naphthoquinones and danthron

To study the anti-tumor chemical components of the pericarps of Juglans mandshurica.. The chemical constituents were isolated and purified by AB-8 macroporous adsorption resin, silica gel, Sephadex LH-20 columns and recrystallization. The structures were elucidated on the basis of physicochemical properties and NMR spectral data analysis.. From the pericarps of Juglans mandshurica, twelve compounds were separated and identified as 3-methoxy juglone(1), 3-ethoxy juglone(2), 1,8-di-hydroxy anthraquinone (3), juglone (4), 2α, 3α, 19α-trihydroxy ursolic acid (5), 1α, 3β-dihydroxy-olean-18-ene (6), methyl gallate (7), pterocarine(8), quercetin(9), kaempferol(10), daucosterol(11), and β-sitosterol(12).. Compounds 1 - 3 and 6 are isolated from the pericarps of Juglans mandshurica for the first time. Compounds 5 and 7 are isolated from Juglans genus for the first time.

Topics: Anthraquinones; Antineoplastic Agents, Phytogenic; Drugs, Chinese Herbal; Gallic Acid; Juglans; Kaempferols; Naphthoquinones; Phytochemicals; Seeds; Sitosterols; Triterpenes; Ursolic Acid

Quinones were studied for their growth inhibitory effect on cultured malignant cells. HCT-15 cells derived from human colon carcinoma were used for these experiments. Quinones used were arbutin in the benzoquinone group, juglone and lawsone in the naphthaquinone group, alizarin, emodin, 1,8-dihydroxyanthraquinone, and anthraquinone in the anthraquinone group, and xanthone. Cultured cells were incubated with various concentrations of the quinones for four days in a 5% CO2 incubator, after which cell numbers were counted and significance of differences was analyzed by Student's t test. Anthraquinones and naphthaquinones used in these experiments were more effective than the monocyclic quinone. The 50% suppression dose was less than 12.5 micrograms/ml for them. The number of OH groups seemed to play an important role in the degree of the cell growth inhibition: anthraquinones with 2 or 3 OH groups were more effective than those with no OH group like, 9,10-dioxoanthracene and xanthone. In fact, anthraquinones with no OH group and xanthone were not significantly effective. Flow cytometric histograms revealed a specific pattern; that is, lawsone and juglone in the naphthaquinone group and alizarin and 1,8-dihydroxy-anthraquinone in the anthraquinone group blocked mainly the S phase, and emodin in the anthraquinone group blocked the G1 to S phase of the cell cycle.

Topics: Anthraquinones; Antineoplastic Agents; Arbutin; Cell Division; Colonic Neoplasms; Humans; Naphthoquinones; Quinones; Tumor Cells, Cultured; Xanthenes; Xanthones

Unsubstituted anthraquinone, 4 substituted anthraquinones (emodin, danthron, physcion, a new compound M-108-C) and 3 dimers (skyrin, rugulosin, rugulin) were tested using the Ames/Salmonella assay (strains TA98, TA100, TA1537 and TA102). Danthron and emodin were found to be mutagenic for TA1537 with or without metabolic activation, physcion only with metabolic activation. A significant difference was found between the mutagenic activities of emodin (16.2 His+/nmole) and danthron (6.5 His+/nmole) as well as a high specific mutagenic activity for physcion (11.6 His+/nmole). These results on structure-mutagenic activity relationships suggest that the 6-methyl group plays an important role in the mutagenic activity after metabolic activation. Furthermore, and contrary to emodin, physcion exhibited a weak mutagenic activity for TA102, probably due to the formation of a different metabolite. Such information is necessary to evaluate the potential carcinogenic hazard of these compounds.

Topics: Anthraquinones; Emodin; Microsomes; Molecular Structure; Mutagenicity Tests; Mutagens; Naphthoquinones; Salmonella typhimurium

Epidermal strips, free of sebaceous gland and hair follicle contamination, were prepared from mouse tail skin. Epidermal homogenates synthesized prostaglandins and 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE) from exogenously added [1-14C]arachidonic acid. The effects of pH, assay time, substrate concentration, and several selective inhibitors upon the lipoxygenase and cyclooxygenase pathways were determined. Ultracentrifugation of the crude homogenate at 105,000 g sedimented both activities, and pellet 12-HETE synthesis increased 2-fold relative to the crude homogenate. Recombination of the 105,000 g pellet and supernatant gave yields of prostaglandins and 12-HETE essentially equivalent to that of crude homogenate. When tested in homogenate with 4.5 microM arachidonic acid, anthralin specifically inhibited 12-HETE production with IC50 of 50.0 microM; no significant effect against cyclooxygenase was observed over the dose range of 2-200 microM. 1,8-Dihydroxy-9,10-anthraquinone (DHAQ) also specifically inhibited 12-HETE synthesis, but the dose response curve was flatter and maximum inhibition was only 55% at 200 microM. 6-Chloro-2,3-dihydroxy-1,4-naphthoquinone (CDNQ), an agent with topical antipsoriatic activity, also inhibited 12-HETE synthesis with an IC50 of 25 microM, but simultaneously stimulated prostaglandin production, up to 2.5-fold at 200 microM. When tested with washed human platelets, anthralin again specifically inhibited 12-HETE production with an IC50 of 10 microM, while DHAQ inhibited lipoxygenase activity by only 40% at 25 microM. When tested in platelets, CDNQ gave 33% inhibition of 12-HETE production at 200 microM, although prostaglandin synthesis was stimulated over the range of 25-200 microM. It is proposed that certain antipsoriatic agents may exert their action through modulation of arachidonic acid metabolism.

Topics: Animals; Anthracenes; Anthralin; Anthraquinones; Arachidonate Lipoxygenases; Arachidonic Acid; Arachidonic Acids; Blood Platelets; Cyclooxygenase Inhibitors; Epidermis; Female; Humans; Lipoxygenase Inhibitors; Male; Mice; Naphthoquinones; Prostaglandin-Endoperoxide Synthases; Psoriasis