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The Journal of Pharmacology and... Jul 1956
Topics: Electric Stimulation; Heart; Veratrum Alkaloids
PubMed: 13332578
DOI: No ID Found -
The Journal of Clinical Investigation Jan 1953
Topics: Biomedical Research; Kidney; Protoveratrines; Veratrum Alkaloids
PubMed: 13011211
DOI: 10.1172/JCI102714 -
British Medical Journal Feb 1954
Topics: Hypersensitivity; Hypertension; Immune System Diseases; Veratrum Alkaloids
PubMed: 13115709
DOI: 10.1136/bmj.1.4857.316 -
Bioorganic & Medicinal Chemistry Apr 2023Cyclopamine (1), the teratogenic steroidal alkaloid isolated from corn lily (Veratrum californicum), has recently gained renewed interest due to its anticancer...
Cyclopamine (1), the teratogenic steroidal alkaloid isolated from corn lily (Veratrum californicum), has recently gained renewed interest due to its anticancer potential, that has been translated into the FDA approval of three Hedgehog (Hh) pathway inhibiting antitumor drugs. A chemical analysis of mother liquors obtained from crystallization of cyclopamine, extracted from roots and rhizomes of V. californicum, resulted in the isolation of two unprecedented cyclopamine analogues, 18-hydroxycyclopamine (2) and 24R-hydroxycyclopamine (3), the first compounds of this class to show modifications on rings D-F. The stereostructures of these new natural compounds have been established based on a detailed MS and 1D/2D NMR investigation. The isolated compounds were evaluated with the dual-luciferase bioassay for their inhibition of the hedgehog pathway in comparison to cyclopamine, providing new insights into the structure-activity relationships for this class of compounds.
Topics: Veratrum; Hedgehog Proteins; Veratrum Alkaloids; Alkaloids
PubMed: 37001245
DOI: 10.1016/j.bmc.2023.117265 -
The Journal of Organic Chemistry Sep 2013Organocatalyzed enantioselective allylation of 2-iodocyclohexenone followed by methylation and oxy-Cope rearrangement delivered enantiomerically enriched 2-methyl...
Organocatalyzed enantioselective allylation of 2-iodocyclohexenone followed by methylation and oxy-Cope rearrangement delivered enantiomerically enriched 2-methyl 3-allyl cyclohexanone, which engaged in acid-catalyzed Robinson annulation to give the bicyclic enone. Subsequent elaboration of the pendant allyl group into an α-diazo β-keto ester set the stage for Rh-mediated cyclization to deliver the tricyclic A-B-C core of the Veratrum alkaloids.
Topics: Cyclization; Cyclohexanones; Molecular Structure; Veratrum Alkaloids
PubMed: 23859604
DOI: 10.1021/jo401158d -
Planta Medica Dec 1993
Topics: Animals; Antihypertensive Agents; Female; Magnetic Resonance Spectroscopy; Male; Molecular Structure; Plants, Medicinal; Plants, Toxic; Rats; Rats, Wistar; Veratrum; Veratrum Alkaloids
PubMed: 8302959
DOI: 10.1055/s-2006-959767 -
The Journal of Pharmacology and... Nov 1954
Topics: Ephedrine; Heart; Isoproterenol; Phenylephrine; Tyramine; Veratrum Alkaloids
PubMed: 13212646
DOI: No ID Found -
Natural Product Communications Aug 2013Four steroidal alkaloids extracted from the roots and rhizomes of Veratrum californicum were separated by high performance liquid chromatography (HPLC) and identified...
Four steroidal alkaloids extracted from the roots and rhizomes of Veratrum californicum were separated by high performance liquid chromatography (HPLC) and identified using high resolution electrospray ionization time of flight tandem mass spectrometry (ESI-TOF-MS/MS) as veratrosine, cycloposine, veratramine, and cyclopamine. This paper compares ethanol and benzene as extraction solvents, HPLC solvent conditions leading to good separation of steroidal alkaloids, and MS/MS fragmentation patterns for the four steroidal alkaloids which have been released to the public database MassBank.jp. The reported Soxhlet extraction method nearly triples the recovery of steroidal alkaloids from V. californicum.
Topics: Chromatography, High Pressure Liquid; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry; Veratrum; Veratrum Alkaloids
PubMed: 24079166
DOI: No ID Found -
Vitamins and Hormones 2012Dysregulated Hedgehog (Hh) signaling has been implicated in a growing number of human cancers. Although first identified as an important developmental signaling pathway... (Review)
Review
Dysregulated Hedgehog (Hh) signaling has been implicated in a growing number of human cancers. Although first identified as an important developmental signaling pathway crucial for cellular proliferation, differentiation, and migration during organogenesis in invertebrates, these fundamental processes have been co-opted in human cancers. Initial evidence for the Hh pathway in tumor biology comes from mutations of signaling pathway components in a hereditary cancer syndrome that typically results in basal-cell carcinoma and medulloblastoma. Subsequent analysis revealed that Hh pathway mutations are found in sporadic tumors as well as activated Hh signaling in several epithelial cancers independent of Hh pathway mutation status. Further, recent evidence has demonstrated paracrine Hh signaling within stromal cells of the tumor microenvironment with implications for drug delivery. Several Hh antagonists targeting the Hh receptor, Smoothened (SMO), have been developed and show efficacy in preclinical studies and early-stage clinical trials in humans. However, major issues with these small molecule compounds include rapid acquired resistance, potential developmental toxicities secondary to use in children, and limited efficacy in cancers driven by Hh signaling downstream of the SMO receptor.
Topics: Animals; Antineoplastic Agents; Hedgehog Proteins; Humans; Neoplasms; Tumor Microenvironment; Veratrum Alkaloids
PubMed: 22391319
DOI: 10.1016/B978-0-12-394622-5.00023-7 -
The Journal of Pharmacology and... Aug 1957
Topics: Alkaloids; Amines; Esters; Heart; Veratrum Alkaloids
PubMed: 13476366
DOI: No ID Found