| J Plant Physiol . 2017 Nov;218:66-73. |
| Involvement of allelopathy in inhibition of understory growth in red pine forests[Pubmed: 28779633] |
| Japanese red pine (Pinus densiflora Sieb. et Zucc.) forests are characterized by sparse understory vegetation although sunlight intensity on the forest floor is sufficient for undergrowth. The possible involvement of pine allelopathy in the establishment of the sparse understory vegetation was investigated. The soil of the red pine forest floor had growth inhibitory activity on six test plant species including Lolium multiflorum, which was observed at the edge of the forest but not in the forest. Two growth inhibitory substances were isolated from the soil and characterized to be 15-hydroxy-7-oxodehydroabietate and 7-oxodehydroabietic acid. Those compounds are probably formed by degradation process of resin acids. Resin acids are produced by pine and delivered into the soil under the pine trees through balsam and defoliation. Threshold concentrations of 15-hydroxy-7-oxodehydroabietate and 7-oxodehydroabietic acid for the growth inhibition of L. multiflorum were 30 and 10μM, respectively. The concentrations of 15-hydroxy-7-oxodehydroabietate and 7-oxodehydroabietic acid in the soil were 312 and 397μM, respectively, which are sufficient concentrations to cause the growth inhibition because of the threshold. These results suggest that those compounds are able to work as allelopathic agents and may prevent from the invasion of herbaceous plants into the forests by inhibiting their growth. Therefore, allelopathy of red pine may be involved in the formation of the sparse understory vegetation. |
| Appl Occup Environ Hyg . 1999 Mar;14(3):171-176. |
| Conjugation of 7-oxodehydroabietic acid to lysine, a haptenation mechanism for an oxidized resin acid with dermal sensitizing properties[Pubmed: 10453631] |
| This article explores protein conjugation of 7-oxodehydroabietic acid, a resin acid found in both aerosol from soldering with rosin flux and in rosin solids. In a murine model, conjugation (haptenation) of resin acids to proteins is required to generate antibodies against rosin. Hydroperoxy resin acids are dermal sensitizers, with haptenation thought to occur via radical mechanisms. Dermal sensitization to 7-oxodehydroabietic acid has been observed, although no radical haptenation mechanism has been proposed to explain the sensitizing properties of this compound. Conjugation of L-lysine to 7-oxodehydroabietic acid was predicted, with a Schiff base (or imine) linkage formed between C-7 of the resin acid and a free amino group of lysine. Fast atom bombardment mass spectrometry provided evidence of the conjugate; a small peak was seen for the conjugate (M+H)+ ion in aqueous ethanol with 20 mM concentrations of the free resin and amino acids. A larger conjugate peak was observed with addition of tertiary amine as a mild basic catalyst, and the intensity of the conjugate peak exceeded that of the precursors upon replacement of the ethanol with benzene. Resin acids accumulate in the plasma membrane, a non-aqueous environment apparently conducive to conjugation of 7-oxodehydroabietic acid with lysine side chains of membrane proteins. The result would be dehydroabietic acid covalently bound to protein, which could lead to interaction with immune cells having resin acid specificity. The haptenation mechanism presented may be involved in allergic contact dermatitis and occupational asthma observed from exposure to resin acid solids and aerosols. As sampling and analytical methods have been previously demonstrated for 7-oxodehydroabietic acid, this compound may be a useful exposure marker with relevance to negative health effects such as occupational asthma. |
| Contact Dermatitis . 2021 Dec;85(6):671-678. |
| Tracing colophonium in consumer products[Pubmed: 34291483] |
| Background: Colophonium (rosin) can cause allergic contact dermatitis, mainly due to autoxidation of abietic acid (AbA). Products containing ≥0.1% colophonium should be labeled with EUH208 - "Contains rosin; colophony. May produce an allergic reaction." How should this be measured?
Objective: To compare the results from different strategies for estimating colophonium levels in consumer products: (a) from AbA, and (b) the sum of all major resin acids. To investigate the ratio of 7-oxodehydroabietic acid (7-O-DeA)/AbA as indication of autoxidation.
Methods: Resin acids were extracted from consumer products, derivatized, and then separated by gas chromatography/mass spectrometry (GC/MS).
Results: Resin acids were detected in 9 of 15 products. No product contained colophonium ≥0.1%. Estimation based on AbA resulted in underestimation of the colophonium levels in four of nine products. For three products, the obtained levels from this strategy were only one of two compared to when estimating from the sum of all resin acids. The ratio 7-O-DeA/AbA varied from 74% to 1.4%.
Conclusions: We propose to measure colophonium based on the sum of all detectable major resin acids, including 7-O-DeA. The ratio of 7-O-DeA/AbA should be used as a marker of autoxidation, indicating an increased risk of sensitization. The presented analytical method is simple to use and suitable for further screening studies. |
| Environ Mutagen . 1979;1(4):361-369. |
| Mutagenicity of resin acids identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay[Pubmed: 399918] |
| Ten resin acids which have been identified as constituents of pulp and paper mill effluents have been examined for potential mutagenicity in the Salmonella/mammalian-microsome assay. Only neoabietic acid has been found to be mutagenic. Neoabietic acid showed dose-related increases in mutagenicity in strains TA1535, TA100, TA1538, and TA98, but not in strain TA1537. Metabolic activation with a preparation of Aroclor 1254-induced liver homogenate (S9) slightly reduced the mutagenic responses. Negative responses were found for abietic acid, dehydroabietic acid, levopimaric acid, 7-oxodehydroabietic acid, monochlorodehydroabietic acid, dichlorodehydroabietic acid, pimaric acid, isopimaric acid, and sandaracopimaric acid. |
| Contact Dermatitis. 1988 Sep;19(3):166-174 |
| Contact allergy to dehydroabietic acid derivatives isolated from Portuguese colophony[Pubmed: 3191677] |
| 7-oxodehydroabietic acid and 15-hydroxydehydroabietic acid were isolated as their methyl esters from Portuguese colophony of the gum rosin type and identified as contact allergens. Another oxidation product of dehydroabietic acid, 15-hydroxy-7-oxodehydroabietic acid, was synthesized and identified as a component of Portuguese gum rosin. 7-oxodehydroabietic acid was found to a be a grade III allergen according to the GPMT method. Guinea pigs induced with gum rosin showed only a low response to the isolated compounds, while patients with a known allergy to gum rosin reacted to a greater extent. The results imply that the content of oxidized dehydroabietic acids in gum rosin is too low to give a marked sensitization in the animals. However, the patients might have come in contact with the allergens in technically modified rosins. The compounds showed a pattern of cross-reactivity in the animal experiments as well as among the patch tested patients. |
| Ann Occup Hyg . 2004 Apr;48(3):267-275. |
| Dermal exposure to terpenic resin acids in Swedish carpentry workshops and sawmills[Pubmed: 15059803] |
| Objectives: The aim of this study was to evaluate dermal exposure to the resin acids abietic acid, dehydroabietic acid and 7-oxodehydroabietic acid during collecting in sawmills and during sawing in carpentry workshops, respectively.
Methods: Sampling was performed by fastening patches at 12 different areas on a sampling overall, one patch on the front of a cap, one patch on the chest inside the clothing and one patch on the inner lower right leg. Exposure of the hands was assessed by fastening patches on cotton gloves representing the dorsal sides and the palms of the left and right hands. Sampling was performed on 30 different occasions in the sawmills and in the carpentry workshops with mean sampling times of 120 and 59 min, respectively. The acids were solvent desorbed from the patches. Identification and quantification of the resin acids was performed by gas chromatography-mass spectrometry.
Results: The geometric means (GMs) of the potential body exposures to abietic acid, dehydroabietic acid and 7-oxodehydroabietic acid during sawing and collecting of wood from pine and spruce were 3346 and 17 247 micro g/h, respectively. The GM of the potential exposure on the hands was 3020 micro g/h in the carpentry workshops and 4365 micro g/h in the sawmills. Resin acids were detected on the inner chest and inner lower front right leg, respectively.
Conclusions: There is a potential dermal exposure to terpenic resin acids in carpentry workshops as well as in sawmills. The hands have the highest exposure during sawing as well as during collecting. There is a spatial distribution of contaminants, with the outer chest, arms and legs showing the highest exposures. Resin acids also contaminated the inner chest and inner lower leg. It is necessary to take action to reduce dermal exposure to these allergenic substances. |
| Fitoterapia . 2016 Sep;113:151-157. |
| Diterpenoids from Callicarpa kwangtungensis and their NO inhibitory effects[Pubmed: 27491749] |
| A phytochemical investigation of the leaves of Callicarpa kwangtungensis led to the isolation of three new diterpenoids (1-3), callipenes A-C, and eleven known analogues (4-14). Their structures were established on the basis of extensive analysis of NMR spectroscopic data, X-ray diffraction data, and experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 are rare abietane diterpenoids possessing a peroxide bridge. All of the isolates were found to inhibit LPS-induced NO production in BV-2 cells. |
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