Synthesis of 5-(3-Hydroxypropyl)-7-methoxy-2-(3‘-methoxy-4‘-hydroxyphenyl)-3- benzo[b]furancarbaldehyde, a Novel Adenosine A1Receptor Ligand from the Root ofSalvia miltiorrhiza

Kuo, Yueh‐Hsiung; Wu, Chien-Huang

doi:10.1021/np9603939

Cited by 15 publications

(14 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product was reprotected with a benzyl group, treated with diisobutyl aluminum hydride in dry tetrahydrofuran, selective-oxidized with manganese dioxide in ethyl acetate, and then finally deprotected with titanium tetrachloride in dichloromethane to obtain the target molecule as a yellowish solid. The desired product was confirmed by 1 H NMR and electron ionization/mass spectrometry and gave spectral data identical with literature values (Yang et al, 1991(Yang et al, , 1992Kuo and Wu, 1996) Cell Lines. Human oral epidermoid carcinoma KB cells, nasopharyngeal carcinoma HONE-1 cells, colorectal carcinoma HT29 cells, nonsmall cell lung cancer H460 cells, and glioblastoma multiforme DBTRG cells were maintained in RPMI 1640 medium supplied with 5% fetal bovine serum.…”

Section: Methodssupporting

confidence: 74%

See 1 more Smart Citation

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Chang

Kuo

et al. 2004

Mol Pharmacol

Self Cite

View full text Add to dashboard Cite

Aqueous extracts of Salvia miltiorrhizae Bunge have been extensively used in the treatment of cardiovascular disorders and cancer in Asia. Recently, a compound, 5-(3-hydroxypropyl)-7-methoxy-2-(3Ј-methoxy-4Ј-hydroxyphenyl)-3-benzo[b]furancarbaldehyde (salvinal), isolated from this plant showed inhibitory activity against tumor cell growth and induced apoptosis in human cancer cells. In the present study, we investigated the cytotoxic effect and mechanisms of action of salvinal in human cancer cell lines. Salvinal caused inhibition of cell growth (IC 50 range, 4 -17 M) in a variety of human cancer cell lines. Flow cytometry analysis showed that salvinal treatment resulted in a concentration-dependent accumulation of cells in the G 2 /M phase. We observed, using Hoechst 33258 dye staining, that salvinal blocked the cell cycle in mitosis. In vitro and in vivo examinations showed that salvinal inhibited tubulin polymerization in a concentration-dependent manner. Immunocytochemical studies demonstrated that salvinal treatment caused the changes of cellular microtubule network, similar to the effect of colchicine. In addition, salvinal treatment resulted in upregulation of cyclin B1 levels, activation of Cdc2 kinase, and Cdc25c phosphorylation. Furthermore, elevation of levels of MPM-2 phosphoepitopes in salvinal-treated cells in a concentration-dependent manner was also observed. Similar to the effect of other antitubulin agent, hyperphosphorylation of Bcl-2, induction of DNA fragmentation and activation of caspase-3 activity occurred in salvinal-treated cells. In particular, salvinal exhibited similar inhibitory activity against parental KB, Pglycoprotein-overexpressing KB vin10 and KB taxol-50 cells, and multidrug resistance-associated protein (MRP)-expressing etoposide-resistant KB 7D cells. Taken together, our data demonstrate that salvinal inhibits tubulin polymerization, arrests cell cycle at mitosis, and induces apoptosis. Notably, Salvinal is a poor substrate for transport by P-glycoprotein and MRP. Salvinal may be useful in the treatment of human cancers, particularly in patients with drug resistance.

show abstract

Section: Methodssupporting

confidence: 74%

“…Salvinal (Fig. 1) was synthesized at the Department of Chemistry, National Taiwan University (Taipei, Taiwan) with use of the method described by Kuo and Wu (1996). In brief, methyl ferulate was oxidized in acetone solution with aqueous ferric chloride to yield dihydrobenzofuran.…”

Section: Methodsmentioning

confidence: 99%

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Chang

Kuo

et al. 2004

Mol Pharmacol

Self Cite

View full text Add to dashboard Cite

show abstract

“…These compounds were synthesized employing previously procedures reported with modifications. [24][25][26] All the structures were confirmed on the basis of NMR, EI-MS and IR data and comparison with the literature.…”

Section: Synthesis Of Dihydrobenzofuran Neolignans 1-8mentioning

confidence: 67%

Antifungal Activity of Dihydrobenzofuran Neolignans

Dias

Aquaroni

Pietro

et al. 2017

MOJPB

View full text Add to dashboard Cite

“…It has been reported that diferulate 5 can be obtained in 30% yield from radical coupling of ferulate by ferric chloride oxidation in aqueous acetone. 28 However, we were not able to obtain the claimed yield for diferulate 5 by following the exact procedure described in that paper. Instead, only 5% of diferulate 5 was isolated because huge amounts of unreacted starting materials remained.…”

Section: ■ Results and Discussionmentioning

confidence: 87%

Rapid Syntheses of Dehydrodiferulates via Biomimetic Radical Coupling Reactions of Ethyl Ferulate

Wei

Azarpira

et al. 2012

J. Agric. Food Chem.

View full text Add to dashboard Cite

Dehydrodimerization of ferulates in grass cell walls provides a pathway toward cross-linking polysaccharide chains limiting the digestibility of carbohydrates by ruminant bacteria and in general affecting the utilization of grass as a renewable bioresource. Analysis of dehydrodiferulates (henceforth termed diferulates) in plant cell walls is useful in the evaluation of the quality of dairy forages as animal feeds. Therefore, there has been considerable demand for quantities of diferulates as standards for such analyses. Described here are syntheses of diferulates from ethyl ferulate via biomimetic radical coupling reactions using the copper(II)-tetramethylethylenediamine [CuCl(OH)-TMEDA] complex as oxidant or catalyst. Although CuCl(OH)-TMEDA oxidation of ethyl ferulate in acetonitrile produced mixtures composed of 8-O-4-, 8-5-, 8-8- (cyclic and noncyclic), and 5-5-coupled diferulates, a catalyzed oxidation using CuCl(OH)-TMEDA as catalyst and oxygen as an oxidant resulted in better overall yields of such diferulates. Flash chromatographic fractionation allowed isolation of 8-8- and 5-5-coupled diferulates. 8-5-Diferulate coeluted with 8-O-4-diferulate but was separated from it via crystallization; the 8-O-4 diferulate left in the mother solution was isolated by rechromatography following a simple tetrabutylammonium fluoride treatment that converted 8-5-diferulate to another useful diferulate, 8-5-(noncyclic) diferulate. Therefore, six of the nine (5-5, 8-O-4, 8-5-c, 8-5-nc, 8-5-dc, 8-8-c, 8-8-nc, 8-8-THF, 4-O-5) diferulic acids that have to date been found in the alkaline hydrolysates of plant cell walls can be readily synthesized by the CuCl(OH)-TMEDA catalyzed aerobic oxidative coupling reaction and subsequent saponification described here.

show abstract

Synthesis of 5-(3-Hydroxypropyl)-7-methoxy-2-(3‘-methoxy-4‘-hydroxyphenyl)-3- benzo[b]furancarbaldehyde, a Novel Adenosine A₁Receptor Ligand from the Root ofSalvia miltiorrhiza

Cited by 15 publications

References 16 publications

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Antifungal Activity of Dihydrobenzofuran Neolignans

Rapid Syntheses of Dehydrodiferulates via Biomimetic Radical Coupling Reactions of Ethyl Ferulate

Contact Info

Product

Resources

About