Antibacterial profiling of abietane-type diterpenoids

Helfenstein, Andreas; Vahermo, Mikko; Nawrot, Dorota A.; Demirci, Fatih; İşcan, Gökalp; Krogerus, Sara; Yli‐Kauhaluoma, Jari; Moreira, Vânia M.; Tammela, Päivi

doi:10.1016/j.bmc.2016.10.019

Cited by 49 publications

(29 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Abietane diterpene resin acids were also stimulated by the treatment, particularly concerning palustric acid intermediates. These diterpenes are reported to function as antioxidants to protect membranes from oxidative stress (Munné-Bosch et al, 1999) and to display antibacterial and antifungal activity (Helfenstein et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

A Combined Phenotypic and Metabolomic Approach for Elucidating the Biostimulant Action of a Plant-Derived Protein Hydrolysate on Tomato Grown Under Limited Water Availability

et al. 2019

View full text Add to dashboard Cite

Plant-derived protein hydrolysates (PHs) are an important category of biostimulants able to increase plant growth and crop yield especially under environmental stress conditions. PHs can be applied as foliar spray or soil drench. Foliar spray is generally applied to achieve a relatively short-term response, whereas soil drench is used when a long-term effect is desired. The aim of the study was to elucidate the biostimulant action of PH application method (foliar spray or substrate drench) on morpho-physiological traits and metabolic profile of tomato grown under limited water availability. An untreated control was also included. A high-throughput image-based phenotyping (HTP) approach was used to non-destructively monitor the crop response under limited water availability (40% of container capacity) in a controlled environment. Moreover, metabolic profile of leaves was determined at the end of the trial. Dry biomass of shoots at the end of the trial was significantly correlated with number of green pixels ( R 2 = 0.90) and projected shoot area, respectively. Both drench and foliar treatments had a positive impact on the digital biomass compared to control while the photosynthetic performance of the plants was slightly influenced by treatments. Overall drench application under limited water availability more positively influenced biomass accumulation and metabolic profile than foliar application. Significantly higher transpiration use efficiency was observed with PH-drench applications indicating better stomatal conductance. The mass-spectrometry based metabolomic analysis allowed the identification of distinct biochemical signatures in PH-treated plants. Metabolomic changes involved a wide and organized range of biochemical processes that included, among others, phytohormones (notably a decrease in cytokinins and an accumulation of salicylates) and lipids (including membrane lipids, sterols, and terpenes). From a general perspective, treated tomato plants exhibited an improved tolerance to reactive oxygen species (ROS)-mediated oxidative imbalance. Such capability to cope with oxidative stress might have resulted from a coordinated action of signaling compounds (salicylic acid and hydroxycinnamic amides), radical scavengers such as carotenoids and prenyl quinones, as well as a reduced biosynthesis of tetrapyrrole coproporphyrins.

show abstract

Section: Discussionmentioning

confidence: 99%

A Combined Phenotypic and Metabolomic Approach for Elucidating the Biostimulant Action of a Plant-Derived Protein Hydrolysate on Tomato Grown Under Limited Water Availability

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Abietic acid and dehydroabietic acid, in a shortage of antibiotics and antimicrobial resistance problems looming against the growing respect, showing potential value. Helfenstein et al ( 2017 ) discovered a dehydroabietic acid derivative 64 containing a serine side chain; its MIC 90 against Staphylococcus aureus ATCC 25923 was 60 μg/mL, and the IC 50 value on Balb/c 3T3L cells was 45 μg /mL ( Figure 8C ).…”

Section: Application Of Amino Acids In the Structural Modification Of Natural Productsmentioning

confidence: 99%

Application of Amino Acids in the Structural Modification of Natural Products: A Review

Deng

et al. 2021

Front. Chem.

View full text Add to dashboard Cite

Natural products and their derivatives are important sources for drug discovery; however, they usually have poor solubility and low activity and require structural modification. Amino acids are highly soluble in water and have a wide range of activities. The introduction of amino acids into natural products is expected to improve the performance of these products and minimize their adverse effects. Therefore, this review summarizes the application of amino acids in the structural modification of natural products and provides a theoretical basis for the structural modification of natural products in the future. The articles were divided into six types based on the backbone structures of the natural products, and the related applications of amino acids in the structural modification of natural products were discussed in detail.

show abstract

“…Abietanes are a family of natural tricyclic diterpenoids with interesting pharmacological activity including antitumor, antimicrobial, antiviral, antiulcer, and anti-inflammatory activities [5,6,7,8,9]. Interestingly, dehydroabietic acid (DHAA) and its derivatives have exhibited a broad spectrum of biological activities including antibacterial [10,11,12,13], antifungal [14], antiprotozoal [15], antiviral [16], antiulcer [17], antiherpetic [18] and anti-aging [19]. Especially, a number of DHAA derivatives have been reported in recent years which showed significant antitumor property through DNA binding, apoptosis or oncosis inducing mechanisms [20,21,22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety

Huang

et al. 2019

Molecules

View full text Add to dashboard Cite

To discover novel potent cytotoxic diterpenoids, a series of hybrids of dehydroabietic acid containing 1,2,3-triazole moiety were designed and synthesized. The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS and elemental analysis techniques. The in vitro cytotoxicity of these compounds was evaluated by standard MTT (methyl thiazolytetrazolium) assay against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), BEL-7402 (liver) human carcinoma cell lines and human normal liver cell (HL-7702). The screening results revealed that most of the hybrids showed significantly improved cytotoxicity over parent compound DHAA. Among them, [1-(3-fluorobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3c), and [1-(2-nitrobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3k) displayed better antiproliferative activity with IC50 (50% inhibitory concentration) values of 5.90 ± 0.41 and 6.25 ± 0.37 µM toward HepG2 cells compared to cisplatin, while they exhibited lower cytotoxicity against HL-7702. Therefore, the 1,2,3-triazole-hybrids could be a promising strategy for the synthesis of antitumor diterpenoids and it also proved the essential role of 1,2,3-triazole moiety of DHAA in the biological activity.

show abstract

Antibacterial profiling of abietane-type diterpenoids

Cited by 49 publications

References 26 publications

A Combined Phenotypic and Metabolomic Approach for Elucidating the Biostimulant Action of a Plant-Derived Protein Hydrolysate on Tomato Grown Under Limited Water Availability

A Combined Phenotypic and Metabolomic Approach for Elucidating the Biostimulant Action of a Plant-Derived Protein Hydrolysate on Tomato Grown Under Limited Water Availability

Application of Amino Acids in the Structural Modification of Natural Products: A Review

Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety

Contact Info

Product

Resources

About