Phytochemical investigation of the alkaloid extract of Palicourea sessilis by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their structures confirmed by means of HRMS, NMR, and ECD measurements as 4-N-methyllyaloside (3), 4-N-methyl-3,4-dehydrostrictosidine (4), 4β-hydroxyisodolichantoside (6), and 4α-hydroxyisodolichantoside (7), as well as the known alkaloids alline (1), N-methyltryptamine (2), isodolichantoside (5), and 5-oxodolichantoside (8). In addition, the acetylcholinesterase inhibitory activity of the compounds was evaluated up to 50 μM.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.jnatprod.7b00681 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Bis-Iridoid Glycosides and Triterpenoids from and Their Potential as Inhibitors of ACC1 and ACL.
Molecules
December 2024
Zhejiang Provincial Key Laboratory of Plant Evolutionary Ecology and Conservation, School of Pharmaceutical Sciences, Taizhou University, Taizhou 318000, China.
A comprehensive phytochemical investigation of the twigs/leaves and flower buds of , a rare deciduous shrub native to China, led to the isolation of 39 structurally diverse compounds. These compounds include 11 iridoid glycosides (- and -), 20 triterpenoids (, , and -), and 8 phenylpropanoids (-). Among these, amabiliosides A () and B () represent previously undescribed bis-iridoid glycosides, while amabiliosides C () and D () feature a unique bis-iridoid-monoterpenoid indole alkaloid scaffold with a tetrahydro--carboline-5-carboxylic acid moiety.
View Article and Find Full Text PDFExperimental and Computational NMR Studies of Large Alkaloids Exemplified With Vindoline Trimer: Advantages and Limitations.
Magn Reson Chem
January 2025
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia.
The complete H and C NMR assignments of a trimeric vindoline together with its individual components, dimeric vindolicine and monomeric vindoline, are performed based on a thorough analysis of the ROESY, COSY, HSQC, and HMBC spectra in combination with the state-of-the-art quantum-chemical calculations. A spatial structure of vindoline trimer is determined by means of computational conformational analysis in combination with the probability distribution map of its basic conformers. On the example of monoterpene indole alkaloid, the trimer vindoline, the present study reveals the power of modern computational NMR to perform identification and stereochemical studies of large natural compounds with some limitations, which may arise in the quantum chemical computing workflow.
View Article and Find Full Text PDFMonoterpene indole alkaloids (MIAs) are a large, structurally diverse class of bioactive natural products. These compounds are biosynthetically derived from a stereoselective Pictet-Spengler condensation that generates a tetrahydro-β-carboline scaffold characterized by a 3 stereocenter. However, a subset of MIAs contain a non-canonical 3 stereocenter.
View Article and Find Full Text PDFPhotoinduced electron transfer enables cytochrome P450 enzyme-catalyzed reaction cycling.
Plant Physiol Biochem
December 2024
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610213, China. Electronic address:
Cytochrome P450 enzymes (CYPs), the members of the largest superfamily of enzymes in plant kingdom, catalyze a variety of functional group transformations involved in metabolite biosynthesis, end-product derivatization, and exogeneous molecule detoxification. Nevertheless, CYPs' functional characterization and practically industrial application have been largely encumbered by their critical dependency on the reducing equivalent for the catalytic cycling, driven by the tedious electron relay mediated by CYP reductase (CPR). Here, we report a photoinduced electron transfer system that initiates and sustains the CYP-catalyzed reaction cycling.
View Article and Find Full Text PDFPaeoniflorin Inhibits the Activation of Microglia and Alleviates Depressive Behavior by Regulating SIRT1-NF-kB-NLRP3/Pyroptosis Pathway.
Int J Mol Sci
November 2024
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, China.
Inflammation assumes a vital role in the pathogenesis of depression and in antidepressant treatment. Paeoniflorin (PF), a monoterpene glycoside analog possessing anti-inflammatory attributes, exhibits therapeutic efficacy on depression-like behavior in mice. The objective of this study was to evaluate the antidepressant effects of PF on depression elicited by the chronic unpredictable mild stress (CUMS) model and the precise neural sequence associated with the inflammatory process.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!