Fatty acid and 3‐hydroxy fatty acid composition of two <i>Hypericum</i> species from Turkey

Özen, Hasan Çetin; Başshan, Mehmet; Keskin, Cumali; Toker, Zuhal

doi:10.1002/ejlt.200300828

Cited by 14 publications

(5 citation statements)

References 8 publications

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“…The 3‐hydroxy fatty acids are an important class of microbial lipids that have been extensively used as biomarkers to aid microbial characterisation 35 . This class of compound is an unusual plant component, but the 3OH‐C18:0 was previously detected in leaves and flowers of some Hypericum species 36 . Besides 3OH‐C18:0, two other long chain fatty acids, C18:1 and C18:2, were identified only in rosemary leaf extracts.…”

Section: Resultsmentioning

confidence: 99%

“…35 This class of compound is an unusual plant component, but the 3OH-C18:0 was previously detected in leaves and flowers of some Hypericum species. 36 Besides 3OH-C18:0, two other long chain fatty acids, C18:1 and C18:2, were identified only in rosemary leaf extracts. Previous authors have detected these compounds in the essential oil of rosemary leaves.…”

Section: Antioxidant Activitymentioning

confidence: 94%

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Metabolomics and chemometrics of seven aromatic plants: Carob, eucalyptus, laurel, mint, myrtle, rosemary and strawberry tree

Falco

Grauso

Fiore

et al. 2022

Phytochemical Analysis

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Introduction: Arbutus unedo L. (strawberry tree), Ceratonia siliqua L. (carob), Eucalyptus camaldulensis Dehnh. (eucalyptus), Laurus nobilis L. (laurel), Mentha aquatica L. (water mint), Myrtus communis L. (common myrtle), and Rosmarinus officinalis L. (rosemary) are aromatic plants from the Mediterranean region whose parts and preparations are used for their nutritional properties and health benefits.Objectives: To evaluate and compare the metabolites profile, total phenol content (TPC), and antioxidant activity of plant leaves for their future use. Gas chromatography-mass spectrometry (GC-MS) was used for metabolomics. Data comparison was performed by chemometrics.Methodology: Polar and apolar extracts were analysed using untargeted GC-MS metabolomics followed by chemometrics (principal component analysis, heatmap correlation and dendrogram) to identify, quantify and compare the major organic compounds in the plants. Additionally, nuclear magnetic resonance (NMR) spectroscopy was used for the laurel polar extract to identify D-gluco-L-glycero-3-octulose whose presence was unclear from the GC-MS data. TPC and antioxidant assays were performed using classical methods (Folin-Ciocalteu, 2,2 0 -azinobis-(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH)) and correlated to the phytochemical profiles.Results: Forty-three metabolites were identified including amino acids, organic acids, carbohydrates, phenols, polyols, fatty acids, and alkanes. Eight metabolites (D-fructose, D-glucose, D-mannose, gallic acid, quinic acid, myo-inositol, palmitic and stearic acids) were in common between all species. D-Gluco-L-glycero-3-octulose (37.29 ± 1.19%), D-pinitol (31.33 ± 5.12%), and arbutin (1.30 ± 0.44%,) were characteristic compounds of laurel, carob, and strawberry tree, respectively. Carob showed the highest values of TPC and antioxidant activity.Conclusion: GC-MS metabolomics and chemometrics analyses are fast and useful methods to determine and compare the metabolomics profiling of aromatic plants of food and industrial interest.

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Section: Resultsmentioning

confidence: 99%

Section: Antioxidant Activitymentioning

confidence: 94%

Metabolomics and chemometrics of seven aromatic plants: Carob, eucalyptus, laurel, mint, myrtle, rosemary and strawberry tree

Falco

Grauso

Fiore

et al. 2022

Phytochemical Analysis

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“…Developing recombinant ALT enzymes with greatly increased 3-OH FA productivity could be achievable in the near future, as certain features of the ALT catalytic domain that can be manipulated to boost affinity for 3-OH fatty acyl-ACPs were uncovered in the present study. The capability of ALTs to act on 3-hydroxy-ACP intermediates of fatty acid biosynthesis could also prove useful in plant systems; however, while 3-hydroxy fatty acids are well-known components of bacterial endotoxins, they are rarely documented as plant metabolites outside of fatty acid biosynthesis, especially in the medium-chain length range [63][64][65]. It is unknown whether recombinant ALTs with preference for 3-hydroxyacyl-ACPs in E. coli would retain these preferences in planta.…”

Section: Alt Variants Have Unique Potential As Metabolic Engineering ...mentioning

confidence: 99%

Determinants of substrate specificity in a catalytically diverse family of acyl-ACP thioesterases from plants

Kalinger

Rowland

2023

BMC Plant Biol

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Background ACYL-LIPID THIOESTERASES (ALTs) are a subclass of plastid-localized, fatty acyl-acyl carrier protein (ACP) thioesterase enzymes from plants. They belong to the single hot dog-fold protein family. ALT enzymes generate medium-chain (C6-C14) and C16 fatty acids, methylketone precursors (β-keto fatty acids), and 3-hydroxy fatty acids when expressed heterologously in E. coli. The diverse substrate chain-length and oxidation state preferences of ALTs set them apart from other plant acyl-ACP thioesterases, and ALTs show promise as metabolic engineering tools to produce high-value medium-chain fatty acids and methylketones in bacterial or plant systems. Here, we used a targeted motif-swapping approach to explore connections between ALT protein sequence and substrate specificity. Guided by comparative motif searches and computational modelling, we exchanged regions of amino acid sequence between ALT-type thioesterases from Arabidopsis thaliana, Medicago truncatula, and Zea mays to create chimeric ALT proteins. Results Comparing the activity profiles of chimeric ALTs in E. coli to their wild-type counterparts led to the identification of interacting regions within the thioesterase domain that shape substrate specificity and enzyme activity. Notably, the presence of a 31-CQH[G/C]RH-36 motif on the central α-helix was shown to shift chain-length specificity towards 12–14 carbon chains, and to be a core determinant of substrate specificity in ALT-type thioesterases with preference for 12–14 carbon 3-hydroxyacyl- and β-ketoacyl-ACP substrates. For an ALT containing this motif to be functional, an additional 108-KXXA-111 motif and compatible sequence spanning aa77–93 of the surrounding β-sheet must also be present, demonstrating that interactions between residues in these regions of the catalytic domain are critical to thioesterase activity. The behaviour of chimeric enzymes in E. coli also indicated that aa77–93 play a significant role in dictating whether an ALT will prefer ≤10-carbon or ≥ 12-carbon acyl chain-lengths, and aa91–96 influence selectivity for substrates of fully or partially reduced oxidation states. Additionally, aa64–67 on the hot dog-fold β-sheet were shown to be important for enabling an ALT to act on 3-hydroxy fatty acyl-ACP substrates. Conclusions By revealing connections between thioesterase sequence and substrate specificity, this study is an advancement towards engineering recombinant ALTs with product profiles suited for specific applications.

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“…Chapter 5: Summary of findings and future research directions While medium-chain fatty acids (FAs) and β-keto fatty acids (β-keto FAs) had been previously reported as products of Arabidopsis and wild tomato ALT enzymes, this work demonstrated that ALTs also generate medium-chain 3-hydroxy fatty acids (3-OH FAs). This is highly novel, as medium-chain 3-OH FAs had not been previously recorded as products of plant acyl-ACP thioesterases, and are rarely documented in plants outside of their role as intermediates in de novo fatty acid synthesis (Racovita et al, 2015;Clericuzio et al, 2017;Özen et al, 2004). As a result of ALT activity, many more plant species than presently known may produce medium-chain 3-OH FAs as secondary metabolites, with biological functions that are as of yet unexplored.…”

Section: -Conclusionmentioning

confidence: 95%

“…Developing recombinant ALT enzymes with greatly increased 3-OH FA productivity could be achievable in the near future, as certain features of the ALT catalytic domain that can be manipulated to boost affinity for 3-OH fatty acyl-ACPs were uncovered in the present study. The capability of ALTs to act on 3-hydroxy-ACP intermediates of fatty acid biosynthesis could also prove useful in plant systems; however, while 3-hydroxy fatty acids are well-known components of bacterial endotoxins, they are rarely documented as plant metabolites outside of fatty acid biosynthesis, especially in the mediumchain length range (Racovita et al, 2015;Clericuzio et al, 2017;Özen et al, 2004). It is unknown whether recombinant ALTs with preference for 3-hydroxyacyl-ACPs in E. coli would retain these preferences in planta.…”

Section: -Alt Variants Have Unique Potential As Metabolic Engineering...mentioning

confidence: 99%

Characterization of acyl-lipid thioesterase (ALT) enzymes from plants

Kalinger

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Fatty acid and 3‐hydroxy fatty acid composition of two Hypericum species from Turkey

Cited by 14 publications

References 8 publications

Metabolomics and chemometrics of seven aromatic plants: Carob, eucalyptus, laurel, mint, myrtle, rosemary and strawberry tree

Metabolomics and chemometrics of seven aromatic plants: Carob, eucalyptus, laurel, mint, myrtle, rosemary and strawberry tree

Determinants of substrate specificity in a catalytically diverse family of acyl-ACP thioesterases from plants

Characterization of acyl-lipid thioesterase (ALT) enzymes from plants

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