Asteraceae family: a review of its allelopathic potential and the case of Acmella oleracea and Sphagneticola trilobata

Abstract Asteraceae family is as an interesting target for researching natural alternatives for crop protection. Many species from this family grow as weeds, and some of them can influence the development of other species by the allelopathy phenomenon. This paper aimed to review the literature for the main genera and species of the Asteraceae family with allelopathic or phytotoxic potential, as well as the classes of secondary metabolites present in this family and responsible for such activity. Artemisia, Ambrosia, Bellis, Bidens, Helianthus and Tagetes were identified as the main genera with phytotoxic or allelopathic activity. Among the secondary metabolites from this family, terpenes, polyacetylenes, saponins, sesquiterpene lactones, phenolic acids and flavonoids were described as responsible for inhibiting the development of other species. In addition, the phytotoxic potential of Acmella oleracea and Sphagneticola trilobata against the weeds Calopogonium mucunoides. and Ipomoea purpurea was described for the first time. At 0.2 mg/mL, crude extract and fractions of A. oleracea inhibited above 60% of C. mucunoides root growth. Hydroalcoholic extract and fractions of S. trilobata, except hexane, significantly affected I. purpurea root growth, ranging from 38 ± 14% to 59 ± 8% of inhibitory effect at different concentrations (0.19 mg/mL to 1.13 mg/mL).

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Effect of guaianolides in the meiosis reinitiation of amphibian oocytes

Zygote ◽

10.1017/s0967199416000265 ◽

2016 ◽

Vol 25 (1) ◽

pp. 10-16 ◽

Cited By ~ 2

Author(s):

J. Zapata-Martínez ◽

G. Sánchez-Toranzo ◽

F. Chaín ◽

C.A.N. Catalán ◽

M.I. Bühler

Keyword(s):

Biological Activities ◽

Wide Spectrum ◽

Sesquiterpene Lactones ◽

Inhibitory Effect ◽

Biological Molecules ◽

Plant Metabolites ◽

Major Mechanism ◽

Bufo Arenarum ◽

Asteraceae Family

SummarySesquiterpene lactones (STLs) are a large and structurally diverse group of plant metabolites generally found in the Asteraceae family. STLs exhibit a wide spectrum of biological activities and it is generally accepted that their major mechanism of action is the alkylation of the thiol groups of biological molecules. The guaianolides is one of various groups of STLs. Anti-tumour and anti-migraine effects, an allergenic agent, an inhibitor of smooth muscle cells and of meristematic cell proliferation are only a few of the most commonly reported activities of STLs. In amphibians, fully grown ovarian oocytes are arrested at the beginning of meiosis I. Under stimulus with progesterone, this meiotic arrest is released and meiosis progresses to metaphase II, a process known as oocyte maturation. There are previous records of the inhibitory effect of dehydroleucodin (DhL), a guaianolide lactone, on the progression of meiosis. It has been also shown that DhL and its 11,13-dihydroderivative (2H-DhL; a mixture of epimers at C-11) act as blockers of the resumption of meiosis in fully grown ovarian oocytes from the amphibian Rhinella arenarum (formerly classified as Bufo arenarum). The aim of this study was to analyze the effect of four closely related guaianolides, i.e., DhL, achillin, desacetoxymatricarin and estafietin as possible inhibitors of meiosis in oocytes of amphibians in vitro and discuss some structure–activity relationships. It was found that the inhibitory effect on meiosis resumption is greater when the lactone has two potentially reactive centres, either a α,β–α′,β′-diunsaturated cyclopentanone moiety or an epoxide group plus an exo-methylene-γ-lactone function.

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Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes

Zygote ◽

10.1017/s0967199413000695 ◽

2014 ◽

Vol 23 (3) ◽

pp. 406-411

Author(s):

G. Sánchez-Toranzo ◽

J. Zapata-Martínez ◽

C. Catalán ◽

M.I. Bühler

Keyword(s):

Sesquiterpene Lactones ◽

Plant Secondary Metabolites ◽

Inhibitory Effect ◽

Inhibitory Effects ◽

Different Types ◽

Low Toxicity ◽

Rhinella Arenarum ◽

High Degree ◽

Asteraceae Family

SummaryThe sesquiterpene lactones (STLs) are a large class of plant secondary metabolites that are generally found in the Asteraceae family and that have high diversity with respect to chemical structure as well as biological activity. STLs have been classified into different groups, such as guaianolides, germacranolides, and melampolides etc., based on their carboxylic skeleton. In amphibians, fully grown ovarian oocytes are arrested at the beginning of meiosis I. Under the stimulus of progesterone, this meiotic arrest is released and meiosis progresses to metaphase II, a process known as oocyte maturation. The purpose of this work was to determine whether sesquiterpene lactones from the germacranolide and melampolide groups act as inhibitor agents on the meiosis of amphibian oocytes in vitro. Results for germacranolides indicated that the addition of deoxyelephantopins caused a high degree of inhibition and that minimolide showed a moderate inhibitory effect, whereas glaucolide A was inactive. Furthermore, the addition of melampolides (uvedalin, enhydrin, polymatin A and polymatin B) showed inhibitory effects. For enhydrin and uvedalin, inhibitory effects were observed at the higher concentrations assayed. The results of this study suggest that the inhibitory activity of the tested sesquiterpene lactones on the meiosis of Rhinella arenarum oocytes is not dependent on the group to which they belong, i.e. not on the carboxylic skeleton, but probably due to the arrangement and type of function groups present in the molecules. All assayed lactones in the germacranolide group showed low toxicity. In contrast, important differences in toxicity were observed for lactones from the melampolide group: enhydrin and uvedalin showed low toxicity, but polymatin A and B were highly toxic.

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Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and α-glycosidase inhibitors

Zeitschrift für Naturforschung C ◽

10.1515/znc-2020-0026 ◽

2020 ◽

Vol 75 (5-6) ◽

pp. 153-159

Author(s):

Tuba Aydin

Keyword(s):

Secondary Metabolites ◽

Carbonic Anhydrase ◽

Folk Medicine ◽

Inhibitory Effect ◽

Glycosidase Inhibitors ◽

Meoh Extract ◽

Chemical Structures ◽

Liquid Chromatography Tandem Mass ◽

First Time

AbstractHelichrysum plicatum species are used in Turkish folk medicine as lithagogue, diuretic, and nephritic. Research on the methanol (MeOH) extract of flowers of H. plicatum DC. subsp. plicatum resulted in the isolation of eight known compounds (1–8). The chemical structures of the compounds were determined as β-sitosterol (1), apigenin (2), nonacosanoic acid (3), astragalin (4), β-sitosterol-3-O-β-D-glucopyranoside (5), helichrysin A (6), helichrysin B (7), and isosalipurposide (8) by spectroscopic and chromatographic/spectrometric methods, including 1D and 2D nuclear magnetic resonance and liquid chromatography-tandem mass spectrometry. Nonacosanoic acid (3) was isolated for the first time from H. plicatum DC. subsp. plicatum. The MeOH extract and isolated compounds were evaluated for their in vitro human carbonic anhydrase I (hCAI) and II (hCAII), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase inhibitory activities. The IC50 values of H. plicatum DC. subsp. plicatum MeOH extract for hCAI, hCAII, AChE, BChE, and α-glycosidase were found to be 77.87, 52.90, 115.50, 117.46, and 81.53 mg/mL, respectively. The compounds showed IC50 values of 1.43–4.47, 1.40–4.32, 1.69–2.90, 1.09–3.89, and 1.61–3.80 μM against hCAI, hCAII, AChE, BChE, and α-glycosidase, respectively. In summary, H. plicatum DC. subsp. plicatum secondary metabolites demonstrated strong inhibitory effects especially against hCAI and hCAII, whereas the MeOH extract showed a weak inhibitory effect on all enzymes.

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Genetic background of sesquiterpene lactones biosynthesis in Asteraceae. A review

Agronomy Science ◽

10.24326/as.2021.3.4 ◽

2021 ◽

Vol 76 (3) ◽

pp. 49-60

Author(s):

Magdalena Sozoniuk

Keyword(s):

Transcription Factors ◽

Metabolic Engineering ◽

Secondary Metabolites ◽

Genetic Background ◽

Host Plants ◽

Biosynthetic Pathway ◽

Sesquiterpene Lactones ◽

Biosynthesis Pathway ◽

Heterologous System ◽

Asteraceae Family

Asteraceae family is a rich source of many sesquiterpene lactones (STLs). These secondary metabolites exhibit multidirectional activity including anti-tumor, anti-inflammatory or antimicrobial, just to name a few. Promising approach of metabolic engineering offers a way of increasing the production of STLs by reconstruction of their biosynthetic pathway in a heterologous system. Moreover, their production in host plants might be increased through overexpression of biosynthetic genes and/or transcription factors (TFs) positively regulating the pathway. Either of the strategies requires extensive knowledge on the genetic background of STLs biosynthesis pathway. This review summarizes molecular investigations concerning biosynthesis of these medicinally essential metabolites.

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COMPONENTS OF ARTEMISIA SOGDIANA

chemistry of plant raw material ◽

10.14258/jcprm.2020015548 ◽

2020 ◽

pp. 207-214

Author(s):

Rimma Fail'yevna Mukhamatkhanova ◽

Khayrulla Mamadievich Bobakulov ◽

Il'dar Dzhamil'yevich Sham’yanov ◽

Rasul Yangiberdievich Оkmanov ◽

Haji Akber Aisa ◽

...

Keyword(s):

Pharmaceutical Industry ◽

Secondary Metabolites ◽

Aerial Part ◽

Sesquiterpene Lactones ◽

Biologically Active ◽

Phytochemical Study ◽

Alcohol Extract ◽

Effective Use ◽

Medicinal Flora ◽

First Time

Phytochemical research and effective use of medicinal flora in the future create the basis for the development of the domestic pharmaceutical industry and allow not only to fill the deficit of drugs, but also contribute to the development of new, environmentally friendly and a number of qualities of unique, export-oriented preparations. The plants of the genus Artemisia L. are rich sources of biologically active secondary metabolites. Phytochemical study of secondary metabolites of plants of the genus Artemisia has led to the creation on their basis, in particular, on the sesquiterpene lactones, antitumor (Artemisinin and its derivatives; Arglabin), antiatherosclerotic (Leucomisin (preparation Oligvon)), cardiotonic (Tauremisin), anthelmintic (α-Santonin) and antimalarial (Artemisinin and its derivatives) preparations. In order to search for natural biologically active compounds, we studied the components of the alcohol extract of the aerial part of Artemisia sogdiana Bunge, collected during budding in the Zaamin district of the Jizzakh region of Uzbekistan. The result of phytochemical research for the first time from this plant is isolated a phenolic compound xanthoxylin, sesquiterpene lactone artesin, flavonoids genkwanin and eupatilin, the structure of which is established on the basis of spectral data.

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A New Flavanone from the Leaves of Chromolaena odorata

Natural Product Communications ◽

10.1177/1934578x1501000918 ◽

2015 ◽

Vol 10 (9) ◽

pp. 1934578X1501000

Author(s):

Lakshmareddy Emani ◽

Suryachandrarao Ravada ◽

Bharani Meka ◽

Machiraju Garaga ◽

Trimurtulu Golakoti

Keyword(s):

Secondary Metabolites ◽

Natural Source ◽

Chromolaena Odorata ◽

Perennial Plant ◽

Phytochemical Investigation ◽

Anti Oxidant ◽

First Time ◽

Asteraceae Family

Chromolaena odorata (Syn: Eupatorium odoratum) is a perennial plant belonging to the Asteraceae family. Extracts of C. odorata have shown strong anti-oxidant and moderate anti-adipogenenesis activities. Detailed phytochemical investigation of C. odorata led to the isolation of 21 secondary metabolites, which include a new flavanone (3), and a chalcone, 3,2′-dihydroxy-4,4′,5′,6′-tetramethoxychalcone (2), reported for the first time from a natural source, besides three known compounds 1, 4 and 5, all of which are reported for the first time from C. odorata. Some of these compounds exhibited potent anti-oxidant and anti-adipogenesis activities and these may be partly responsible for the activity of the extract.

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The impact of traditional plants and their secondary metabolites in the discovery of COVID-19 treatment

Current Pharmaceutical Design ◽

10.2174/1381612826666201118103416 ◽

2020 ◽

Vol 26 ◽

Author(s):

Shabana Bibi ◽

Ayesha Sarfraz ◽

Ghazala Mustafa ◽

Zeeshan Ahmed ◽

Muhammad Aurang Zeb ◽

...

Keyword(s):

Secondary Metabolites ◽

Test System ◽

Chemical Information ◽

System Type ◽

The Family ◽

Comprehensive Search ◽

Coronavirus Infection ◽

The Impact ◽

First Time ◽

Plant Sources

Background: Coronavirus Disease-2019 belongs to the family of viruses which cause a serious pneumonia along with fever, breathing issues and infection of lungs for the first time in China and later spread worldwide. Objective: Several studies and clinical trials have been conducted to identify potential drugs and vaccines for Coronavirus Disease-2019. The present study listed natural secondary metabolites identified from plant sources with antiviral properties and could be safer and tolerable treatment for Coronavirus Disease-2019. Methods: A comprehensive search on the reported studies was conducted using different search engine such as Google scholar, SciFinder, Sciencedirect, Medline PubMed, and Scopus for the collection of research articles based on plantderived secondary metabolites, herbal extracts, and traditional medicine for coronavirus infections. Results: Status of COVID-19 worldwide and information of important molecular targets involved in COVID-19 is described and through literature search, is highlighted that numerous plant species and their extracts possess antiviral properties and studied with respect to Coronavirus treatments. Chemical information, plant source, test system type with mechanism of action for each secondary metabolite is also mentioned in this review paper. Conclusion: The present review has listed plants that have presented antiviral potential in the previous coronavirus pandemics and their secondary metabolites which could be significant for the development of novel and a safer drug which could prevent and cure coronavirus infection worldwide.

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

Pharmaceutics ◽

10.3390/pharmaceutics13050713 ◽

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.

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Secondary Metabolites from Artemisia Genus as Biopesticides and Innovative Nano-Based Application Strategies

Molecules ◽

10.3390/molecules26103061 ◽

2021 ◽

Vol 26 (10) ◽

pp. 3061

Author(s):

Bianca Ivănescu ◽

Ana Flavia Burlec ◽

Florina Crivoi ◽

Crăița Roșu ◽

Andreia Corciovă

Keyword(s):

Secondary Metabolites ◽

Negative Impact ◽

Crop Protection ◽

Duration Of Action ◽

Worldwide Distribution ◽

Artemisia Species ◽

Extended Duration ◽

Reduced Toxicity ◽

Available Information ◽

Potential Use

The Artemisia genus includes a large number of species with worldwide distribution and diverse chemical composition. The secondary metabolites of Artemisia species have numerous applications in the health, cosmetics, and food sectors. Moreover, many compounds of this genus are known for their antimicrobial, insecticidal, parasiticidal, and phytotoxic properties, which recommend them as possible biological control agents against plant pests. This paper aims to evaluate the latest available information related to the pesticidal properties of Artemisia compounds and extracts and their potential use in crop protection. Another aspect discussed in this review is the use of nanotechnology as a valuable trend for obtaining pesticides. Nanoparticles, nanoemulsions, and nanocapsules represent a more efficient method of biopesticide delivery with increased stability and potency, reduced toxicity, and extended duration of action. Given the negative impact of synthetic pesticides on human health and on the environment, Artemisia-derived biopesticides and their nanoformulations emerge as promising ecofriendly alternatives to pest management.

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Brassinolide Enhances the Level of Brassinosteroids, Protein, Pigments, and Monosaccharides in Wolffia arrhiza Treated with Brassinazole

Plants ◽

10.3390/plants10071311 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1311

Author(s):

Magdalena Chmur ◽

Andrzej Bajguz

Keyword(s):

Plant Growth ◽

Growth And Development ◽

Inhibitory Effect ◽

Dependent Manner ◽

Plant Growth And Development ◽

Concentration Dependent Manner ◽

Spectrophotometric Methods ◽

Synthetic Inhibitor ◽

Wolffia Arrhiza ◽

First Time

Brassinolide (BL) represents brassinosteroids (BRs)—a group of phytohormones that are essential for plant growth and development. Brassinazole (Brz) is as a synthetic inhibitor of BRs’ biosynthesis. In the present study, the responses of Wolffia arrhiza to the treatment with BL, Brz, and the combination of BL with Brz were analyzed. The analysis of BRs and Brz was performed using LC-MS/MS. The photosynthetic pigments (chlorophylls, carotenes, and xanthophylls) levels were determined using HPLC, but protein and monosaccharides level using spectrophotometric methods. The obtained results indicated that BL and Brz influence W. arrhiza cultures in a concentration-dependent manner. The most stimulatory effects on the growth, level of BRs (BL, 24-epibrassinolide, 28-homobrassinolide, 28-norbrassinolide, catasterone, castasterone, 24-epicastasterone, typhasterol, and 6-deoxytyphasterol), and the content of pigments, protein, and monosaccharides, were observed in plants treated with 0.1 µM BL. Whereas the application of 1 µM and 10 µM Brz caused a significant decrease in duckweed weight and level of targeted compounds. Application of BL caused the mitigation of the Brz inhibitory effect and enhanced the BR level in duckweed treated with Brz. The level of BRs was reported for the first time in duckweed treated with BL and/or Brz.

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