3606-45-9Relevant articles and documents
Studies on the alkaloids of fumariaceous plants. IX. Alkaloids of Bocconia frutescens.
Tani,Takao
, p. 699 - 701 (1967)
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The synthesis and biological evaluation of sanguinarine derivatives as anti-non-small cell lung cancer agents
Ding, Ke,Jiang, Liang,Lu, Xiaoyun,Wang, Xiaolu,Wang, Yuting,Xu, Fang,Zhang, Zhang
, p. 293 - 296 (2020)
A novel series of sanguinarine (SA) derivatives were synthesized and evaluated as anti-non-small cell lung cancer (NSCLC) agents. The compounds inhibited A549 and H1975 NSCLC cells with IC50 values of 0.96->30 ΜM and 0.79->30 ΜM, respectively. Compounds 8d-8j exhibited low micromolar inhibitory activity and indicated that the C6-position of SA was tolerated to be substituted by hydrophilic groups and CN. Further investigation of their mechanism of action showed that compound 8h induced apoptosis of A549 and H1975 cells by inhibiting the Akt signaling pathway and elevating the reactive oxygen species (ROS). This study provided a strategy for developing new anti-cancer agents.
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Howell et al.
, p. 364,368,369 (1972)
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FORMATION OF ALKALOIDS IN CORYDALIS OPHIOCARPA CALLUS CULTURE
Iwasa, K.,Takao, N.
, p. 611 - 614 (1982)
Corydalis ophiocarpa callus tissue was examined for its isoquinoline alkaloid content.The culture has good biosynthetic capabilities for transformation of exogenous alkaloids.Key Word Index - Corydalis ophiocarpa; Papaveraceae; callus tissue; biotransformation; isoquinoline alkaloids.
Visible-Light-Promoted Biomimetic Reductive Functionalization of Quaternary Benzophenanthridine Alkaloids
Wang, Lin,Wang, Xinhao,Wang, Wei,Liu, Wei,Liu, Yisong,Xie, Hongqi,Reiser, Oliver,Zeng, Jianguo,Cheng, Pi
supporting information, p. 2390 - 2397 (2021/08/20)
Reduction of an iminium C=N double bond is the most important phase I metabolism process associated with the cytotoxic property of quaternary benzophenanthridine alkaloids (QBAs). Inspired by the light-mediated reduction of QBAs with nicotinamide adenine dinucleotide, a visible-light-promoted reductive functionalization reaction of QBAs is reported in this study. C4-Alkyl-1,4-dihydropyridines (DHPs) enable the direct reductive alkylation of QBA independently, serving as both single-electron-transfer reductant reagents under irradiation with 455 nm blue light in the absence of photocatalysts and additional additives. Our protocol can be further applied to the semisynthesis of natural 6-substituted dihydrobenzophenanthridine derivatives such as O-acetyl maclekarpine E.
Sanguinarine is reduced by NADH through a covalent adduct
Sandor, Roman,Slanina, Jiri,Midlik, Adam,Sebrlova, Kristyna,Novotna, Lucie,Carnecka, Martina,Slaninova, Iva,Taborsky, Petr,Taborska, Eva,Pes, Ondrej
, p. 77 - 84 (2017/11/07)
Sanguinarine is a benzo[c]phenanthridine alkaloid with interesting cytotoxic properties, such as induction of oxidative DNA damage and very rapid apoptosis, which is not mediated by p53-dependent signaling. It has been previously documented that sanguinarine is reduced with NADH even in absence of any enzymes while being converted to its dihydro form. We found that the dark blue fluorescent species, observed during sanguinarine reduction with NADH and misinterpreted by Matkar et al. (Arch. Biochem. Biophys. 2008, 477, 43–52) as an anionic form of the alkaloid, is a covalent adduct formed by the interaction of NADH and sanguinarine. The covalent adduct is then converted slowly to the products, dihydrosanguinarine and NAD+, in the second step of reduction. The product of the reduction, dihydrosanguinarine, was continually re-oxidized by the atmospheric oxygen back to sanguinarine, resulting in further reacting with NADH and eventually depleting all NADH molecules. The ability of sanguinarine to diminish the pool of NADH and NADPH is further considered when explaining the sanguinarine-induced apoptosis in living cells.
