Dehydroabietic acid

( > 99%)

CAS Number:  1740-19- 8

Chemical Formula: C20H28O2

Properties

 Purity > 99%
 Melting point 63 - 65 °C
 Storage temperature -20 °C
 Main hazards Danger
 Molecular Weight 300.442
Dehydroabietic acid

Available modifications

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Publications related to Dehydroabietic acid

Development of ultrasonic-assisted closed in-syringe extraction and derivatization for the determination of labile abietic acid and dehydroabietic acid in cosmetics.

Liu J. et. al

J Chromatogr A. 2014 Dec 5;1371:20-9.

Two resin acids, abietic acid (AA) and dehydroabietic acid (DHAA), in cosmetics may cause allergy or toxicoderma, but remain inaccurately investigated due to their lability. In this work, an accurate, sensitive, efficient and convenient method, utilizing the ultrasonic-assisted closed in-syringe extraction and derivatization (UCSED) prior to high performance liquid chromatography (HPLC) coupled with fluorescence detection (FLD) and on-line tandem mass spectra (MS/MS), has been developed. Analytes are extracted by acetonitrile (10/1, v/m) in a sealed syringe under safe condition (60°C; 15 min; nitrogen atmosphere) and then in-syringe derivatized by 2-(2-(anthracen-10-yl)-1H-naphtho[2,3-d]imidazol-1-yl) ethyl-p-toluenesulfonate (ANITS) (8-fold, 93°C, 30 min, DMF as co-solvent, K2CO3 as catalyst). In UCSED, derivatization contributes to increase both analytical sensitivity and stability of analytes. Excellent linearity (r2≥0.9991) is achieved in wide range (75-3000 ng/mL (AA); 150-4500 ng/mL (DHAA)). Quite low detection limits (AA: 8.2-10.8 ng/mL; DHAA: 19.4-24.3 ng/mL) and limits of analyte concentration (LOAC) (AA: 30.0-44.5 ng/mL; DHAA: 70.9-86.7 ng/mL) ensure the trace analysis. This method is applied to the analysis of cosmetic samples, including depilatory wax strip, liquid foundation, mascara, eyeliner, eyebrow pencil and lip balm. No additional purification is required and no matrix effect is observed, demonstrating obvious advantages over conventional pretreatment such as solid phase extraction (SPE). Accuracy (RE: -3.2% to 2.51%), precision (RSD: 1.29-2.84%), recovery (95.20-103.63%; 95.51-104.22%) and repeatability (<0.23%; <2.87%) are significantly improved. Furthermore, this work plays a guiding role in developing a reasonable method for labile analytes.

Molecular mechanism of pharmacological activation of BK channels.

Gessner G. et. al

Proc Natl Acad Sci U S A. 2012 Feb 28;109(9):3552-7.

Large-conductance voltage- and Ca(2+)-activated K(+) (Slo1 BK) channels serve numerous cellular functions, and their dysregulation is implicated in various diseases. Drugs activating BK channels therefore bear substantial therapeutic potential, but their deployment has been hindered in part because the mode of action remains obscure. Here we provide mechanistic insight into how the dehydroabietic acid derivative Cym04 activates BK channels. As a representative of NS1619-like BK openers, Cym04 reversibly left-shifts the half-activation voltage of Slo1 BK channels. Using an established allosteric BK gating model, the Cym04 effect can be simulated by a shift of the voltage sensor and the ion conduction gate equilibria toward the activated and open state, respectively. BK activation by Cym04 occurs in a splice variant-specific manner; it does not occur in such Slo1 BK channels using an alternative neuronal exon 9, which codes for the linker connecting the transmembrane segment S6 and the cytosolic RCK1 domain--the S6/RCK linker. In addition, Cym04 does not affect Slo1 BK channels with a two-residue deletion within this linker. Mutagenesis and model-based gating analysis revealed that BK openers, such as Cym04 and NS1619 but not mallotoxin, activate BK channels by functionally interacting with the S6/RCK linker, mimicking site-specific shortening of this purported passive spring, which transmits force from the cytosolic gating ring structure to open the channel's gate

Fungal biotransformation products of dehydroabietic acid.

van Beek T.A. et. al

J Nat Prod. 2007 Feb;70(2):154-9.

Dehydroabietic acid (DHA) (1) is one of the main compounds in Scots pine wood responsible for aquatic and microbial toxicity. The degradation of 1 by Trametes versicolor and Phlebiopsis gigantea in liquid stationary cultures was followed by HPLC-DAD-ELSD. Both fungi rapidly degraded DHA relative to a control. More breakdown products were observed for T. versicolor than for P. gigantea. After 13 days, four compounds were identified by means of spectroscopic methods in P. gigantea cultures: 1beta-hydroxy-DHA (2), 1beta,7alpha-dihydroxy-DHA (3), 1beta,16-dihydroxy-DHA (5), and tentatively 1beta-hydroxy-7-oxo-DHA (4). In T. versicolor cultures, 1beta,16-dihydroxy-DHA (5), 7beta,16-dihydroxy-DHA (6), 1beta,7beta,16-trihydroxy-DHA (7), 1beta,16-dihydroxy-7-oxo-DHA (8), 1beta,15-dihydroxy-DHA (9), and 1beta,7alpha,16-trihydroxy-DHA (10) were identified after 9 days of incubation. Thus the biotransformation of 1 by the two fungi was different, with only 5 being produced by both strains. Compounds 3, 7, 8, and 10 are reported for the first time as natural products.

Dehydroabietic acid, a phytochemical, acts as ligand for PPARs in macrophages and adipocytes to regulate inflammation.

Kang M.-S. et. al

Biochem Biophys Res Commun. 2008 May 2;369(2):333-8.

Obesity is characterized by an enhanced infiltration of macrophages to adipose tissues, which is closely associated with the low-grade inflammatory state and obesity-related pathologies such as type 2 diabetes and cardiovascular diseases. We showed here that dehydroabietic acid (DAA) is a potent PPARalpha/gamma dual activator. Furthermore, we examined the anti-inflammatory effects of DAA in stimulated macrophages and in the coculture of macrophages and adipocytes. DAA significantly suppressed the production of proinflammatory mediators such as MCP-1, TNF-alpha, and NO in stimulated RAW 264 macrophages and in the coculture of RAW 264 macrophages and 3T3-L1 adipocytes. These results suggest that DAA is a valuable medicinal and food component for improving inflammatory changes associated with obesity-related diabetes.

Friction of fatty acids in nanometer-sized contacts of different adhesive strength.

Ruths M. et. al

Langmuir. 2008 Feb 19;24(4):1509-16.

The effects of adhesion, contact area, and pressure on the lubricating properties of self-assembled monolayers on steel have been investigated with friction force microscopy. The adsorbed molecules were fatty acids with varying degrees of unsaturation (0-2 double bonds; stearic, oleic, and linoleic acid) and a rosin acid (dehydroabietic acid), adsorbed from n-hexadecane solution. The friction of these loose-packed monolayers was studied in dry N2 gas and in ethanol. Low adhesion (in ethanol) resulted in a linear increase in friction force at low loads, that is, F = muL, whereas higher adhesion (in N2 gas) gave an apparent area-dependence at low loads of the form F = S(c)A, where S(c) is the critical shear stress. A recent model for the contact mechanics of a compliant elastic film confined between stiffer substrates was applied to the data obtained in dry N2. Using this approach, we obtained interfacial energies of the compliant monolayers in good agreement with van der Waals-Lifshitz theory. With a low monolayer elastic modulus of E'(1)=0.2 GPa, we obtained a slightly higher value of Sc for stearic acid than that established for more close-packed stearic acid monolayers. An increase of mu and S(c) was found with increasing degree of unsaturation of the fatty acid.

Antibacterial activity of Pinus elliottii and its major compound, dehydroabietic acid, against multidrug-resistant strains.

Leandro L.F. et. al

J Med Microbiol. 2014 Dec;63(Pt 12):1649-53.

Antibiotic-resistant bacteria have emerged from the widespread use of antibiotics worldwide and have prompted the search for new sources of antimicrobial substances. Pinus spp. contain several bioactive compounds consisting mainly of terpenes, terpenoids and some other aromatic and aliphatic constituents. These compounds exert important biological effects, and pine oils have found wide application in the industry. In the present study, we have evaluated the potential activity of the resin-oil of Pinus elliottii and its major compound dehydroabietic acid (DA) against multiresistant bacteria by MIC, minimum bactericidal concentration and time-kill assays. The MIC of the resin-oil of P. elliottii varied between 25 and 100 µg ml(-1). As for DA, the MIC and minimum bactericidal concentration varied between 6.25 and 50 and between 6.25 and 100 µg ml(-1), respectively. The time-kill assay conducted with DA at 6.25 µg ml(-1) evidenced bactericidal activity against Staphylococcus epidermidis (American Type Culture Collection 14990) within 24 h. On the basis of these results, the resin-oil of P. elliottii and its major compound DA play an important part in the search for novel sources of agents that can act against multiresistant bacteria.

Novel BK channel openers containing dehydroabietic acid skeleton: structure-activity relationship for peripheral substituents on ring C.

Cui Y.M. et. al

Bioorg Med Chem Lett. 2008 Oct 1;18(19):5201-5.

A series of dehydroabietic acid (DHAA, 2) derivatives was synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKalpha channels. Systematic modifications of the peripheral functionality of ring C of DHAA showed that the introduction of a nitro or (thio)urea group in ring C greatly enhanced the BK channel-opening activity.

Highly enantioselective synthesis of gamma-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on dehydroabietic amine: a doubly stereocontrolled approach to pyrrolidine carboxylic acids.

Jiang X. et. al

Org Lett. 2009 Jan 1;11(1):153-6.

A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)- or (R)-gamma-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly optically pure gamma-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids.

Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice.

Kang M.S. et. al

Biofactors. 2009 Sep-Oct;35(5):442-8.

Terpenoids, which are contained in a large number of dietary and herbal plants, have many biological effects. In this study, the effects of dehydroabietic acid (DAA), a diterpene, on glucose and lipid metabolism were examined using obese diabetic KK-Ay mice. We showed here that DAA treatment decreased not only plasma glucose and insulin levels but also plasma triglyceride (TG) and hepatic TG levels. To examine the mechanism underlying the effects of DAA, the production of inflammatory cytokines was measured. It was shown that the DAA treatment suppressed the production of monocyte chemoattractant protein-1 (MCP-1) and tumor necrosis factor-alpha (TNFalpha) (proinflammatory cytokines) and increased that of adiponectin (an anti-inflammatory cytokine). As a result of the changes in the production of inflammatory cytokines caused by the DAA treatment, the accumulation of macrophages in adipose tissues was reduced. These results indicate that treatment with DAA improves the levels of plasma glucose, plasma insulin, plasma TG, and hepatic TG through the decrease in the macrophage infiltration into adipose tissues, suggesting that DAA is a useful food-derived compound for treating obesity-related diseases.

A large gene cluster in Burkholderia xenovorans encoding abietane diterpenoid catabolism.

Smith D.J. et. al

J Bacteriol. 2007 Sep;189(17):6195-204

Abietane diterpenoids are defense compounds synthesized by trees that are abundant in natural environments and occur as significant pollutants from pulp and paper production. Burkholderia xenovorans LB400 has diverse catabolic capabilities and represents an important group of heterotrophic bacteria in soil environments. The genome sequence of LB400 revealed homologs of the dit genes of Pseudomonas abietaniphila BKME-9, which encode abietane diterpenoid degradation. LB400 grew on abietic acid (AbA), dehydroabietic acid (DhA), palustric acid (PaA), and 7-oxo-DhA. A Xeotron microarray set, with probes for 8450 of the estimated 9000 LB400 genes, was used to compare the transcriptomes of LB400 growing on DhA versus on succinate. On DhA, 97 genes were upregulated, 43 of which were within an 80-kb cluster located on the 1.47-Mbp megaplasmid of LB400. Upregulated genes in this cluster encode a permease, a ring-hydroxylating dioxygenase system (DitA), a ring-cleavage dioxygenase (DitC), a P450 monooxygenase (DitQ), and enzymes catalyzing beta-oxidation-type reactions. Disruption of the ditA1 gene, encoding the alpha-subunit of DitA, abolished growth on these abietanes. Analyses of the metabolism of abietanes by cell suspensions of wild-type LB400 and the ditA1 mutant indicate a convergent pathway, with 7-oxo-DhA as a common intermediate for ring hydroxylation by DitA. Also, 7-oxo-PaA was identified as a metabolite of both AbA and PaA. Sequence analysis indicates that genes encoding this pathway have been horizontally transferred among Betaproteobacteria and Gammaproteobacteria.

A cytochrome P450 involved in the metabolism of abietane diterpenoids by Pseudomonas abietaniphila BKME-9.

Smith D.J. et. al

J Bacteriol. 2004 Jun;186(11):3631-9.

Diterpenoids are naturally occurring plant compounds which have pharmaceutical properties. We have sequenced a 10.4-kbp extension of the dit cluster in Pseudomonas abietaniphila BKME-9, containing genes involved in abietane diterpenoid biodegradation. The ditQ gene was found to encode a cytochrome P450 monooxygenase, P450dit, and to be homologous to the tdtD gene of Pseudomonas diterpeniphila A19-6a. Knocking out ditQ had little effect on growth of BKME-9 on abietic acid but severely impaired growth on dehydroabietic acid (DhA) and palustric acid (PaA), increasing doubling times from 3.8 to 15 h on DhA and from 5.6 to 18.5 h on PaA. A xylE transcriptional fusion showed that transcription of ditQ was induced by a range of diterpenoids. Substrate binding assays of P450dit expressed in Escherichia coli revealed that DhA binds to the enzyme and yields a type I binding spectrum with a Kd of 0.4 microM. These results indicate that P450dit is involved in the metabolism of DhA and PaA and are consistent with its putative role in converting DhA to 7-hydroxy-DhA. Finally, an amino acid sequence identity of greater than 72% and conserved gene arrangement support the hypothesis that the dit gene cluster of P. abietaniphila BKME-9 and the tdt cluster of P. diterpeniphila A19-6a contain functional homologues.

Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives.

Sepúlveda B. et. al

Pharmacol Res. 2005 Nov;52(5):429-37.

Dehydroabietic acid derivatives have been reported to display antisecretory and antipepsin effect in animal models. Some 19 dehydroabietic acid diterpenes were prepared and assessed for gastroprotective activity in the HCl/EtOH-induced gastric lesions in mice as well as for cytotoxicity in human lung fibroblasts (MRC-5) and human epithelial gastric (AGS) cells. At a single oral dose of 100 mg kg(-1), highest gastroprotective effect was provided by dehydroabietanol, its corresponding aldehyde, dehydroabietic acid (DHA) and its methyl ester, N-(m-nitrophenyl)-, N-(o-chlorophenyl)- and N-(p-iodophenyl)abieta-8,11,13-trien-18-amide (compounds 12-14), N-2-aminothiazolyl- and N-benzylabieta-8,11,13-trien-18-amide (compounds 18-19) being as active as lansoprazole at 20 mg kg(-1) and reducing the lesion index by at least 75%. In the compound series including the alcohol, ester, aldehyde, acid and methyl ester at C-18 (compounds 1-9), highest activity was related with the presence of an alcohol, aldehyde, acid or methyl ester at C-18, the activity being strongly reduced after esterification. The cytotoxicity of the compounds 1-9 towards AGS cells and fibroblasts was higher than the values for the amides 10-19. In the compounds 10-19, the best gastroprotective effect was observed for the aromatic amides 12-14 (75-85% inhibition of gastric lesions) bearing a nitro or halogen function in the N-benzoyl moiety. Lowest cytotoxicity was found for the amides, with IC(50) values >1000 microM for fibroblasts and from 200 up to >1000 microM for AGS cells, respectively. The N-2-aminothiazolyl- and N-benzylamide derivatives were also very active as gastroprotectors with higher cytotoxicity against AGS cells.

Synthesis and biological evaluation of dehydroabietic acid derivatives.

González M.A. et. al

Eur J Med Chem. 2010 Feb;45(2):811-6.

A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.

Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid.

Gu W. and Wang S.

Eur J Med Chem. 2010 Oct;45(10):4692-6.

A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, (1)H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.

Distinct roles for two CYP226 family cytochromes P450 in abietane diterpenoid catabolism by Burkholderia xenovorans LB400.

Smith D.J. et. al

J Bacteriol. 2008 Mar;190(5):1575-83.

The 80-kb dit cluster of Burkholderia xenovorans LB400 encodes the catabolism of abietane diterpenoids. This cluster includes ditQ and ditU, predicted to encode cytochromes P450 (P450s) belonging to the poorly characterized CYP226A subfamily. Using proteomics, we identified 16 dit-encoded proteins that were significantly more abundant in LB400 cells grown on dehydroabietic acid (DhA) or abietic acid (AbA) than in succinate-grown cells. A key difference in the catabolism of DhA and AbA lies in the differential expression of the P450s; DitU was detected only in the AbA-grown cells, whereas DitQ was expressed both during growth on DhA and during growth on AbA. Analyses of insertion mutants showed that ditQ was required for growth on DhA, ditU was required for growth on AbA, and neither gene was required for growth on the central intermediate, 7-oxo-DhA. In cell suspension assays, patterns of substrate removal and metabolite accumulation confirmed the role of DitU in AbA transformation and the role of DitQ in DhA transformation. Spectral assays revealed that DitQ binds both DhA (dissociation constant, 0.98 +/- 0.01 microM) and palustric acid. Finally, DitQ transformed DhA to 7-hydroxy-DhA in vitro. These results demonstrate the distinct roles of the P450s DitQ and DitU in the transformation of DhA and AbA, respectively, to 7-oxo-DhA in a convergent degradation pathway.

Dehydroabietic acid (DHAA) alters metabolic enzyme activity and the effects of 17β-estradiol in rainbow trout (Oncorhynchus mykiss).

Pandelides Z. et. al

Ecotoxicol Environ Saf. 2014 Mar;101:168-76.

Recent studies have shown that dehydroabietic acid (DHAA), a resin acid present in pulp and paper mill effluent, affects liver energy metabolism and may have anti-estrogenic effects in fish. A chronic-exposure toxicity experiment using immature rainbow trout (Oncorhynchus mykiss) was conducted in order to assess the endocrine disrupting and liver metabolic effects of the model estrogen 17β-estradiol (E2) and the wood extractives DHAA and β-sitosterol (BS), regularly present in pulp and paper mill effluents. Exposure to 5ppm of E2 significantly increased hepatosomatic index (HSI), vitellogenin (VTG) and plasma sorbitol dehydrogenase (SDH). This latter effect was reduced by mixing E2 with DHAA, indicating that DHAA does not cause its endocrine disrupting effects indirectly due to liver damage. Exposure to 0.5ppm of DHAA as well as all the DHAA mixed treatments caused significant increases in liver citrate synthase (CS), activity after 7 days, however, the fish returned to control values by 28 days. Results indicate that DHAA may alter metabolic enzyme activity as well as alter the effects of E2 in juvenile rainbow trout.

Analysis of abietic acid and dehydroabietic acid in food samples by in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry.

Mitani K. et. al

J Chromatogr A. 2007 Mar 30;1146(1):61-6.

A simple and sensitive method for the determination of abietic acid and dehydroabietic acid in food samples was developed using a fully automated method consisting of in-tube solid-phase microextraction (SPME) coupled with liquid chromatography-mass spectrometry (LC/MS). These compounds were separated within 5min by HPLC using an ODS-3 column and 5mM ammonium formate/acetonitrile (10/90, v/v). Electrospray ionization conditions in the negative ion mode were optimized for MS detection of abietic acid and dehydroabietic acid. The optimum in-tube SPME conditions were 20draw/eject cycles of 40microL of sample using a Supel Q PLOT capillary column as an extraction device. The extracted compounds were easily desorbed from the capillary by passage of the mobile phase, and no carryover was observed. Using the in-tube SPME LC/MS method, good linearity of the calibration curve (r>0.9998) was obtained in the concentration range from 0 to 50ng/mL, and the detection limits (S/N=3) of abietic acid and dehydroabietic acid were 2.9 and 2.1pg/mL, respectively. The in-tube SPME method showed above 75-fold greater sensitivity than the direct injection method (5microL injection). This method was applied successfully to analysis of food samples without interference peaks. The recoveries of abietic acid and dehydroabietic acid spiked into liquid samples were above 79%, and the relative standard deviations were below 6.6%. These compounds were detected at ng/mL or ng/g levels in various liquid or solid food samples contacted with paper.

Dehydroabietic acid activates peroxisome proliferator-activated receptor-γ and stimulates insulin-dependent glucose uptake into 3T3-L1 adipocytes.

Takahashi N. et. al

Biofactors. 2011 Jul-Aug;37(4):309-14.

Dehydroabietic acid (DAA) is a food-derived terpenoid with various bioactivities. Our previous study has revealed that DAA activates peroxisome proliferator-activated receptor-γ (PPARγ) in luciferase assay and suppresses chronic inflammation in obese adipose tissues. In this study, we examined the effects of DAA on adipocyte differentiation. DAA treatment stimulated the adipocyte differentiation of 3T3-L1 preadipocytes. The DAA treatment increased the mRNA expression levels of adipocyte differentiation marker genes such as aP2, lipoprotein lipase (LPL), and PPARγ. In particular, the expression level of adiponectin, which is an adipocytokine with stimulatory effects on insulin sensitivity, was increased at both the mRNA and protein levels by the DAA treatment. Moreover, the DAA treatment stimulated insulin-dependent glucose uptake into differentiated 3T3-L1 adipocytes. These findings indicate that DAA stimulates adipocyte differentiation and insulin sensitivity in 3T3-L1 cells, suggesting that DAA is a valuable food-derived compound for the management of metabolic syndrome.

Determination of resin acids during production of wood pellets--a comparison of HPLC/ESI-MS with the GC/FID MDHS 83/2 method.

Axelsson S. et. al

J Environ Monit. 2011 Oct;13(10):2940-5.

Resin acids are constituents of natural and technical products of widespread use. Exposure is known to cause health effects in the airways and on the skin. Liquid chromatography/positive ion electrospray-mass spectrometry (HPLC/pos ESI-MS) was investigated for determination of 7-oxodehydroabietic (7-OXO), dehydroabietic (DHAA) and abietic acid (AA) in wood dust-containing air samples as a derivatisation-free alternative to the GC/FID HSE method 83/2, developed by the Health and Safety Executive UK. The resin acid 7-OXO was measured as a marker for oxidised resin acids, which are known to be the main contact allergens in colophonium. The found detection limits were 0.42 ng m(-3) for 7-OXO, 5.2 ng m(-3) for DHAA and 9.4 ng m(-3) for AA, respectively, which are considerably lower than with the GC/FID method (24, 115 and 89 ng m(-3)). The two methods correlated well, although consistently and significantly lower concentrations of 7-OXO were detected with LC/MS. The higher concentration of this compound with MDHS 83/2 is suggested to be an artefact from the derivatisation step in the presence of soluble wood dust remains.

Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior.

Duan W. et. al

Carbohydr Res. 2009 Jan 5;344(1):9-13.

A new type of chitosan derivative, dehydroabietic acid-modified chitosan (DAMC), was synthesized by the acylation reaction of chitosan with dehydroabietic acid chloride (DHAC) under microwave irradiation. The resulting product (DAMC) was characterized by FT-IR, UV, (1)H NMR, X-ray diffraction (XRD), scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. The degree of substitution (DS) of DAMC was 16.5%. And chitosan and DAMC were used as carriers of fenoprofen calcium (FC), and their controlled release behavior in artificial intestinal juice was studied. The results showed that the controlled release of FC from the carrier of DAMC is better than that from original chitosan.

Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels.

Gravato C. et. al

Ecotoxicol Environ Saf. 2005 Jun;61(2):221-9.

This study represents the first attempt to investigate the genotoxic effects and oxidative stress of resin acids in Mediterranean mussels (Mytilus galloprovincialis Lmk). Mussels were exposed to 2.7 microM abietic acid (AA) and dehydroabietic acid (DHAA) for 6, 12, 18, and 24h. Gill and hepatopancreas conjugation activity, antioxidant defense system, lipid peroxidation (LPO), and DNA damage were determined as reduced glutathione (GSH), glutathione S-transferase (GST) activity, glutathione peroxidase (GPx) activity, catalase (CAT) activity, LPO, and DNA strand breaks. AA caused significant GST inhibition in mussel gills at 12, 18, and 24h. Activity of the antioxidant enzymes, namely, GPx and CAT, was inhibited at 24 and 18 h, respectively, in mussel gills. A significant increase in gill LPO was observed at 24h. The DNA integrity of mussel hepatopancreas significantly decreased after 12 and 24 h exposure to AA. A significant increase in LPO was observed after 6h exposure to DHAA, in either mussel gills or hepatopancreas. DNA integrity was significantly decreased in mussel hepatopancreas after 12 and 24 h exposure to DHAA. AA induced oxidative damage and genotoxicity in mussels, because it promoted increases in LPO in gills and DNA strand breaks in hepatopancreas. DHAA promoted oxidative damage and genotoxicity in mussels, as significant increases were observed in LPO in gills and hepatopancreas and in DNA strand breaks in hepatopancreas.

Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives.

Huang X.C. et. al

Bioorg Med Chem Lett. 2013 Oct 1;23(19):5283-9.

A series of novel α-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma cell), HepG2 (human liver cancer cell) and SKOV3 (human ovarian cancer cell) human cancer cell lines were evaluated and compared with commercial anticancer drug 5-fluorouracil (5-FU), employing standard MTT assay. The pharmacological screening results revealed that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most demonstrated more potent inhibitory activities compared with the commercial anticancer drug 5-FU. The action mechanism of representative compound 7c was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicated that the compound can induce cell apoptosis in NCI-H460 cells. Cell cycle analysis showed that compound 7c mainly arrested NCI-H460 cells in G1 stage.

Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells.

Häkkinen S.T. et. al

J Biotechnol. 2012 Jan 20;157(2):287-94.

The aim of this study was to use whole cell catalysts as tools for modification of selected resin acids in order to obtain value-added functional derivatives. The enzymatic bioconversion capacities of two plant species were tested towards dehydroabietic acid. Dehydroabietic acid (DHA) is an abundant resin acid in conifers, representing a natural wood protectant. It is also one of the constituents found in by-products of the kraft chemical pulping industry. DHA was fed to tobacco (Nicotiana tabacum) and Madagascar periwinkle (Catharanthus roseus) plant cell and tissue cultures and bioconversion product formation was monitored using NMR analysis. Both plant species took up DHA from culture medium, and various types of typical detoxification processes occurred in both cultures. In addition, diverse responses to DHA treatment were observed, including differences in uptake kinetics, chemical modification of added substrate and changes in overall metabolism of the cells. Interestingly, Catharanthus roseus, a host species for pharmaceutically valuable terpenoid indole alkaloids, exhibited a very different bioconversion pattern for exogenously applied DHA than tobacco, which does not possess a terpenoid indole pathway. In tobacco, DHA is readily glycosylated in the carbonyl group, whereas in periwinkle it is proposed that a cytochrome P450-catalyzed enzymatic detoxification reaction takes place before the formation of glycosylated product.

Synthesis, structure analysis and cytotoxicity studies of novel unsymmetrically n,n'-substituted ureas from dehydroabietic Acid.

Rao X et. al

Chem Pharm Bull (Tokyo). 2008 Nov;56(11):1575-8.

A series of novel unsymmetrically N,N'-substituted ureas were synthesized from dehydroabietic acid and their structures were characterized by IR, 1H-NMR, 13C-NMR spectroscopy and single crystal X-ray diffraction. Three six-membered rings of urea 4c exhibited plane, half-chair and chair configurations, respectively. Their cytotoxicity activities against SMMC7721 liver cancer cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) method. The results showed that the title compounds exhibited highly effective cytotoxicity activities against SMMC7721 cells. Their IC50 values are between 8.8 and 14.2 micromol/l. The change of N' substituted groups resulted little difference to the cytotoxicity activities of ureas, which indicated that the cytotoxicity of this kind of ureas depend strongly on the tricyclic hydrophenanthrene structure.

Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br.

Xu X. et. al

Carbohydr Res. 2011 Sep 27;346(13):2024-7.

A new type of cellulose derivative, cellulose dehydroabietate (CDA), was synthesized by the O-acylation reaction of cellulose with dehydroabietic acid chloride (DHAC) using ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) as a solvent and 4-dimethyl-aminopyridine (DMAP) as a catalyst. The resulting CDA was characterized by means of FT-IR, X-ray diffraction (XRD), scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. Also, some properties of CDA were determined. These results showed that CDA has better solubility, water-repellency, and resistance to acids and bases than raw cellulose, and these properties increase with the DS of CDA.

Effects of dehydroabietic acid and abietic acid on survival, reproduction, and growth of the crustacean Daphnia magna.

Kamaya Y. et. al

Ecotoxicol Environ Saf. 2005 May;61(1):83-8.

Resin acids, a class of wood extractives, are potential toxic constituents in many pulp and paper mill effluents. In the present investigation, the effects of two predominant resin acids, dehydroabietic acid (DHA) and abietic acid (ABA), on survival, reproduction, and growth of the freshwater crustacean Daphnia magna were assessed over its life cycle. Based on the experimentally determined acute toxicity data (48-h EC(50)'s) for DHA (7.48 mg/L) and ABA (7.98 mg/L), D. magna was treated chronically with each resin acid at nominal concentrations of 0, 0.25, 0.5, 1.0, 2.0, 4.0, and 8.0mg/L for 21 days. Both DHA and ABA at concentrations as high as 4.0mg/L did not affect physiological and reproductive parameters such as time to maturation, number of molting, number of broods, and number of offspring produced from surviving daphnids, while significant mortality was observed only at 8.0mg/L in both cases. However, a small but statistically significant decrease in Daphnia growth (body length) at the end of exposure was detected at concentrations as low as 0.5mg/L for DHA and 1.0mg/L for ABA, respectively. These results indicated that both DHA and ABA had the potential to exhibit weak growth inhibition without apparent negative effects on reproduction to D. magna at nonlethal concentration levels. This slight effect is not expected to be ecologically significant because the concentrations of DHA and ABA in biologically treated pulp and paper mill effluents are well below the effective levels observed in the present study.