Inhibition of beta-ionone on SGC-7901 cell proliferation and upregulation of metalloproteinases-1 and -2 expression.
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AIM: To observe the effect of beta-ionone on the proliferation of human gastric adenocarcinoma cell line SGC-7901 and the inhibition of metalloproteinase. METHODS: Using growth inhibition, Zymograms assays and reverse transcription-polymerase-chain reaction (RT-PCR), we examined cell growth rates, activities of matrix metalloproteinases-2 (MMP-2) and -9 (MMP-9), and expression of metalloproteinases-1 (TIMP-1) and -2 (TIMP-2) in SGC-7901 cells after the treatment with beta-ionone for 24 h and 48 h, respectively. RESULTS: beta-ionone had an inhibitory effect on the growth of SGC-7901 cells. Eight days after the treatment with beta-ionone at concentrations of 25, 50, 100 and 200 micromol/L, the inhibition rates were 25.9%, 28.2%, 74.4% and 90.1%, respectively. The IC50 value of beta-ionone for SGC-7901 cells was estimated to be 89 micromol/L. The effects of beta-ionone on MMP-2 and MMP-9 activities in SGC-7901 cells were not observed. However, the levels of TIMP-1 and TIMP-2 transcripts were elevated in cells treated with beta-ionone in a dose-dependent manner. CONCLUSION: beta-ionone can inhibit the proliferation of SGC-7901 cells, upregulate the expression of TIMP-1 and TIMP-2 expression, and may influence metastasis of cancer. (+info)
Apoptosis of human gastric adenocarcinoma cells induced by beta-ionone.
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AIM: To investigate the effect of beta-ionone on the growth and apoptosis of gastric adenocarcinoma cell line SGC-7901. METHODS: Using MTT, fluorescence dye (Hoechst-33258), transmission electron microscopy and the TUNEL assay, we examined growth and apoptosis of SGC-7901 cells treated with beta-ionone at various concentrations (i.e. 25, 50, 100 and 200 micromol/L) for 24 h, 48 h. RESULTS: The growth of SGC-7901 cells was inhibited by beta-ionone. Seven days after treatment with beta-ionone at four concentrations, the inhibition rates were 12.04%, 30.59%, 78.25% and 94.15%, respectively. The IC(50) value of beta-ionone for SGC-7901 cells was estimated to be 89 micromol/L. The apoptotic morphology was demonstrated in SGC-7901 cells treated with beta-ionone by Hoechst-33258 staining and electron microscopy. Apoptosis was also shown in beta-ionone-treated SGC-7901 cells by the TUNEL assay. CONCLUSION: beta-ionone can inhibit cell proliferation and induce apoptosis of SGC-7901 cells. However, the mechanism needs to be further investigated. (+info)
Biotransformation of alpha-isomethylionone to 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)propan-2-one.
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The main biodegradation product of (+/-)-alpha-isomethylionone (2) with standard activated sludge was characterized as (+/-)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)propan-2-one (1) by its analysis and synthesis. Both enantiomers (1a and 1b) of 1 were synthesized by starting from (R)- and (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (3a and 3b), respectively. (+info)
Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers.
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Carotenoids are thought to be the precursors of terpenoid volatile compounds that contribute to flavor and aroma. One such volatile, beta-ionone, is important to fragrance in many flowers, including petunia (Petunia hybrida). However, little is known about the factors regulating its synthesis in vivo. The petunia genome contains a gene encoding a 9,10(9',10') carotenoid cleavage dioxygenase, PhCCD1. The PhCCD1 is 94% identical to LeCCD1A, an enzyme responsible for formation of beta-ionone in tomato (Lycopersicon esculentum; Simkin AJ, Schwartz SH, Auldridge M, Taylor MG, Klee HJ [2004] Plant J [in press]). Reduction of PhCCD1 transcript levels in transgenic plants led to a 58% to 76% decrease in beta-ionone synthesis in the corollas of selected petunia lines, indicating a significant role for this enzyme in volatile synthesis. Quantitative reverse transcription-PCR analysis revealed that PhCCD1 is highly expressed in corollas and leaves, where it constitutes approximately 0.04% and 0.02% of total RNA, respectively. PhCCD1 is light-inducible and exhibits a circadian rhythm in both leaves and flowers. beta-Ionone emission by flowers occurred principally during daylight hours, paralleling PhCCD1 expression in corollas. The results indicate that PhCCD1 activity and beta-ionone emission are likely regulated at the level of transcript. (+info)
Geranylgeraniol and beta-ionone inhibit hepatic preneoplastic lesions, cell proliferation, total plasma cholesterol and DNA damage during the initial phases of hepatocarcinogenesis, but only the former inhibits NF-kappaB activation.
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Chemopreventive activities of the isoprenoids geranylgeraniol (GGO) and beta-ionone (BI) were evaluated during initial phases of hepatocarcinogenesis. Rats received 8 or 16 mg/100 g body wt GGO (GGO8 and GGO16 groups) or BI (BI8 and BI16 groups), or only corn oil (CO group, controls) daily for 7 weeks. Incidence (%) and the mean number of visible hepatocyte nodules/animal were inhibited in the GGO8 (64% and 21 +/- 40), GGO16 (33% and 3 +/- 5), BI8 (50% and 13 +/- 34) and BI16 (42% and 9 +/- 19) groups compared with the CO group (100% and 34 +/- 51) (P < 0.05, except for the GGO8 group). Number/cm(2) liver section, mean area (mm(2)) and % liver section area occupied by persistent hepatic placental glutathione S-transferase positive preneoplastic lesions (PNL) were reduced in the GGO8 (11 +/- 9; 0.26 +/- 0.35; 2.7 +/- 3.0), GGO16 (6 +/- 6; 0.18 +/- 0.16; 0.9 +/- 0.9), BI8 (9 +/- 5; 0.13 +/- 0.20; 1.1 +/- 1.2) and BI16 (8 +/- 6; 0.08 +/- 0.09; 0.6 +/- 0.4) groups compared with the CO group (26 +/- 18; 0.29 +/- 0.34; 7.0 +/- 5.5) (P < 0.05). GGO16 and BI16 groups showed smaller visible hepatocyte nodules, reduced PNL cell proliferation and total plasma cholesterol levels compared with the CO group (P < 0.05), but did not show any differences (P > 0.05) in PNL apoptosis. DNA damage expressed as comet length (microm) was reduced in the GGO8 (96.7 +/- 1.5), GGO16 (94.2 +/- 1.5), BI8 (97.1 +/- 1.1) and BI16 (95.1 +/- 1.5) groups compared with the CO group (102.1 +/- 1.7) (P < 0.05). In comparison with normal animals, the CO group animals showed increased (P < 0.05) nuclear levels of nuclear factor kappa B (NF-kappaB) p65 subunit in hepatic cells, which were decreased (P < 0.05) in the GGO16 group animals. Anticarcinogenic actions of these isoprenoids seem to follow a dose-response relationship. Results indicate that GGO and BI could be represented as promising chemopreventive agents against hepatocarcinogenesis. Inhibition of cell proliferation and DNA damage seems to be important for the anticarcinogenic actions of isoprenoids, while the inhibition of NF-kappaB activation seems to be specifically related to GGO actions. (+info)
Synthesis of optically active vomifoliol and roseoside stereoisomers.
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A synthesis of optically active vomifoliol stereoisomers 1-4 and their glucosides, roseoside stereoisomers 5-8, was accomplished via alpha-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of alpha,beta-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also performed. (+info)
A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa.
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A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated. (+info)
Staphylionosides A-K: megastigmane glucosides from the leaves of Staphylea bumalda DC.
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Chemical investigation of leaves of Staphylea bumalda DC., collected in the suburbs of Hiroshima City, afforded 11 new megastigmane glucosides, named staphylionosides A-K (3-13), along with two known megastigmane glucosides (1, 2). The relative structures were elucidated from spectroscopic evidence, and the absolute structures of the aglycones were determined by means of the combination of beta-D-glucosylation-induced shift-trends and the modified Mosher's method. (+info)