Search results for "Ferruginol"
showing 9 items of 9 documents
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…
Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine
2012
Short syntheses of bioactive (+)-ferruginol in five or six synthetic steps starting from commercially available (+)-dehydroabietylamine are described. The oxygenated function at C12 was introduced via a Friedel–Crafts acylation of N-phthaloyldehydroabietylamine followed by Baeyer–Villiger oxidation. Then, overall deprotection of functional groups, reductive deamination or biomimetic oxidative deamination, and final Wolff–Kishner reduction provided (+)-ferruginol in 21 and 23% overall yields, respectively.
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…
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…
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.
Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group.
2014
The abietane-type diterpenoid (+)-ferruginol, a bioactive compound isolated from New Zealand’s Miro tree (Podocarpus ferruginea), displays relevant pharmacological properties, including antimicrobial, cardioprotective, anti-oxidative, anti-plasmodial, leishmanicidal, anti-ulcerogenic, anti-inflammatory and anticancer. Herein, we demonstrate that ferruginol (1) and some phthalimide containing analogues 2–12 have potential antimalarial activity. The compounds were evaluated against malaria strains 3D7 and K1, and cytotoxicity was measured against a mammalian cell line panel. A promising lead, compound 3, showed potent activity with an EC50 = 86 nM (3D7 strain), 201 nM (K1 strain) and low cyto…
Rearranged abietane diterpenoids from the root of two Teucrium species
1992
Abstract From the root of Teucrium fruticans , two new rearranged abietane diterpenoids, teuvincenones F and G, have been isolated together with the known diterpene teuvincenone E. The acetone extract of the root of T. polium subsp. expansum yielded three previously known compounds (ferruginol and teuvincenones A and B) and two new 17(15 → 16)- abeo -abietane derivatives (teuvincenones H and I). The structures of the new diterpenoids [12,16-epoxy-11,14-dihydroxy-17(15 → 16), 18(4 → 3)- diabeo -abieta-3,5,8,11,13,15-hexaene-2,7-dione (teuvincenone F), (16 S )-12,16-epoxy-11,14-dihydroxy-17(15 → 16)- abeo -abieta-8,11,13-triene-3,7-dione (teuvincenone G), 12,16-epoxy-6,11,14-trihydroxy-17(15 …