, eudesmanolides, guaianolides. Differentiation of saturated and unsaturated sesquiterpene lactones was one of the advantages of 1hnmr application in this method. Topical herbal therapies an alternative and complementary choice to combat acne author. Sesquiterpene lactones constitute a major class of bioactive natural products.
Biological activities of natural sesquiterpene lactones. Biological activities of sesquiterpene lactones isolated from the genus centaurea l. Return to article details promising biological activities of sesquiterpene lactones download download pdf promising biological activities of sesquiterpene lactones. Sesquiterpene lactones from dimerostemma species asteraceae. They have been known to cause allergic contact dermatitis in humans, livestock poisoning and to act as mollucidides against the snails of the genus biomphalaria 4. Complexation of sesquiterpene lactones with cyclodextrins. Here, we investigated the anticancer activity of sesquiterpene lactones sls isolated from ambrosia arborescens and of synthetic derivatives in breast cancer cell lines, with a specific focus on activity. Media in category sesquiterpene lactones the following 50 files are in this category, out of 50 total. It is important to note that arnica belongs to the sunflower family asteraceae and may engender allergic reactions as a result of its sesquiterpene lactones and polyacetylenes. Sesquiterpene lactones have a distinctive biological activity.
Centaurea, sesquiterpene lactones, dna, cell viability, toxicity, glutathione. Isolation and oxidative modifications of sesquiterpene lactones nunez, isabel salkeld, ph. As noted by numerous workers 26,28, the structures and reactivities of these sesquiterpene lactones fig. The main publications on this sesquiterpenolide, from its isolation of natural sources in 1972 to the current days, are included. Across a broad range of helianthus annuus, differences in composition of sesquiterpene lactones extracted from disc florets were found between wild and cultivated sunflowers and also between distinct groups of inbreds used to produce sunflower. Background in recent years, a growing interest has developed in the field of biological activity of plant metabolites. All extracts were found to be more or less deter rent to the granary weevil beetle, the confused flour beetle, and larvae of the khapra beetle.
Several general ideas about the structural requirements for activity, based on the in vitro bioassays and the in silico prediction of their adme properties are discussed. Ann aibor, mi 48106 reproduced with permission of the owner. Sesquiterpene lactones sls 1 found in plants are remarkably diverse in terms of their structure, properties, and proposed functions. The induced sesquiterpene lactone phytoalexin, lettucenin a, was found in the lactuca spp. The activity is connected to presence of, unsaturated. Sesquiterpene lactones also act as plant growth regulators and are responsible for allelopathic properties of many plants. The originally proposed structure of antheindurolide b was revised. Table 2 includes those sesquiterpene lactones that exhibit antitumor activity. The most important allergens in the compositae family are sesquiterpene lactones, which are present in the.
Topical herbal therapies an alternative and complementary. The louisiana state university and agricultural and mechanical col. Various activities of sesquiterpene lactones suggest their evolu tionary significance in plants as deterrents against herbivores and antiofungal. Ps mx18 issue 2 201606 patient information sheet sesquiterpene lactone mix mx18 your patch testing results indicate that you have a contact allergy to one or more chemicals in the sesquiterpene lactone. Sesquiterpene lactones, produced in light and capable of inhibiting auxininduced elongation growth of coleoptile and hypocotyl segments, were isolated from young leaves of helianthus annuus spring and hager, planta in press, 1982. Jan 16, 2016 arnica is used for a variety of medical conditions, generally to improve or relieve pain, reduce swelling, act as a local antimicrobial to prevent infections, etc. Sesquiterpene lactones sls are probably the largest class of secondary metabolites in plants, with over 5000 structures reported to date 14. Synthesis and biological studies of some new derivatives of.
Biological activities of sesquiterpene lactones 267 in the search for feeding deterrents of plant origin against selected storage pests, extracts of 11 species of composites were examined 156. Investigations of chemical analyses and biological potential exhibited that flavonoids and sesquiterpene lactones, in particular germacranolides, eudesmanolides, elemanolides, and guaianolides, are compounds responsible for the biological potential of plants. University rohtak, haryana, sohna road, faridabad121002, india. Advances in their chemistry and biological aspects. It may be used as an antiseptic, antibacterial, or antiinflammatory and as a calming agent by aromatherapists.
This suggests biological activities of sesquiterpene lactones 275 that the individual lactones from this group of secondary plant metabolites may play a role in defense of plants against pathogens, herbivor ous insects and mammals, and in competition with other plants. Detection of sesquiterpene lactones in ten artemisia species. A qsar analysis article in international journal of quantum chemistry 1091. In recent years, a growing interest has developed in the field of biological activity of plant metabolites. Different stl subtypes have been reported as antileishmanial compounds. Constituents and biological activities of artemisia herbaalba 2 carbacholine induced contraction of guineapig trachea 6. It is evident that a majority of structurally diverse biologically potent sesquiterpene lactones have emerged as potential anticancer agents.
Promising biological activities of sesquiterpene lactones abstract. Screening of several biological activities induced by different sesquiterpene lactones isolated from centaurea behen l. Sesquiterpene lactones from plants of the family asteraceae. A highly stereoselective divergent synthesis of bicyclic. Anticancer stem cell activity of a sesquiterpene lactone. Identification of a novel sesquiterpene biosynthetic. New regimens are constantly being pursued in cancer treatment, especially in the context of treatmentresistant cancer stem cells cscs that are assumed to be involved in cancer recurrence. Sesquiterpene lactones advances in their chemistry and. Pages in category sesquiterpene lactones the following 25 pages are in this category, out of 25 total. Research in this area considering antimicrobial, antioxidant, cytotoxic, antiinflammatory, and other. Biological activity sesquiterpene lactones have a distinctive biological activity. Sesquiterpene lactones sls are a group of secondary metabolites that represent a diverse and unique class of natural products and are important constituent of essential oils, formed from headtotail condensation of three isoprene units and subsequent cyclization and oxidative transformation to produce a cis or transfused lactone. Biological activities of sesquiterpene lactones isolated. The results are generalized of the results of a study of 109 species of plants of the family compositae asteraceae growing on the territory of kazakhstan.
184 1391 202 745 1026 208 173 788 852 957 1223 1177 1312 839 968 1302 1427 441 984 492 1003 1236 1032 371 835 1391 1355 927 1017 85 1073 46 628 646 1155 529 72 1170 381 813 1079 820 305 1338