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Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides
Abstract
Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P. subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera.
... There have been a number of scientific efforts to evaluate the antioxidant, anti-inflammatory, and wound-healing activities of Plantago extracts and isolated compounds. Previous studies have confirmed that Plantago species are rich in natural antioxidants, and their methanolic and ethanolic extracts exhibit reactive oxygen species (ROS) scavenging activity [20]. This property demonstrates their potential as agents against many chronic diseases, including age-related cardiovascular and neurological diseases as such illnesses are influenced or brought on by oxidative stress, or in other words, by the abundance of ROS and other free radicals in the body [21]. ...
... This property demonstrates their potential as agents against many chronic diseases, including age-related cardiovascular and neurological diseases as such illnesses are influenced or brought on by oxidative stress, or in other words, by the abundance of ROS and other free radicals in the body [21]. However, the results demonstrating the antioxidant potential of Plantago species are difficult to compare due to the different extraction protocols and analysis methods used [20]. Several studies have been conducted to confirm the anti-inflammatory properties of Plantago species, particularly P. lanceolata [20]. ...
... However, the results demonstrating the antioxidant potential of Plantago species are difficult to compare due to the different extraction protocols and analysis methods used [20]. Several studies have been conducted to confirm the anti-inflammatory properties of Plantago species, particularly P. lanceolata [20]. As inflammation is a pathological component of many autoimmune diseases, as well as cancer, and as it might play an important role in Lyme disease pathogenesis, research into effective anti-inflammatory drugs is an important field in drug discovery [22]. ...
Lyme disease, caused by Borrelia burgdorferi sensu lato infection, is the most widespread vector-borne illness in the Northern Hemisphere. Unfortunately, using targeted antibiotic therapy is often an ineffective cure. The antibiotic resistance and recurring symptoms of Lyme disease are associated with the formation of biofilm-like aggregates of B. burgdorferi. Plant extracts could provide an effective alternative solution as many of them exhibit antibacterial or biofilm inhibiting activities. This study demonstrates the therapeutic potential of Plantago major and Plantago lanceolata as B. burgdorferi inhibitors. Hydroalcoholic extracts from three different samples of each plant were first characterised based on their total concentrations of polyphenolics, flavonoids, iridoids, and antioxidant capacity. Both plants contained substantial amounts of named phytochemicals and showed considerable antioxidant properties. The major non-volatile constituents were then quantified using HPLC-DAD-MS analyses, and volatile constituents were quantified using HS-SPME-GC-MS. The most prevalent non-volatiles were found to be plantamajoside and acteoside, and the most prevalent volatiles were β-caryophyllene, D-limonene, and α-caryophyllene. The B. burgdorferi inhibiting activity of the extracts was tested on stationary-phase B. burgdorferi culture and its biofilm fraction. All extracts showed antibacterial activity, with the most effective lowering the residual bacterial viability down to 15%. Moreover, the extracts prepared from the leaves of each plant additionally demonstrated biofilm inhibiting properties, reducing its formation by 30%.
... Rønsted et al. identified the isolated compounds by nuclear magnetic resonance spectroscopy [15,22]. Their findings showed that the distribution pattern of the iridoids in 34 species of Plantago has a good correlation with the classification of Rahn [89]. ...
... Their findings showed that the distribution pattern of the iridoids in 34 species of Plantago has a good correlation with the classification of Rahn [89]. The qualitative studies of Plantago atrata, Plantago bellardii, Plantago coronopus, Plantago holosteum, and Plantago reniformis have been reported [15,87]. In some studies, aucubin and catalpol have been isolated from the genus Plantago (Table 4). ...
... Basic Iridoid biosynthesis from the pathway I and II, adapted from Jensen (1992)[14] Rønsted et al. have revealed the biosynthesis of aucubin and catalpol, mainly in Plantago major(Figure 4)[15]. ...
Background: Plantago species contain aucubin and catalpol iridoid glycosides used in traditional medicine for many purposes.
Objectives: To accelerate the utilization of aucubin and catalpol in Plantago species, research should be focused on introducing advanced purification and detection methods. In this regard, the therapeutic activities of aucubin and catalpol compounds are mentioned to confirm their effectiveness in medicinal uses.
Methods: An extensive literature search was conducted using the keywords “Aucubin and Catalpol + Plantago” in the public domains of Google scholar.
Results: The iridoid patterns exhibited a significant correlation with morphological and other chemical specifications of the representatives of the genus Plantago. Commonly, iridoid glycosides are detected with gas chromatography, liquid chromatography, thin-layer chromatography, high-performance liquid chromatography (HPLC), high-performance thin-layer chromatography (HPTLC), and capillary electrophoresis techniques. The most common methods are HPLC and HPTLC. Aucubin and catalpol are active compounds possessing biological activities, including anti-cancer, anti-aging, anti-inflammatory, anti-oxidant, hepatoprotective, osteoprotective, and neuroprotective properties.
Conclusion: This review article comprehensively summarizes cytotoxic activities and detection methods of aucubin and catalpol in Plantago species. The results suggest that Plantago species and their metabolites may benefit human health beyond their traditional uses.
... The major phenolics in the genus Plantago are phenylethanoid glycosides represented mainly by acteoside and plantamajoside (Rønsted et al., 2000;Rønsted et al., 2003). Acteoside (verbascoside), which occurs in over 20 plant families of Asteridae (Schlauer et al., 2004;Alipieva et al., 2014), exhibits a wide range of activities: antioxidant, antiproliferative, cytotoxic, anticancer, antimetastatic, anti-inflammatory, and immunomodulatory (Alipieva et al., 2014). ...
... Micropropagated Plantago media has never been investigated for the presence of secondary metabolites. The methanol extracts prepared from the shoots and roots were analyzed for the phenolic compounds and were found to contain phenylethanoids acteoside and plantamajoside previously reported for P. media plants from the natural sites (Rønsted et al., 2000;Rønsted et al., 2003;Olennikov et al., 2011). The studied extracts showed absence of flavonoids, as it was previously observed in the case of in vitro cultures of P. lanceolata (Budzianowska et al., 2004). ...
... Plants of the genus Plantago can be used in medicine due to their anti-inflammatory, analgesic, anti-cancer, antiviral, and anti-ulcer effects; they also have expectorant and diuretic properties [4,6-9]. The main groups of compounds with a wide spectrum of biological activity that can be found in P. media are phenylethanoid glycosides [10][11][12], iridoid glucosides [13,14], phenolic acids [15,16], flavonoids [15,17], and polysaccharides [12,18]. In the micropropagated plants of P. media, there were mainly phenylethanoid glycosides present, and no flavonoids were detected [19]. ...
... The phenylethanoid glycosides occurring in Plantago are represented mainly by acteoside (verbascoside) and also its positional isomer-isoacteoside, which is a water-soluble, low-molecular secondary metabolite [10,11,20]. The phenylethanoid glycosides are associated with a wide range of biological and pharmacological activities [21][22][23]. ...
Abstract: (1) Background: The aim of the study was to compare the potency of Plantago media L. (Plan-taginaceae) extracts on Acanthamoeba sp. trophozoites, which are opportunistic protozoan parasites leading to several dangerous diseases; (2) Methods: The chromatographically (TLC, HPLC-DAD) characterized water fractions of the extracts from biomass from in vitro cultures (shoots and roots), leaves, and inflorescences from field cultivation were used for the study of the acanthamoebic activity in a Thoma haemocytometer chamber; (3) Results: The anti-amoebic effect at the lowest concentration (1.0 mg/mL) was demonstrated only by the extract of the leaves from the cultivation (50.50% inhibition). The remaining samples inhibited the growth of parasites from a concentration of 5.0 mg/mL in the range of 41.36% inflorescences to 63.89% shoots in vitro. Quantitative determinations of phenolic compounds in the tested extracts indicate a tendency to increase the potency of the anti-amoebic effect with the content of a phenylethanoid glycoside-acteoside. The maximum content of this compound was determined in leaves from field cultivation (6.64%) and the minimum in inflorescences (0.65%). This is confirmed by the range of the lowest IC 50 values (the strongest biological activity) for the tested samples, 0.95-1.80 mg/mL for leaves from cultivation, and the high values, 9.70-5.30 mg/mL for inflorescences and in-vitro-derived roots. The strength of the biological activity of the extracts correlated with the content of acteoside, which constituted 84-93% of the sum of phenolic compounds determined; (4) Conclusions: The performed investigations proved the anti-acanthamoebic efficacy of Plantago media organs, including those obtainable by biotechnological methods, and indicated phenylethanoid glycosides, their main phenolic constituents, to be responsible for the activity. To our knowledge, this is the first report on the amoebicidal activity of Plantago media extracts from biomass produced by biotechnological methods and organs of an intact plant.
... Due to a dearth of valid taxonomic characters, the intrageneric classification of the genus Plantago is controversial and inadequate. Several morphological features, including trichomes and seeds, as well as chemotaxonomic analyses [63][64][65] , have been employed in attempts to identify and classify the species. ...
... Plantago species synthesize multiple polyphenols, e.g., lignin, iridoid, and caffeoyl phenylethanoid glucosides 11,63,79 . Polyphenols confer plant tolerance to biotic and abiotic stresses such as pathogen attacks, oxidants, and ultraviolet radiation 61,80 . ...
Plantago is a major genus belonging to the Plantaginaceae family and used in herbal medicine, functional food, and pastures. Several Plantago species are also characterized by their global distribution, but the mechanism underpinning this is not known. Here, we present a high-quality, chromosome-level genome assembly of Plantago major L., a species of Plantago, by incorporating Oxford Nanopore sequencing and Hi-C technologies. The genome assembly size was approximately 671.27 Mb with a contig N50 length of 31.30 Mb. 31,654 protein-coding genes were identified from the genome. Evolutionary analysis showed that P. major diverged from other Lamiales species at ~62.18 Mya and experienced two rounds of WGD events. Notably, many gene families related to plant acclimation and adaptation expanded. We also found that many polyphenol biosynthesis genes showed high expression patterns in roots. Some amino acid biosynthesis genes, such as those involved in histidine synthesis, were highly induced under metal (Ni) stress which led to the accumulation of corresponding metabolites. These results suggest persuasive arguments for the global distribution of P. major through multiscale analysis. Decoding the P. major genome provides a valuable genomic resource for research on dissecting biological function, molecular evolution, taxonomy, and breeding.
... While most research on Plantago secondary chemistry has focused on aucubin, catalpol, and verbascoside, the genus produces a range of other secondary metabolites including other IGs, as well as coumarins, flavonoids, and alkaloids (Rønsted et al. 2000(Rønsted et al. , 2003Willinger and Dobler 2001;Fons et al. 2008;Janković et al. 2012). Many of these compounds likely play defensive roles based on their function in other systems but are understudied in the Plantago ecological literature. ...
... Another question is how herbivory-chemistry relationships across a given environmental gradient compare between co-occurring Plantago species that differ in secondary chemistry and palatability with herbivores (Kuiper and Bos 1992;Rønsted et al. 2000;Barton and Bowers 2006;Pankoke et al. 2013). Such questions could be asked for Plantago congeners with contrasting range sizes, native/introduced status in a given region, and distance from the center of their environmental niche space to provide insight into the effects of biogeography and niche on biotic interactions, as well as on the relative importance of abiotic and biotic determinants of range size and structure. ...
AbstractA central challenge in ecology and evolutionary biology is to understand how variation in abiotic and biotic factors combine to shape the distribution, abundance, and diversity of focal species. Environmental gradients, whether natural (e.g., latitude, elevation, ocean proximity) or anthropogenic (e.g., land-use intensity, urbanization), provide compelling settings for addressing this challenge. However, not all organisms are amenable to the observational and experimental approaches required for untangling the factors that structure species along gradients. Here we highlight herbaceous plants in the genus Plantago as models for studying the ecology and evolution of species interactions along abiotic gradients. Plantago lanceolata and P. major are native to Europe and Asia but distributed globally, and they are established models for studying population ecology and interactions with herbivores, pathogens, and soil microbes. Studying restricted range congeners in comparison with those cosmopolitan species can provide insight into abiotic and biotic determinants of range size and population structure. We highlight one such species, P. rugelii, which is endemic to eastern North America. We give an overview of the literature on these focal Plantago species and explain why they are logical candidates for studies of species interactions across environmental gradients. Finally, we emphasize collaborative and community science approaches that can facilitate such research and note the amenability of Plantago for authentic research projects in science education.
... The taxonomy of Plantago is notoriously difficult, owing to the relatively few morphological characters available and its evolutionary trend toward morphological reduction and simplification [4,5]. Traditionally, several morphological features, including trichomes and seeds, as well as chemotaxonomic analyses [6][7][8], have been employed in attempts to identify and classify the species. However, none of these methods have yielded a conclusive result that is considered satisfactory, not even with 91 mainly morphological and embryological characters [2]. ...
Plantago (plantains, Plantaginaceae) is a cosmopolitan genus including over 250 species used as functional foods, forage, and traditional medicine. Among them, Plantago lanceolata is commonly used as an ingredient of herbal products, but the close similarity to other Plantago species can cause misidentifications with potentially serious consequences for product safety/quality. To test the possibility of developing species-specific barcoding markers, we de novo assembled plastome sequences of individuals of Plantago argentea, Plantago atrata, P. lanceolata, and Plantago maritima. These genomes were characterized in comparison with both previously sequenced conspecific accessions and other publicly available plastomes, thus providing an assessment of both intraspecific and interspecific genetic variation in Plantago plastomes. Additionally, molecular evolutionary analyses indicated that eleven protein-coding genes involved in different plastid functions in Plantago plastomes underwent positive selection, suggesting they might have contributed to enhancing species’ adaptation during the evolutionary history of Plantago. While the most variable mutational hotspots in Plantago plastomes were not suitable for the development of species-specific molecular markers, species-specific polymorphisms could discriminate P. lanceolata from its closest relatives. Taken together, these results highlight the potential of plastome sequencing for the development of molecular markers to improve the identification of species with relevance in herbal products.
... For Plantago spp., we analysed two iridoid glycosides (IGs), catapol and aucubin (Rønsted et al., 2000), while two cyanogenic glycosides (CNGs), linamarin and lotaustralin (Sun et al., 2018), were analysed for Lotus spp. For the detailed explanation of the chemical analytical procedures employed, see Methods S1. ...
Asynchronous migration of insect herbivores and their host plants towards higher elevations following climate warming is expected to generate novel plant–insect interactions. While the disassociation of specialised interactions can challenge species' persistence, consequences for specialised low‐elevation insect herbivores encountering novel high‐elevation plants under climate change remain largely unknown. To explore the ability of two low‐elevation Lepidoptera species, Melitaea celadussa and Zygaena filipendulae, to undergo shifts from low‐ to high‐elevation host plants, we combined a translocation experiment performed at two elevations in the Swiss Alps with experiments conducted under controlled conditions. Specifically, we exposed M. celadussa and Z. filipendulae to current low‐ and congeneric high‐elevation host plants, to test how shifts in host plant use impact oviposition probability, number of eggs clutches laid, caterpillar feeding preference and growth, pupation rate and wing size. While our study shows that both M. celadussa and Z. filipendulae can oviposit and feed on novel high‐elevation host plants, we reveal strong preferences towards ovipositing and feeding on current low‐elevation host plants. In addition, shifts from current low‐ to novel high‐elevation host plants reduced pupation rates as well as wing size for M. celadussa, while caterpillar growth was unaffected by host plant identity for both species. Our study suggests that populations of M. celadussa and Z. filipendulae have the ability to undergo host plant shifts under climate change. However, these shifts may impact the ability of populations to respond to rapid climate change by altering developmental processes and morphology. Our study highlights the importance of considering altered biotic interactions when predicting consequences for natural populations facing novel abiotic and biotic environments.
... Chromatographic separation of methanolic extract of V. leiocarpum led to isolation of catalpol (1), [19] ajugol (2), [20] eriodictyol (3), [21] luteolin (4), [22] and 10-O-cinnamoyl catalpol (5), [23] and apigenin (6), [24] 6-deoxy melittoside (7), [25] poliumoside (8), [26] verbascoside (9), [27] isoverbascoside (10), [28] ferruginoside C (11), [29] ferruginoside D (12), harpagoside (13), [30] trans-cinnamic acid, (14) [31] and ursolic acid (15). [32] The structures of the isolated molecules ( Figure 1) were identified by comparing NMR data with those previous reports. ...
A novel phenylethanoid, ferruginoside D, together with fourteen known compounds were isolated from the Verbascum leiocarpum for the first time. Chemical structures of isolated compounds were determined by spectroscopic analysis including HR‐ESI‐MS and NMR spectra. The antioxidant, α‐glucosidase inhibitory properties, and antiproliferative activities against multiple cell lines (A172, C6, HeLa, A2780, SW620, HT29, Beas2B, RPE, and HSF) of the isolated compounds were evaluated in vitro. According to the results, iridoids, flavonoids (luteolin and apigenin), and phenylethanoids (poliumoside and isoverbascoside) with strong antiproliferative potential were also found to have cytostatic effects. Furthermore, the investigation revealed that compounds luteolin, poliumoside, verbascoside, isoverbascoside, ferruginoside C, ferruginoside D, and ursolic acid show potent alpha‐glucosidase inhibitory activity, while compounds luteolin, verbascoside, and isoverbascoside exhibit substantial antioxidant activity. The new compound (ferruginoside D) was found moderately active against cancer cell lines, with strong alpha‐glucosidase inhibitory activity, and moderate antioxidant properties.
... P. lanceolata, a well-known medicinal plant, has antispasmodic, anti-inflammatory, antioxidant, antibacterial, antiasthmatic, and cytotoxic activities [3][4][5][6][7][8]. It contains mainly iridoids and phenylethanoid glycosides [9][10][11] with biologically active compounds, especially aucubin [12], acteoside [13] and plantamajoside [14]. Flavonoids were also identified, mainly apigenin and luteolin glucuronides [15,16], and a few flavonol, 3-O-glycoside, at a much lower content than that of flavones [17,18]. ...
The aim of the study is to investigate whether the bioactive compounds isolated from P. lanceolata inflorescences, namely, phenylethanoid glucosides, acteoside, plantamajoside, and a flavonoid, isorhamnetin-3-O-rutinoside-4′-O-glucoside, possessed cytotoxic activity against the selected cancer cell lines. The potential antitumor effects of two phenylethanoid glycosides and one flavonoid were evaluated via MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay on seven human carcinoma cell lines (MCF-7, MDA-MB-231, Caco-2, HepG2, OVCAR-3, U138-MG, U251-MG) and one nontumorigenic mammary epithelial cell line (MCF-12A). For the first time, acteoside was studied in ovarian cancer cell line OVCAR-3, and plantamajoside in all cell lines except breast adenocarcinoma MDA-MB-281 and hepatocarcinoma HepG2. The phenylethanoid glycosides showed stronger cytotoxic activity than that of the glycoside flavonoid. Acteoside and plantamajoside, at concentrations of 200 and 300 μM, respectively, had a highly toxic effect on the selected two cancer cell lines of breast adenocarcinoma MDA-MB-231 and MCF-7, ovarian cancer cell line OVCAR-3, glioblastoma cell line U138-MG, and hepatocarcinoma cell line HepG2. Both glycosides were significantly less cytotoxic towards nontumorigenic cell line MCF-12A; the effect appeared at a concentration of 400 μM. For the first time, the activity of acteoside and plantamajoside was compared in one parallel investigation. The results are discussed against a broad background of existing knowledge on biological effects, their mechanisms, and structure–activity relationships. Phenylethanoids may be potential compounds with cytotoxic activity against the selected cancer types.
... Mussaenosidic acid is widely represented in representatives of Plantaginaceae family, including Plantago alpina L., P. arborescens Poir., P. nivalis Boiss., P. sempervirens Crantz, P. webbii Barneoud, Globularia vulgaris L., Wulfenia orientalis Boiss. (Rønsted et al. 2000;Kuruüzüm-Uz et al. 2003;Taskova et al. 2006), Linaria aegyptiaca (Ferhat et al. 2010), L. macroura (Degot et al. 1983). It was also found in Scrophulariaceae (Sun et al. 2017;Zhang et al. 2000), Orobanceae (Taskova et al. 2006) and Rubiaceae (Zhang et al. 2008a). ...
The tribe Antirrhineae of Plantaginaceae family is well known for various garden ornamentals (Antirrhinum L., Linaria Mill., Cymbalaria Hill.), numerous medicinal plants (Anarrhinum orientale Benth., Nanorrhinum ramosissimum (Wall.) Betsche, Linaria japonica Miq. etc.), besides, the Linaria genus is famous for the fact that it contains naturally-transgenic plants. Medicinal properties are caused by the presence of a certain spectrum of specialized metabolites. A major role among them in tribe Antirrhineae is played by iridoid glycosides, in particular antirrhinoside, antirrhide, linarioside and 6-O-acetylantirrinoside. This review summarizes the literature data on biosynthesis, methods of analysis, the diversity and distribution of these compounds in the representatives of the tribe, that makes it possible to use the obtained data for chemotaxonomy and pharmacology, and also indicates gaps in our knowledge regarding the biochemistry of such taxonomic groups as Anarrhinum, Maurandya, Gambelia, Chaenorhinum, Antirrhinum and Linaria. The general picture of the state of research indicates directions for future work. Despite the different degrees of study of the tribe representatives, we can conclude the presence of antirrhinoside as a marker of this group of plants.
... This species is also used as animal feed, and its importance in improving their physiological conditions has been evaluated (Deaker et al., 1994;Rumball et al., 1997;Stewart, 1996). P. lanceolata contains iridoid glycosides (aucubin and catalpol), phenylpropanoid glycosides (acteoside), flavonoids (luteolin and luteolin-7-O-glucoside), and phenylcarboxylic acids (Rønsted et al., 2000). Quantitative ...
This study was designed in order to determine optimal parameters for ultrasound‐assisted extraction (UAE) of polyphenols from plantain herb using response surface methodology (RSM) as well as UV‐ visible spectrophotometric and reverse‐phase high‐performance liquid chromatographic (RP‐HPLC) method. Solvent extraction was performed based on four factors‐five levels central composite design (CCD). The influence of extraction time (X1: 5–65 min), ethanol concentration (X2: 10–90 %), solid to solvent ratio (X3: 1:10–1:50) and extraction temperature (X4: 20–80 ºC) on total polyphenols content (TPC) as well on content of dominant individual polyphenolic compounds (acteoside and luteolin‐7‐O‐glucoside) was analysed. The optimal extraction parameters were as follows: extraction time of 64 min, ethanol concentration of 45%, solid to solvent ratio of 1:49, and extraction temperature of 40 °C. Under these optimal conditions, the experimental values for total phenolics and acteoside and luteolin‐7‐O‐glucoside content in plantain herb extract were 42.15, 24.15 and 0.87 mg/g DW, respectively. Experimental validation of optimized parameters was performed and close agreement with predicted values suggested effectiveness of the applied model and the achievement of RSM in optimizing the extraction parameters.
... P. major contains important compounds, such as polysaccharides, flavonoids [6,7] , phenolic compounds [8] , monoterpenoids, and triterpenoids [9] , lipids, and caffeic acid derivatives [10] . Moreover, caffeoyl phenylethanoid glycosides and iridoids glycosides are the most distinctive category of compounds that show important correspondence in their chemotaxonomy significance [11][12][13] . ...
Background:
To study the anticancer activity of Plantago major, we assessed the effect of ethanolic, methanolic and acetonic extracts of this plant on HCT-116, SW-480, and HEK-293 cell lines as control.
Methods:
The cytotoxic activity, biocompatibility, and toxicity were evaluated by MTT assay, hemolysis, and Artemia salina-LD50 (on mice) tests, respectively. The analysis of the extracts was performed by GC-MS analysis.
Results:
The results showed that all the extracts had the most antiproliferative properties on the HCT-116 cell line. The P. major root extract was more effective than the aerial parts, and IC50 values for ethanolic, methanolic and acetonic root extracts were 405.59, 470.16, and 82.26 µg/mL, respectively on HCT-116 cell line at 72 h. Hemolysis degree of the ethanolic extract of aerial and root parts were approximately 1% at 400 μg/mL.. Using the ethanolic extracts, the Artemia survived every concentration, and no toxicity was observed. One week after the oral administration of different parts of P. major extracts, none of the mice died, even those were administered 2000 mg/kg. The results of GC/MS analysis showed that P. major extracts contain potential anticancer compounds, such as stearic acid (8.61%) in aerial parts of methanolic extract and 1,2- Benzenedicarboxylic acid, mono(2-ethylhexyl)ester (88.07% and 40.63%) in aerial and root parts of acetonic extract of P. major.
Conclusion:
Our findings suggest that the P. major is a source of potential compounds with antiproliferative properties.
... In contrast, for the plants species that showed lower phenolic contents (<20 GAE mg/g dry weigh) other compounds have been reported: Glycosides such as the caffeoyl phenylethanoid glycosides in some Plantago species [34,35]; verbascoside, calceolariosides A-E, forsythoside A and isoarenarioside in Chilean species of Calceolaria [36]; and kaempferol and quercetin glycosides in some Adiantum species [37]. ...
The antioxidant activities of the aqueous extracts of seven wild plants were investigated, using both in vitro and in vivo assays. The former relied on the use of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the latter, on the sensibility towards hydrogen peroxide of the yeast sod1 mutant. The studied plants were all wild, collected at the Ccamarrara hill (4000 m.a.s.l. Cusco, Peru), and of the following species: Plantago australis, Baccharis latifolia, Ageratina sternbergiana, Stevia macbridei, Ageratina cuzcoensis, Calceolaria myriophylla, and Adiantum orbignyanum. The DPPH assay demonstrated high antioxidant contents in the dry leaves of all tested plants, with AAEAC values (ascorbic acid equivalent antioxidant capacity) ranging from 20.6 to 72.7 mg/g dry leaves. The antioxidant activities were also evident in the yeast assay, which also allowed distinction between the intracellular and extracellular effects. These in vitro and in vivo studies demonstrate the need to further investigate native wild plants from the Andes as important sources for water-soluble antioxidant compounds.
... On the contrary, we found that the diversity of GSLs was not explained by phylogeny. This is in contrast to the phylogenetic conservatism reported across different families of plants (Wink, 2003;Wink & Mohamed, 2003;Winkler & Mitter, 2008), or within genera, such as the production of aliphatic and branched-chain GSLs in the genus Streptanthus (Cacho et al., 2015), the production of cardenolides in the genus Asclepias Rasmann & Agrawal, 2011), or the production of iridoid glycosides in the genus Plantago (Rønsted et al., 2000). However, we interpret the lack of phylogenetic signal in GSL production in our system with The effects were tested using MCMCGLMM analyses by including phylogenetic relatedness among the 14 Cardamine species as a random factor. ...
Biologists still strive to identify the ecological and evolutionary drivers of phytochemical variation that mediate biotic interactions. We hypothesized that plant species growing at sites characterized by high herbivore pressure would converge to produce highly toxic blends of secondary metabolites, independent of phylogenetic constraints.
To address the role of shared evolutionary history and ecological niches in driving variation in plant phytochemistry, we combined targeted metabolomics with insect herbivore bioassays and with a set of growth‐related traits of several Cardamine species growing along the entire elevational gradient of the Alps.
We observed that Cardamine phytochemical profiles grouped according to previously established growth form categorizations within specific abiotic conditions, independently of phylogenetic relationship. We also showed that novel indices summarizing functional phytochemical diversity better explain plant resistance against chewing and sap‐feeding herbivores than classic diversity indices.
We conclude that multiple functional axes of phytochemical diversity should be integrated with the functional axis of plant growth forms to study phenotypic convergence along large‐scale ecological gradients.
... Compound 12 showed deprotonated ion in the mass spectrum at m/z = 359. The fragmentation pattern was like compounds 3 and 4. Based on literature review, compound 12 was tentatively identified as deoxyloganic acid [47]. Compound 15 had major ion in the mass spectrum at m/z = 435 corresponding to M+HCOO •− adduct (Table 1). ...
The aim of this study was to compare the chemical composition, as well as antioxidant, anti-inflammatory, antiacne, and cytotoxic activites of various extracts of Cephalaria gigantea and C. uralensis. It is worth underlining that we are the first to characterize the composition and evaluate the biological properties of extracts from Cephalaria gigantea and C. uralensis. Thus, the LC-DAD-MS 3 analysis revealed the presence of 41 natural products in studied extracts. The 5-O-caffeoylquinic acid, isoorinetin, and swertiajaponin were the main detected compounds. Among the tested samples, ethanol extract of the aerial parts of C. uralensis (CUE) possessed the most suitable biological properties. It exhibited moderate ability to scavenge free radicals and good capacity to inhibit cyclooxygenase-1, as well as cyclooxygenase-2. Moreover, CUE possessed moderate antibacterial activity against all tested bacterial strains (S. aureus, S. epidermidis, and P. acnes), and importantly, it was non-toxic towards normal skin fibroblasts. Taking into account the value of calculated therapeutic index (>10), it is worth noting that CUE can be subjected to in vivo study. Thus, CUE constitutes a very promising antiacne agent.
... Plantain is reported to have a beneficial effect on wound healing, digestive and circulatory system organs and skin conditions alongside its various other anti-inflammatory, antibacterial, anti-cancer and immunomodulator effects. The plant contains several active ingredients, primarily iridoid glycosides (aucubin, aucubigenin, catalpol, melittoside) as well as caffeic acid derivatives (plantamajoside and acteoside), alkaloids and flavonoids (Rønsted et al., 2000;Samuelsen, 2000). An important iridoid glycoside, aucubin is noted for its antimicrobial, hepatoprotective, neuroprotective, anti-inflammatory and antitumoral effects (Rakotondramasy et al., 2010;Xue et al., 2012;Kim et al., 2014). ...
This study aims to assess the pharmacodynamics of aucubin, the active ingredient in plantain (Plantago), in vitro
rat bladder, and trachea tissues, and explore its cell-protective effects on primary lung and kidney cell lines. The study was
carried out by repeated applications of acetylcholine, atropine, verapamil, and oxybutynin, alongside Ca++ in a calcium-free
environment, on urinary bladder tissue, and repeated applications of acetylcholine, atropine, carbachol, and mecamylamine
on trachea tissue. At the same time, cell viability and catalase and superoxide dismutase activities were measured in primary
cell lines. The results indicated that aucubin had a relaxant effect on the urinary bladder and trachea tissues. It was conceived
that aucubin acted as a cholinergic antagonist through different sub receptors (muscarinic-3 receptors). The results also
indicated that aucubin caused a statistically insignificant increase in remaining at the level of the control group in cell
viability in the primary lung and kidney cell lines at increasing concentrations (1-10 µM), while causing a significant reduction
in cell viability at 20 and 50 µM concentrations in the same cell lines. In conclusion, it is suggested that plantain, which is
used in folk medicine, and its active ingredient aucubin might have beneficial effects on bronchoconstriction and other
respiratory conditions, as well as on pulmonary and renal diseases, urinary incontinence, etc
... see Figure S1). Plantago major, like most of the species in the Plantaginaceae, produce methylcyclopentanoid monoterpenes or iridoids, with several in the form of glycosides and caffeoyl phenylethanoid glycosides (hereafter referred to as IGs and CPGs, respectively; Boros & Stermitz, 1990;Rønsted, Göbel, Franzyk, Jensen, & Olsen, 2000), that serve as resistance compounds against herbivores (Bowers, 1988;). ...
Ecotypic differences in plant growth and anti‐herbivore defence phenotypes are determined by the complex interactions between the abiotic and the biotic environment.
Root‐associated microbes (RAMs) are pervasive in nature, vary over climatic gradients and have been shown to influence the expression of multiple plant functional traits related to biomass accumulation and biotic interactions. We addressed how variation in climatic conditions between lowland and subalpine habitats in the Alps and RAMs can independently or interactively affect plant growth and anti‐herbivore defence trait expression.
To address the contribution of climate and RAMs on growth and chemical defences of high‐ and low‐elevation Plantago major ecotypes, we performed a full‐factorial reciprocal transplant field experiment at two elevations. We coupled it with plant functional trait measurements and metabolomics analyses.
We found that local growing climatic conditions mostly influenced how the ecotypes grew, but we also found that the high‐ and low‐elevation ecotypes improved biomass accumulation if in the presence of their own‐elevation RAMs. We also found that while chemical defence expression was affected by climate, they were also more highly expressed when plants were inoculated with low‐elevation RAMs.
Synthesis. Our research demonstrated that root‐associated microbes (RAMs) from contrasted elevations impact how plants grow or synthesize toxic secondary metabolites. At low elevation, where biotic interactions are stronger, RAMs enhance plant biomass accumulation and the production of toxic secondary metabolites.
... Plantago species are rich in iridoids, iridoid glycosides, polyphenols, flavonoids, polysaccharides, and triterpene acids (Rønsted, Göbel, Franzyk, Jensen, & Olsen, 2000;Samuelsen et al., 1999;Tarvainen, Suomela, Kallio, & Yang, 2010;Velázquez-Fiz, Díaz-Lanza, & Fernández-Matellano, 2000;Zubair, Nybom, Lindholm, & Rumpunen, 2011). ...
Plantain (Plantago) species are traditionally used as food products and folkloric medicines in many countries. This study evaluated the antioxidant effects, phytochemical content, and phenolics profile of Plantago lanceolata (ribwort plantain) as an important herb in Turkey. Five different methods were used to measure the antioxidant activity including β-carotene bleaching, DPPH radical scavenging, reducing power, metal chelating, and phosphomolybdenum total antioxidant assays. Total content of phenolics and flavonoids were also determined. Profiling of phenolic compounds was done using liquid chromatography–electrospray tandem mass spectrometry. Methanolic extracts showed the highest antiradical and reducing activities. Water extracts had strong β-carotene bleaching (71% at 0.4 mg/mL) and ferrous ion chelating (95% at 0.25 mg/mL) abilities. Methanol extracts had high antioxidant capacity in the phosphomolybdenum assay (145 mg AAE/g extract). Phenolics profiling showed 28 phenolic acids, flavonoid, and phenylethanoid glycoside compounds. A high amount of verbascoside (94.8 mg/g dry aerial parts of plant) was obtained followed by chlorogenic acid, rosmarinic acid, hesperidin, and hyperoside. Plantago lanceolata has considerable potential for use in new food and pharmaceutical products. Also, it could be regarded as a rich source of verbascoside.
... Phytochemical investigation of the genus revealed the presence of polysaccharides, phenylpropanoid glycosides, alkaloids, triterpenes, flavonoids, and phenolic acids as the main bioactive compounds present in the aerial parts [17][18][19][20]. The aim of the present study was to evaluate the allelopathic potential of Plantago major extracts on the germination and early seedling growth of purslane. ...
... Catalpol is an iridoid glucoside widely found in plants belonging to several families of the order Lamiales, such as Plantaginaceae [1], Lamiaceae, and Bignoniaceae [2]. It was named after plants of genus Catalpa, in which it was first discovered in 1962 [3]. ...
This review aimed to provide a general view of catalpol in protection against diabetes and diabetic complications, as well as its pharmacokinetics and safety concerns. The following databases were consulted with the retrieval of more than 100 publications through June 2019: PubMed, Chinese National Knowledge Infrastructure, WanFang Data, and web of science. Catalpol exerts an anti-diabetic effect in different animal models with an oral dosage ranging from 2.5 to 200 mg/kg in rats and 10 to 200 mg/kg in mice. Besides, catalpol may prevent the development of diabetic complications in kidney, heart, central nervous system, and bone. The underlying mechanism may be associated with an inhibition of inflammation, oxidative stress, and apoptosis through modulation of various cellular signaling, such as AMPK/PI3K/Akt, PPAR/ACC, JNK/NF-κB, and AGE/RAGE/NOX4 signaling pathways, as well as PKCγ and Cav-1 expression. The pharmacokinetic profile reveals that catalpol could pass the blood-brain barrier and has a potential to be orally administrated. Taken together, catalpol is a well-tolerated natural compound with promising pharmacological actions in protection against diabetes and diabetic complications via multi-targets, offering a novel scaffold for the development of anti-diabetic drug candidate. Further prospective and well-designed clinical trials will shed light on the potential of clinical usage of catalpol.
... The AChE inhibition properties of some Plantaginaceae species have been previously reported [14][15][16], supporting the possible contribution of further family species as natural therapeutics for AD treatment. Plantaginaceae plants are known for their iridoid constituents [17,18]. Taking into account the neuroprotective potential of such phytochemicals, resulting from the exhibited inhibitory impact on AChE, iridoids deemed to be promising compounds worth to explore by targeting the enzyme. ...
Plants are an important source of natural iridoids. This study demonstrates for the first time the acetylcholinesterase (AChE) inhibitory activity of iridoids belonging to the class of antirrhinosides. As iridoids distinguish the chemical composition of most species of the Plantaginaceae family, the active AChE inhibitors were investigated in the hydro-alcoholic extract of Anarrhinum pubescens Fresen. High-performance thin-layer chromatography (HPTLC) in combination with the AChE inhibition assay is a time and material saving methodology, and thus was employed to directly point to the individual enzyme inhibitors occurring in the plant. The effect-directed screening successfully discovered three active metabolites. These were characterized as antirrhinoside-derived iridoids. Two of these are here reported as newly isolated natural compounds. Identification of the two new metabolites was based on analysis of their collected spectroscopic data (HRMS, 1D and 2D NMR). Their structures were elucidated to be 6-O-, 6'-O-di-trans-cinnamoyl-antirrhinoside (1) and 5-O-, 6-O-difoliamenthoyl-antirrhinoside (3), while the previously known compound 6-O-foliamenthoyl-(6'-O-cinnamoyl)-antirrhinoside (2) was assigned by extensive analysis of its HRMS and HRMS/MS data. The activity of the isolated compounds was referred to the known AChE inhibitor rivastigmine, i.e. their activity were calculated and expressed as values equivalently to rivastigmine. This neuroprotective potential of iridoids mediated through AChE inhibition promote them to compete as natural curatives for neurodegenerative disorders like Alzheimer's disease.
... Within P. subg. Coronopus, our molecular phylogenetic results agree with other DNA-based phylogenetic analyses , chromosome base-number and morphology (Rahn, 1996), seed coat (Shehata & Loutfy, 2006), and phytochemistry (Rønsted & al., 2000), confirming a sister relationship of P. sect. Maritima and P. sect. ...
Plantago sect. Coronopus contains our two focal species (P. coronopus L., P. crassifolia Forssk.), both with an overall conspicuous bi‐hemispheric distribution range (Mediterranean and Middle Eastern regions in the Northern Hemisphere and South Africa in the Southern Hemisphere). We have evaluated up to 27 morphological characters from 96 herbarium specimens representing five out of seven species of that section that are currently recognised using principal coordinate analysis, linear discriminant analyses, agglomerative clustering, and classification tree analyses, in order to test the current taxonomic concepts of our two focal species. Furthermore, we used 54 individuals representing six out of those seven species of P. sect. Coronopus to construct molecular phylogenetic hypotheses by sequencing nuclear ribosomal DNA from the internal transcribed spacer region (ITS), the plastid trnL‐F region, the plastid intergenic spacer region trnH‐psbA and adopting maximum likelihood and Bayesian inference analyses. In the Northern Hemisphere, an Irano‐Arabian clade initially identified as P. coronopus and shown as distinct in both morphological and phylogenetical terms fits a wider circumscription of P. crypsoides Boiss. due to lack of the prominent short and thick inflorescence scape following Boissier's description. The morphological differences between P. crassifolia from the Mediterranean region and P. crassifolia from South Africa (often named P. carnosa Lam.) were marginal, yet the molecular phylogenetic analyses of both nuclear and plastid markers clearly separated these evolutionary entities. Therefore, we re‐instated the name P. carnosa as the correct name for South African P. crassifolia. Plantago carnosa differs from P. crassifolia by the combination of having stronger woody rootstocks, which are more often branched, by broader leaves (≥1.6 mm wide) and the fact that specimens more often turn brown when dried. Our dataset provides the best sampled phylogenetic hypothesis for P. sect. (and subg.) Coronopus to date, and reveals discordance between nuclear and plastid genealogies within P. sect. Maritima, which requires further investigation.
... A series of chemotaxonomic studies have also been conducted (e.g. Jensen et al., 1996;Rønsted et al., 2000Rønsted et al., , 2003Taskova et al., 2002). However, none of these characters have enabled a satisfying infrageneric classification of the genus. ...
Plantago is a cosmopolitan genus including over 250 species, concentrated in temperate and high-elevation tropical regions. The taxonomy of Plantago is very difficult, mainly because of its reduced morphology, which features relatively few characters for species classification. Consequently, the infrageneric classification of the genus remains controversial and inadequate. In this study we applied high-throughput plastid genome skimming to provide powerful phylogenetic resolution to clarify the relationships within subg. Plantago, which is the largest, most broadly distributed and poorest understood subgenus of Plantago. Ninety-four samples covering ~56% of all species and representing all sections of subg. Plantago as well as an outgroup were successfully sequenced. The resulting phylogenetic topology was used, complemented by field and herbarium studies, to revise the sectional classification of subg. Plantago and present a complete listing of the accepted species in the subgenus. Our phylogenetic results were also tested for their usefulness in clarifying the taxonomic placement of some taxonomically complicated species in the subgenus. We conclude that a combination of morphological studies and state-of-the art high-throughput DNA data provide a useful toolbox for resolving outstanding taxonomic puzzles exemplified by the genus Plantago.
... Concentrations were normalized to plant weight and expressed as μg/mg. Other Iridoid glycosides and caffeoyl phenylethanoid glycosides were putatively identified based on their retention time and chemical formula by comparing them to previous detection in P. major or in species of Plantago genus (Rønsted, Göbel, Franzyk, Jensen, & Olsen, 2000) and database (Dictionary of Natural ...
Along ecological gradients, phenotypic differentiation can arise through natural selection on trait diversity and magnitude, and environment‐driven plastic changes. The magnitude of ecotypic differentiation versus phenotypic plasticity can vary depending on the traits under study. Using reciprocal transplant‐common gardens along steep elevation gradients, we evaluated patterns of ecotypic differentiation and phenotypic plasticity of several growth and defense‐related traits for two coexisting but unrelated plant species, Cardamine pratensis and Plantago major. For both species, we observed ecotypic differentiation accompanied by plasticity in growth‐related traits. Plants grew faster and produced more biomass when placed at low elevation. In contrast, we observed fixed ecotypic differentiation for defense and resistance traits. Generally, low‐elevation ecotypes produced higher chemical defenses regardless of the growing elevation. Yet, some plasticity was observed for specific compounds, such as indole glucosinolates. The results of this study may suggest that ecotypic differentiation in defense traits is maintained by costs of chemical defense production, while plasticity in growth traits is regulated by temperature‐driven growth response maximization. Using reciprocal transplant‐common gardens along steep elevation gradients, we evaluated patterns of ecotypic differentiation and phenotypic plasticity of two coexisting but unrelated plant species, Cardamine pratensis, and Plantago major. For both species, we observed ecotypic differentiation accompanied by plasticity in growth related traits. In contrast, we observed fixed ecotypic differentiation for defence and resistance traits.
... Phytochemical studies revealed several compounds in P. australis, some of which present pharmacological activities that have been previously described. Among them are iridoid glucoside aucubine and phenolic compounds salidroside, isoverbascoside and verbascoside, which were described in hydroethanolic extracts (Andary et al., 1988;Rønsted et al., 2000). Verbascoside, also known as acteoside, is an ester structurally formed by phenylpropanoid caffeic acid, phenylethanoid hydroxytyrosol and sugar alpha-L-rhamnopyranosyl-(1-> 3)-β-D-glucopyranose. Belonging to caffeoyl phenylethanoid glycoside group, it is found in numerous plant families, including Plantaginaceae, and therefore is one of the most studied compounds in Plantago (Li et al., 2014;Zhang et al., 2015;Wen et al., 2016). ...
... This specie of plant is largely used in folk medicine for the treatment of various pathological conditions due to its actions as anti-inflammatory, healing agent and an analgesic (Kujawska and Pieroni, 2015;Trojan-Rodrigues et al., 2012). Studies on the phytochemical composition demonstrated that P. australis has secondary metabolites that exhibit biological activity, including phenolic compounds, such as verbascoside (Rønsted et al., 2000). ...
The large plantain has been widely used since ancient times to treat many diseases, including constipation, cough and ulcers. The purpose of this study is to review the traditional use, botanical characteristics, pharmacological activity, phytochemical effects and toxicity of Plantago major. Some o f its traditional properties, including wound healing, antipyretic, antitussive, anti-infective, anti-hemorrhagic, anti-inflammatory, diuretic, laxative, astringent and hemostatic, have been confirmed by recent studies. Phytochemical studies have shown that Plantago major contains volatile compounds, triterpenoids, phenolic acids and flavonoids. Current pharmacological studies have proven some of the traditional uses of Plantago major. However, additional studies of this plant are needed, since it can be used for the production of various natural preparations.The healing properties of the great plantain have been recognized all over the world for hundreds of years. This plant contains a number of effective chemical components, such as flavonoids, alkaloids, terpenoids, phenolic acid derivatives, iridoid glycosides, fatty acids, polysaccharides and vitamins, which contribute to its specific therapeutic effect. Accordingly, studies have shown that the large plantain is effective as a wound healing agent, as well as as an anti-cancer, antidiabetic, antidiarrheal, anti-inflammatory, antinociceptive, antibacterial and antiviral agent. It also fights fatigue and cancer, is an antioxidant and neutralizes free radicals.
A clear trend of replacing synthetic cosmetic ingredients with natural ones can be observed in modern cosmetology. This entails the need to search for bioactive ingredients in the natural environment, especially in plants. This paper presents a comprehensive overview of dermatological, cosmetic, and pharmacological properties of highly potent plants, namely Acmella oleracea (A. oleracea), Centella asiatica (C. asiatica), Psoralea corylifolia (P. corylifolia), Plantago lanceolata L. (P. lanceolata L.), and Solidago virgaurea L. (S. virgaurea L.). Biological activity and phytochemical constituents are presented for all plants, but special attention is paid to ingredients of particular value to the cosmetics industry. The advantages of spilanthol and bakuchiol as a replacement for the popular botulinum toxin and retinol are discussed. Natural habitats, ethnomedical importance, cultivation area, as well as extraction methods of active plant ingredients are presented in detail. A wide spectrum of biological activity indicates the enormous potential of the presented plants in formulating new cosmetic and dermatological preparations.
Plantago atrata Hoppe (dark plantain; Plantaginaceae) is a lesser-studied narrow-leaved Plantain species and in the present review, we summarize the knowledge about the plant. The distribution of this alpine species and reported subspecies is described. Emphasis is made on P. atrata taxonomic features including botanical characteristics and phylogenetic discrimination via DNA barcoding and metabolic composition. The ecological significance of this plant species is discussed from floristic and nutrient value points of view. The collected information would serve as a basis for further in-depth research on physiological and phytochemical aspects of P. atrata , which would enable the understanding of this plant’s high-altitude adaptation and its possible contribution to beneficial applications for other organisms.
The main phenylethanoid glycosides in the Plantago genus are acteoside (verbascoside) and plantamajoside, compounds with broad biological effects. This is a report on Plantago ovata callus induction, proliferation and establishment as well as the content of those phenylethanoids in that cell biomass. In the experimental studies, callus initiated from various seedling explants (roots, hypocotyls and leaves) was cultured on MS (Murashige-Skoog) media augmented with 2,4-D (2,4-dichloroacetic acid) and KIN (kinetin) or NAA (α-naphthaleneacetic acid) and BAP (6-benzylaminopurine). Callus proliferating on MS without NH4NO3 (ammonium nitrate) supplemented with 2,4-D (1.0 mg/l) and KIN (0.5 mg/l or 1.0 mg/l) turned out to be a good growth system for biomass production—mean increase of fresh weigh calculated on three following passages was 9.1 ± 1.8. The phytochemical analyses and antiradical DPPH (1,1-diphenyl-2-picryl-hydrazyl) tests revealed that the antioxidant activity is due to the presence of phenylethanoid glycosides. The quantitative screening of the callus extract by TLC (thin-layer chromatography) video densitometric method showed the highest content of acteoside (9.58 ± 0.75 mg/g dry weight) in root-derived and plantamajoside (8.15 ± 0.81 mg/g d.w.) in hypocotyl-derived callus biomass. In in vitro redifferentiated cultures of P. ovata, compounds with a demonstrated therapeutic effect, can be obtained in a manner that is completely independent of cultivation or harvesting from the wild.
Graphical abstract
Plantago ovata Forsck., is a herbaceous annual medicinal plant, usually known as commonly psyllium or Isabgol. It has been used traditionally used for various purposes in folk medicines. It is mostly grown for mucilaginous seeds husk, which is most effect laxative. It is native to Asia and Europe and has rooted throughout the world in tropical and temperate regions of the world. Isabgol consists of phenolics, flavonoids, terpenoids and iridoid glycosides. Hemicellulose is present in excess amount in Isabgol, with a xylan backbone linked with rhamnose, arabinose and arabinoxylans. Isabgol is a natural polymer which is mainly composed of polysaccharide chain consisting (1 > 3) and (1 > 4)-ß– xylan system. This chapter described the use of histological, physicochemical, and chromatographic analyses.
Catalpol, an iridoid glucoside isolated from Rehmannia glutinosa, has gained attention due to its potential use in treating cardio-cerebrovascular diseases (CVDs). This extensive review delves into recent studies on catalpol's protective properties in relation to various CVDs, such as atherosclerosis, myocardial ischemia, infarction, cardiac hypertrophy, and heart failure. The review also explores the compound's anti-oxidant, anti-inflammatory, and anti-apoptotic characteristics, emphasizing the role of vital signaling pathways, including PGC-1α/TERT, PI3K/Akt, AMPK, Nrf2/HO-1, estrogen receptor (ER), Nox4/NF-κB, and GRP78/PERK. The article discusses emerging findings on catalpol's ability to alleviate diabetic cardiovascular complications, thrombosis, and other cardiovascular-related conditions. Although clinical studies specifically addressing catalpol's impact on CVDs are scarce, the compound's established safety and well-tolerated nature suggest that it could be a valuable treatment alternative for CVD patients. Further investigation into catalpol and related iridoid derivatives may unveil new opportunities for devising natural and efficacious CVD therapies.
Plantago australis Lam. Subsp. hirtella (Kunth) Rahn is a medicinal plant used as a diuretic, anti-inflammatory, antibacterial, throat cancer treatment and for the control of diabetes. P. australis was collected in the state of Morelos, México. The hydroalcoholic extract (HAEPa) of P. australis was obtained by maceration and concentrated in vacuo. Once dry, it was evaluated through an oral glucose tolerance test (OGTT) in normoglycemic mice and in a non-insulin-dependent diabetic mice model. The expression of PPARγ and GLUT-4 mRNA was determined by rt-PCR, and GLUT-4 translocation was confirmed by confocal microscopy. The toxicological studies were conducted in accordance with the guidelines suggested by the OECD, sections 423 and 407, with some modifications. HAEPa significantly decreased glycemia in OGTT curves, as well as in the experimental diabetes model compared to the vehicle group. In vitro tests showed that HAEPa induced an α-glucosidase inhibition and increased PPARγ and GLUT-4 expression in cell culture. The LD50 of HAEPa was greater than 2000 mg/kg, and sub-chronic toxicity studies revealed that 100 mg/kg/day for 28 days did not generate toxicity. Finally, LC-MS analysis led to the identification of verbascoside, caffeic acid and geniposidic acid, and phytochemical approaches allowed for the isolation of ursolic acid, which showed significant PPARγ overexpression and augmented GLUT-4 translocation. In conclusion, HAEPa induced significant antidiabetic action by insulin sensitization through PPARγ/GLUT-4 overexpression.
Secondary plant chemistry mediates a variety of communication signals among species, playing a fundamental role in the evolutionary diversification of communities and ecosystems. Herein, we explored diet-mediated host plant effects on development and immune response of a generalist insect herbivore. Vanessa cardui (Nymphalidae) caterpillars were reared on leaves of three host plants that vary in secondary metabolites, Plantago lanceolata (Plantaginaceae), Taraxacum officinale (Asteraceae) and Tithonia diversifolia (Asteraceae). Insect development was evaluated by larval and pupal viabilities, survivorship, and development rate. Immune response was measured as phenoloxidase (PO) activity. Additionally, chemical profiles of the host plants were obtained by liquid chromatograph-mass spectrometry (LC–MS) and the discriminant metabolites were determined using a metabolomic approach. Caterpillars reared on P. lanceolata exhibited the highest larval and pupal viabilities, as well as PO activity, and P. lanceolata leaves were chemically characterized by the presence of iridoid glycosides, phenylpropanoids and flavonoids. Taraxacum officinale leaves were characterized mainly by the presence of phenylpropanoids, flavones O-glycoside and germacranolide-type sesquiterpene lactones; caterpillars reared on this host plant fully developed to the adult stage, however they exhibited lower larval and pupal viabilities compared to individuals reared on P. lanceolata. Conversely, caterpillars reared on T. diversifolia leaves, which contain phenylpropanoids, flavones and diverse furanoheliangolide-type sesquiterpene lactones, were not able to complete larval development and exhibited the lowest PO activity. These findings suggested that V. cardui have adapted to tolerate potentially toxic metabolites occurring in P. lanceolata (iridoid glycosides), however caterpillars were not able to cope with potentially detrimental metabolites occurring in T. diversifolia (furanoheliangolides). Therefore, we suggest that furanoheliangolide-type sesquiterpene lactones were responsible for the poor development and immune response observed for caterpillars reared on T. diversifolia.
Natural products have been a key source of drug lead discovery. However, their identification has long been a challenge even with the state-of-the-art analysis technologies like high-resolution mass spectrometry (MS) due to their complexity. Emerging in silico chemical structure prediction tools have provided time-saving and highly efficient approaches for identification of these complex samples. Nevertheless, the interpretation of these MS annotations into key supporting evidence towards specific questions is still a bottleneck in medicinal and biological fields. Here we present a deep clustering-based MS data visualization strategy (MCnebula), integrated with the influential open-source automatic MS annotation platform SIRIUS and in vivo and in vitro methods, to screen and validate potential lead compounds from natural products. MCnebula could provide multi-layer clustering profiles with chemical ontologies and comparative analysis of differential treatments. Plantaginis Semen (PS) is commonly used for treating kidney disease and usually stir-fried with salt water to enhance its anti-renal fibrosis effect, but the reason behind this remains unclear. Taking PS as an example, we comprehensively identified and compared the raw and processed PS extracts with SIRIUS-MCnebula, and screened potential anti-renal fibrotic lead compounds using weighted fold change analysis. Eighty-nine components were identified in PS with isoacteoside, calceolarioside B, 2'-acetylacteoside, and plantainoside D being screened and validated to treat renal fibrosis. The novel developed mass spectral data visualization strategy combined with biological function investigation and validation workflow could not only accelerate the discovery of lead compounds from medicinal natural products, but also shed new light on the traditional processing theory.
Twelve undescribed cyclopentanoid monoterpenes, Jiopiasins A–K and 6-epi-rehmaglutin A, and 19 known compounds were isolated from the whole plant of Rehmannia piasezkii Maxim. The structures of these compounds, especially their absolute stereochemistry, were established by extensive spectroscopic analysis, various quantum chemical calculations, and/or X-ray diffraction analyses. Furthermore, in vitro assays, some compounds exhibited moderate hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage.
The investigations were targeted to obtain in vitro culture of Plantago ovata, which would be efficient in the production of plant biomass and phenolic compounds with multiple biological activities, like acteoside and plantamajoside - the main phenylethanoid glycosides present in the Plantago genus. In these experimental studies, roots were obtained by natural development from seedlings germinated in vitro and from in vitro multiplied shoots as well as by direct organogenesis on seedling leaf explants and indirect organogenesis from callus cultured on various explants. Callus-regenerated roots agitated in MS (Murashige and Skoog) liquid medium supplemented with phytohormones NAA (1-naphthaleneacetic acid) 0.25 mg/L and BAP (benzylaminopurine) 0.5 mg/L turned out to be a good growth system for root biomass production - mean increase of root fresh weight calculated on three following passages was 6641.07%. The quantitative screening of the root extract by HPTLC video densitometric method showed the content of acteoside 33.02 mg/g dry weight (d.w.) (538.9 mg/L of culture) and plantamajoside 6.39 mg/g d.w. (104.0 mg/L of culture) in root biomass obtained with the yield 16.32 g d.w. /L within 4 weeks. The content of those compounds in the in vitro shoots was significantly lower – 4.20 and 4.28 mg/g, d.w., respectively. Although the high level of acteoside in the root culture decreased in the following 8 weeks of the culture, it is still satisfactorily high (8.25 mg/g, d.w.). This is the first report on the adventitious root cultures of Plantago ovata and the content of those phenylethanoids in that well-grown plant material. The proposed approach provides an alternative to the soil-grown plants, source of plant metabolites, due to the possibility of the fast, regular and scalable production of plant biomass containing the compounds of interest as the main constituents.
For the first time inflorescences of a plant species from the genus Plantago (Pantaginaceae)—Plantago lanceolata L. (Ribwort Plantain), a known medicinal plant, were subjected to studies of phenolic compounds, which resulted in an isolation of two new compounds: a flavonoid—isorhamnetin 3-O-α-L-⁴C1-arabinopyranosyl-(1→2)-β-D-⁴C1-glucopyranoside) (1) and a phenylethanoid glycoside—2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinofuranosyl-(1→2)-[α-L-¹C4-rhamnopyranosyl-(1→3)][E-caffeoyl-1→4]-β-D-⁴C1-glucopyranoside (14), along with fourteen known compounds—eight flavonoids (2–9) and six phenylethanoid glycosides (10–13, 15–16). The chemical structures were established by 1 D and 2 D NMR and HRESIMS spectral methods. The known phenylethanoids were the same as reported for leaves or aerial parts of P. lanceolata or other Plantago species. The flavonoids appeared to be only flavonols, mainly isorhamnetin 3-O- and 3,4’-O- glycosides, and thus completely different from flavones, mainly luteolin and apigenin glucuronides, previously reported in the leaves. The possible medicinal and chemotaxonomic relevance of the phenolics found in P. lanceolata inflorescences were taken into consideration.
Catalpol has gained increasing attention for its potential contributions in controlling glycolipid metabolism and diabetic complications, which makes used as a very promising scaffold for seeking new anti-diabetic drug candidates. Acylation derivatives of catalpol crotonate (CCs) were designed as drug ligands of glutathione peroxidase (GSH-Px) based on molecular docking (MD) using Surfex-Docking method. Catalpol hexacrotonate (CC-6) was synthesized using microwave assisted method and characterized by FT-IR, NMR, HPLC and HRMS. The MD results indicate that with the increasing of esterification degree of hydroxyl, the C log P of CCs increased significantly, and the calculated total scores (Total_score) of CCs are all higher than that of catalpol. It shows that CCs maybe served as potential lead compounds for neuroprotective agents. It was found that the maximum Total_score of isomers in one group CCs is often not that the molecule with minimum energy. MD calculations show that there are five hydrogen bonds formed between CC-6 and the surrounding amino acid residues. Molecular dynamics simulation results show that the binding of CC-6 with GSH-Px is stable. CC-6 was screened for SH-SY5Y cells viability by MTT (3-(4, 5-dimethylthiazolyl-2)-2, 5-diphenyltetrazolium bromide) assay, the result indicates CC-6 can effectively reverse SZT induced cells apoptosis with dose-dependent manner, which can indirectly show that CC-6 is a potential neuroprotective agent.
Catalpol, an effective component of China's functional food Rehmannia glutinosa Libosch, has a wide range of pharmacological effects. However, it is unclear whether catalpol exhibits protective and therapeutic potential against rheumatoid arthritis. In this study, the effects of catalpol in rats with collagen II-induced arthritis (CIA) and in LPS-stimulated SW982 human synovial cells were investigated. Catalpol significantly reduced paw swelling and thickness in rats with CIA. Histopathology revealed that catalpol alleviated articular cartilage damage, infiltration of inflammatory cells and synovial hyperplasia. Catalpol also inhibited protein and mRNA levels of IL-6, IL-8 and MMP-1, and the expression of COX-2 and mPGEs-1 in LPS-stimulated SW982 cells. Furthermore, the phosphorylation levels of ERK, JNK, p65, IκBα and c-Jun were suppressed by catalpol. Taken together, these findings showed that catalpol had inhibitory effects against arthritis, which may be related to decreased production of pro-inflammatory mediators and suppression of the MAPK, NF-κB and AP-1 pathways.
Using various chromatographic separations, five iridoid glucosides (1―5) and five phenylethanoid glycosides (6―10) were isolated from the Plantago major whole plants and included two new compounds: 10-acetylarborescoside (1) and plantainoside G (6). Their structures were elucidated by detailed analysis of 1D and 2D NMR data, HR QTOF MS data, and experimental and calculated ECD data. The isolated compounds exhibited moderate inhibitory effects on NO overproduction in LPS-stimulated BV2 microglial cells, with IC50 values ranging from 44.2–62.3 μM.
Ethnopharmacological relevance
World-wild distributed plantains (genus Plantago L.) are extensively used in the traditional, but some of them are also accepted in the modern medicine. Wide range of usages is mainly connected to the inflammation processes.
Aim of the study
To support usage of renowned P. lanceolata L. and P. major L., underinvestigated P. altissima L., P. argentea Chaix, P. holosteum Scop. and P. media L. methanol extracts, and their typical constituents (aucubin, apigenin, apigenin-7-O-glucoside, luteolin, luteolin-7-O-glucoside, chlorogenic and ursolic acid) in treatment of inflammation disorders, we conducted study on plantain potential to inhibit production of inflammatory mediators, prostaglandin E2 (PGE2) and tromboxane A2 (TXA2).
Materials and methods
LPS-stimulated monocytes were used as a model-system to examine anti-inflammatory potential of plantains and their constituents. Produced PGE2 and TXA2 were quantified by LC-MS/MS; qPCR was applied to examine related gene (PLA2, COX-1, COX-2, mPGES-1, mPGES-2, cPGES, TXAS) expression; LC-MS/MS and LC-UV/VIS techniques to analyze extracts composition.
Results
In general, examined plantain extracts showed similar inhibition activity of PGE2 and TXA2 production as aspirin at low-dose concentration. Underinvestigated P. altissima can be pointed out, since it exerted the strongest effect on both PGE2 production and related gene expression. Notable suppression of TXA2 production by P. lanceolata and P. major was observed. But, PCA analysis showed no obvious grouping, implicating that different mechanisms of action are responsible for each sample activity. In most cases, positive correlation was found between content of apigenin and ursolic acid and extracts suppression of PGE2 and TXA2 production and related genes expression.
Conclusions
P. altissima can be regarded as promising anti-inflammatory agent, while novel aspect of P. lanceolata and P. major application (anti-aggregation) can be suggested. P. argentea and P. media could be considered as a good source of ursolic acid.
The Puna is an extensive highland, or high mountain plateau, typical of the central area of the cordillera de los Andes. The vegetation is substantially affected by the climatic conditions. The dominant flora is the shrub steppe with dispersed bushes. Local edaphic microclimates determine the existence of small sectors with different physiognomies. The species Acacia caven (Molina) Molina var. caven, Chenopodium ambrosioides L, Anemia tomentosa (Savigny) Sw. var. anthriscifolia (Schrad.) Mickel, Plantago australis Lam. subsp. Australis, and Alternanthera pungens Kunth. that grow in the region are described in respect to their botanical characteristics, ethnomedical uses, chemicals, biological activity, toxicity, and establishment of in vitro cultures and legal status, when corresponding.
Potential health benefit effects and versatile pharmacological activities of several iridoids and secoiridoids have created interests among synthetic chemists and biotechnologists to make them popular targets of chemical synthesis and biosynthesis. The presence of oxidative substituents in the cyclopentane ring of iridoids, several groups have been used these compounds as starting materials for regioselective and stereoselective synthesis of potential bioactive alkaloids, prostaglandin analogues and other bioactive natural products.
Background: Native Americans have had a rich ethnobotanical heritage for treating diseases, ailments, and injuries. Cherokee traditional medicine has provided numerous aromatic and medicinal plants that not only were used by the Cherokee people, but were also adopted for use by European settlers in North America. Methods: The aim of this review was to examine the Cherokee ethnobotanical literature and the published phytochemical investigations on Cherokee medicinal plants and to correlate phytochemical constituents with traditional uses and biological activities. Results: Several Cherokee medicinal plants are still in use today as herbal medicines, including, for example, yarrow (Achillea millefolium), black cohosh (Cimicifuga racemosa), American ginseng (Panax quinquefolius), and blue skullcap (Scutellaria lateriflora). This review presents a summary of the traditional uses, phytochemical constituents, and biological activities of Cherokee aromatic and medicinal plants. Conclusions: The list is not complete, however, as there is still much work needed in phytochemical investigation and pharmacological evaluation of many traditional herbal medicines.
The new iridoid 10-acetylaucubin and the well known iridoids aucubin. melittoside and monomelittoside as well as the rare 6-epiaucubin and 3,4-dihydroaucubin were isolated from aerial parts of Plantago carinata Schrad. This is the first isolation of 6-epiaucubin from Planta-ginaceae plants and of 3,4-dihydroaucubin and monomelittoside from P. carinata Schrad.
Plantago altissima L., Plantago lanceolata L., Plantago atrata Hoppe and Plantago argentea Chaix. were examined for iridoids. In all four species aucubin and catalpol were found. Globularin and methyl ester of the desacetylasperulosidic acid were isolated for the first time from Plantaginaceae plants (P. altissima and P. lanceolata). Asperuloside was found for the first time in P. altissima as well as dihydroaucubin in P. atrata.
10-Hydroxymajoroside, a second representative of the rare majoroside type iridoid glucosides, along with the well known aucubin, has been isolated from Plantago cornuti.
In Littorella uniflora two iridoid glucosides already known from the Plantaginaceae family are present: aucuboside and catalpol. The present and an earlier study of sugars and sucrose alcohols indicate a biochemical relationships of Littorella to Plantago.
The systematic positions of genera previously assigned to the Buddlejaceae are investigated using Bremer support and parsimony jackknife analyses of cpDNA ndhF and rbcL sequence data. The differences between these two methods are discussed: resampling methods such as the jackknife help identify and assess confidence in qualitatively supported groups, whereas Bremer support provides an absolute quantitative measure of that support. The close relationship of Buddlejaceae s. str. (comprising Buddleja, Nicodemia, Emorya, and Gomphostigma) to Scrophulariaceae s. str. is confirmed. Previous suggestions that Desfontainia and Plocosperma are not related to the Scrophulariales sensu Thorne are corroborated, as are the close relationships of Sanango to Gesneriaceae and of Retzia to Stilbaceae previously unsuggested monophyletic groups revealed include Androya and Myoporum, together appearing as sister group to the Scrophulariaceae/Buddlejaceae clade Nuxia and the Stilbaceae clade, Peltanthera and the Sanango/Gesneriaceae clade, and Polypremum and Tetrachondra. The latter genus is not part of Scrophulariales sensu Theme, which otherwise is well supported. Oleaceae is resolved as sister group to the rest of the clade. Within the order a gesneriad clade, a stilbacean clade, two 'scroph' clades, Acanthaceae, Bignoniaceae, Lamiaceae, and Verbenaceae occur as distinct lineages. The relationships among these are poorly resolved and the position of Lindenbergia is uncertain.
Phylogenetic analysis of DNA sequences of the chloroplast genes rcbL and ndhf revealed a highly supported clade composed of the families Plantaginaceae, Callitrichaceae, and Hippuridaceae in close association with the model organism Antirrhinum majus and other members of family Scrophulariaceae. Plantago has miniature actinomorphic wind-pollinated flowers that have evolved from zygomorphic animal-pollinated precursors. The aquatic Hippuridaceae have reduced windpollinated flowers with one reproductive organ per whorl, and three, rather than four, whorls. In monoecious aquatic Callitrichaceae, further reduction has occurred such that there is only one whorl per flower containing a single stamen or carpel. Optimization of character states showed that these families descended from an ancestor similar to Antirrhinum majus. Recent studies of plant developmental genetics have focused on distantly related species. Differences in the molecular mechanisms controlling floral development between model organisms are difficult to interpret due to phylogenetic distance. In order to understand evolutionary changes in floral morphology in terms of their underlying genetic processes, closely related species exhibiting morphological Variation should be examined. Studies of genes that regulate morphogenesis in the clade described here could aid in the elucidation of a general model tot such fundamental issues as how changes in floral symmetry, organ number, and whorl number are achieved, as well as providing insight on the evolution of dicliny and associated changes in pollination syndrome.
Einjährige oder perennierende Kräuter, seltener Halbsträucher mit parallelnervigen, oft in einer grundständigen Rosette vereinigten, meist ungeteilten Blättern. Blüten klein, zwittrig (Plantago, Bougueria) oder eingeschlechtig (Littorella), in meist reichblütigen, ährigen Blütenständen. Kelch meist 4zählig, am Grunde röhrig verwachsen; Krone 4zählig, sympetal; Staubblätter 4 (seltener 3, 2 oder 1), mit sehr langen Filamenten und versatilen Antheren (Windbestäubung); Fruchtknoten oberständig, ein-, zwei- oder mehrfächerig mit einer bis vielen Samenanlagen mit: einem Integument in jedem Fache. Kapselfrüchte (Plantago) oder Nüsse (Littorella und Bougueria). Samen mit reichlich Endosperm.
The main iridoids, aucuboside and catalpol, were isolated from Plantago lanceolata L., P. major L. and P. media L. leaves. Their quantitative analysis were determinated by HPLC. Their respective contents were estimated according to the vegetative cycle.
The distribution of the chemical compounds iridoids, anthraquinones, and verbascosides is demonstrated in Dahlgrenograms. An analysis of iridoid biosynthesis and structure allows distinction of two main groups of compounds. Thus, the biosynthetic route I gives rise to the Seco-iridoids and their derivatives, and another (route II) to aucubin and similar decarboyxlated iridoid glucosides. Seco-iridoids from route I are widely distributed in Cornanae, Loasanae, and Gentiananae but never in Lamianae. Aucubinlike compounds derived by route II are commonly found in Lamianae and in three small families in Cornanae, but are not found in Gentiananae. Ericanae contain both groups, but not within the same order. Likewise, two biosynthetically different groups of anthraquinones can be distinguished, one of which is found solely in Gentiananae and in Lamianae, and thus suggests the monophyletic origin of these taxa. The distribution of the verbascosides, a group of caffeic acid esters, and cornoside, a compound that is often vicarious for iridoids, is shown to be limited to Lamianae and Oleaceae (Gentiananae), barring a few exceptions. This, together with other evidence, may suggest that Oleaceae systematically belong close to Scrophulariaceae, despite the presence of seco-iridoids in Oleaceae. The results of an investigation of the family Loganiaceae, as delineated recently by Leeuwenberg, are presented and analyzed in light of the above distributional patterns. The chemical data, combined with a few morphological characters, reveal that the tribes Spigelieae, Loganieae, Strychneae, Gelsemieae, and Antonieae show many similarities and are characterized by containing seco-iridoids (biosynthetic route 1), by having intraxylary phloem and nuclear endosperm formation, and by lacking verbascosides. The tribe Potalieae share this set of characters, but because of the presence of a unique combination of compounds, elsewhere only found in Gentianaceae, it may fit better in that family. The tribes Plocospermeae, Buddlejeae, and Retzieae, as well as the genus Polypremum from Spigelieae, do not belong in the Gentianaceae, because they are all different in the above set of characters. Chemically (and morphologically), they are more closely related to Scrophulariaceae and its allies or, alternatively, Oleaceae. Our studies have revealed nothing conclusive about tribe Desfontainieae.
A new flavanone glucoside, plantagoside (1) was isolated from the seeds of Plantago major var. japonica NAKAI (Plantaginaceae) together with aucubin, geniposidic acid, acteoside and syringin. The structure of plantagoside was elucidated to be 1 on the basis of chemical and spectral evidence.
Antioxidative components in the methanol extract of seeds of Plantago asiatica L. were investigated by using our test method based on the air oxidation of linoleic acid. Geniposidic acid, an iridoid glucoside, was found to be the most potent antioxidative component. The 50% inhibitory concentration (IC50) of geniposidic acid was 1.56×10-2% (thiobarbituric acid value), and this value was superior to that of dl-α-tocopherol (IC50 : 1.95×10-1%). The antioxidative effects of other related iridoid glucosides (aucubin, geniposide, gardenoside) were also tested, but their activities were clearly weaker than that of geniposidic acid.
A new iridoid glucoside, hygrophiloside, has been isolated from Hygrophila difformis. Hygrophiloside is apparently identical to the so-called ‘Cardanthera-Pseudoindican’. Its structure has been established by spectroscopic means and by reduction to isoaucubin.
From the roots of Rehmannia glutinosa var. purpurea and R. glutinosa var. hueichingensis, besides four known iridoid glucosides, catalp
The new iridoid glucoside from the rare Δ8,9 type, 10-acetoxymajoroside, was isolated from Plantago cornuti and P. major along with known iridoids. The main constituents in V. cymbalaria were the known catalpol, amphicoside and verproside together with alpinoside, aucubin, 6-O-veratroylcatalpol and verminoside. The iridoid alpinoside with a 8,9-double bond was found for the first time in genus Veronica.
Two species of Plantago, namely P. Alpina and P. altissima were investigated. From the former, nine iridoid glucosides and verbascoside were isolated. Together with the known iridoids gardoside, geniposidic acid, 8-epi-loganic acid, mussaenosidic acid, aucubin, monomelittoside and melittoside, two new glucosides were found: 10-O-acetylgeniposidic acid and alpinoside, another compound with a 10-O-acetyl group. From P. altissima verbascoside and isoverbascoside were isolated together with the known iridoids gardoside, 8-epi-loganic acid, catalpol, aucubin, and hookerioside as well as the new compound desacetylhookerioside.
Feeding experiments with deuterium-labelled 8-epi-deoxyloganic acid, bartsioside and aucubin gave incorporation of all compounds into catalpol both in Scutellaria albida and Paulownia tomentosa. Dilution experiments with labelled 8-epi-deoxyloganic acid and unlabelled aucubin showed that aucubin is an intermediate in the biosynthesis of catalpol in these two species. 8-epi-Deoxyloganic acid was incorporated into tomentoside in P. tomentosa.
A new iridoid glucoside, majoroside, along with the known aucubin have been isolated from Plantago major from Bulgaria and Mongolia. Majoroside is the first Δ8-iridoid glucoside. The structure was established on the basis of chemical and spectroscopic studies.
Melampyrum arvense and M. cristatum contain, besides aucubin, 8-epiloganin and melampyroside, a new natural iridoid glucoside: gardoside methyl ester. In addition, M. arvense contains mussaenoside and M. cristatum mussaenosidic acid, another novel iridoid glucoside.
Plantago patagonica from plants grown in a greenhouse and from a field population in Boulder, Colorado, were sampled for iridoid glycosides. Both aucubin and catalpol were found in P. patagonica, however, not all individual plants contained detectable amounts of both these compounds. Plants grown in the greenhouse (n=8) contained means of 0.26% (±0.04 S.E.) aucubin and 0.23% (±0.05 S.E.) catalpol, whereas field-collected plants (n=61) contained means of 0.02% (±0.006 S.E.) aucubin and 0.36% (±0.02 S.E.) catalpol.
The new iridoid 10-acetylmonomelittoside and the known iridoid glucosides aucubin and monomelittoside were isolated from fresh leaves of two varieties of Plantago media. This is the first isolation of monomelittoside from Plantaginaceae.
The 13C NMR and 360 MHz 1H NMR signals of melittoside and its acetate have been assigned.
Two minor iridoids isolated from the leaves of Thevetia peruviana were shown to be 10-O-β-D-fructofuranosyltheviridoside and 6′-O-β-D-glucopyranosyltheviridoside.
From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a beta-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy.
The four known phenolic compounds, 3,4-dihydroxyphenethyl alcohol-6-O-caffeoyl-beta-D-glycoside, acteoside (verbascoside), plantagenin and plantamajoside, and a new phenylpropanoid glycoside, hellicoside, were isolated from aerial parts of Plantago asiatica, which is used in oriental medicine 'Plantaginis Herba'. The structure of hellicoside was deduced from chemical and spectral evidence to be 3,4,7-trihydroxy-beta-phenethyl-O-beta-D-glucopyranosyl-(1-3)-4-O-caffeoyl-beta-D-glucopyranoside. Plantamajoside and hellicoside showed high inhibition of cyclic AMP phosphodiesterase and 5-lipoxygenase. Acteoside showed high inhibition of lens aldose reductase.
In a study based on morphological, embryological and chemical data of the Plantaginaceae, within the subclass Sympetalae or Asteridae, the superorder Lamianae is shown to be monophyletic. However, it was not possible to reconstruct the phylogeny within Lamianae or to find a sister-group for the monophyletic Plantaginaceae — Hydrostachyaceae for the latter is rejected. Three or rarely four genera have previously been recognized within Plantaginaceae, but in both casesPlantagoappears as polyphyletic, which is considered unacceptable. Six clades are recognized as subgenera withinPlantago: subgen.Plantago(c. 131 species), subgen.Coronopus(c. 11 species), subgen.Littorella(three species), subgen.Psyllium(c. 16 species), subgen.Bougueria(one species), and subgen.Albicans(51 species). WithinP. subgen.Plantago, the paraphyletic sect.Plantago(c. 42 species) is found in all parts of the world except South America, New Zealand, Australia, and New Guinea, where sect.Oliganthosand sect.Mesembryniaevicariate. It is not possible to infer the phylogeny within sect.Plantago, for example between the endemic species from distant Pacific Islands; their common ancestor might be a species that once had a very wide distribution. Keys to genera, subgenera, sections and series are given. Only one genus,PlantagoL., is recognized. The following proposals are made in the Appendix:P. ser.OliganthosRahn, ser. nov.;P. ser.Carpophorae(Rahn) Rahn, stat. nov. (= sect. C.);P. ser.Microcalyx(Pilg.) Rahn, stat. nov. (= sect.M.);P. unibracteataRahn, nom. nov. (= P. unifloraHook.f. non L.);P. subgen.Littorella(P.J.Bergius) Rahn, stat. nov. (= LittorellaP.J.Bergius);P. araucanaRahn, nom. nov. (= Littorella australisGriseb. nonPlantago australisLam.);P. americana(Fernald) Rahn, comb. nov.(= Littorellaa.);P. subgen.Bougueria(Decne.) Rahn, stat. nov. (= BougueriaDecne.);P. nubicola(Decne.) Rahn, comb. nov. (= Bougueria n. Decne.);P. subgen.AlbicansRahn, subgen. nov. Ten lectotypes are selected.
Feeding experiments with deuterium-labelled 8-epi-iridodial, 8-epi-iridotrial and 8-epi-iridotrial glucoside gave incorporation of all compounds into aucubin and harpagide in Scrophularia umbrosa, whereas the same compounds did not show significant incorporation into aucubin in Buddleya albiflora.
Six new phenylethanoid glycosides, plantainosides A–F, were isolated from a water extract of the whole plants of Plantago asiatica together with eight known phenylethanoid glycosides. Their structures were determined on the basis of chemical and spectral evidence.
The structure of plantamajoside, a phenylpropanoid glycoside isolated from Plantago major subs major, is deduced from chemical, spectral and other physical evidence, to be 3,4-dihydroxy-β-phenethyl-O-β-d-glucopyranosyl-(1 →3)-4-O-caffeoyl-β-d-glucopyranoside. The Minimum Inhibitory Concentration value has been evaluated for seven plant pathogenic bacteria and for E. coli (ML 30) and S. aureus (502 A) after preliminary investigations by the agar diffusion method.
77 leaf samples representing 68 taxa of Rosaceae were investigated for the presence of sorbitol. A procedure for the quantitative estimation of sorbitol in dry plant tissues was elaborated; it made use of extraction by percolation and capillary GLC analysis of the silylated extracts. All Maloideae and Prunoideae and most Spiraeoideae were found to accumulate sorbitol. The subfamily Rosoideae was found to be heterogeneous in this respect; in most tribes sorbitol is totally lacking, but in Kerrieae, Adenostomeae and part of Dryadeae sorbitol is present in variable amounts. A clear-cut correlation between sorbitol accumulation and basic chromosome number seems to exist in Rosaceae.
To compare and contrast the inter- and intra-population variation in Plantago rhodosperma, individuals from four populations in Kansas (Russell, Woodston, Stockton A and Stockton B) were sampled. The following five characteristics were compared: (1) size of the plants, using area of the largest leaf as an index, (2) number of trichomes on the upper and lower leaf surfaces, (3) iridoid glycoside concentration of leaves and scapes, (4) leaf nitrogen concentration, and (5) allozyme variability. The Russell and Woodston populations were significantly smaller than those from Stockton A and B, and had greater trichome densities on the upper leaf surface. The Stockton B population had significantly more aucubin in the leaves than the other populations sampled. However, the aucubin concentration in the scapes did not differ among populations. The Stockton A and B populations had significantly higher leaf nitrogen concentrations than Russell, but Woodston was not significantly different from either of the other two. There was little inter- populational allozyme variation, although the Russell population showed allozyme variability among individuals for the enzyme PGI. The allozyme data suggest that P. rhodosperma is an allopolyploid.
Polypremum procumbens (Buddlejaceae) was found to contain sorbitol, cornoside, salidroside and conandroside. One collection of Peltanthera floribunda (Buddlejaceae) contained verbascoside, two others the cornoside-derived rengyolone (=halleridone). From Tetrachondra hamiltonii (Tetrachondraceae) was isolated sorbitol, cornoside and verbascoside. Iridoids were not found in any of the taxa. The taxonomic significance of the different chemical constituents is discussed, and the data demonstrate a close relationship between Polypremum and Tetrachondra. They may also suggest an inclusion of Peltanthera in Gesneriaceae. These findings are in concert with recently published chloroplast DNA sequence data.
Plantago hookeriana contains a new iridoid glucoside, hookerioside, in addition to the known compounds catalpol, aucubin, 8-epi-loganic acid, 10-benzoylcatalpol and verbascoside. Hookerioside contains two unusual structural features, an 8,9-double bond and a carboxyl-1-β-d-glucopyranosyl group at C-4.
Within the genusPlantago, subg.Psyllium is characterized by the accumulation of the iridoids plantarenaloside and bartsioside. The latter compound was identified as constituent ofP. sempervirens for the first time. The structures of iridoids were determined by UV, IR,13C-NMR and1H-NMR. Both compounds are of chemotaxonomic value, as they are typical only of subg.Psyllium withinPlantago. The distribution of plantarenaloside within subg.Psyllium suggests the heterogeneity of this taxon.
Deuterium-labelled samples of I-epi-deoxyloganic acid, deoxygeniposidic acid, geniposidic acid, and bartsioside (6-deoxyaucubin) all gave high incorporations into aucubin in Scrophularia umbrosa whereas labelled 6,10-dideoxyaucubin did not give a significant incorporation. In S. racemosa, 8-epi-deoxyloganic acid gave a high incorporation into aucubin and harpagide while 8-epi-loganic acid was not incorporated. Dilution experiments with labelled 8-epi-deoxyloganic acid and unlabelled geniposidic acid or scandoside showed that geniposidic acid is an intermediate in the biosynthesis of aucubin whereas scandoside apparently is not. The pathway from 8-epi-deoxyloganic acid to aucubin has thus been established, showing that decarboxylation takes place at the geniposidic acid stage.
The 13C NMR data of 51 iridoid glucosides or glucoside acetates are tabulated. The collection includes 20 pairs of C-6, C-7 or C-8 epimers. Three parameters in using the data for the configurational assignment of 6-O-substituents are given. The chemical shift for C-9 in a range of substituted compounds is shown to be numerically related to the stereochemistry at C-8. This allows the determination of the configuration at this centre for most types of substitution patterns by calculation of the C-9 shift using increments for each substituent. Such increments are given for 25 substituents in three different solvents. A method for simulation of spectra of unknown iridoid glucosides is presented. By this method, the structures of five novel iridoid glucosides have been elucidated, and that of tecomoside has been revised. The methods used to assign the configurations to C-6 and C-8 epimeric iridoid glucosides by 1H NMR spectroscopy are discussed and a table with sel