Displaying all 19 publications

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  1. Usman A, Razak IA, Fun HK, Chantrapromma S, Zhang Y, Xu JH
    Acta Crystallogr C, 2002 Sep;58(Pt 9):o543-4.
    PMID: 12205382
    In the title compound, C(24)H(17)NO(2)S, the dioxine and thiazoline rings are distorted from planarity towards a half-chair and an envelope conformation, respectively. The configurations of the dioxine ring, the thiazoline ring and the attached phenyl ring are conditioned by the sp(3) state of the two bridgehead C atoms. The phenanthrene system is nearly coplanar with the dioxine ring, while the attached phenyl ring is orthogonal to the thiazoline ring.
    Matched MeSH terms: Phenanthrenes
  2. Usman A, Razak IA, Fun HK, Chantrapromma S, Zhang Y, Xu JH
    Acta Crystallogr C, 2002 Aug;58(Pt 8):o477-9.
    PMID: 12154304
    In the title compounds, C(24)H(17)NO(3), (I), and C(43)H(27)NO(5), (II), the dioxine ring is not planar and tends toward a boat conformation. The oxazoline ring adopts a twisted conformation in molecule (I) but is essentially planar in molecule (II). The configuration of the dioxine-oxazoline system is determined by the sp(3) state of the two shared atoms. The phenanthrene moiety is nearly coplanar with the dioxine ring, while the phenyl ring is perpendicular to the attached oxazole ring. The triclinic unit cell of (II) contains two crystallographically independent molecules related by a pseudo-inversion centre.
    Matched MeSH terms: Phenanthrenes
  3. Von Lau E, Gan S, Ng HK
    J Environ Manage, 2012 Sep 30;107:124-30.
    PMID: 22595079 DOI: 10.1016/j.jenvman.2012.04.029
    Experimental extraction tests are conducted to investigate feasibility of saturated palm kernel oil (PKO) and unsaturated soybean oil (SO) to extract polycyclic aromatic hydrocarbons (PAHs) from contaminated sand. The extraction rates and efficiencies for lowly contaminated (LC) and highly contaminated (HC) sands at temperatures of 30 °C and 70 °C are evaluated using empirical first order kinetic dissolution models. In LC sand, the extraction is dominated by the diffusion of PAHs adsorbed onto particle surfaces and the direct dissolution of PAH phase. In HC sand, a rapid diffusion of PAHs adsorbed onto particle surfaces and a direct dissolution of PAH phase occur followed by a slower diffusion of PAHs entrapped within the pores and micropores. Larger diffusion resistance during HC sand extractions results in an average 10.8% reduction in extraction efficiencies compared to LC sand. Increased temperature generally increases the mass transfer rates and extraction efficiencies. Additionally, the physicochemical properties of both oils and PAHs also determine the extent of PAH extraction into oil.
    Matched MeSH terms: Phenanthrenes/isolation & purification*
  4. Awang K, Hadi AH, Saidi N, Mukhtar MR, Morita H, Litaudon M
    Fitoterapia, 2008 Jun;79(4):308-10.
    PMID: 18313862 DOI: 10.1016/j.fitote.2007.11.025
    The bark of Cryptocarya crassinervia provided two new phenantrene alkaloids, 2-hydroxyatherosperminine (1) and N-demethyl-2-methoxyatherosperminine (2).
    Matched MeSH terms: Phenanthrenes/chemistry*
  5. Hadibarata T, Tachibana S, Askari M
    J Microbiol Biotechnol, 2011 Mar;21(3):299-304.
    PMID: 21464602
    Phenanthrene degradation by Polyporus sp. S133, a new phenanthrene-degrading strain, was investigated in this work. The analysis of degradation was performed by calculation of the remaining phenanthrene by gas chromatography-mass spectrometry. When cells were grown in phenanthrene culture after 92 h, all but 200 and 250 mg/l of the phenanthrene had been degraded. New metabolic pathways of phenanthrene and a better understanding of the phenoloxidases and dioxygenase mechanism involved in degradation of phenanthrene were explored in this research. The mechanism of degradation was determined through identification of the several metabolites; 9,10-phenanthrenequinone, 2,2'-diphenic acid, salicylic acid, and catechol. 9,10-Oxidation and ring cleavage to give 9,10-phenanthrenequinone is the major fate of phenanthrene in ligninolytic Polyporus sp. S133. The identification of 2,2'-diphenic acid in culture extracts indicates that phenanthrene was initially attacked through dioxigenation at C9 and C10 to give cis-9,10-dihydrodiol. Dehydrogenation of phenanthrene-cis-9,10-dihydrodiol to produce the corresponding diol, followed by ortho-cleavage of the oxygenated ring, produced 2,2'-diphenic acid. Several enzymes (manganese peroxidase, lignin peroxidase, laccase, 1,2-dioxygenase, and 2,3-dioxygenase) produced by Polyporus sp. S133 was detected during the incubation. The highest level of activity was shown at 92 h of culture.
    Matched MeSH terms: Phenanthrenes/analysis; Phenanthrenes/metabolism*
  6. Jantan I, Raweh SM, Yasin YH, Murad S
    Phytother Res, 2006 Jun;20(6):493-6.
    PMID: 16619347
    Six aporphine and one phenanthrenoid alkaloids isolated from Aromadendron elegans Blume were investigated for their ability to inhibit arachidonic acid (AA), collagen and ADP induced platelet aggregation in human whole blood. The antiplatelet activity of the compounds was measured in vitro by the Chrono Log whole blood aggregometer using an electrical impedance method. Of the compounds tested, (-)-N-acetylnornuciferine, (-)-N-acetylanonaine and 1-(N-acetyl-N-methylamino)ethyl-3,4,6-trimethoxy-7-hydroxyphenanthrene showed strong inhibition on platelet aggregation caused by all three inducers. (-)-N-acetylanonaine was the most effective antiplatelet compound as it inhibited both arachidonic acid, collagen and ADP-induced platelet aggregation with IC(50) values of 66.1, 95.1 and 80.6 microm, respectively.
    Matched MeSH terms: Phenanthrenes/isolation & purification; Phenanthrenes/pharmacology
  7. Venny, Gan S, Ng HK
    Environ Sci Pollut Res Int, 2014 Feb;21(4):2888-97.
    PMID: 24151025 DOI: 10.1007/s11356-013-2207-7
    Extensive contamination of soils by highly recalcitrant contaminants such as polycyclic aromatic hydrocarbons (PAHs) is an environmental problem arising from rapid industrialisation. This work focusses on the remediation of soil contaminated with 3- and 4-aromatic ring PAHs (phenanthrene (PHE) and fluoranthene (FLUT)) through catalysed hydrogen peroxide propagation (CHP). In the present work, the operating parameters of the CHP treatment in packed soil column was optimised with central composite design (H2O2/soil 0.081, Fe(3+)/soil 0.024, sodium pyrophosphate (SP)/soil 0.024, pH of SP solution 7.73). The effect of contaminant aging on PAH removals was also investigated. Remarkable oxidative PAH removals were observed for the short aging and extended aging period (up to 86.73 and 70.61 % for PHE and FLUT, respectively). The impacts of CHP on soil biological, chemical and physical properties were studied for both spiked and aged soils. Overall, the soil functionality analyses after the proposed operating condition demonstrated that the values for soil respiration, electrical conductivity, pH and iron precipitation fell within acceptable limits, indicating the compatibility of the CHP process with land restoration.
    Matched MeSH terms: Phenanthrenes/metabolism; Phenanthrenes/chemistry*
  8. Karami A, Romano N, Hamzah H, Simpson SL, Yap CK
    Environ Pollut, 2016 May;212:155-165.
    PMID: 26845363 DOI: 10.1016/j.envpol.2016.01.055
    Information on the biological responses of polyploid animals towards environmental contaminants is scarce. This study aimed to compare reproductive axis-related gene expressions in the brain, plasma biochemical responses, and the liver and gill histopathological alterations in diploid and triploid full-sibling juvenile African catfish (Clarias gariepinus). Fish were exposed for 96 h to one of the two waterborne phenanthrene (Phe) concentrations [mean measured (SD): 6.2 (2.4) and 76 (4.2) μg/L]. In triploids, exposure to 76 μg/L Phe increased mRNA level of fushi tarazu-factor 1 (ftz-f1). Expression of tryptophan hydroxylase2 (tph2) was also elevated in both ploidies following the exposure to 76 μg/L Phe compared to the solvent control. In triploids, 76 μg/L Phe increased plasma alkaline phosphatase (ALP) and lactate dehydrogenase (LDH) levels compared to the other Phe-exposed group. It also elevated lactate and glucose contents relative to the other groups. In diploids, however, biochemical biomarkers did not change. Phenanthrene exposures elevated glycogen contents and the prevalence of histopathological lesions in the liver and gills of both ploidies. This study showed substantial differences between diploids and triploids on biochemical and molecular biomarker responses, but similar histopathological alterations following acute Phe exposures.
    Matched MeSH terms: Phenanthrenes/metabolism; Phenanthrenes/toxicity*
  9. Karami A, Romano N, Galloway T, Hamzah H
    Environ Res, 2016 Nov;151:58-70.
    PMID: 27451000 DOI: 10.1016/j.envres.2016.07.024
    Despite the ubiquity of microplastics (MPs) in aquatic environments and their proven ability to carry a wide variety of chemicals, very little is known about the impacts of virgin or contaminant-loaded MPs on organisms. The primary aim of this study was to investigate the impacts of virgin or phenanthrene (Phe)-loaded low-density polyethylene (LDPE) fragments on a suite of biomarker responses in juvenile African catfish (Clarias gariepinus). Virgin LDPE (50 or 500µg/L) were preloaded with one of two nominal Phe concentrations (10 or 100µg/L) and were exposed to the fish for 96h. Our findings showed one or both Phe treatments significantly increased the degree of tissue change (DTC) in the liver while decreased the transcription levels of forkhead box L2 (foxl2) and tryptophan hydroxylase2 (tph2) in the brain of C. gariepinus. Exposure to either levels of virgin MPs increased the DTC in the liver and plasma albumin: globulin ratio while decreased the transcription levels of tph2. Moreover, MPs modulated (interacted with) the impact of Phe on the DTC in the gill, plasma concentrations of cholesterol, high-density lipoprotein (HDL), total protein (TP), albumin, and globulin, and the transcription levels of fushi tarazu-factor 1 (ftz-f1), gonadotropin-releasing hormone (GnRH), 11 β-hydroxysteroid dehydrogenase type 2 (11β-hsd2), and liver glycogen stores. Results of this study highlight the ability of virgin LDPE fragments to cause toxicity and to modulate the adverse impacts of Phe in C. gariepinus. Due to the wide distribution of MPs and other classes of contaminants in aquatic environments, further studies are urgently needed to elucidate the toxicity of virgin or contaminant-loaded MPs on organisms.
    Matched MeSH terms: Phenanthrenes/analysis; Phenanthrenes/toxicity*
  10. Nasrullah AA, Zahari A, Mohamad J, Awang K
    Molecules, 2013 Jul 08;18(7):8009-17.
    PMID: 23884132 DOI: 10.3390/molecules18078009
    A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug/mL and 42.87 ug/mL, respectively.
    Matched MeSH terms: Phenanthrenes/isolation & purification; Phenanthrenes/pharmacology; Phenanthrenes/chemistry
  11. Bakhtiari, Alireza Riyahi, Mohamad Pauzi Zakaria, Mohammad Ismail Yaziz, Mohamad Nordin Lajis, Bi, Xinhui, Mohamad Reza Mohamad Shafiee, et al.
    MyJurnal
    Surface sediment samples were collected from five locations at the downstream of Klang River in January 2007 to examine the spatial distribution, composition, and sources of 19 parent polycyclic aromatic hydrocarbons (PAHs) and aliphatic hydrocarbon (n-alkanes) using gas chromatographymass spectrometry. The total concentrations of the 19 PAHs in the sediments were found to range from 1304 to 2187 ng g-1 sediment. Meanwhile, total concentrations of n-alkanes ranged from 17008 to 27116 μg g-1 sediment. The concentration of n-alkanes in the sediment was significantly correlated (r = 0.991, p = 0.001) with the content of sediment organic carbon. In this study, all the sediments exhibited phenanthrene/anthracene (PHE/ANT >15) fluoranthene/(fluorantene+pyrene) (FLT/FLT+PYR < 0.4), ethylphenanthrenes/phenanthrene (MP/P >1), combustion PAHs/total PAHs (CombPAH/Σ19PAH
    Matched MeSH terms: Phenanthrenes
  12. Storey S, Ashaari MM, Clipson N, Doyle E, de Menezes AB
    Front Microbiol, 2018;9:2815.
    PMID: 30519226 DOI: 10.3389/fmicb.2018.02815
    Bioremediation offers a sustainable approach for removal of polycyclic aromatic hydrocarbons (PAHs) from the environment; however, information regarding the microbial communities involved remains limited. In this study, microbial community dynamics and the abundance of the key gene (PAH-RHDα) encoding a ring hydroxylating dioxygenase involved in PAH degradation were examined during degradation of phenanthrene in a podzolic soil from the site of a former timber treatment facility. The 10,000-fold greater abundance of this gene associated with Gram-positive bacteria found in phenanthrene-amended soil compared to unamended soil indicated the likely role of Gram-positive bacteria in PAH degradation. In contrast, the abundance of the Gram-negative PAHs-RHDα gene was very low throughout the experiment. While phenanthrene induced increases in the abundance of a small number of OTUs from the Actinomycetales and Sphingomonadale, most of the remainder of the community remained stable. A single unclassified OTU from the Micrococcaceae family increased ~20-fold in relative abundance, reaching 32% of the total sequences in amended microcosms on day 7 of the experiment. The relative abundance of this same OTU increased 4.5-fold in unamended soils, and a similar pattern was observed for the second most abundant PAH-responsive OTU, classified into the Sphingomonas genus. Furthermore, the relative abundance of both of these OTUs decreased substantially between days 7 and 17 in the phenanthrene-amended and control microcosms. This suggests that their opportunistic phenotype, in addition to likely PAH-degrading ability, was determinant in the vigorous growth of dominant PAH-responsive OTUs following phenanthrene amendment. This study provides new information on the temporal response of soil microbial communities to the presence and degradation of a significant environmental pollutant, and as such has the potential to inform the design of PAH bioremediation protocols.
    Matched MeSH terms: Phenanthrenes
  13. Loh SH, Sanagi MM, Wan Ibrahim WA, Hasan MN
    Talanta, 2013 Mar 15;106:200-5.
    PMID: 23598117 DOI: 10.1016/j.talanta.2012.12.032
    A new microextraction procedure termed multi-walled carbon nanotube-impregnated agarose film microextraction (MWCNT-AFME) has been developed. The method utilized multi-walled carbon nanotubes (MWCNTs) immobilized in agarose film to serve as adsorbent in solid phase microextraction (SPME). The film was prepared by mixing the MWCNTs in agarose solution and drying the mixture in oven. Extraction of selected polycyclic aromatic hydrocarbons was performed by inserting a needle through circular MWCNT-impregnated agarose films (5 mm diameter) and the assembly was dipped into an agitated sample solution prior to micro high performance liquid chromatography-ultraviolet analysis. Back extraction was then performed using ultrasonication of the films in 100 μL of solvent. The film was discarded after single use, thus avoiding any analyte carry-over effect. Due to the mesoporous nature of the agarose film, the MWCNTs were immobilized easily within the film and thus allowing for close contact between adsorbent and analytes. Under the optimized extraction conditions, the technique achieved trace LODs in the range of 0.1 to 50 ng L(-1) for the targeted analytes, namely fluoranthene, phenanthrene and benzo[a]pyrene. The method was successfully applied to the analysis of spiked green tea beverage samples with good relative recoveries in the range of 91.1 to 107.2%. The results supported the feasibility of agarose to serve as adsorbent holder in SPME which then minimizes the consumption of chemicals and disposal cost of organic wastes.
    Matched MeSH terms: Phenanthrenes/isolation & purification*
  14. Venny, Gan S, Ng HK
    Sci Total Environ, 2012 Mar 1;419:240-9.
    PMID: 22285087 DOI: 10.1016/j.scitotenv.2011.12.053
    This work focuses on the remediation of polycyclic aromatic hydrocarbon (PAH)-contaminated soil using modified Fenton (MF) treatment coupled with a novel chelating agent (CA), a more effective technique among currently available technologies. The performance of MF treatment to promote PAH oxidation in artificially contaminated soil was investigated in a packed column with a hydrogen peroxide (H(2)O(2)) delivery system simulating in-situ soil flushing which is more representative of field conditions. The effectiveness of process parameters H(2)O(2)/soil, Fe(3+)/soil, CA/soil weight ratios and reaction time were studied using a 2(4) three level factorial design experiments. An optimised operating condition of the MF treatment was observed at H(2)O(2)/soil 0.05, Fe(3+)/soil 0.025, CA/soil 0.04 and 3h reaction time with 79.42% and 68.08% PAH removals attainable for the upper and lower parts of the soil column respectively. The effects of natural attenuation and biostimulation process as post-treatment in the remediation of the PAH-contaminated soil were also studied. In all cases, 3-aromatic ring PAH (phenanthrene) was more readily degraded than 4-aromatic ring PAH (fluoranthene) regardless of the bioremediation approach. The results revealed that both natural attenuation and biostimulation could offer remarkable enhancement of up to 6.34% and 9.38% in PAH removals respectively after 8 weeks of incubation period. Overall, the results demonstrated that combined inorganic CA-enhanced MF treatment and bioremediation serves as a suitable strategy to enhance soil quality particularly to remediate soils heavily contaminated with mixtures of PAHs.
    Matched MeSH terms: Phenanthrenes/metabolism*
  15. Ng NT, Sanagi MM, Wan Ibrahim WN, Wan Ibrahim WA
    Food Chem, 2017 May 01;222:28-34.
    PMID: 28041555 DOI: 10.1016/j.foodchem.2016.11.147
    Agarose-chitosan-immobilized octadecylsilyl-silica (C18) film micro-solid phase extraction (μSPE) was developed and applied for the determination of phenanthrene (PHE) and pyrene (PYR) in chrysanthemum tea samples using high performance liquid chromatography-ultraviolet detection (HPLC-UV). The film of blended agarose and chitosan allows good dispersion of C18, prevents the leaching of C18 during application and enhances the film mechanical stability. Important μSPE parameters were optimized including amount of sorbent loading, extraction time, desorption solvent and desorption time. The matrix match calibration curves showed good linearity (r⩾0.994) over a concentration range of 1-500ppb. Under the optimized conditions, the proposed method showed good limits of detection (0.549-0.673ppb), good analyte recoveries (100.8-105.99%) and good reproducibilities (RSDs⩽13.53%, n=3) with preconcentration factors of 4 and 72 for PHE and PYR, respectively.
    Matched MeSH terms: Phenanthrenes/analysis*
  16. LIANG SUN TAN, SAW HONG LOH
    MyJurnal
    Polycyclic aromatic hydrocarbons (PAHs) are hazardous and persistent organic pollutants that usually exist at low concentrations in the environment. In this study, dispersive liquid-liquid microextraction (DLLME) technique coupled with high performance liquid chromatography-fluorescence detection (HPLC-FD) was optimized for the analysis of selected PAHs, namely phenanthrene (PHE), fluoranthene (FLA) and benzo[a]pyrene (BaP) in apple juice. Under the optimal extraction conditions (the mixture of 200 µL of acetone and 50 µL of 1-octanol was applied to extract the selected PAHs for 1 min), the DLLME-HPLC-FD showed excellent linearity over the concentration range of 5 to 200 µg/L for both PHE and FLA, and 0.01 to 5 µg/L for BaP with correlation coefficients, r ≥ 0.9956. The method offered ultra-trace detection of selected PAHs in the range of 0.002 to 0.5 µg/L, and negligible matrix effects in determining selected PAHs with relative recovery average within the range of 92.6 to 109.6% in apple juice. The advantages of applying this method for the extraction of PAHs include rapidity, simple operation, as well as small consumption of organic extraction solvent, which is beneficial for routine analysis.
    Matched MeSH terms: Phenanthrenes
  17. Al Farraj DA, Hadibarata T, Yuniarto A, Alkufeidy RM, Alshammari MK, Syafiuddin A
    Bioprocess Biosyst Eng, 2020 Dec;43(12):2305-2314.
    PMID: 32812060 DOI: 10.1007/s00449-020-02415-4
    The present study aimed to determine the degradation and transformation of three-ring PAHs phenanthrene and anthracene by Cryptococcus sp. MR22 and Halomonas sp. BR04 under halophilic conditions. The growth progress of Cryptococcus sp. MR22 and Halomonas sp. BR04 on anthracene and phenanthrene was monitored by colony-forming unit (CFU) technique. The growth of the bacteria was maintained at a maximum concentration of 200 mg/L of all tested hydrocarbon, indicating that Cryptococcus sp. MR22 and Halomonas sp. BR04 significantly perform in the removal of the PAH-contaminated medium at low concentrations. The fit model to represent the biodegradation kinetics of both PAHs was first-order rate equation The extract prepared from cells supplemented with three different substrates exhibited some enzymes such as hydroxylase, dioxygenase, laccase and peroxidase. The results suggest that both strains had an impressive ability in the degradation of aromatic and aliphatic hydrocarbon but also could tolerate in the extreme salinity condition.
    Matched MeSH terms: Phenanthrenes/chemistry*
  18. Mahendran R, Lim SK, Ong KC, Chua KH, Chai HC
    Clin Exp Nephrol, 2021 Nov;25(11):1163-1172.
    PMID: 34254206 DOI: 10.1007/s10157-021-02111-x
    BACKGROUND: Autosomal dominant polycystic kidney disease (ADPKD) is a monogenic kidney disorder that impairs renal functions progressively leading to kidney failure. The disease affects between 1:400 and 1:1000 ratio of the people worldwide. It is caused by the mutated PKD1 and PKD2 genes which encode for the defective polycystins. Polycystins mimic the receptor protein or protein channel and mediate aberrant cell signaling that causes cystic development in the renal parenchyma. The cystic development is driven by the increased cyclic AMP stimulating fluid secretion and infinite cell growth. In recent years, natural product-derived small molecules or drugs targeting specific signaling pathways have caught attention in the drug discovery discipline. The advantages of natural products over synthetic drugs enthusiast researchers to utilize the medicinal benefits in various diseases including ADPKD.

    CONCLUSION: Overall, this review discusses some of the previously studied and reported natural products and their mechanisms of action which may potentially be redirected into ADPKD.

    Matched MeSH terms: Phenanthrenes/pharmacology
  19. Ang KP, Tan HK, Selvaraja M, Kadir AA, Somchit MN, Akim AM, et al.
    Planta Med, 2011 Nov;77(16):1782-7.
    PMID: 21614753 DOI: 10.1055/s-0030-1271119
    Development of early stage atherosclerosis involves the activation of endothelial cells by oxidized low-density lipoprotein (oxLDL) with subsequent increases in endothelial permeability and expression of adhesion molecules favoring the adherence of monocytes to the endothelium. Cryptotanshinone (CTS), a major compound derived from the Chinese herb Salvia miltiorrhiza, is known for its protective effects against cardiovascular diseases. The aim of this study was to determine whether CTS could prevent the oxLDL-induced early atherosclerotic events. OxLDL (100 µg/mL) was used to increase endothelial permeability and induce monocyte-endothelial cell adhesion in human umbilical vein endothelial cells (HUVECs). Endothelial nitric oxide (NO) concentrations, a permeability-regulating molecule, and expressions of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) were measured. Results show that a) endothelial hyperpermeability was suppressed by 94 % (p 
    Matched MeSH terms: Phenanthrenes/pharmacology*
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