1.Induction of apoptosis in K562 cells by dicyclohexylammonium salt of hyperforin through a mitochondrial-related pathway.
Liu JY1, Liu Z, Wang DM, Li MM, Wang SX, Wang R, Chen JP, Wang YF, Yang DP. Chem Biol Interact. 2011 Apr 25;190(2-3):91-101. doi: 10.1016/j.cbi.2011.02.026. Epub 2011 Mar 3.
Hyperforin is an abundant phloroglucinol-type constituent isolated from the extract of the flowering upper portion of the plant Hypericum perforatum L. The dicyclohexylammonium salt of hyperforin (DCHA-HF) has exhibited antitumor and antiangiogenic activities in various cancer cells. Here, the antitumor effects of DCHA-HF on the chronic myeloid leukemia K562 cell line were investigated for the first time. DCHA-HF exhibited dose- and time-dependent inhibitory activities against K562 cells, with IC(50) values of 8.6 and 3.2 μM for 48 h and 72 h of treatment, respectively, which was more effective than that of the hyperforin. In contrast, little cytotoxic activity was observed with DCHA-HF on HUVECs. DCHA-HF treatment resulted in induction of apoptosis as evidenced from DNA fragmentation, nuclear condensation and increase of early apoptotic cells by DAPI staining analysis, TUNEL assay and Annexin V-FITC/PI double-labeled staining analysis, respectively.
2.In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models.
Gobbi M1, Moia M, Funicello M, Riva A, Morazzoni P, Mennini T. Planta Med. 2004 Jul;70(7):680-2.
Cytokine hypersecretion might be involved in the onset and maintenance of depressive disorders and it has been suggested that St. John's wort extracts (Hypericum perforatum, SJW) might exert their antidepressant-like effects by affecting peripheral interleukin-6 (IL6) expression. We found that hyperforin, one putative active principle of SJW, and its dicyclohexylammonium salt (hyperforin-DCHA), inhibited the substance P (SP)-induced [L6 release inhuman astrocytoma cells (U373MG) with an Cs50 of 1.6 pM, indicating that hyperforin is likely to account for the inhibitory effect previously found in the same experimental model with SJW ex-tracts. [3H]SP binding experiments in parallel on the same intact cells indicate that hyperforin-DCHA does not interact with neuro-kinin-I receptors but very likely interacts with some intracellular steps leading to the synthesis and/or release of IL6. Hyperforin-DCHA also inhibited, with a similar IC50, the IL6 release induced in U373MG cells by two other classic proinflammatory stimuli,ILl and lipopolysaccharide (LPS), as well as the LPS-induced IL6 release in whole rat blood.
3.Silicon-mediated changes in polyamines participate in silicon-induced salt tolerance in Sorghum bicolor L.
Yin L1,2,3, Wang S1,2, Tanaka K3, Fujihara S4, Itai A3, Den X1,2, Zhang S1,2. Plant Cell Environ. 2016 Feb;39(2):245-58. doi: 10.1111/pce.12521. Epub 2015 Apr 17.
Silicon (Si) is generally considered a beneficial element for the growth of higher plants, especially under stress conditions, but the mechanisms remain unclear. Here, we tested the hypothesis that Si improves salt tolerance through mediating important metabolism processes rather than acting as a mere mechanical barrier. Seedlings of sorghum (Sorghum bicolor L.) growing in hydroponic culture were treated with NaCl (100 mm) combined with or without Si (0.83 mm). The result showed that supplemental Si enhanced sorghum salt tolerance by decreasing Na(+) accumulation. Simultaneously, polyamine (PA) levels were increased and ethylene precursor (1-aminocyclopropane-1-carboxylic acid: ACC) concentrations were decreased. Several key PA synthesis genes were up-regulated by Si under salt stress. To further confirm the role of PA in Si-mediated salt tolerance, seedlings were exposed to spermidine (Spd) or a PA synthesis inhibitor (dicyclohexylammonium sulphate, DCHA) combined with salt and Si.
4.Chirospecific synthesis of D and Lp-chlorohomophenylalanine N-t-BOC DCHA salts.
Cessac JW1, Rao PN, Kim HK. Amino Acids. 1994 Feb;6(1):97-105. doi: 10.1007/BF00808125.
The chirospecific conversions of D-glucosamine hydrochloride and D-mannosamine hydrochloride to the configurationally stable L and D isomers of N-t-butyloxycarbonylserinal were carried out byt-butylcarbonylation followed by sodium borohydride reduction and sodium meta-periodate oxidation. Reaction of the L and D aldehydes with the Wittig reagent prepared from 4-chlorobenzyltriphenylphosphonium chloride and butyl lithium followed by catalytic hydrogenation, Jones oxidation and salt formation with dicyclohexylamine gave the DCHA salts of the D and L isomers ofp-chlorohomophenylalanine N-t-Boc in high enatiomeric excess. The optical purity of the title compounds was established by hydrolysis to the respective free amino acids, followed by chiral derivatization and HPLC analysis.
