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Molecular and phytochemical systematics of the subtribe Hypochaeridinae (Asteraceae, Cichorieae)

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The systematics of the Hypochaeridinae subtribe was re-evaluated based on a combination of published and new molecular data. Newly emerging clades were additionally characterized using published and new phytochemical data. In addition to flavonoids and sesquiterpene lactones, which recently had been reviewed as chemosystematic markers in the Cichorieae, we analysed the reported occurrences of caffeic acid derivatives and their potential as chemosystematic markers. The molecular results required changes in the systematics of the subtribe: the genus Hedypnois proved to be very closely related to a few Mediterranean members of Leontodon section Leontodon. This clade comprises all members of the genus Hedypnois, Leontodon siculus (Guss.) Nyman, L. boryi DC., L. rosani (Ten.) DC., and L. villarsii (Willd.) Loisel. and is more closely related to Leontodon section Asterothrix than to all members of Leontodon section Leontodon. Instead of splitting Leontodon into even a higher number of segregate genera we propose to include Hedypnois into Leontodon s.str., thus comprising members of sections Asterothrix, Leontodon, and Thrincia sensu Widder (1975) plus the taxa currently assigned to the genus Hedypnois. Leontodon sections Leontodon and Astrerothrix are merged into a single section Leontodon. The newly defined genus Leontodon is supported by high bootstrap values and characterized by the unique occurrence of hydroxyhypocretenolides. The monophyly of the genus Hypochaeris is not supported. There are two separate molecular clades within Hypochaeris. The clade Hypochaeris I comprises the majority of the European and Mediterranean as well as all South American taxa of Hypochaeris s.l. while the clade Hypochaeris II only encompasses H. achyrophorus L., H. glabra L., H. laevigata Benth. & Hook.f., and H. radicata L.
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... Peak separation was achieved by a Phenomenex (Torrance, CA, USA) Luna C18 5 µm (250 mm × 4.6 mm) column, at 35 • C in thermostatic oven (Agilent P/N G1316A), and a binary gradient elution with 5% (v/v) acetic acid in deionized water (solvent A) and methanol (solvent B), at a flow rate of 1 mL min −1 . The following elution profile was adopted: 0-25 min Therefore, phenolic profiles are generally characteristic of a certain species and could be used in some cases as chemotaxonomic markers for species and sub-species identification [24][25][26][27]. ...
... Differently from TPC, qualitative phenolic composition of wild edible herbs is scarcely influenced by geographical and pedoclimatic factors, rather it seems to depend on genetic factors. Therefore, phenolic profiles are generally characteristic of a certain species and could be used in some cases as chemotaxonomic markers for species and sub-species identification [24][25][26][27]. ...
... only, and not also of CFTA and CHLA; on the other hand, in T. officinale juice, besides all components found in this work, Shütz et al. [28] reported the presence of 3,4-and 4,5-DCQA, L-7-rut., and of other unidentified L-and a Q-glycosides. As for U. picroides, according with the present results, Enke et al. [27] reported the presence of CHLA and 3,5-DCQA, but not of flavonoids; on the other hand Petropoulos et al. [4] found CHLA, Q-3-gluc., K-3-gluc. and other Q-and K-glycosides; while Giner et al. [26] reported the presence of CHLA, DCQA, Q-3-gluc., Q-3-galactoside (galact.), ...
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The study aimed to assess the influence of three cooking methods (boiling, steaming, and microwave-cooking) on (i) composition in individual phenolic compounds, (ii) total phenolic content (TPC), and (iii) total antioxidant activity (TAA) of eight Mediterranean wild edible species (Asparagus acutifolius, Asphodeline lutea, Beta vulgaris, Helminthotheca echioides, Sonchus oleraceus, Taraxacum officinale, Urospermum picroides, Urtica dioica). In raw greens, several caffeic acid derivatives (chicoric, caftaric, chlorogenic, neochlorogenic, 1,5-and 3,5-dicaffeoylquinic acids) and flavonoids (glycosides of apigenin, luteolin, quercetin, isorhamnetin, kaempferol) were identified. Cooking treatments did not affect qualitative phenolic composition, while quantitative changes were recorded in some phenolic compounds and in TPC. Generally, boiling decreased TPC and TAA, while chicoric, caftaric, chlorogenic acids and quercetin-3-rutinoside increased in some species after steaming and microwave-cooking, showing positive correlation with TAA. Results confirmed steaming and microwave-cooking as mild procedures able to increase antioxidant capacity of some species, producing beneficial effects on their nutraceutical properties.
... The phylogenetic relationships of Leontodon section Asterothrix, of which L. tenuiflorus is a member (Widder, 1975;Zidorn, 2012), are shown in Fig. 4. The displayed tree topology is a based on a maximum likelihood phylogram reported by Enke et al. (2012). Based on the preliminary survey described above and based on the fact that in previous extensive investigations of L. hispidus, compound 3 was never detected, the newly discovered sesquiterpenoid 3 might be a chemophenetic marker of the section Asterothrix (Fig. 4). ...
... only been found in Hypochaeris cretensis (L.) Bory & Chaub. (they were actually named after this species) and members of Leontodon section Leontodon (Enke et al., 2012); in contrast, an additional previous record from Crepis aurea (L.) Cass. was proven to be erroneous (Michalska et al., 2013). ...
Article
Leontodon tenuiflorus (Gaudin) Rchb. yielded ixerisoside D, sonchuside A , and the previously undescribed 4,6-O-dihypocretenoyl-D-glucopyranoside. This is the first report of a hypocretenoid from Leontodon section Asterothrix.
... In addition, macro-molecular data showed that the genus Hedypnois [currently considered to encompass three species (Kilian et al., 2020)] should also be included into Leontodon section Leontodon, though Hedypnois in its traditional delimitation is, by the lack of a plumose pappus, morphologically easily distinguished from all other taxa of Leontodon (Kilian et al., 2020). Chemophenetically (Zidorn, 2019) however, Hedypnois taxa and all taxa of Leontodon section Leontodon analyzed so far, share a unique phytochemical character, the occurrence of hydroxyhypocretenolides (Enke et al., 2012). Hypocretenolides are a unique subclass of guaianolides featuring a 12,5-instead of a 12,6-lactone ring. ...
... 11,13β-Dihydro-14-hydroxyhypocretenolide-β-D-glucopyranoside 16 was present in all investigated taxa and is subsequently reported for the first time in samples of L. filii, L. hochstetteri, and L. rigens. Thus, so far, all Leontodon section Leontodon taxa, which have been analyzed with regards to their medium-polar natural compounds profile, have also been identified as sources of hydroxyhypocretenolides (Zidorn et al., 2007;Enke et al., 2012). Carine and Schaefer (2010) suggested that the three endemic Azorean Leontodon taxa formed by inter-island allopatric speciation. ...
Article
The genera Leontodon s.str. and Hedypnois are so far the only known sources of hydroxyhypocretenolides, a rare subclass of guaianolide type sesquiterpene lactones. In this study the three endemic species from the Azorean Archipelago, L. filii, L. hochstetteri, and L. rigens, were analyzed together with L. hispidus and L. × grassiorum, a hybrid originating from L. hispidus and L. hochstetteri. Flowering heads were analyzed by UHPLC-DAD-MS with regards to their phenolics' profiles, establishing qualitatively identical profiles for all taxa. The following phenolics were detected in flowering heads of all investigated taxa: caffeoyltartaric acid, cichoric acid, chlorogenic acid, 3,5-di-O-caffeoylquinic acid, luteolin, luteolin 7-O-β-d-glucopyranoside, luteolin 4′-O-β-d-glucopyranoside, and luteolin 7-O-β-d-glucuronide. In UHPLC-DAD-MS analyses of the rhizomes, no flavonoids were detected. In rhizomes, caffeoyltartaric acid was only detected in L. hispidus. However, in addition to caffeoylquinic acid derivatives already found in the flowering heads, 1,5-di-O-caffeoylquinic acid, 3,4-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid were detected in rhizomes of all investigated taxa. The chemophenetically most interesting group of hydroxyhypocretenolides was detected in rhizomes of all investigated taxa. 11,13β-Dihydro-14-dihydroxyhypocretenolide was detected in L. filii and L. hochstetteri, while 11,13β-dihydro-14-hydroxyhypocretenolide-β-d-glucopyranoside was present in all Azorean taxa. 1,10-Epoxy-14-hydroxyhypocretenolide-β-d-glucopyranoside and 1,10-epoxy-14-hydroxyhypocretenolide-β-d-glucopyranoside-6′-O-p-hydroxyphenylacetic acid ester were restricted to the Azorean taxa and the hybrid L. × grassiorum, while the dimeric sesquiterpenoid 14-hydroxyhypocretenolide-β-d-glucopyranoside-4′,14″-hydroxyhypocretenoate ester was restricted to L. hispidus and L. × grassiorum.
... The limit between naturalized taxa and taxa which only occur as casuals is often not clear cut and moreover prone to change over time. The following species are listed by Christiansen (1953) as introduced casuals or taxa temporarily escaped from culture [the list includes also the taxa which have been covered in the sections above; nomenclature has been updated according to The Plant List (2019) Enke et al. (2012), the latter two taxa should be better named Leontodon rhagadioloides (L.) Enke & Zidorn and Leontodon rhagadioloides subsp. tubaeformis (Ten.) ...
... In the Cichorieae found in Schlewsig-Holstein (as in the rest of the world), phenolics, sesquiterpene lactones, and triterpenes occur in nearly all species studied in some detail, and in particular for sesquiterpene lactones, the array of compounds found is often characteristic for each studied taxon. Therefore, these compounds can also be used to chemophenetically characterize taxa, lacking obvious morphologic characters (Enke et al. 2012;Zidorn 2019). In contrast, flavonoids and phenolic acids vary less dramatically between genera and species. ...
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Recent international developments make access to biological resources across international borders more difficult than in the past. Local access to biological resources, including plant natural products, thus becomes more important. In order to evaluate the opportunities to access bioactive natural products in our region, we here start a series of dedicated articles assessing the chemical diversity of plant taxa, native and naturalized, in the region of Schleswig-Holstein, Germany. The region has only a limited biodiversity with about 1500 species of higher plants growing in the wild. Our aims are the following: (1) A complete review of the natural products reported from taxa occurring in Schleswig-Holstein from any part of their distribution range. (2) Proof or disproof, whether these substances are also occurring in populations of the taxa at hand occurring in the wild in Schleswig-Holstein. (3) To establish analytical GLC-MS and/or HPLC-DAD-MS systems to identify and quantify these compounds. (4) Initiation of dedicated efforts to unravel the array of secondary metabolites contained in species from the Schleswig-Holstein region not yet investigated. (5) Search for chemically defined intraspecific taxa, i.e. chemically differing lineages of morphologically indistinguishable plant taxa, by comparing plants from Schleswig-Holstein with plants collected in other regions. The survey into the plant natural products’ chemodiversity of the flora of Schleswig-Holstein begins with a review of the natural products from Schleswig-Holstein members of the Cichorieae tribe of the Asteraceae family. The Cichorieae tribe of the Asteraceae family, which encompasses 94 genera and about 1500 species and innumerous microtaxa worldwide (Kilian et al. in Systematics, evolution and biogeography of the Compositae, IAPT, Vienna, 2009), is represented by only 17 genera in Schleswig-Holstein: Arnoseris, Chondrilla, Cicerbita, Cichorium, Crepis, Hieracium, Hypochaeris, Lactuca, Lapsana, Leontodon, Picris, Pilosella, Scorzonera, Scorzoneroides, Sonchus, Taraxacum, and Tragopogon. In total, 48 species (50 taxa including the two species with two distinct subspecies each in the region and treating the sections in the hyper-species-rich genus Taraxacum as species here), occur in Schleswig-Holstein. For all of the genera and all but six of the species (Hieracium fuscocinereum, Lactuca macrophylla, Sonchus palustris, and Taraxacum sections Celtica, Hamata, and Obliqua), the array of plant natural products has already been investigated to some degree. However, for only two taxa (Pilosella officinarum and Tragopogon pratensis subsp. minor) also plants from the region of Schleswig-Holstein have been studied and for only very few taxa, such as Cichorium intybus and Taraxacum officinale, all major classes of natural products have been investigated in detail so far.
... Atendiendo a tales criterios y a los aportados por Gallo (2017), la sistemática y nomenclatura de las plantas del grupo que crecen en el Principado de Asturias es la siguiente: En lo que se refiere a los otros géneros propuestos por Grulich (1984), los resultados del trabajo de Nikulina et al. (2016) (2017) proponen discriminar Thrincia de Leontodon. Tal postura sistemática la apoyan en criterios morfológicos, además de en los resultados de análisis de secuencias del ADN nuclear y cloroplástico (Enke et al., 2012;Moura et al., 2015). ...
... Atendiendo a tales criterios y a los aportados por Gallo (2017), la sistemática y nomenclatura de las plantas del grupo que crecen en el Principado de Asturias es la siguiente: En lo que se refiere a los otros géneros propuestos por Grulich (1984), los resultados del trabajo de Nikulina et al. (2016) (2017) proponen discriminar Thrincia de Leontodon. Tal postura sistemática la apoyan en criterios morfológicos, además de en los resultados de análisis de secuencias del ADN nuclear y cloroplástico (Enke et al., 2012;Moura et al., 2015). ...
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... Atendiendo a tales criterios y a los aportados por Gallo (2017), la sistemática y nomenclatura de las plantas del grupo que crecen en el Principado de Asturias es la siguiente: En lo que se refiere a los otros géneros propuestos por Grulich (1984), los resultados del trabajo de Nikulina et al. (2016) (2017) proponen discriminar Thrincia de Leontodon. Tal postura sistemática la apoyan en criterios morfológicos, además de en los resultados de análisis de secuencias del ADN nuclear y cloroplástico (Enke et al., 2012;Moura et al., 2015). ...
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... Atendiendo a tales criterios y a los aportados por Gallo (2017), la sistemática y nomenclatura de las plantas del grupo que crecen en el Principado de Asturias es la siguiente: En lo que se refiere a los otros géneros propuestos por Grulich (1984), los resultados del trabajo de Nikulina et al. (2016) (2017) proponen discriminar Thrincia de Leontodon. Tal postura sistemática la apoyan en criterios morfológicos, además de en los resultados de análisis de secuencias del ADN nuclear y cloroplástico (Enke et al., 2012;Moura et al., 2015). ...
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... Atendiendo a tales criterios y a los aportados por Gallo (2017), la sistemática y nomenclatura de las plantas del grupo que crecen en el Principado de Asturias es la siguiente: En lo que se refiere a los otros géneros propuestos por Grulich (1984), los resultados del trabajo de Nikulina et al. (2016) (2017) proponen discriminar Thrincia de Leontodon. Tal postura sistemática la apoyan en criterios morfológicos, además de en los resultados de análisis de secuencias del ADN nuclear y cloroplástico (Enke et al., 2012;Moura et al., 2015). ...
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