Disease relevance of ABIETIC ACID

• At naturally occurring concentrations (relative to abietic acid) all unoxidized resin acids were found to play an insignificant part, individually, in colophony dermatitis, except abietic acid (purity 99%), which was found to be a weak but important allergen [1].
• In addition, to beta-sitosterol and abietic acid, several other wood-derived compounds including betulin, isorhapontigenin, isorhapontin, and pinosylvin were estrogenic in breast cancer cells (MCF-7 or T-47D) [2].
• Contact urticaria from abietic acid [3].
• The role of abietic acid as the main sensitizer in colophony was confirmed in a case of contact dermatitis occurring in a sportsman with an acute eczematous reaction due to a leg bandage [4].
• Since the lipoxygenase pathway leads to the biosynthesis of leukotrienes this result supports the view that abietic acid may be used in the treatment of allergic reactions [5].

High impact information on ABIETIC ACID

• The marked difference in potency as BK channel openers between PiMA and abietic acid, despite only very small differences in their chemical structures, may provide insight into the fundamental structure-activity relationship governing BKalpha activation [6].
• Our results suggest that plicatic acid, a unique constituent of cedar wood, and abietic acid, the major constituent in pine resin, can produce lytic damage to alveolar, tracheal, and bronchial epithelial cells [7].
• Abietic acid also caused destruction of the alveolar epithelium [7].
• Abietic acid activates peroxisome proliferator-activated receptor-gamma (PPARgamma) in RAW264.7 macrophages and 3T3-L1 adipocytes to regulate gene expression involved in inflammation and lipid metabolism [8].
• The present work indicates that abietic acid suppresses the protein expression of tumor necrosis factor-alpha and cyclooxygenase 2, which are involved in inflammation, in lipopolysaccharide-stimulated macrophages [8].

Biological context of ABIETIC ACID

• Abietic acid was the next most toxic compound for all the species, with an IC50 in the range of 21.4 to 203 mg/liter [9].
• The present work suggests a novel possibility that abietic acid, a naturally occurring compound, can be used not only for anti-inflammation but also for regulating lipid metabolism and atherosclerosis [8].
• The activity of abietic acid induces PPARgamma target gene expression in RAW264.7 macrophages and 3T3-L1 adipocytes [8].
• Diterpenoid resin acid biosynthesis in conifers: enzymatic cyclization of geranylgeranyl pyrophosphate to abietadiene, the precursor of abietic acid [10].
• Hydrogenation of the conjugated double bonds of abietic acid decreases its susceptibility to air oxidation and would thus reduce the allergenicity of rosin [11].

Anatomical context of ABIETIC ACID

• These data indicate that abietic acid is a PPARgamma ligand and that its anti-inflammatory effect is partly due to the activation of PPARgamma in stimulated macrophages [8].
• The transcellular transport of [(3)H]digoxin across Caco-2 cell monolayers was then examined in the presence of (R)-(+)-citronellal, abietic acid, and glycyrrhetic acid [12].
• The interaction of abietic acid with phospholipid membranes [13].

Associations of ABIETIC ACID with other chemical compounds

• To determine if plicatic acid from cedar wood and abietic acid from pine resin could directly damage lung cells, we exposed monolayers of rat type II and human A549 alveolar epithelial cells, intact rat lungs, and rat tracheal explants to solutions of plicatic and abietic acids [7].
• Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis [14].
• To investigate whether esterification of rosin with polyalcohols changes its allergenic potential, abietic acid, the main component of rosin, was esterified with glycerol at high temperature [15].
• The technique, using HPLC, is based on the analysis of abietic acid and dehydroabietic acid, major components of rosin [16].
• The major product formed was isolated and identified, using nuclear magnetic resonance (NMR), infra-red (IR) and mass spectrometry (MS) analyses, as glyceryl triabietate (GTA), an ester between one glycerol molecule and 3 abietic acid molecules [15].

Gene context of ABIETIC ACID

• In this work the in vitro antioxidant activity of an abietic acid-derived catechol (methyl 11,12-dihydroxyabietate-8,11,13-trien-18-oate, MDTO) was evaluated [17].
• In this study, it was shown that abietic acid, an abietane diterpenoid, inhibited soybean 5-lipoxygenase (linoleate: oxygen oxidoreductase, EC 1.13.11.12) and an IC(50) of 29.5 +/- 1.29 microM was determined [5].

Analytical, diagnostic and therapeutic context of ABIETIC ACID

• The concentration of abietic acid in the adhesives was determined with HPLC [18].
• High performance liquid chromatography was used to identify abietic acid present in a breathing zone sample [19].
• These results indicate that abietic acid exerts in-vivo anti-inflammatory activity after oral or topical administration and has partial ability to prevent the production of some inflammatory mediators [20].
• The minimum inhibitory concentrations (MIC) were 32-64 microg/mL and compared with a commercially obtained resin acid, abietic acid, with MICs of 64 microg/mL [21].
• The interaction of abietic acid with model membranes of dipalmitoylphosphatidylcholine (DPPC) and dielaidoylphosphatidylethanolamine (DEPE) has been studied by differential scanning calorimetry and 31P-nuclear magnetic resonance spectroscopy [13].

References