Synthesis and biological activity of nitrogen-containing derivatives of methyl dehydroabietate

Толмачева, И. А.; Tarantin, A. V.; Boteva, A. A.; Аникина, Л. В.; Vikharev, Yu. B.; Гришко, В. В.; Толстиков, А. Г.

doi:10.1007/s11094-006-0161-0

Cited by 11 publications

(7 citation statements)

References 10 publications

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“…Up to date, RA-derived compounds with different pharmacological effects—anti-inflammatory [77], antimicrobial [12,78], fungicidal [12,22,23,79], anxiolytic [80], antiviral [23], antitumor [23,43,81], and anti-angiogenic [82]—have been described. In addition, RA derivatives can be used as intermediates in the synthesis of bioactive compounds [13,83] and pharmaceuticals [84,85].…”

Section: Biotransformation Of Ras To Bioactive Compoundsmentioning

confidence: 99%

Microbial Conversion of Toxic Resin Acids

et al. 2019

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Organic wood extractives—resin acids—significantly contribute to an increase in the toxicity level of pulp and paper industry effluents. Entering open ecosystems, resin acids accumulate and have toxic effects on living organisms, which can lead to the ecological imbalance. Among the most effective methods applied to neutralize these ecotoxicants is enzymatic detoxification using microorganisms. A fundamental interest in the in-depth study of the oxidation mechanisms of resin acids and the search for their key biodegraders is increasing every year. Compounds from this group receive attention because of the need to develop highly effective procedures of resin acid removal from pulp and paper effluents and also the possibility to obtain their derivatives with pronounced pharmacological effects. Over the past fifteen years, this is the first report analyzing the data on distribution, the impacts on living organisms, and the microbial transformation of resin acids. Using the example of dehydroabietic acid—the dominant compound of resin acids in effluents—the review discusses the features of interactions between microorganisms and this pollutant and also highlights the pathways and main products of resin acid bioconversion.

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Section: Biotransformation Of Ras To Bioactive Compoundsmentioning

confidence: 99%

Microbial Conversion of Toxic Resin Acids

et al. 2019

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“…Despite the numerous biological activities that have been reported for DAA (Kang et al, 2009;Ohwada et al, 2003;Savluchinske-Feio et al, 2007;Tagat et al, 1994;Takahashi et al, 2011;Tanaka et al, 2008;Tolmacheva et al, 2006;Wada et al, 1985), the anti-aging effect of DAA has surprisingly not been studied. We used the Caenorhabditis elegans (C. elegans) wild-type N2 strain as a model organism of aging, to observe the lifespan extension effects of DAA.…”

Section: Daa Extends the Lifespan Of Wild-type C Elegans N2mentioning

confidence: 99%

“…DAA improves diabetes and hyperlipidemia in obese diabetic mice (Kang et al, 2009), activates peroxisome proliferatoractivated receptor-γ (PPAR-γ) and stimulates insulin-dependent glucose uptake into 3T3-L1 adipocytes (Takahashi et al, 2011). DAA has also shown antiulcer, antimicrobial, anxiolytic, antiviral, and antitumor activities (Savluchinske-Feio et al, 2007;Tagat et al, 1994;Tanaka et al, 2008;Tolmacheva et al, 2006;Wada et al, 1985). Recent studies have confirmed that DAA is a chemical modulator that opens large-conductance calcium-activated BK channels (Ohwada et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

The natural phytochemical dehydroabietic acid is an anti-aging reagent that mediates the direct activation of SIRT1

Kim

Kang

Lee

et al. 2015

Molecular and Cellular Endocrinology

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“…DHA is a naturally occurring tricyclic diterpenic resin acid, which can easily be obtained from Pinus rosin or commercial disproportionated rosin [ 6 ]. Recently, DHA and its derivatives were claimed to possess a wide range of biological and pharmacological activities, such as antiprotozoal [ 7 ], antiulcer [ 8 ], anti-inflammatory [ 9 ], immunomodulatory, antiviral [ 10 ], antimicrobial [ 11 , 12 ], antifungal [ 13 ], anxiolytic [ 14 ], anti-aging [ 15 ], gastroprotective [ 16 ], and BK channel-opening [ 17 ] activities. In addition, in recent years a number of DHA derivatives have been reported to have anticancer activity in many human cancer cells such as cervical carcinoma cells, hepatocarcinoma cells, lung cancer cells, prostate cancer cells, ovarian cancer cells, and breast cancer cells [ 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Anticancer Activity of Novel Dehydroabietic Acid-Based Acylhydrazones

Wang

Duan

et al. 2017

Molecules

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In order to develop novel chemotherapeutic agents with potent anticancer activities, a series of dehydroabietic acid (DHA) derivatives bearing an acylhydrazone moiety were designed and synthesized by the condensation between dehydroabietic acylhydrazide (3) and a variety of substituted arylaldehydes. The inhibitory activities of these compounds against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), and BEL-7402 (liver) human carcinoma cell lines were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay in vitro. The screening results revealed that many of the compounds showed moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed similar potent inhibitory activities to the commercial anticancer drug cisplatin, while they exhibited lower cytotoxicity against normal human liver cell (HL-7702). Particularly, compound 4w, N’-(3,5-difluorobenzylidene)-2-(dehydroabietyloxy)acetohydrazide, with an IC50 (50% inhibitory concentration) value of 2.21 μM against HeLa cell, was about 17-fold more active than that of the parent compound, and showed remarkable cytotoxicity with an IC50 value of 14.46 μM against BEL-7402 cell. These results provide an encouraging framework that could lead to the development of potent novel anticancer agents.

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Synthesis and biological activity of nitrogen-containing derivatives of methyl dehydroabietate

Cited by 11 publications

References 10 publications

Microbial Conversion of Toxic Resin Acids

Microbial Conversion of Toxic Resin Acids

The natural phytochemical dehydroabietic acid is an anti-aging reagent that mediates the direct activation of SIRT1

Synthesis and In Vitro Anticancer Activity of Novel Dehydroabietic Acid-Based Acylhydrazones

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