Search results for "Abietic acid"
showing 10 items of 14 documents
Synthesis and biological evaluation of abietic acid derivatives
2009
A series of C18-oxygenated derivatives of abietic acid were synthesized and evaluated for their cytotoxic, antimycotic, and antiviral activities. In general, the introduction of an aldehyde group at C18 did improve the resultant bioactivity, while the presence of an acid or alcohol led to less active compounds.
Identification of diterpenes in canvas painting varnishes by gas chromatography-mass spectrometry with combined derivatisation.
2004
A derivatisation method that combines the formation of ethyl esters from the carboxylic groups and trimethylsilyl ethers from hydroxyl groups of the components of diterpenic resins is presented in this paper. This methodology involves two experimental steps: (1) formation of ethyl esters using ethyl chloroformate; and (2) the esterified compounds are lead to react with trimethylsilylimidazole to form the corresponding trimethylsilyl ethers. The main advantage of the proposed method is the possibility of performing simultaneously the analysis of amino acids from proteins, fatty acids from drying oils, and diterpenic compounds from natural resins usually found in works of art. This methodolog…
ChemInform Abstract: Aromatic Abietane Diterpenoids: Their Biological Activity and Synthesis
2016
Covering: 1980s–2014 In this study, the biological properties of natural abietane-type diterpenoids with an aromatic C ring are reviewed. An overview of the synthetic studies of this group of abietanes, including dehydroabietic acid, callitrisic acid and ferruginol, is presented. The review contains about 160 references.
Acetylcholinesterase and antioxidant evaluation of C18-functionalized ferruginol analogues
2019
Nearly 200 years ago, the study of the chemistry of terpenoids started with the analysis of turpentine oil, investigating the first resin acid, abietic acid from pine oleoresin.[1] Abietic acid occurs in plants of the genus Abies and is the first member of a class of plant metabolites, the abietane-type diterpenoids. They are characterized by a tricyclic ring system and have shown a wide range of chemical diversity and biological activity. [2,3] Medicinal chemists have studied derivatives of two readily available materials such as dehydroabietic acid and dehydroabietylamine. [3] To date, there is only one commercial drug, Ecabet® [ecabet sodium], based on abietanes, which is used for the tr…
Synthesis and biological evaluation of dehydroabietic acid derivatives.
2010
A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.
Aromatic abietane diterpenoids: their biological activity and synthesis
2015
Covering: 1980s–2014 In this study, the biological properties of natural abietane-type diterpenoids with an aromatic C ring are reviewed. An overview of the synthetic studies of this group of abietanes, including dehydroabietic acid, callitrisic acid and ferruginol, is presented. The review contains about 160 references.
Synthetic derivatives of aromatic abietane diterpenoids and their biological activities
2014
Naturally occurring aromatic abietane diterpenoids (dehydroabietanes) exhibit a wide range of biological activities. A number of synthetic studies aimed at modifying the abietane skeleton in order to obtain new potential chemotherapeutic agents have been reported. In this study, the biological activities of synthetic derivatives of aromatic abietane diterpenoids are reviewed.
Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
2020
[EN] The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid
Ancient wood of the Acqualadrone rostrum: Materials history through gas chromatography/mass spectrometry and sulfur X-ray absorption spectroscopy
2012
In 2008 the rostrum from an ancient warship was recovered from the Mediterranean near Acqualadrone, Sicily. To establish its provenance and condition, samples of black and brown rostrum wood were examined using sulfur K-edge X-ray absorption spectroscopy (XAS) and gas chromatography/mass spectrometry (GC/MS). GC/MS of pyrolytic volatiles yielded only guaiacyl derivatives, indicating construction from pinewood. A derivatized extract of black wood yielded forms of abietic acid and sandaracopimaric acid consistent with pine pitch waterproofing. Numerical fits to the sulfur K-edge XAS spectra showed that about 65% of the endogenous sulfur consisted of thiols and disulfides. Elemental sulfur was…
Pyrolysis-gas chromatography : mass spectrometry analysis of di- and triterpenoids
2017
The objective of this work was to study a specific class of extractives existing in lignocellulosic biomass and more precisely in wood materials, and their thermochemical behavior during pyrolysis. The focus was centered on the class of terpenes and terpenoids; specifically two model compounds, abietic acid and betulinol, were chosen to represent the subclasses of di- and triterpenoids, respectively. The model compounds were investigated via pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) and the main objective was to study their product profiles and characteristic fragmentations, as well as the influence of specific variables (pyrolysis temperature and time) on pyrolysis products…