Chelerythrine chloride

The plant is known to contain chelerythrine chloride, which inhibits the aggregation of rabbit platelet in vitro via inhibition on thromboxane formation and phosphoinosi-tides breakdown (30). Chelerythrine, which occurs in members of the family Papaver-aceae, has been reported to inhibit the enzymatic activity of protein kinase C and to exert cell-growth inhibitory effect via the induction of apoptosis in numerous cancer cell lines (31,32). What is the topoisomerase activity of chelerythrine ... 

Fig. 6.15 FAC-MS chromatograms of dual indicators for protein kinase Ca [32]. (a) In the chromatograms, the red lines correspond to a void marker, the blue lines correspond to the substrate-site indicator chelerythrine chloride and the magenta lines correspond to the ATP-site indicator PDl53035. Arrows...

The compound chelerythrine chloride inhibited platelet aggregation induced by ADP, arachidonic acid, PAF, collagen, ionophore A23187, and thrombin in washed rabbit platelets. Less inhibition was observed in platelet-rich plasma. Treatment of washed platelets with chelerythrine... 

Ko, F.N., I.S. Chen, S.J. Wu, et al. 1990. Antiplatelet effects of chelerythrine chloride isolated from Zanthoxylum simulans. Biochim. Biophys. Acta 1052(3) 360-365. 

Z. F. Zhang, Y. Guo, J. B. Zhang, and X. H. Wei, Induction of apoptosis by chelerythrine chloride through mitochondrial pathway and Bcl-2 family proteins in human hepatoma SMMC-7721 cell. Arch. Pharm. Res., 34 (2011) 791-800. 

Treatment of arnottianamide with lithium aluminum hydride furnished the base deoxoarnottianamide which was 0-methylated using Rodionow conditions to afford methyl deoxoarnottianamide. Subsequently, in a transformation with biogenetic implications, reaction of the known benzophenanthridine alkaloid chelerythrine chloride with /w-chloroperbenzoic acid in HMPA at 40° gave arnottianamide in 707o (see Scheme 21.1). ... 

The benzyne route to aromatic benzophenanthridines was investigated initially by Kessar. Treatment of the A -(o-bromobenzyl)-l-naphthylamine 6 with potassium amide in liquid ammonia, followed by oxidation with manganese dioxide, furnished the aromatic benzophenanthridine 7 which was readily converted to chelerythrine chloride. ... 

Figure 8 CREB phosphorylation by hypoxia does not require Ca, PCK, RSK-2, MAPK, or p38. Cells were pretreated with various drugs or vehicle (0.1% dimethyl sulfoxide) as indicated. Cells were then exposed to either normoxia (C, 21% O2) or hypoxia (H, 5% O2) for 6 hr, and whole-cell lysates were immunoblotted with an antibody specific for Ser phospho-CREB. (a) Cells were preincubated for 40 min in serum-fi ee medium in the presence of Ca and vehicle (—) or in serum-iree medium formulated without Ca and supplemented with 1 mM EGTA-I-100 pM BAPTA-AM (-h). The medium was then replaced (minus drug or vehicle) and cells were exposed to either normoxia or hypoxia, (b) Cells were pretreated for 40 min in serum-free medium with either vehicle (—) or 20 pM chelerythrine chloride, an inhibitor of PKC (CHL -P), and exposed to either normoxia or hypoxia, (c) Cells were pretreated for 40 min in serum-fi ee medium with either vehicle (—) or 0.3 pM Ro 31-8220, an inhibitor of RSK and p70 S6 kinase (-P), and exposed to either normoxia or hypoxia, (d) Cells were pretreated for 40 min in serum-lree medium with either vehicle (—) or 50 pM PD098059, an inhibitor of MEKl and the downstream MAPKS (-P), and exposed to either normoxia or hypoxia, (e) Cells were pretreated for 1 hr in serum-fiee medium with either vehicle (—) or 10 nM rapamycin, an inhibitor of p70 S6 kinase (-P), and exposed to either normoxia or hypoxia, (f) Cells were pretreated for 1 hr in serum-fiee medium with either vehicle (—) or 20 pM SB203580, an inhibitor of p38a kinase and MAPKAP kinase (-P), and then exposed to either normoxia or hypoxia. In all of these experiments, hypoxia did not alter the total levels of CREB.

The bark of this West Indian tree yielded lupeol and d-sesamine in addition to five quaternary alkaloids, namely, chelerythrine, 1-canadine methochloride, candicine, and d-tambetarine, all isolated as chlorides as well as alkaloid-A (mp 266°-268°), which is not to be confused with alkaloid-A from Stephania rotunda (209). The plant has also been referred to as Z.follis oblongo-ovatis Browne, Z. clavaherculis SW., Z. caribaeum Hitchc., Fagara martinicense Lam. 

Iwamide (156 R = H), a new product from Xanthoxylum arnottianum, has been synthesized from decarine (157), and similar syntheses of arnottianamide (156 R = Me) and isoarnottianamide have been achieved from chelerythrine and nitidine chlorides (Scheme 4). ... 

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