dihydrochelerythrine and dihydrosanguinarine

A series of C(6)-substituted dihydrobenzo[c]phenanthridines were synthesized by mild copper-catalyzed C(sp

Topics: Antineoplastic Agents; Apoptosis; Benzophenanthridines; Cell Line, Tumor; Cell Proliferation; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Isoquinolines; MCF-7 Cells; Models, Molecular; Molecular Structure; Structure-Activity Relationship

Ongoing study on the chemical constituents of the roots of Macleaya microcarpa led to the isolation of eight compounds of derivatives of triterpenes and organic acids in addition to some previously identified benzophenanthridines. The eight compounds were identified by spectroscopic methods as well as comparison with literature values as 1-oxo-2, 22 (30)-hopandien-29-oic acid (1), 3-oxo-12-oleanen-30-oic acid (2), 3α-hydroxy-12-oleanen-30-oic acid (3), 3β-hydroxy-12-oleanen-30-oic acid (4), ferulic acid (5), ferulic acid 4-O-β-D-glucoside (6), 3-O-feruloylquinic acid (7), and methyl 3-O-feruloylquinate (8). Of which, 1 is a new triterpenoid of hopanes and 2-8 are isolated from M microcarpa for the first time. In order to discover natural active compounds as potential agents of anti-ulcerative colitis (UC), an in vitro drug high-throughput screening model targeted x-box-binding protein 1 (xbp1) was employed to evaluate the activity of the major chemical constituents of M microcarpa. The result confirmed that two dihydrobenzophenanthridines, dihydrosanguinarine (9) and dihydrochelerythrine (10), showed a certain activity on activating the transcription of xbpl, a transcription factor (TF) associated with the occurrence, development, and potential treatment of UC, with their relative activating ratios being 1.76 and 1.77 times, respectively, as compared with control group.

Topics: Anti-Ulcer Agents; Benzophenanthridines; DNA-Binding Proteins; Isoquinolines; Papaveraceae; Plant Roots; Regulatory Factor X Transcription Factors; Transcription Factors; Transcription, Genetic; Triterpenes

The antifungal activities of dihydrosanguinarine and dihydrochelerythrine, isolated from the leaves of Macleaya microcarpa, were evaluated on 12 plant pathogenic fungi; the two compounds exhibited the highest antifungal activity against Botrytis cinerea Pers. Among the 11 tested plant pathogenic fungi in vitro, the two compounds showed the highest antifungal activity against B. cinerea Pers, with 95.16% and 98.32% mycelial growth inhibition at 50 µg mL⁻¹, respectively. In addition, the two compounds inhibited spore germination in vitro in a concentration-dependent manner. They also showed potent protective and curative effects against Erysiphe graminis and B. cinerea in vivo. This is the first report on the antifungal activity of dihydrosanguinarine and dihydrochelerythrine against pathogenic plant fungi.

Topics: Antifungal Agents; Benzophenanthridines; Botrytis; Fungi; Isoquinolines; Papaveraceae; Plant Leaves

Ichthyophthirius multifiliis is a holotrichous protozoan that invades the gills and skin surfaces of fish and can cause morbidity and high mortality in most species of freshwater fish worldwide. The present study was undertaken to investigate the antiparasitic activity of crude extracts and pure compounds from the leaves of Macleaya microcarpa. The chloroform extract showed a promising antiparasitic activity against I. multifiliis. Based on these finding, the chloroform extract was fractionated on silica gel column chromatography in a bioactivity-guided isolation affording two compounds showing potent activity. The structures of the two compounds were elucidated as dihydrosanguinarine and dihydrochelerythrine by hydrogen and carbon-13 nuclear magnetic resonance spectrum and electron ionization mass spectrometry. The in vivo tests revealed that dihydrosanguinarine and dihydrochelerythrine were effective against I. multifiliis with median effective concentration (EC(50)) values of 5.18 and 9.43 mg/l, respectively. The acute toxicities (LC(50)) of dihydrosanguinarine and dihydrochelerythrine for richadsin were 13.3 and 18.2mg/l, respectively. The overall results provided important information for the potential application of dihydrosanguinarine and dihydrochelerythrine in the therapy of serious infection caused by I. multifiliis.

Topics: Animals; Antiprotozoal Agents; Benzophenanthridines; Biological Assay; Ciliophora Infections; Confidence Intervals; Cyprinidae; Fish Diseases; Gills; Hymenostomatida; Isoquinolines; Lethal Dose 50; Magnetic Resonance Spectroscopy; Mass Spectrometry; Papaveraceae; Parasitic Sensitivity Tests; Plant Extracts; Plant Leaves; Time Factors

The herb of Chelidonium majus Linn is known to possess a variety of biological activities and applied in the therapy of various infectious diseases.. To evaluate the in vitro antifungal activity of the active components from Chelidonium majus against clinical drug-resistant yeast isolates.. Active compounds were obtained using bioassay-guided method. Six species of yeast fungi were exposed to the compounds. Minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) were determined according to the standard broth microdilution method.. Of the six compounds determined, 8-hydroxydihydrosanguinarine (1) and 8-hydroxydihydrochelerythrine (2) demonstrated potent activity with the MIC ranges of 2-80 and 4-100 microg/mL, respectively. Dihydrosanguinarine (3), dihydrochelerythrine (4), sanguinarine (5) and chelerythrine (6) had some degree of antifungal activity.. The overall results provided important information for the potential application of the 8-hydroxylated alkaloids from Chelidonium majus in the therapy of serious infection caused by drug-resistant fungi.

Topics: Alkaloids; Antifungal Agents; Benzophenanthridines; Candida; Chelidonium; Drug Evaluation, Preclinical; Drug Resistance; Heterocyclic Compounds, 4 or More Rings; Humans; Isoquinolines; Microbial Sensitivity Tests; Molecular Structure; Plant Extracts; Plants, Medicinal; Reference Standards