Sesquiterpene Lactones: More Than Protective Plant Compounds With High Toxicity

Padilla-González, Guillermo F.; Santos, Felipe Antunes; Costa, Fernando B. Da

doi:10.1080/07352689.2016.1145956

Cited by 90 publications

(87 citation statements)

References 142 publications

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“…On the other hand, the allelopathic activity of the LS sample could be attributed to the bioactivity of the major compounds of the oxygenated sesquiterpenes (α‐acorenol, trans ‐longipinocarveol, and γ‐eudesmol). Oxygenated terpenes were characterized by their pronounced biological activity, compared with non‐oxygenated terpenes . Besides this, some of these compounds have been reported as antimicrobial, antioxidant, and anticancer agents; however, the allelopathic activity of this compound is still not known.…”

Section: Resultsmentioning

confidence: 99%

Interspecific variation, antioxidant and allelopathic activity of the essential oil from three Launaea species growing naturally in heterogeneous habitats in Egypt

Elshamy

Abd‐ElGawad

El‐Amier

et al. 2019

Flavour & Fragrance J

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Essential oils (EOs) from the aerial parts of three Launaea species collected from two different habitats were extracted [Launaea mucronata collected from coastal desert (LMC) and from inland desert (LMD), Launaea nudicaulis collected from coastal desert (LNC) and from inland desert (LND), Launaea spinosa (LS)]. The EOs were analysed by gas chromatography mass spectrometry (GC‐MS) and tested for antioxidant activity as well for allelopathic activity against purslane. A total of 117 compounds were identified from all samples, including 64 from LS, 50 from LMC, 39 from LMD, 24 from LNC, and 20 from LND, representing 100% of the total oil mass. The oxygenated sesquiterpenes were the major compounds of the EOs from LS, LMC, LMD, LNC, and LND, representing 62.73, 61.02, 58.35, 43.22, and 48.33%, respectively, whereas the monoterpene hydrocarbons were minor compounds in all samples. α‐Acorenol (31.42%), trans‐longipinocarveol (12.04%), and γ‐eudesmol (6.31%) represented the major compounds of the EO from LS, whereas hexahydrofarnesyl acetone and n‐heneicosane represented the major compounds from LMC, LMD, LNC, and LND. Correlations between the EOs of the five samples were studied via principal component analysis and agglomerative hierarchical clustering, based on the chemical composition of the EOs. There was a significant variation between Launaea species regarding both the quality and the quantity of EO composition, whereas no significant difference was observed based on the habitats (coastal and inland deserts). The EOs of the five Launaea samples exhibited meaningful antioxidant activities, as follows: LND > LNC > LMD > LMC > LS. Moreover, the EOs of the five Lanaea samples exhibited significant allelopathic activity against purslane weed in a concentration‐dependent manner. LMD and LMC showed the highest effect, with germination inhibition of 96.1 and 87.9% at 250 μL L−1, and radicle growth inhibition of 92.6 and 89.7%, but LS was the least effective extract. Our results showed that the variation in the quality and quantity of EO composition is mainly species specific, with a slight correlation with habitats.

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Section: Resultsmentioning

confidence: 99%

Interspecific variation, antioxidant and allelopathic activity of the essential oil from three Launaea species growing naturally in heterogeneous habitats in Egypt

Elshamy

Abd‐ElGawad

El‐Amier

et al. 2019

Flavour & Fragrance J

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“…Lupeol showed the highest concentration in leaves (2853 mg kg −1 dw), followed by inflorescences (2265 mg kg −1 dw), flowers (1892 mg kg −1 dw), and stems (774 mg kg −1 dw) . These secondary metabolites play a key role in plants as deterrents against herbivores and as antifungal, antibacterial, and allelopathic agents, insect repellents, and animal allergens . Moreover, STLs contribute to the bitter taste of cardoon and artichoke, attributed to four guaianolides, namely cynaropicrin, dehydrocynaropicrin, grosheimin and cynatriol …”

Section: Bioactive Compoundsmentioning

confidence: 99%

Cardoon as a Sustainable Crop for Biomass and Bioactive Compounds Production

Barracosa

Pires

2019

Chemistry & Biodiversity

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Cardoon is a multi-purpose and versatile Mediterranean crop, adapted to climate change, with a wide spectrum of potential applications due its added value as a rich source of fibers, oils and bioactive compounds. The Cynara species are a component of the Mediterranean diet and have been used as food and medicine since ancient times. The important role of cardoon in human nutrition, as a functional food, is due to its high content of nutraceutical and bioactive compounds such as oligofructose inulin, caffeoylquinic acids, flavonoids, anthocyanins, sesquiterpenes lactones, triterpenes, fatty acids and aspartic proteases. The present review highlights the characteristics and functions of cardoon biomass which permits the development of innovative products in food and nutrition, pharmaceutics and cosmetics, plant protection and biocides, oils and energy, lignocellulose materials, and healthcare industries following the actual trends of a circular economy.

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“…As a unit, the GAS/GAO tandem produces GAA leading to the simplest germacranolide (e.g. costunolide)the non-enzymatic degradation and cyclization of which opens the gateway to diverse elemene, eudesmane and guaiene classes of STLs [5,27]. The evolution history was inferred based on the maximum likelihood method and the JTT matrix-based model.…”

Section: Bsgas1 Forms a Cluster Named Clade I Which Includes Gass Fmentioning

confidence: 99%

Discovery of germacrene A synthases in Barnadesia spinosa: The first committed step in sesquiterpene lactone biosynthesis in the basal member of the Asteraceae

Nguyen

Faraldos

Vardakou

et al. 2016

Biochemical and Biophysical Research Communications

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The Andes-endemic Barnadesioideae lineage is the oldest surviving and phylogenetically basal subfamily of the Asteraceae (Compositae), a prolific group of flowering plants with world-wide distribution (∼24,000 species) marked by a rich diversity of sesquiterpene lactones (STLs). Intriguingly, there is no evidence that members of the Barnadesioideae produce STLs, specialized metabolites thought to have contributed to the adaptive success of the Asteraceae family outside South America. The biosynthesis of STLs requires the intimate expression and functional integration of germacrene A synthase (GAS) and germacrene A oxidase (GAO) to sequentially cyclize and oxidize farnesyl diphosphate into the advanced intermediate germacrene A acid leading to diverse STLs. Our previous discovery of GAO activity conserved across all major subfamilies of Asteraceae, including the phylogenetically basal lineage of Barnadesioideae, prompted further investigation of the presence of the gateway GAS in Barnadesioideae. Herein we isolated two terpene synthases (BsGAS1/BsGAS2) from the basal Barnadesia spinosa (Barnadesioideae) that displayed robust GAS activity when reconstituted in yeast and characterized in vitro. Despite the apparent lack of STLs in the Barnadesioideae, this work unambiguously confirms the presence of GAS in the basal genera of the Asteraceae. Phylogenetic analysis reveals that the two BsGASs fall into two distinct clades of the Asteraceae's GASs, and BsGAS1 clade is only retained in the evolutionary closer Cichorioideae subfamily, implicating BsGAS2 is likely the ancestral base of most GASs found in the lineages outside the Barnadesioideae. Taken together, these results show the enzymatic capacities of GAS and GAO emerged prior to the subsequent radiation of STL-producing Asteraceae subfamilies.

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Sesquiterpene Lactones: More Than Protective Plant Compounds With High Toxicity

Cited by 90 publications

References 142 publications

Interspecific variation, antioxidant and allelopathic activity of the essential oil from three Launaea species growing naturally in heterogeneous habitats in Egypt

Interspecific variation, antioxidant and allelopathic activity of the essential oil from three Launaea species growing naturally in heterogeneous habitats in Egypt

Cardoon as a Sustainable Crop for Biomass and Bioactive Compounds Production

Discovery of germacrene A synthases in Barnadesia spinosa: The first committed step in sesquiterpene lactone biosynthesis in the basal member of the Asteraceae

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