scholarly journals Identification of Sesquiterpene Lactones in the Bryophyta (Mosses) Takakia: Takakia Species are Closely Related Chemically to the Marchantiophyta (Liverworts)

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Yoshinori Asakawa ◽  
Kaeko Nii ◽  
Masanobu Higuchi
Keyword(s):  
Secondary Metabolites ◽  
Sesquiterpene Lactones ◽  
Volatile Components ◽  
Minor Components ◽  
Chemical Markers ◽  
Significant Chemical

Takakia lepidozioides has been considered to be the most primitive liverwort morphologically and classified initially in the Marchantiophyta (liverworts). However, the Takakia have been reclassified from liverworts to mosses on the basis of the similarity of the male sporophyte of T. ceratophylla to that of some mosses. Reinvestigation of secondary metabolites of fresh T. lepidozioides resulted in identification of eudesmane-type sesquiterpene lactones and hydrocarbon that are significant chemical markers of several liverworts. T. lepidozioides also produces a small amount of hop-22(29)-ene, together with coumarin, which produce the characteristic odor of T. lepidozioides, and 1,4-hydroquinone; these are the predominant volatile components, whereas dihydrocoumarin, 1,4-benzoquinone, dihydrobenzofuran, α-asarone and α-tocopherol are minor components. These chemical results indicated that T. lepidozioides is more closely related to the Marchantiophyta than the Bryophyta. T. lepidozioides is morphologically similar to the liverwort Haplomitrium species. However, both species are totally different chemically.

scholarly journals Volatile Components from Selected Mexican, Ecuadorian, Greek, German and Japanese Liverworts

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Agnieszka Ludwiczuk ◽  
Fumihiro Nagashima ◽  
Rob S. Gradstein ◽  
Yoshinori Asakawa
Keyword(s):  
Diethyl Ether ◽  
Brown Algae ◽  
Sesquiterpene Lactones ◽  
Evolutionary Relationship ◽  
Volatile Components ◽  
Chemical Markers ◽  
Chemical Similarity ◽  
Important Chemical ◽  
Crude Extracts

Twenty-one liverworts from Mexico, Ecuador, Greece, Germany and Japan were extracted with diethyl ether and the crude extracts analyzed by TLC and GC/MS. Several volatile sesqui- and diterpenoids, and also bibenzyls were identified. Many of these compounds are important chemical markers of liverworts genus or family. Sacculatane-type diterpene dialdehydes occur in the Pelliaceae family, while bibenzyls, especially with a prenyl group are characteristic of the Japanese Radula perrottetii. Eudesman-type sesquiterpene lactones and pinguisane-type sesquiterpenoids are significant markers of Frullania tamarisci and Trocholejeunea sandvicensis, respectively. The Greek Fossombronia angulosa contained exactly the same compounds previously found in brown algae. Such chemical similarity suggests that some families of liverworts and algae may have an evolutionary relationship.

scholarly journals Chemotaxonomic Value of Magastigmane Glucosides of Cichorium calvum

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900
Author(s):  
Klaudia Michalska ◽  
Alex Beharav ◽  
Wanda Kisiel
Keyword(s):  
Secondary Metabolites ◽  
Wild Species ◽  
Sesquiterpene Lactones ◽  
Morphological Characters ◽  
Chemical Markers ◽  
Molecular Analyses ◽  
First Report ◽  
Aerial Parts ◽  
Chemical Discrimination ◽  
Related Wild Species

Morphological characters and molecular analyses of Cichorium calvum and C. pumilum do not allow clear discrimination between these closely related wild species. Therefore, the aim of this study was to characterize the secondary metabolites of C. calvum and to select chemical markers which are unique to this species. From roots of C. calvum, ten sesquiterpene lactones were isolated, including seven lactucin-type guaianolides reported earlier from C. pumilum. Aerial parts also afforded secondary metabolites common to both species, along with the megastigmane glucosides staphylionoside D, saussureoside B and komaroveside A. This is the first report of the occurrence of these norisoprenoids in Cichorium species and the second record of their isolation from plants. Therefore, chemical discrimination of C. calvum is possible on the basis of its norisoprenoid composition.

scholarly journals Comparative Metabolite Profile, Biological Activity and Overall Quality of Three Lettuce (Lactuca sativa L., Asteraceae) Cultivars in Response to Sulfur Nutrition

Pharmaceutics ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 713
Author(s):  
Muna Ali Abdalla ◽  
Fengjie Li ◽  
Arlette Wenzel-Storjohann ◽  
Saad Sulieman ◽  
Deniz Tasdemir ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Plant Growth ◽  
Sesquiterpene Lactones ◽  
Critical Role ◽  
Soluble Sugars ◽  
Radical Scavenging ◽  
Metabolite Profile ◽  
Water Soluble ◽  
Radical Scavenger ◽  
Higher Plant

The main objective of the present study was to assess the effects of sulfur (S) nutrition on plant growth, overall quality, secondary metabolites, and antibacterial and radical scavenging activities of hydroponically grown lettuce cultivars. Three lettuce cultivars, namely, Pazmanea RZ (green butterhead, V1), Hawking RZ (green multi-leaf lettuce, V2), and Barlach RZ (red multi-leaf, V3) were subjected to two S-treatments in the form of magnesium sulfate (+S) or magnesium chloride (−S). Significant differences were observed under −S treatments, especially among V1 and V2 lettuce cultivars. These responses were reflected in the yield, levels of macro- and micro-nutrients, water-soluble sugars, and free inorganic anions. In comparison with the green cultivars (V1 and V2), the red-V3 cultivar revealed a greater acclimation to S starvation, as evidenced by relative higher plant growth. In contrast, the green cultivars showed higher capabilities in production and superior quality attributes under +S condition. As for secondary metabolites, sixteen compounds (e.g., sesquiterpene lactones, caffeoyl derivatives, caffeic acid hexose, 5-caffeoylquinic acid (5-OCQA), quercetin and luteolin glucoside derivatives) were annotated in all three cultivars with the aid of HPLC-DAD-MS-based untargeted metabolomics. Sesquiterpene lactone lactucin and anthocyanin cyanidin 3-O-galactoside were only detected in V1 and V3 cultivars, respectively. Based on the analyses, the V3 cultivar was the most potent radical scavenger, while V1 and V2 cultivars exhibited antibacterial activity against Staphylococcus aureus in response to S provision. Our study emphasizes the critical role of S nutrition in plant growth, acclimation, and nutritional quality. The judicious-S application can be adopted as a promising antimicrobial prototype for medical applications.

In the search for new secondary metabolites with biopesticidal properties

2015 ◽  
Vol 62 (4) ◽  
pp. 216-228 ◽  
Author(s):  
Carlos L. Céspedes ◽  
Julio E. Alarcon ◽  
Pedro Aqueveque ◽  
David S. Seigler ◽  
Isao Kubo
Keyword(s):  
Secondary Metabolites ◽  
Chemical Defense ◽  
Insect Pests ◽  
Sesquiterpene Lactones ◽  
Antibacterial Activities ◽  
Natural Compounds ◽  
Insect Growth Regulator ◽  
Bacterial Strains ◽  
Plant Chemical Defense ◽  
Insect Growth

Secondary metabolites are involved in diverse functions in plants, including defense and protective processes. Information concerning the biosynthesis of secondary metabolites in plants points at a constitutive or induced chemical defense, generated for protection against a variety of phytopathogenic attacks. Our phytochemical studies are aimed at finding biopesticides of botanical origin. Some plant taxa of American distribution are toxic to selected insects, fungi and bacterial strains, and their effect has been associated with the presence of phenolics, phenylpropanoids and terpenes. We have isolated some diterpenes, triterpenes, sesquiterpene lactones, flavonoids, and phenylpropanoids from members of the plant families Araucariaceae, Asteraceae, Calceolariaceae, Celastraceae, and Rhamnaceae. In addition, we have identified a number of chemical derivatives of these compound classes from the plants. A major finding indicates that compounds or their derivatives that possess antioxidant, antifungal, insect growth regulator or insecticidal activity and enzymatic inhibitors are natural compounds. Insecticidal activities were assayed against strains of lepidopteran, dipteran, and coleopteran insect pests that affect many crops. Antifungal and antibacterial activities were assayed against phytopathogenic species of filamentous fungi and bacterial strains that are pests on many crops. Our results indicate that the plant-derived compounds obtained from the abovementioned plants have excellent insect growth regulatory activity and a good potency as antifungal agents. However, little is known about the effects of these natural compounds and their derivatives on insect pests. The natural compounds that we have isolated represent a valuable resource for future studies of plant chemical defense and the role of these substances in chemical ecology.

Comparative Histochemical analysis of above-ground parts of Filipendula vulgaris and Filipendula ulmaria growing in Central Kazakhstan

2021 ◽  
pp. 4863-4867
Author(s):  
Yerbolat Tulebayev A. ◽  
Margarita Ishmuratova Yu. ◽  
Irina Losseva V. ◽  
Wirginia Kukuła-Koch ◽  
Ewa Poleszak ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Raw Materials ◽  
Sesquiterpene Lactones ◽  
Biologically Active ◽  
Histochemical Analysis ◽  
Filipendula Ulmaria ◽  
Plant Raw Materials ◽  
Related Substances ◽  
Histochemical Tests ◽  
The Republic

The histochemical analysis of medicinal plants and raw materials makes it possible to establish the presence of certain groups of active and related substances or products of their metabolism, as well as to study their localization in tissues. The article presents the results of histochemical analysis of leaves, flowers, petioles and stems of Filipendula vulgaris and Filipendula ulmaria. These types of plant are used in traditional medicine as an anti-inflammatory, antipyretic and bactericidal agent. Our research objective - to determine the peculiarities of the localization features of individual groups of secondary metabolites in the aerial part of meadowsweet and meadowsweet growing in the territory of Central Kazakhstan at the microscopic level. Materials and Methods. Transverse sections of petioles, stem and whole flower; transverse and superficial sections of leaves of Filipendula vulgaris and Filipendula ulmaria were fixed in Strauss-Fleming solution, after which histochemical reactions were carried out to locate and identify essential oils, phenolic acids, flavonoids, sesquiterpene lactones, polysaccharides and alkaloids. The study of microscopic signs, as well as histochemical tests were carried out according to the methods of the State Pharmacopoeia of the Republic of Kazakhstan using a light microscope Biomed-4. Results and Discussion. The localization of biologically active substances in the studied types of plant raw materials was determined by histochemical methods using light microscopy. The presence of phenolic compounds, flavonoids, traces of essential oil, alkaloids and sesquiterpene lactones was established. The absence of polysaccharides in the investigated micropreparations was established. Conclusions. For the first time, the localization of secondary metabolites in the tissues of Filipendula vulgaris and Filipendula ulmaria was studied by histochemical tests. The results of histochemical studies can be used to confirm the authenticity, identification and standardization of the aerial parts of Filipendula vulgaris and Filipendula ulmaria.

scholarly journals The Health Promoting Bioactivities of Lactuca sativa can be Enhanced by Genetic Modulation of Plant Secondary Metabolites

Metabolites ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 97 ◽  
Author(s):  
Hammad Ismail ◽  
Anna L. Gillespie ◽  
Danielle Calderwood ◽  
Haroon Iqbal ◽  
Colene Gallagher ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Lactuca Sativa ◽  
Genetic Manipulation ◽  
Sesquiterpene Lactones ◽  
Plant Secondary Metabolites ◽  
Rol Genes ◽  
In Vitro Bioactivity ◽  
New Paradigm ◽  
Plant Metabolites

Plant secondary metabolites are protective dietary constituents and rol genes evidently increase the synthesis of these versatile phytochemicals. This study subjected a globally important vegetable, lettuce (Lactuca sativa) to a combination of untargeted metabolomics (LC-QTof-MS) and in vitro bioactivity assays. Specifically, we examined the differences between untransformed cultured lettuce (UnT), lettuce transformed with either rolABC (RA) or rolC (RC) and commercially grown (COM) lettuce. Of the 5333 metabolite features aligned, deconvoluted and quantified 3637, 1792 and 3737 significantly differed in RA, RC and COM, respectively, compared with UnT. In all cases the number of downregulated metabolites exceeded the number increased. In vitro bioactivity assays showed that RA and RC (but not COM) significantly improved the ability of L. sativa to inhibit α-glucosidase, inhibit dipeptidyl peptidase-4 (DPP-4) and stimulate GLP-1 secretion. We putatively identified 76 lettuce metabolites (sesquiterpene lactones, non-phenolic and phenolic compounds) some of which were altered by several thousand percent in RA and RC. Ferulic acid levels increased 3033–9777%, aminooxononanoic acid increased 1141–1803% and 2,3,5,4′tetrahydroxystilbene-2-O-β-d-glucoside increased 40,272–48,008%. Compound activities were confirmed using commercially obtained standards. In conclusion, rol gene transformation significantly alters the metabolome of L.sativa and enhances its antidiabetic properties. There is considerable potential to exploit rol genes to modulate secondary metabolite production for the development of novel functional foods. This investigation serves as a new paradigm whereby genetic manipulation, metabolomic analysis and bioactivity techniques can be combined to enable the discovery of novel natural bioactives and determine the functional significance of plant metabolites.

scholarly journals Optimization of extraction conditions for secondary biomolecules from various plant species

2016 ◽  
Vol 70 (4) ◽  
pp. 473-483 ◽  
Author(s):  
Filip Sibul ◽  
Dejan Orcic ◽  
Emilija Svircev ◽  
Neda Mimica-Dukic
Keyword(s):  
Secondary Metabolites ◽  
Extraction Efficiency ◽  
Sesquiterpene Lactones ◽  
Lupinus Albus ◽  
Plant Secondary Metabolites ◽  
Solvent Mixtures ◽  
Artemisia Absinthium ◽  
Extraction Solvent ◽  
Anthriscus Sylvestris ◽  
Rumex Alpinus

Extraction of plant secondary metabolites is an essential step in isolation of natural products. Non-optimized extraction conditions can lead to losses, degradation and modification of the biomolecules. In this paper, the influence of different solvent mixtures, solvent amounts, temperature, extraction time, and procedures for defatting on yield and profile of various classes of secondary metabolites was investigated. Rumex alpinus was used for the extraction of anthraquinones, Glycine max for isoflavonoids, Chaerophyllum bulbosum for flavonoids and phenolic acids, Anthriscus sylvestris for lignans and coumarins, alkaloids were extracted from Lupinus albus and sesquiterpene lactones from Artemisia absinthium. Extraction efficiency was evaluated by use of LC-DAD-ESI-MS/MS. The compromise extraction solvent for all of the examined compounds is 80 % methanol, mixed in ratio 13 : 1 with plant material. Maceration should last for six hours, repeated four times with fresh solvent. Defatting of the extracts does not lead to significant losses of the compounds of interest. It is acceptable to use extraction and evaporation temperature of 60?C, while the extracts should be stored in the dark, on -20?C.

scholarly journals Sesquiterpene lactones – occurrence and biological properties. A review

2018 ◽  
Vol 73 (3) ◽  
pp. 83-95
Author(s):  
KATARZYNA OLESIŃSKA
Keyword(s):  
Biological Activity ◽  
Secondary Metabolites ◽  
Plant Pathogens ◽  
Higher Plants ◽  
Sesquiterpene Lactones ◽  
Biological Properties ◽  
Chemical Structures ◽  
Potential Source ◽  
Active Substances ◽  
Carbon Pathways

Sesquiterpene lactones are secondary metabolites commonly found in higher plants as well as mosses, lichens, and fungi. Currently, over 5000 of such compounds have been identified with a majority isolated from Asteraceae plants. They are characterised by different chemical structures associated with the presence of various carbon pathways and functional groups, which exert an impact on their pharmacological activity. These colourless substances are soluble in fats, alcohols, or water. They are often bitter ingredients regarded as bitter compounds. They are accumulated mainly in leaves, flower parts and seeds; less frequently, they are present in roots. Sesquiterpene lactones exhibit multidirectional biological activity: some of them have anticancer, anti-inflammatory, antidiabetic, analgesic, antiparasitic, antifungal, and bacteriostatic effects. Therefore, high hopes are placed on the medical and pharmaceutical use of these substances. Lactone compounds are also regarded as a potential source of new active substances used in agriculture to combat plant pathogens

scholarly journals An Analysis of Volatile Components of the Liverworts Dumortiera hirsuta subsp. hirsuta and Dumortiera hirsuta subsp. nepalensis (Dumortieraceae) from Panama and Taxonomic Observations on the Species

2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Armando A. Durant-Archibold ◽  
Noris Salazar Allen ◽  
Anette Garrido ◽  
Jose Gudiño Ledezma ◽  
Mahabir P. Gupta
Keyword(s):  
Mass Spectrometry ◽  
Gas Chromatography ◽  
Chemical Composition ◽  
Solid Phase Microextraction ◽  
Solid Phase ◽  
Gas Chromatography Mass Spectrometry ◽  
Volatile Components ◽  
Chemical Markers ◽  
Headspace Solid Phase Microextraction ◽  
First Time

We report for the first time the chemical composition of volatile components (VOCs) of two subspecies, D. hirsuta subsp. hirsuta and D. hirsuta subsp. nepalensis, of the liverwort Dumortiera hirsuta from Panama by using headspace-solid phase microextraction-gas chromatography-mass spectrometry in order to assess distinguishing markers between the two species. Forty VOCs were identified in total for both subspecies. Of these, 34 are reported for the first time in D. hirsuta. Furthermore, both subspecies showed clear differences in the type and amount of VOCs. The major compounds in D. hirsuta subsp. hirsuta were α-gurjunene, β-selinene, α-guaiene, α-humulene and β-caryophyllene; while in D. hirsuta subsp. nepalensis were ledene, α-gurjunene, β-caryophyllene and α-guaiene, respectively. Two oxygenated sesquiterpenes, globulol and nerolidol, could be considered as possible distinguishing chemical markers between these two subspecies. We conclude that both morphotypes of D. hirsuta are chemically different.

scholarly journals Chemical Profiling of Volatile Components of the Gametophyte and Sporophyte Stages of the Hornwort Leiosporoceros dussii (Leiosporocerotaceae) From Panama by HS-SPME-GC-MS

2019 ◽  
Vol 14 (8) ◽  
pp. 1934578X1986887
Author(s):  
Anette Garrido ◽  
Jose Gudiño Ledezma ◽  
Armando A. Durant-Archibold ◽  
Noris Salazar Allen ◽  
Juan Carlos Villarreal A ◽  
...  
Keyword(s):  
Solid Phase Microextraction ◽  
Solid Phase ◽  
Chemical Constituents ◽  
Gas Chromatography Mass Spectrometry ◽  
Bornyl Acetate ◽  
Volatile Components ◽  
Chemical Markers ◽  
Chemical Profiling ◽  
Volatile Organic ◽  
First Time

We report for the first time the chemical profiling of volatile organic compounds (VOCs) of gametophyte and sporophyte life stages of Leiosporoceros dussii, from Panama by using headspace-solid phase microextraction-gas chromatography-mass spectrometry in order to assess distinguishing chemical markers between the male and female gametophytes, and sporophytes of this hornwort. A total of 27 VOCs were identified in L. dussii. Furthermore, the gametophyte and sporophyte showed clear differences in the type and amount of VOCs. The main constituents of L. dussii female thalli were menthacamphor (17.8%), hexanol (12.3%), and menthyl acetate (12.3%), while the major compounds of the male thalli were hexanol (25.3%), β-ionone (21.1%), benzeneacetaldehyde (17.6%), and β-cyclocitral (14.0%). The main VOCs of the sporophytes were hexanal (19.3%), β-cyclocitral (17.6%), 2-nonenal (15.8%), hexanol (12.5%), and β-ionone (10.2%). Unique compounds found in the female thalli were 3-pentanone, 3-octenol, nonanol, estragole, and menthyl acetate, and in the male thalli were methyl heptenone, nonanal, neoisomenthol, and bornyl acetate. Isomenthol, thymol, isomenthol acetate, and β-methylnaphthalene were only found in the sporophyte. The characteristic VOCs identified in L. dussii suggest a difference between the chemical constituents of L. dussii and other hornworts species. The presence of simple VOCs when compared with compounds previously characterized in another hornwort genera may support the distinct genetic nature of this species.

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