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[Purification, glucose-6-phosphate dehydrogenase inhibition, and HPLC analysis of four 1,8-dihydroxyanthrones].
Pharm Acta Helv. 1989; 64(1):8-15.PA

Abstract

With regard to the examination of their antipsoriatic properties, four 1,8-dihydroxyanthrones were prepared in a purity greater than 99%: Dithranol (1, anthralin) by chromatographic purification, chrysarobin (2) either by work-up from commercial chrysarobin or by an oxidative cleavage (FeCl3) of aloin, followed by a reduction (SnCl2/HCl) of the produced anthraquinone derivative (6), aloe emodin anthrone (3) by the action of aquous sodium tetraborate on aloin and frangula emodin anthrone (4) by the SnCl2/HCl-reduction of frangula emodin (7) isolated from the dry extract of the bark of alder buckthorn. UV/VIS, IR, 1H-NMR and mass spectra confirmed the structures of the four anthrones which all distinctly inhibited G-6-P dehydrogenase (0.05 mmol, desactivation in 6 h). For clinical studies the anthrones were incorporated into white petrolatum with exclusion of oxygen (under Ar). The anthrone content of the preparations was determined by HPLC (LiChrosorb RP-18, 7 microns [280 x 4 mm]; 1.5 ml/min MeOH/water/HOAc [80:20:0.2]) after extraction with CH2Cl2 (tR = 1: 10.4 min, 2: 15.3 min, 3: 4.7 min, 4: 7.7 min).

Authors

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Pub Type(s)

English Abstract
Journal Article

Language

ger

PubMed ID

2717648

Citation

Rychener, M, and W Steiger. "[Purification, Glucose-6-phosphate Dehydrogenase Inhibition, and HPLC Analysis of Four 1,8-dihydroxyanthrones]." Pharmaceutica Acta Helvetiae, vol. 64, no. 1, 1989, pp. 8-15.
Rychener M, Steiger W. [Purification, glucose-6-phosphate dehydrogenase inhibition, and HPLC analysis of four 1,8-dihydroxyanthrones]. Pharm Acta Helv. 1989;64(1):8-15.
Rychener, M., & Steiger, W. (1989). [Purification, glucose-6-phosphate dehydrogenase inhibition, and HPLC analysis of four 1,8-dihydroxyanthrones]. Pharmaceutica Acta Helvetiae, 64(1), 8-15.
Rychener M, Steiger W. [Purification, Glucose-6-phosphate Dehydrogenase Inhibition, and HPLC Analysis of Four 1,8-dihydroxyanthrones]. Pharm Acta Helv. 1989;64(1):8-15. PubMed PMID: 2717648.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [Purification, glucose-6-phosphate dehydrogenase inhibition, and HPLC analysis of four 1,8-dihydroxyanthrones]. AU - Rychener,M, AU - Steiger,W, PY - 1989/1/1/pubmed PY - 1989/1/1/medline PY - 1989/1/1/entrez SP - 8 EP - 15 JF - Pharmaceutica acta Helvetiae JO - Pharm Acta Helv VL - 64 IS - 1 N2 - With regard to the examination of their antipsoriatic properties, four 1,8-dihydroxyanthrones were prepared in a purity greater than 99%: Dithranol (1, anthralin) by chromatographic purification, chrysarobin (2) either by work-up from commercial chrysarobin or by an oxidative cleavage (FeCl3) of aloin, followed by a reduction (SnCl2/HCl) of the produced anthraquinone derivative (6), aloe emodin anthrone (3) by the action of aquous sodium tetraborate on aloin and frangula emodin anthrone (4) by the SnCl2/HCl-reduction of frangula emodin (7) isolated from the dry extract of the bark of alder buckthorn. UV/VIS, IR, 1H-NMR and mass spectra confirmed the structures of the four anthrones which all distinctly inhibited G-6-P dehydrogenase (0.05 mmol, desactivation in 6 h). For clinical studies the anthrones were incorporated into white petrolatum with exclusion of oxygen (under Ar). The anthrone content of the preparations was determined by HPLC (LiChrosorb RP-18, 7 microns [280 x 4 mm]; 1.5 ml/min MeOH/water/HOAc [80:20:0.2]) after extraction with CH2Cl2 (tR = 1: 10.4 min, 2: 15.3 min, 3: 4.7 min, 4: 7.7 min). SN - 0031-6865 UR - https://www.unboundmedicine.com/medline/citation/2717648/[Purification_glucose_6_phosphate_dehydrogenase_inhibition_and_HPLC_analysis_of_four_18_dihydroxyanthrones]_ L2 - https://antibodies.cancer.gov/detail/CPTC-AKR1B1-1 DB - PRIME DP - Unbound Medicine ER -