Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC(50) of 27.9 μM. Compound 2 was tested for neuroprotective effect and showed significant activity against β-amyloid(25-35)-induced oxidative injury (*P < 0.05) at 10 μM in PC-12 cells.
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http://dx.doi.org/10.1080/10286020.2011.574617 | DOI Listing |
ACS Synth Biol
December 2024
State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Industrial Fermentation Microbiology of the Ministry of Education, Tianjin Key Laboratory of Industrial Microbiology, College of Biotechnology, Tianjin University of Science and Technology, No.29 the 13th Street TEDA, Tianjin 300457, PR China.
Benzylisoquinoline alkaloids (BIAs) are a class of natural compounds found in plants of the family, known for their diverse pharmacological activities. However, the extraction yields of BIAs from plants are limited, and the cost of chemical synthesis is prohibitively high. Recent advancements in systems metabolic engineering and genomics have made it feasible to use microbes as bioreactors for BIAs production.
View Article and Find Full Text PDFFitoterapia
March 2024
School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China. Electronic address:
Cocculus orbiculatus (C. orbiculatus), the root of plants belonging to the Menispermaceae family, has been extensively used to treat various diseases, including malaria and rheumatism. The main chemicals in these plants are alkaloids; however, the spatial distribution of these compounds within the plant roots remains undefined.
View Article and Find Full Text PDFFitoterapia
January 2024
College of Bioscience and Biotechnology, Hunan Agricultural University, Changsha 410128, PR China. Electronic address:
The chemical structure of sinoacutine is formed by a phenanthrene nucleus and an ethylamine bridge. Because it has a similar parent structure to morphine, it is subdivided into morphinane. At present, all reports have pointed out that the basic skeleton of morphine alkaloids is salutaridine (the isomer of sinoacutine), which is generated by the phenol coupling reaction of (R)-reticuline.
View Article and Find Full Text PDFAntioxidants (Basel)
September 2022
Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, 2610 Antwerp, Belgium.
Oxidative stress is an important component of many diseases including cancer, along with inflammatory and neurodegenerative processes. Natural antioxidants have emerged as promising substances to protect the human body against reactive oxygen and nitrogen species. The present study evaluates the inhibition of nitric oxide (NO) production in LPS-stimulated RAW 264.
View Article and Find Full Text PDFJ Enzyme Inhib Med Chem
December 2022
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, and School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China.
Sinomenine, a morphinane-type isoquinoline-derived alkaloid, was first isolated from stems and roots of (Miq.) in 1920. Later discovery by researchers confirmed various essential biological efficacy sinomenine exerted and .
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