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Further sesquiterpene lactones and phenolics from Cichorium spinosum

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... The remaining cooking water is often reserved in closed jars in reduced temperatures and consumed weekly as a remedy for liver disorders [7]. Phytochemical studies of chicories have been mainly focused on the raw or dried plant material and extracts of medium polarity [8,9], with C. spinosum being the less studied [10,11]. Even more limited are the phytochemical studies of the bioactive watersoluble decoctions [12], which are often used in Mediterranean and Greek medical folklore for the treatment of liver disorders and diabetes, and their spasmolytic, anti-cholesterolemic, antiinflammatory, antihypertensive, and detoxifying properties [13,14]. ...
... The flow rate was stable at 10 mL · min −1 during the separation while fractions were collected every 1 min (total of 60 fractions of 10 mL (Fig. S3, Supporting Information) Fractions B, G, and J contained chichoric acid (1), caftaric acid (2), and 8-deacetylmatricarin-8-O-sulphate (8), respectively, in pure form. Fraction C was a mixture of cafeoylmalic acid (4) and kaempferol-3-O-β-D-glucuronide (6), fraction D contained mainly caffeic acid (5) and quercetin-3-O-β-D-glucuronide (7), fraction F contained chlorogenic acid (3) and impurities, while fraction M was a mixture of malic acid (11) and pyroglutamic acid (12). Finally, in fraction N, which constitutes the bigger part of the extract, quinic acid (9) and tartaric acid (10) ...
Article
The Cretan diet, as the basis of the Mediterranean diet, has provided traditional remedies for the general well being of people through the long-established consumption of cooked wild greens and vegetables. The intake of the water decoctions of Cichorium spinosum and Cichorium intybus in the context of the daily dietary regime in Greece has been long associated with "liver detoxifying" properties. In the current study, we performed an in-depth investigation of the water decoctions traditionally prepared from C. spinosum and C. intybus through qualitative UHPLC-HRMS profiling and direct quantification of cichoric and caftaric acid as major antioxidant components of the decoction. In addition, we developed a one-step countercurrent chromatography method for the isolation of the two phenolic acids, along with a sulfoconjugate sesquiterpene lactone present only in the Cretan C. spinosum. All water decoctions were found not to be cytotoxic in human fibroblasts, whereas they all significantly reduced the intracellular reactive oxygen species, which is consistent with the major presence of strong antioxidant compounds such as cichoric acid. This work demonstrates that the intake of these decoctions in doses suggested by Greek traditional use is comparable to the ingestion of a phytomedical preparation of antioxidants. These results contribute to our current knowledge on the beneficial health effect of the Cretan diet. Georg Thieme Verlag KG Stuttgart · New York.
... 21,22 In addition, Melliou et al. 37 studied the phytochemical composition of aerial parts of wild C. spinosum plants collected on Crete island (Greece) and identified four alkylresorcinol derivatives, cichoriol B and a mixture of cichoriol A, C and D, and two sesquiterpene lactones, namely lactucopicrin and 3,4-dihydrolactucopicrin, as the main compounds. Further secondary metabolites of C. spinosum aerial parts from plants of wild origin (Sicily, Italy) have been reported by Michalska and Kisiel,38 who identified four new coumarins and four sesquiterpene lactones. More recently, Petropoulos et al. 39 reported the phenolic composition of a Cretan ecotype of C. spinosum grown under saline conditions, with chicoric acid and quercetin-3-O-glucuronide being the most abundant phenolic acid and flavonoid, respectively. ...
... However, the low values of determination coefficients (R 2 ) do not suggest significant correlations between the studied parameters, which may be attributed to secondary metabolites that could not be detected in the present study, such as sesquiterpene lactones, antioxidant vitamins and glutathione. 22,35,38 Regarding the growing conditions and cultivation practices, significant differences were detected between wild and cultivated plants, as well as between conventionally and organically produced products, with wild ecotypes having significantly lower amounts of phenolic acids and flavonoids and consequently of total phenolic compounds, compared to cultivated plants. According to Williams et al., 44 many factors may affect phenolic composition in plants, including the genotype (cultivar), growing conditions and soil properties, while Sinkovič et al. 29 have reported a significant effect of fertilizer type (organic or conventional) on phenolic profile of C. intybus leaves. ...
Article
Background: Wild greens are considered a rich source of phenolic compounds and antioxidants and an essential part of the so-called Mediterranean diet. In the present study, Cichorium spinosum L. ecotypes, cultivated or collected in situ from wild plants from the eastern Mediterranean were evaluated regarding their phenolic composition and antioxidant activity. Results: Significant differences were observed among the various studied ecotypes regarding their phenolic compounds content and profile, especially between wild and cultivated ecotypes, as well as the phenolic acids content between commercial products and cultivated plants. The antioxidant activity also varied among the various studied ecotypes and growing conditions, with commercial products having the highest antioxidant activity, whereas wild ecotypes showed lower antioxidant activity. Conclusions: In conclusion, C. spinosum leaves are a rich source of chicoric and 5-O-caffeoylquinic acid, while significant differences in total phenolic acids, flavonoids and phenolic compounds content, and antioxidant activity were observed among the studied ecotypes, as well as between the tested growing conditions. According to the results of the present study, further valorization of C. spinosum species has a great potential, since it could be used as a new alternative species in the food industry.
... Previous phytochemical studies performed on the aerial parts of Cichorium species revealed the presence of polyamines, sterols, flavonoids, phenolic acids, anthocyanins, hydroxycinnamic acid derivatives, sesquiterpene lactones, triterpenoids, norisoprenoids and coumarins (Krebsky et al., 1999;Mulinacci et al., 2001;Kisiel and Michalska, 2002;Norbaek et al., 2002;Kisiel et al., 2004;Michalska and Kisiel, 2007;Papetti et al., 2008). Besides these compounds, several polysaccharides including homogalacturonan, rhamnogalacturonan-I, cellulose, xyloglucan, heteroxylan and glucomannan have been determined in the leaves of C. intybus (Sun et al., 2006). ...
... Cichorium spinosum L., 2n=18 (Stamnagathi) is a perennial species in the genus Cichorium which contains approximately 6 to 10 species (C. intybus, C. endivia, C. pumilum, C. spinosum, C. calvum and C. bottae) and belongs to Asteraceae family ( Figure 1 and Table 1) (1). Stamnagathi can be found in Spain, Balearic Islands, Turkey, Italy (Sicily), South Greece (Crete) and Aegean islands. ...
Article
Fifteen Random Amplified Polymorphic DNA (RAPD) markers were used to measure genetic diversity and genetic relationships between five endemic genera of Mediterranean basin (Greece). Three species of Cichorium spinosum were collected; two from island Crete (Greece) and one from island Kythnos, and other two species of Taraxacom sp. (Asteraceae); are from Orhomenos and Athens. Two hundred-forty amplified products and 163 RAPD bands were scored with an average of 67.91% of them revealing polymorphism across accessions. In this research OPD-05 primer with 24 bands showed the highest number of bands, while the OPM-18 and OPB-16, both of them with 8 bands showed the least number of bands. Also OPV-06 primer with 18 polimorphic bands showed the highest number of bands. The least number of polymorphic bandswere found in OPX-18. UBC-292, OPAN-01, OPB-16, OPM-18, OPD-05 primers. Subsequently, OPD-05 primer with 29.16% showed the least percentage of polymorphism degree, whereas OPM-18 and OPB-16 primers with 87.50% showed the highest percentage of polymorphism. UPGMA clustering based on data from polymorphic RAPD bands revealed two distinct group which joined to form one major cluster at 32% level of similarity. Also Cichorium spinosum, Crete and Cichorium spinosum, Kythnos, varieties with 100% similarity are synonyms. The similarity indices of the RAPD dendrogram ranged between 30% and 100% averagely high enough to suggest useful variability for genetic diversity and plant breeding.
... Cichorium spinosum L., 2n= 18 (Stamnagathi) is a perennial species in the genus Cichorium which contains approximately 6 to 10 species (C. intybus, C. endivia, C. pumilum, C. spinosum, C. calvum and C. bottae) and belongs to Asteraceae family ( Figure 1 and Table 1), (1). Stamnagathi can be found in Spain, Balearic Islands, Turkey, Italy (Sicily), South Greece (Crete) and Aegean islands. ...
Article
Full-text available
Fifteen Random Amplified Polymorphic DNA (RAPD) markers were used to measure genetic diversity and genetic relationships between five endemic genera of Mediterranean basin (Greece). Three species of Cichorium spinosum were collected; two from island Crete (Greece) and one from island Kythnos, and other two species of Taraxacom sp. (Asteraceae); are from Orhomenos and Athens. Two hundred-forty amplified products and 163 RAPD bands were scored with an average of 67.91% of them revealing polymorphism across accessions. In this research OPD-05 primer with 24 bands showed the highest number of bands, while the OPM-18 and OPB-16, both of them with 8 bands showed the least number of bands. Also OPV-06 primer with 18 polimorphic bands showed the highest number of bands. The least number of polymorphic bandswere found in OPX-18. UBC-292, OPAN-01, OPB-16, OPM-18, OPD-05 primers. Subsequently, OPD-05 primer with 29.16% showed the least percentage of polymorphism degree, whereas OPM-18 and OPB-16 primers with 87.50% showed the highest percentage of polymorphism. UPGMA clustering based on data from polymorphic RAPD bands revealed two distinct group which joined to form one major cluster at 32% level of similarity. Also Cichorium spinosum, Crete and Cichorium spinosum, Kythnos, varieties with 100% similarity are synonyms. The similarity indices of the RAPD dendrogram ranged between 30% and 100% averagely high enough to suggest useful variability for genetic diversity and plant breeding.
... Alpha-Tocopherol, gamma-To- copherol, 5-O-Caffeoylquinic acid, chicoric acid, caftaric acid kaemp- ferol-3-O-glucuronide, quercetin-3-O-glucuronide, and apigenin-O-glu- curonide are the main bioactive compounds isolated from the leaves of the species ( Brieudes et al., 2016). Moreover, Michalska and Kisiel (2007) and Melliou, Magiatis, and Skaltsounis (2003) detected four alkylresorcinol derivative (cichoriol A, B, C and D), various sesqui- terpene lactones ((4R)-3,4-dihydrolactucopicrin, lactucin and its deri- vatives, leucodin, tanacetin) and four coumarins (umbelliferone, sco- poletin, aesculetin and cichoriin 4). Regarding the health effects of the species, there is limited number of reports which focus mainly on the antioxidant compounds content. ...
Article
Background: Recent trends in the food science industry and consumers’ preferences for diversified diets suggest the consumption of wild greens not only as diet complements but also as healthy and functional foods for targeted conditions, rendering its commercial cultivation of major importance in order to avoid irrational gathering and genetic erosion threats. The Mediterranean basin abounds in wild edible species which have been used for food and medicinal purposes by human throughout the centuries. Many of these species can be found near coastal areas and usually grow under saline conditions, while others can adapt to various harsh conditions including high salinity. Scope and approach: The aim of this review focuses on listing and describing the most important halophyte species that traditionally have been gathered by rural communities of the Mediterranean basin, while special interest will be given on their chemical composition and health-promoting components. Cases of commercially cultivated halophytes will be also presented to highlight their potential as alternative cash crops, while results from in vitro and in vivo health effects will be presented. Key findings and conclusions: The recent literature has provided useful information regarding the potential of wild halophytes as promising ingredients in functional food products and/or as sources of bioactive compounds. However, further research is needed regarding the chemical characterization of these species under commercial cultivation practices, while further clinical and model trials have to be conducted to assess their long-term bioactivity and elucidate potential toxic effects and regulations of safe consumption.
... Hiorthia (Bruno et al. 2002;Staneva et al. 2008). The guaianolide leucodin (100) and the eudesmanolide tanacetin (101) are chemotaxonomic markers of Cichorium spinosum (Michalska and Kisiel 2007), whereas several guaianolides and germacranolides characterize the genus Achillea (Todorova et al. 2006). In Viguiera radula (Heliantheae), the co-occurrence of germacranolides and heliangolides, stored in glandular trichomes, shows the same general sesquiterpene lactone pattern of many other thus far investigated members of section Paradosa (Spring et al. 2003). ...
Chapter
This chapter describes the: Distribution of biodiversity, Chemotaxonomy of specialized compounds, Chemotaxonomy of phenolic compounds ( Asteraceae, Lamiaceae, Leguminosae, other plant families), Chemotaxonomy of terpenoids (Monoterpenes, Sesquiterpenes, Diterpenes, Triterpenes, Tetraterpenes, Polyterpenes) Chemotaxonomy of specialized products containing nitrogen ( Alkaloids, Glucosinolates, Cyanogenic glycosides, nonprotein amino acids), Chemotaxonomic significance of fatty acids and surface alkanes.
... Alternatevely, different active constituents of other Cichorium spp. were reported [27, 30], and few other studies reported different active constituents and medicinal uses of Cichorium endivia [29, 45, 53]. The wild artichoke, Cynara cornigera Lindl. ...
Article
Full-text available
The present study attempts to explore the phytochemical constituents of different extracts from Cynara cornigera and Cichorium endivia plant materials. The two species studied are native in Egypt. Five different solvents, viz., aqueous, methylene chloride, petroleum ether, ethyl acetate, and n-butanol were used. Phytochemical analysis revealed the presence of phenols, flavonoids, sterols (stigmasterol and beta-sitosterol), terpenes (α-amyrin, ursolic and oleanolic acid), and hydrocarbons (n-alkane), the latter found in low amount. The ethyl acetate and water extracts of C. cornigera root showed lower mass fractions of phenolic compounds ranged from 20 to 81 g/100 g, and higher amounts in ethyl acetate extract of the inflorescences and butanol extract of the root where values ranged from 195 to 399 g/100 g. The β-sitosterol and stigmasterol were present in all plant extracts. Oleanolic and ursolic acids were detected in roots, leaves and inflorescences of C. cornigera and in C. endivia shoot. The ethyl acetate extracts from C. cornigera leaf and inflorescence attained higher chemical diversity than the other extracts. Alternatively, sterols and triterpenes were the major constituents. The high chemical diversity of active constituents justifies the future potential use of the two species at commercial level.
... Previous phytochemical studies performed on the aerial parts of Cichorium species revealed the presence of polyamines, sterols, flavonoids, phenolic acids, anthocyanins, hydroxycinnamic acid derivatives, sesquiterpene lactones, triterpenoids, norisoprenoids and coumarins (Krebsky et al., 1999;Mulinacci et al., 2001;Kisiel and Michalska, 2002;Norbaek et al., 2002;Kisiel et al., 2004;Michalska and Kisiel, 2007;Papetti et al., 2008). Besides these compounds, several polysaccharides including homogalacturonan, rhamnogalacturonan-I, cellulose, xyloglucan, heteroxylan and glucomannan have been determined in the leaves of C. intybus (Sun et al., 2006). ...
Article
Ethnobotanical field surveys revealed that various parts of Cichorium intybus L. has been used for wound healing in Turkish folk medicine. The present study aimed at verifying the efficiency of various traditional prescriptions prepared from the aerial parts and roots of C. intybus experimentally and to define the components responsible from the activity by bioassay-guided procedures. Initially, wound healing activity of the aerial parts, leaves, and roots as well as ashes of either leaves or roots were investigated. Subsequently, roots of the plant were submitted to further detailed investigations. The wound healing activity of the methanolic extract, its subextracts, and fractions were evaluated by using in vivo linear incision and circular excision wound models in rats. The hydroxyproline content of the tissues treated with test ointments were also assessed for the activity evaluation. Moreover, in order to find out a possible involvement of antioxidant activity in wound healing, the test samples were also investigated by DPPH radical scavenging activity and total phenolic concentration were also determined. Additionally anti-inflammatory activity was assessed by using the method of Whittle, which is based on the inhibition of acetic acid-induced increase in capillary permeability. Through the bioassay guided fractionation one compound was isolated and its structure was elucidated by spectroscopic methods. For the determination of the activity mechanisms, the fractions were screened for hyaluronidase, collagenase and elastase enzyme inhibitory activities. Methanolic extract of C. intybus roots was found to possess potent wound healing activity. Then this extract was subjected to successive solvent extraction with n-hexane, dichloromethane (DCM), ethyl acetate and n-butanol. Each solvent extracts were also applied on the same wound models. DCM subextract was found to be the most active one and through chromatographic techniques DCM subextract was fractionated into several fractions and compound 1 was isolated as the compound being responsible from the wound healing activity. The experimental study revealed that C. intybus methanolic extract displays wound healing effect and β-sitosterol was determined as the active compound responsible from the activity.
... On the other hand, different active constituents of other Cichorium spp. were reported (Klaudia et al., 2007;Judentiene et al., 2008); few reports were found concerning the different active constituents of Cichorium endivia Kisiel, 2004;Warashina, 2006). Phytochemically, Cynara cornigera has not been analysed to date, Cichorium endivia has not been analysed in detail and apart from the two above mentioned review about root constituents, a single flavonoid has been reported; ...
Chapter
Specialized metabolites produced by plants of the Cichorieae tribe are of the vital interest to both plant breeders and consumers. The compounds are responsible for the taste, aroma, health benefactory properties, plant-plant and plant-insect interactions, as well as pathogen and pest resistance. The chapter deals with a production of the specialized metabolites in various types of plant in vitro cultures and differences in biosynthetic capability of the field-grown plants and their undifferentiated and differentiated tissue and organ cultures in vitro. An attempt was made to draw some conclusions concerning biosynthetic limitations of particular plant tissue culture techniques. Four genera of the Cichorieae tribe that are of importance as popular vegetables and/or traditional medicines, i.e., Cichorium, Lactuca, Scorzonera, and Taraxacum, were described in detail.
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Covering: January 2010 to December 2010. Previous review: Nat. Prod. Rep. 2010, 27, 1681.
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Chapter
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Chapter
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Amounts of the sesquiterpene lactones and the major phenolics were determined in the chicory plant at different times during the growing season. The levels of the sesquiterpene lactones (lactucin, lactupicrin and 8-deoxylactucin) and the hydroxycoumarin cichoriin were found to be highest in the most actively growing regions of the plant. In two-choice and no-choice feeding experiments with borosilicate discs, 8-deoxylactucin, lactupicrin and cichoriin significantly reduced feeding of Schistocerca gregaria at levels comparable to those present in the plant. Cichoriin was still significantly antifeedant at 0.006% dry wt, while aesculin, aesculetin and the caffeic acid ester, chicoric acid were inactive. We conclude that the three sesquiterpene lactones secreted in the latex provide a significant barrier to herbivory in chicory, although the phenolics and notably cichoriin also protect the plant from insect feeding.
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The inter- and intraspecific variability of Cichorium intybus L. was examined to evaluate potential morphological and molecular diagnostic character states. Two diagnostic and one overlapping morphological character clearly delimit the two species C. intybus and C. spinosum. All applied molecular methods (ITS, AFLP, Microsatellites) failed to significantly discriminate between these accepted species. As the morphological traits are fixed and heritable, criteria for species delimitation are fulfilled. These traits, however, are apparently due to mutations of a few crucial loci affecting the morphological diagnostic character states. Intraspecific variability within C. intybus revealed to be highly influenced by plastic response to local environmental factors and subspecific delimitation cannot be supported.
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Ten guaianolides, including three previously unreported natural products, were isolated from the aerial parts of Cichorium intybus (Asteraceae), more commonly known as chicory. Two of the new compounds (8 and 9) were analogues of lactupicrin and 11β,13-dihydrolactupicrin, respectively, with the C-15 oxidized to the aldehyde state. The third new natural product, which we have called intybulide A (10), is an isomer of lactucin with the lactone closed to the C-8 oxygen rather than the C-6.
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The genus Cichorium consists of two widely cultivated species C. intybus (chicory) and C. endivia (endive) and four wild species, C. bottae, C. spinosum, C. calvum, and C. pumilum. A multivariate and an UPGMA (unweighted pair group method average) analysis based on AFLP (amplified fragment length polymorphism) markers were used to establish the genetic relationships among the species and cultivar groups of C. intybus and C. endivia. At the species level, the results correspond with previously obtained phylogenetic relationships in that C. bottae is the most divergent species, and C. intybus and C. spinosum, as well as C. endivia, C. pumilum, and C. calvum formed clusters. Based on the congruence between phylogenetic and genetic analyses, unique markers were expected for all species, however, hardly any specific marker was found except for C. bottae. The analysis of cultivar groups of C. intybus resembled the species analysis in two respects: (i) grouping of cultivars according to cultivar groups, and (ii) lack of markers unique to cultivar groups. In contrast to C. intybus, the cultivar series of C. endivia do not form distinct groups, which would reflect that crosses have been made among the various cultivar groups. The relationships among Cichorium species and cultivars will be useful for setting up a core collection of Cichorium, and stress the importance of inclusion of the wild species in the collection.
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From the roots of Crepis mollis, one new and two known guaianolides were isolated together with eight known guaianolide glycosides, one known germacranolide glycoside and two known phenylpropanoids. The structure and relative configuration of the new compound were established as 9alpha-hydroxy-4beta, 15, 11beta, 13-tetrahydro-dehydrozaluzanin C by spectral methods.
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The isolation and structure elucidation of a new lactucopierin derivative from Cichorium intybus is described. together with the revised structures of several sesquiterpene lactones previously isolated from Cichorium species. The known eudesmanolide magnolialide and the known guaianolide ixerisoside D, reported far the first time from the plant material, along with the previously known chicory sesquiterpene lactones have been also isolated and identified. (C) 2001 Elsevier Science Ltd. All rights: reserved.
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Cichoriin-6'-p-hydroxyphenyl acetate, a new natural product, was isolated from chicory leaves.
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One new alkylresorcinol derivative, cichoriol B, and a mixture of three other ones, cichoriols A, C, and D, were isolated from the dichloromethane extract of Cichorium spinosum, a plant that is used traditionally in the Cretan diet. The methanol extract afforded one new sesquiterpene lactone, (4R)-3,4-dihydrolactucopicrin. The structures of the new compounds were determined by spectroscopic methods, mainly by the concerted application of 1D and 2D NMR techniques (HMQC, HMBC, NOESY).
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The forage potential of chicory (Cichorium intybus L.) has not been realized in southern West Virginia (WV) because ruminants are reluctant to consume the herbage. Chicory contains bitter sesquiterpene lactones that can adversely impact palatability. This study was undertaken to determine whether sesquiterpene lactone concentrations in chicory grown in southern WV differ from those in chicory grown in central Pennsylvania (PA) where chicory is grazed readily. Herbage was collected in 1997 and 1998 from cultivars Grasslands Puna (Puna), INIA le Lacerta (Lacerta), and Forage Feast established at research sites near State College, PA, and Beckley, WV. The total concentration of sesquiterpene lactones in WV-grown cultivars was 0.58% (dry matter basis) in Puna, 0.59% in Lacerta, and 0.79% in Forage Feast in 1997 and ranged from 1.03 (Lacerta) to 1.52% (Forage Feast) in 1998. In PA-grown cultivars, sesquiterpene lactones represented 0.16 (Puna), 0.18 (Lacerta), and 0.27% (Forage Feast) of the forage dry matter in 1997 and ranged from 0.32 (Lacerta) to 0.55% (Forage Feast) in 1998. Concentrations of lactucin, lactucopicrin, and total sesquiterpene lactones in Forage Feast exceeded those in the other cultivars grown at the same site. The lowest concentrations of lactucopicrin and total sesquiterpene lactones observed among WV-grown cultivars were higher (2-fold or more) than the highest concentrations present in cultivars grown the same year in PA. Mineral analyses of soils from the two cultivation sites indicate that P availability may influence sesquiterpene lactone composition of chicory herbage. Results provide a foundation for future studies of environmental effects on sesquiterpene lactone composition and palatability of chicory herbage.
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