Preparation and Application of Mixed Octadecylsilyl- And (3-(C-Methylcalix[4]resorcinarene)-Hydroxypropoxy)-Propylsilyl–appended Silica Particles as Stationary Phase for High-Performance Liquid Chromatography

Tan, Huey Min; Wang, Xiaochong; Soh, Shu Fang; Tan, S. F.; Zhao, Jia; Yong, Eu Leong; Lee, Hian Kee; Gong, Yiwei

doi:10.1080/10739149.2011.651674

Cited by 7 publications

(13 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isolation and purification of Breviflavone B. The ODS-MCR-HPS column [5] is a new type of HPLC column which has two main functional groups MCR [7] and ODS [5]. Since this column can be used under multiple chromatographic modes [5], It showed excellent separation selectivity for polyphenolic compounds and flavonoids.…”

Section: Discussionmentioning

confidence: 99%

“…The ODS-MCR-HPS column [5] is a new type of HPLC column which has two main functional groups MCR [7] and ODS [5]. Since this column can be used under multiple chromatographic modes [5], It showed excellent separation selectivity for polyphenolic compounds and flavonoids. The ODS-MCR-HPS also can be used for separation both chiral and achiral compounds in a complicated sample.…”

Section: Discussionmentioning

confidence: 99%

“…The sample lost was huge and yield of Breviflavone B was very low due to the bare Silica columns used in the normal phase chromatography procedures. Recently, our group reported a new type of HPLC column packed with the mixed octadecylsily (ODS)-and C-methylcalix [4]resorcinarene (MCR)-bonded silica particles (ODS-MCR-HPS) [5]. This column has two main functional groups MCR and ODS (shown in Figure 2).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Isolation of a Novel Chiral Phytoestrogen Breviflavone B from <i>Epimedium</i> Herb by a New Approach of Liquid Chromatography

Soh

Tay

et al. 2013

AMR

Self Cite

View full text Add to dashboard Cite

Breviflavone B is a novel chiral phytoestrogen that mimics the biological functions of 17β-estradiol (E2), an estrogen which is naturally produced in our body. It has exhibited a much higher estrogen receptor (ER) bioactivity than E2 or other phytoestrogens. Breviflavone B specifically activates ER at a low dose without activating other steroid receptors, and inhibits estrogen-stimulated breast cancer cell proliferation at high doses, making it a potential treatment option for breast cancer patients. In this report, a new liquid chromatography aprroach has been developed to isolate Breviflavone B from Epimedium Brevicornum herbal extracts. After passing through DIAION HP20 resin, the ethanolic extract of Epimedium Brevicornum was firstly fractionalized by a Diol column, then further separated by a C18 column using preparative HPLC, and finally purified by an ODS-MCR-HPS column in HPLC under gradient mode. In each stage of separation, the ER bioactivities of the each fraction were measured by estrogen receptor-driven reporter gene bioassays to guide the chromatographic fractionations. The results showed that the new combination of Diol and C18 and ODS-MCR-HPS column chromatography provided better separation selectivity than our previously-reported C18 column chromatography for isolation of Breviflavon B from Epemidium herbs. Pure Breviflavon B was successfully isolated from the ethanolic extract of Epimedium Brevicornum herb via this new approach of chromatographic fractionations guided by the bioassays.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Isolation of a Novel Chiral Phytoestrogen Breviflavone B from <i>Epimedium</i> Herb by a New Approach of Liquid Chromatography

Soh

Tay

et al. 2013

AMR

Self Cite

View full text Add to dashboard Cite

show abstract

“…This methodology is known as “reaction with surface groups”. Using this protocol, silica particles have been chemically modified, obtaining the stationary phases MCR-HPS, BAMCR-HPS [26], and ODS-MCR-HPS [27], which exhibited excellent selectivity and chromatographic behavior in the separation of the position of aromatic isomers and chiral molecules. The second functionalization is the modification of the calix[4]resorcinarene lower rim.…”

Section: Introductionmentioning

confidence: 99%

Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

et al. 2019

View full text Add to dashboard Cite

Functionalization of tetrapropylcalix[4]resorcinarene, tetrapentylcalix[4]resorcinarene, tetranonylcalix[4]resorcinarene, and tetra-(4-hydroxyphenyl)calix[4]resorcinarene by means of aminomethylation reactions with the amino acids β-alanine and l-proline in the presence of aqueous formaldehyde was carried out. When β-alanine was used, the reaction products were tetrabenzoxazines. The reaction with tetra-(4-hydroxyphenyl)calix[4]resorcinarene did not proceed under the experimental conditions; therefore, l-proline was used, and the corresponding tetra-Mannich base was regio- and diasteroselectively formed. The products were characterized via FT-IR, 1H NMR, 13C NMR, and elemental analysis. With these aminomethylated-calix[4]resorcinarenes, the chemical surface modification of the copolymers poly(GMA–co–EDMA) and poly(BMA–co–EDMA–co–MMA) in a basic medium was studied. The results were quite satisfactory, obtaining the corresponding copolymers functionalized by nucleophilic substitution reaction and ring-opening between the carboxyl group of the upper rim of aliphatic calix[4]resorcinarenes and the hydroxyl group of the lower rim in the aromatic calix[4]resorcinarene and the epoxy group of the glycidyl methacrylate residue of each copolymer. The modified copolymers were characterized via FT-IR, scanning electron microscopy imaging, and elemental analysis. Finally, the modified copolymer surfaces exhibited interaction with peptides, showing their potential application in chromatographic separation techniques such as high-performance liquid chromatography.

show abstract

“…

A new type of calix [4] arene-capped (3-(2-O-β-cyclodextrin)-2-hydroxypropoxy) propylsilyl-appended silica particles (C4CD-HPS) has been successfully used as chiral stationary phase (CSP) in capillary electrochromatography (CEC) for separation of enantiomers of 1-phenyl-1-propanol for the first time. C4CD-HPS contains a chiral selector with two recognition sites: calix[4]arene and β-cyclodextrin.

…”

mentioning

confidence: 99%

Enantiomeric Separation of 1-Phenyl-1-Propanol Using Calix[4]Arene-Capped β-Cyclodextrin-Bonded Silica Particles as Chiral Stationary Phase in Capillary Electrochromatography

Zhao

Yong

et al. 2013

AMR

Self Cite

View full text Add to dashboard Cite

A new type of calix [ arene-capped (3-(2-O-β-cyclodextrin)-2-hydroxypropoxy) propylsilyl-appended silica particles (C4CD-HPS) has been successfully used as chiral stationary phase (CSP) in capillary electrochromatography (CEC) for separation of enantiomers of 1-phenyl-1-propanol for the first time. C4CD-HPS contains a chiral selector with two recognition sites: calix [arene and β-cyclodextrin. Due to the cooperative functioning of the calix [arene and β-cyclodextrin, C4CD-HPS has exhibited excellent enantioselectivity for the enantiomers of 1-phenyl-1-propanol. After the multiple phenolic hydroxyl groups in the calix [arene moieties are ionized in the running buffer, the bonded stationary phase C4CD-HPS becomes negatively-charged to provide high electroosmotic flow (EOF) in CEC. Fast and high-resolution separation for enantiomers of 1-phenyl-1-propanol has been easily achieved on C4CD-HPS. This new type of chiral stationary phase has exhibited great potential for fast enantiomeric separations in CEC.

show abstract

Preparation and Application of Mixed Octadecylsilyl- And (3-(C-Methylcalix[4]resorcinarene)-Hydroxypropoxy)-Propylsilyl–appended Silica Particles as Stationary Phase for High-Performance Liquid Chromatography

Cited by 7 publications

References 24 publications

Isolation of a Novel Chiral Phytoestrogen Breviflavone B from <i>Epimedium</i> Herb by a New Approach of Liquid Chromatography

Isolation of a Novel Chiral Phytoestrogen Breviflavone B from <i>Epimedium</i> Herb by a New Approach of Liquid Chromatography

Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

Enantiomeric Separation of 1-Phenyl-1-Propanol Using Calix[4]Arene-Capped β-Cyclodextrin-Bonded Silica Particles as Chiral Stationary Phase in Capillary Electrochromatography

Contact Info

Product

Resources

About