A new cytotoxic phenylbutenoid dimer from the rhizomes of Zingiber cassumunar
ABSTRACT A new phenylbutenoid dimer, (+/-)- trans-3-(4-hydroxy-3-methoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene, was isolated from the rhizomes of Zingiber cassumunar along with the three known compounds, (+/-)- trans-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene, 4-(3,4-dimethoxyphenyl)but-1,3-diene, and 4-(2,4,5-trimethoxyphenyl)but-1,3-diene by bioassay-directed fractionation using the A549 human cancer cell line cytotoxicity assay. Structure of the new compound was elucidated by spectral analysis, including 1D and 2D NMR experiments.
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ABSTRACT: Epitaxially twinned (028)-oriented Bi3.25La0.75Ti3O12 (BLT) thin films were grown on GaN(002)/Al2O3 (0006) substrates by pulsed laser deposition. The BLT layer deposited on GaN substrate showed sixfold-like symmetric peaks in a φ scan of (006) reflection and 12 peaks in that of the (117) reflection. In order to investigate hetero-epitaxial growth, origin of six and 12 peaks in the φ scan, and the domain structure of the BLT thin film, the X-ray analysis including θ–2θ, ω, φ scan, and pole figure measurement were performed. The hetero-epitaxial growth was studied by atomic arrangements and domain distribution with calculated lattice mismatch, interplanar angles, and atomic distances.Journal of Crystal Growth 10/2004; 271(1):50-54. DOI:10.1016/j.jcrysgro.2004.07.020 · 1.69 Impact Factor
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ABSTRACT: High-performance liquid chromatography/electrospray tandem mass spectrometry was developed to distinguish isomers and compounds of similar structures with different configurations in the rhizomes of Z. cassumunar. Energy-resolved breakdown curves were utilized to differentiate four compounds. Compounds 2 (3R,4S) and 4 (3R,4R) were a pair of stereoisomers which could be distinguished easily by breakdown curves. The breakdown curve of compound 1 was identical to that of compound 2, which suggested that the configuration of compound 1 was (3R,4S) or (3S,4R). The breakdown curve of compound 3 was completely different from those of compounds 1, 2 and 4, and it might be that the configuration of the double bond of compound 3 was different from the other three compounds. Hence, the described method using breakdown curves has great potential in the distinguishing of isomers and compounds of similar structure with different configurations.Rapid Communications in Mass Spectrometry 06/2009; 23(11):1654-8. DOI:10.1002/rcm.4050 · 2.64 Impact Factor
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ABSTRACT: Five phenylbutenoid derivatives from the rhizomes of Zingiber cassumunar Roxb. (Zingiberaceae) were evaluated for their P-glycoprotein (P-gp) inhibitory effects in a P-gp over-expressing multidrug resistant (MDR) human breast cancer cell line, MCF-7/ADR. As a result, a phenylbutenoid dimer, (+/-)-trans-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene (1), exhibited highly potent P-gp inhibitory activity, decreasing the IC(50) value of daunomycin (DNM) to 4.31 +/- 0.40 microm in the cells (DNM IC(50) = 37.1 +/- 0.59 microm). The positive control, verapamil decreased the IC(50) value of DNM to 6.94 +/- 0.40 microm. Three phenylbutenoid monomers, 2-4 from this plant, also resulted in a significant decrease in the IC(50) values of DNM compared with the control. In particular, compound 1 markedly enhanced [(3)H]-DNM accumulation and significantly reduced [(3)H]-DNM efflux compared with the control, and this effect was more potent than that of verapamil, a well-known P-gp inhibitor. These results suggest that compound 1 of Z. cassumunar can be developed as a potent chemo-sensitizing agent that reverses P-gp-mediated MDR in human cancer chemotherapy.Phytotherapy Research 04/2009; 23(4):472-6. DOI:10.1002/ptr.2650 · 2.40 Impact Factor