Search results for "Abietane"
showing 10 items of 28 documents
The abietane diterpene taxodione contributes to the antioxidant activity of rosemary by-product in muscle tissue
2019
International audience; Research on rosemary antioxidant activity and its potential use in human health and food applications is focused on rosemary leaves and two main bioactive compounds carnosic acid and carnosol. However, many other, not-yet identified molecules could be present, especially in rosemary by-products. In this study, we first showed that rosemary stem extract was the most efficient in protecting human skeletal muscle cells against oxidation. Then, using bioassay-guided fractionation, we identified taxodione, an abietane diterpene, as the main bioactive molecule in the rosemary stem extract. We demonstrated that taxodione protects skeletal muscle cells from hydrogen peroxide…
A Short and Improved Synthesis of the Antiprotozoal Abietane Diterpenoid (–)-Sugikurojin A
2016
An efficient and straightforward semisynthesis of the antiprotozoal abietane diterpenoid (–)-sugikurojin A, starting from the readily available methyl ester of callitrisic acid (4-epi-dehydroabietic acid) isolated from sandarac resin, is reported. This optimized semisynthetic route provides a convenient source of the antiprotozoal compound, in four steps from methyl callitrisate in 50% overall yield, for further biological studies.
Anti-herpetic and anti-dengue activity of abietane ferruginol analogues synthesized from (+)-dehydroabietylamine
2015
The abietane-type diterpenoid (+)-ferruginol (1), a bioactive compound isolated from several plants, has attracted much attention as consequence of its pharmacological properties, which includes antibacterial, antifungal, antimicrobial, cardioprotective, anti-oxidative, anti-plasmodial, leishmanicidal, anti-ulcerogenic, anti-inflammatory and antitumor actions. In this study, we report on the antiviral evaluation of ferruginol (1) and several analogues synthesized from commercial (+)-dehydroabietylamine. Thus, the activity against Human Herpesvirus type 1, Human Herpesvirus type 2 and Dengue Virus type 2, was studied. Two ferruginol analogues showed high antiviral selectivity index and reduc…
Putative molecular determinants mediating sensitivity or resistance towards carnosic acid tumor cell responses.
2020
Abstract Background Carnosic acid (CA) is one of the main constituents in rosemary extract. It possesses valuable pharmacological properties, including anti-oxidant, anti-inflammatory, anti-microbial and anti-cancer activities. Numerous in vitro and in vivo studies investigated the anticancer profile of CA and emphasized its potentiality for cancer treatment. Nevertheless, the role of multidrug-resistance (MDR) related mechanisms for CA's anticancer effect is not yet known. Purpose We investigated the cytotoxicity of CA against known mechanisms of anticancer drug resistance (P-gp, ABCB5, BCRP, EGFR and p53) and determined novel putative molecular factors associated with cellular response to…
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.
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…
Secondary metabolites from Pinus mugo Turra subsp. mugo growing in the Majella National Park (Central Apennines, Italy).
2013
In this study, we examined the composition regarding secondary metabolites of P. mugo Turra ssp. mugo growing in the protected area of Majella National Park, which is the southernmost station of the habitat of this species. Both the nonpolar and polar fractions were considered. In particular, the essential-oil composition showed a high variety of compounds, and 109 compounds were detected, and 101 were identified, among which abietane-type compounds have a taxonomic relevance. Abietanes were also isolated from the polar fraction, together with an acylated flavonol and a remarkably high amount of shikimic acid.
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.
Biological Profiling of Semisynthetic C19-Functionalized Ferruginol and Sugiol Analogues
2021
[EN] The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure-activity relationship (SAR) elements. In particular, the ferruginol and sugi…