Synthesis of Gingerenone C and 5-Hydroxy-1-(4′-hydroxy-3-methoxyphenyl)-7-(4′′-hydroxyphenyl)-3-heptanone

The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.

Antioxidant Activity of the Natural Flavonoid 7-Hydroxy-5,6,4’-trimethoxyflavone Isolated from the Leaves of Lippia rugosa A. Chev

Phytochemical studies and antioxidant activities were carried out on n-hexane, ethyl acetate, ethanol and methanol extracts of the leaves of Lippia rugosa A. Chev (Verbenaceae), a medicinal plant used traditionally in the Cameroonian savannah’s region to protect foodstuffs and to cure degenerative diseases. Results indicated that theses extracts contain terpenoids, phenolic and flavonoid compounds. Except the n-hexane extract, all of the obtained extracts exhibit antioxidant activities with the ethanol extract being the most effective with an inhibition percentage of 85.668% ± 1.233% and an inhibition concentration (IC50) of 58 μg/ml (R2 = 0.987, P < 0.01) at a concentration of 100 mg/ml. Chromatographic separation on silica gel of the ethanol extract led to the isolation of a pure organic compound which was characterized as 7-hydroxy-5,6,4'-trimethox- yflavone by extensive 1D and 2D NMR spectroscopy, a flavonoid exhibiting antioxidative activity with an inhibitory percentage of 25.506% ± 0.205% and inhibition concentration (IC50) of 221 μg/ml (R2 = 0.966, P < 0.01). This is the first time that 7-hydroxy-5,6,4'-trimethoxyflavone is being isolated from L. rugosa and its antioxidant activity evaluated.

Argentum 5-Hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate:Synthesis,Crystal Structure and Antitumor Activity

In order to improve the water solubility and bioavailability of 5-hydroxy-7-methoxyflavone,argentum 5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate[Ag4(H2O)6](C(16)H(11)O4SO3)4·H2O(1,C(16)H(11)O4SO3=5-hydroxy-7-methoxy-2-phenyl-4H-chromen-4-one-6-sulfonate)was synthesized by sulfonation reaction.The structure of 1 was characterized by FT-IR,elemental analysis and X-ray single-crystal diffraction.Complex 1 belongs to the triclinic system,space group P1,a=8.077(4),b=12.365(4),c=17.735(7)A,V=1685.0(12)A3,Z=1,μ=1.372 mm^–1,Dc=1.936 g/cm^3,F(000)=984,the final R=0.0819 and wR=0.2332 with I>2σ(I).3D structure of 1 exhibits alternating organic and inorganic regions.O–H×××O hydrogen bonds and Ag–O coordination interactions exist among crystal water,coordinated water and sulfo group,which constructed an organic zone.Flavone skeletons form organic region of 1.Sulfo group is the bridge linking these two regions.The in vitro antitumor activity of 1 against human lymphoma cells U937 and human breast cancer cells MCF-7 were evaluated with CCK-8 assay.The result shows that 1 showed inhibitory activity against tumour cell U937 and MCF-7,and indicated that flavone sulfonate derivatives may be potential leads for further biological screenings and may generate drug-like molecules.

野鸦椿的植物化学成分研究

从野鸦椿 (EuscaphisjaponecaKantiz)枝叶的甲醇提取物分离得到 6个化合物 ,通过波谱分析鉴定为 5 ,7 dihydroxy 2 methyl benzopyran 4 one(Ⅰ ) ,3,4 ,5 trihydroxy benzoicacidmethylester(Ⅱ ) ,3,7 dihydroxy 5 octanolide(Ⅲ ) ,methyl 5 ,7 dihydroxy 2 (Z) octenoate(Ⅳ ) ,7 hydroxy 2 octen 5 olide(Ⅴ )和vomifoliol(Ⅵ )。

Two new coumarin glucosides biosynthesized by transgenic hairy roots of Polygonum multiflorum

The glycosylation of hydroxylcoumarin was investigated by using suspension cultures of hairy roots of Polygonum multiflorum. Two new coumarin glucosides （3 and 4） were biosysthesized by regioselectively glycosylation of corresponding substrates （1 and 2） in the system. The structures of two products were identified as 7-hydroxy-4-methylcoumarin 5-O-β-D-glucopyranoside and 7- hydroxy-3,4-dimethylcoumarin 5-O-β-D-glucopyranoside on the ground of chemical and spectroscopic methods, respectively. 2007 Rong Min Yu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A New Chromone Derivative from Stellera chamaejasme L

A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.

A New Halogenated Biindole and A New Apo-carotenone from Green Alga Chaetomorpha basiretorsa Setchell

A new halogenated biindole and a new apo-carotenone have been isolated from the ethanolic extract of the green alga Chaetomorpha basiretorsa Sethcell. On the basis of chemical and spectroscopic methods including 2D NMR technique, their structures have been elucidated as 4,4′-dichloro-5,5′-dibromo-7,7′-dimethoxy-2,2′-bi-1H-indole and 1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′- trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien-2-one, respectively.

New flavan and unusual chalcone glycosides from Drypetes parvifolia

Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.

A novel derivative of Genistein inhibits proliferation of ovarian cancer HO-8910 cells by regulating reactive oxygen species

Objective To investigate the anticancer effect of a novel derivative of genistein(5-hydroxy-4’-nitro-7-propionyloxy-genistein,HNPG)on human ovarian cancer HO-8910 cells and its possible molecular mechanism.Methods HO-8910 cells were cultured in vitro,and the inhibitory effect of HNPG on proliferation was determined using MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide]assay.The effect of HNPG on inducing apoptosis was examined using FCM with Annexin V-FITC and propidium iodide staining.The effect of HNPG on regulating reactive oxygen species(ROS)was measured using FCM with 2’,7’-di chlorodihydro-fluorescein diacetate staining.The effect of HNPG on modulating mitochondrial membrane potential(MMP)was determined using FCM with lipophilic cationic dye 2(6 Amino 3 imino 3H xanthen 9 yl)benzoic acid methyl ester(Rh123)staining.The bioactivity of superoxide dismutase(SOD)and catalase(CAT)and the content of glutathione(GSH)and malondialdehyde(MDA)were detected using enzymelinked immunosorbent assay.The related apoptotic proteins,including bcl-2,bax,cyt-c,and cleavedcaspase-3,were assessed using western blotting.Results HNPG exhibited dramatic antitumor activity against HO-8910 cells in vitro,inhibited proliferation,and induced apoptosis in a time-and dose-dependent manner.These effects were accompanied by reduced bioactivity of SOD and CAT,reduced GSH content,and enhanced MDA content.Simultaneously,the amount of ROS was increased and the level of MMP was reduced,along with upregulation of mitochondrial apoptosis pathway-related proteins,bax,cyt-c,and cleaved-caspase-3;bcl-2 protein was downregulated.Conclusion HNPG inhibited proliferation of human ovarian cancer HO-8910 cells in vitro,which might be related to decreased bioactivity of SOD and CAT.HNPG also reduced GSH content,which resulted in ROS accumulation in cells,damaged the integrity of mitochondrial membrane,and induced cell apoptosis.