Inspired by the intriguing structures and bioactivities of dimeric alkaloids, 11 new thalifaberine-type aporphine-benzylisoquinoline alkaloids, thalicultratines A-K, a tetrahydroprotoberberine-aporphine alkaloid, thalicultratine L, and five known ones were isolated from the roots of Thalictrum cultratum. Their structures were defined on the basis of NMR and HRESIMS data. The antiproliferative activities of compounds 1-17 were evaluated against human leukemia HL-60 and prostate cancer PC-3 cells. Most alkaloids showed potent cytotoxicity against selected cancer cells. Preliminary SARs are discussed. The most active new compound (3), with an IC value of 1.06 μM against HL-60 cells, was selected for mechanism of action studies. The results revealed that compound 3 induced apoptosis and arrested the HL-60 cell cycle at the S phase with the loss of mitochondria membrane potential. The nuclear morphological Hoechst 33258 staining assay was also carried out, and the results confirmed apoptosis.
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http://dx.doi.org/10.1021/acs.jnatprod.7b00387 | DOI Listing |
J Asian Nat Prod Res
February 2024
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, PR China.
Two new aporphine alkaloids, 6a-2'-(3-oxobutenyl)-thaliadin () and -methylthalisopynine (), along with ten known analogs (-), were isolated from the roots of W. T. Wang et S.
View Article and Find Full Text PDFZhongguo Zhong Yao Za Zhi
May 2022
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University Shenyang 110016, China.
The chemical constituents from the roots of Thalictrum cultratum and T. baicalense were investigated. By various isolation methods, such as silica gel, aluminium oxide, ODS, and Sephadex LH-20 column chromatographies, and semi-preparative HPLC, 11 simple isoquinoline alkaloids were isolated from the ethanol extract of the roots of these two plants, including a new compound, named dehydrothalflavine(1), and ten known ones(2-11): N-methylcorydaline(2), N-methylthalidaldine(3), thaliflavine(4), oxyhydrastinine(5), noroxyhydrastinine(6), dimethoxyisoquinolone(7), thalactamine(8), dehydronoroxyhydrastinine(9), 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(10), and isopicnarrhine(11).
View Article and Find Full Text PDFOrg Lett
October 2020
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
Baicalensines A () and B () were isolated from the roots of and structurally characterized using spectroscopic data, C NMR calculations, and the CASE algorithm. Compound , representing a new class of alkaloid dimers, contains berberine conjugated to a ring-opened isoquinoline. Compound is the first reported natural benzylisoquinoline bearing a formyl group at C-3.
View Article and Find Full Text PDFJ Asian Nat Prod Res
January 2021
Department of Thoracic Surgery, Shengjing Hospital of China Medical University, Shenyang 110003, China.
Phytochemical investigation on the 70% EtOH extract of the roots of DC. resulted in the isolation of three new isoquinoline alkaloids, 5,6,7,12-tetramethoxy-2-methyl-13-hydroxy-11-(4'-methoxycarbonylphenoxy)benzylisoquinoline (), 5,6,7,12-tetramethoxy-2-methyl-13-hydroxy-11-(4'-carbonylphenoxy) benzylisoquinoline (), and 3-methoxy-10--acetylprodensiflorin B (). The new structures were elucidated by using spectroscopic data (NMR, IR, UV, and MS).
View Article and Find Full Text PDFMolecules
September 2019
Botanical Garden of Maria Curie-Skłodowska University in Lublin, 20-819 Lublin, Poland.
Plants are an important origin of natural substances that the raw material for various pharmaceutical and therapeutic applications due to the presence of phytochemicals, such as alkaloids. Alkaloids, which are found in different plant species, possess numerous biological activities. Some alkaloids have strong cytotoxic effects on various cancer cells.
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