ODS Column Chromatography Research Articles

A New Monoterpenoid Indole Alkaloid from Tabernaemontana corymbosa

Tabernaemontana corymbosa is used in folk medicine for the treatment of hypertension, sore throat, and abdominal pain by the Dais in Yunnan Province. The crude alkaloid extract of T. corymbosa were successively subjected to D-101 macroporous resin, MCI gel, and ODS column chromatography and purified via preparative HPLC to afford a new aspidospermar-type monoterpenoid indole alkaloid, named tabercarpamine K (1). The structure of 1 was elucidated using spectroscopic methods. Compared to the structure of vincamine, a hydroxyl group is substituted at C-19 and a proton, instead of a hydroxyl, is attached to C-16 in 1.

Anti-inflammatory iridoids from the stems of Cistanche deserticola cultured in Tarim Desert

In order to determine the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The constituents were isolated by silica gel, Sephadex LH-20, MCI gel, ODS column chromatography, and semi-preparative HPLC. Their structures were determined on the basis of MS and NMR spectroscopic analyses, by chemical methods, and/or comparison with literature data. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 mouse microglial cells. Nine iridoids were isolated and identified as cistadesertoside A (1), cistanin (2), cistachlorin (3), 6-deoxycatalpol (4), gluroside (5), kankanoside A (6), ajugol (7), bartsioside (8), and 8-epi-loganic acid (9). Compound 9 exhibited potent inhibition on the NO production with an IC50 value being 5.2 μmol·L−1, comparable to the positive control quercetin (4.3 μmol·L−1). Compound 1 was a new iridoid, and compounds 5, 6, and 8 were isolated from this species for the first time.

Iminimycin A, the new iminium metabolite produced by Streptomyces griseus OS-3601.

A new natural product, designated iminimycin A, was isolated from the cultured broth of a streptomycin-producing microbial strain, Streptomyces griseus OS-3601, via a physicochemical screening method using HP-20, silica gel and ODS column chromatographies and subsequent preparative HPLC. Iminimycin A is an indolizidine alkaloid, containing of an unusual iminium group and a cyclopropane ring with a triene side chain. The absolute configuration of iminimycin A was elucidated by NMR studies and electronic circular dichroism analysis. Iminimycin A shows anti-bacterial activity against Bacillus subtilis, Kocuria rhizophila and Xanthomonas campestris pv. orizae, and cytotoxic activity against HeLa S3 and Jurkat cells with IC50 values of 43 and 36 μM, respectively.

Flavonoids from Heartwood of Dalbergia cochinchinensis

ObjectiveTo study the flavonoids from the heartwood of Dalbergia cochinchinensis. MethodsThe chemical constituents were isolated and purified by combination of silica gel, macroporous resin, Sephadex LH-20, and ODS column chromatography. Their structures were identified by means of spectral analysis. ResultsFifteen flavonoids were isolated and identified as pinocembrin (1), liquiritigenin (2), galangin (3), 7-hydroxy-6-methoxyflavone (4), naringenin (5), alpinetin (6), 2,3-dimethoxyxanthone (7), 6,4′-dihydroxy-7-methoxy-flavan (8), mucronulatol (9), 7,8-dihydroxyflavanone (10), 5,7,3′,5′-tetrahydroxyflavanone (11), 4,2′,5′-trihydroxy-4′-methoxychalcone (12), isoliquiritigenin (13), butein (14), and 3′,5′,5,7-tetrahydroxy-6-C-β-D-glucopyranosyl-flavanone (15), respectively. ConclusionCompounds 7, 8, 10, and 15 are isolated from the plants of Dalbergia L. f. for the first time, and compounds 1, 3, 5, 6, 9, 11, 12, and 14 are isolated from this plant for the first time.

Alkyl Glycosides from the Flowers of Magnolia obovata

The flowers of M. obovata were extracted with aqueous MeOH and fractionated into EtOAc, n-BuOH, and H2O fractination. Three alkyl glycosides were isolated from the EtOAc fraction through repeated silica gel and ODS column chromatography. The structures were identified to be 2-methylbutan-1-ol-β-D-galactopyranoside (1), 2-methylbutan-1-ol-β-D-glucopyranoside (2), and 2-methylpropan-1-ol-β-D-glucopyranoside (3) on the basis of spectroscopic analyses such as fast atom bombardment mass spectrometry, infrared spectroscopy, 1D nuclear magnetic resonance (NMR) (1H and 13C-NMR), and 2D NMR (gCOSY, gHSQC, and gHMBC). These compounds were isolated for the first time from the flower of M. obovata in this study.

Tricin derivatives as anti-inflammatory and anti-allergic constituents from the aerial part of Zizania latifolia

Methanol extract of Zizania latifolia was partitioned with EtOAc, n-BuOH, and H2O. From the EtOAc layers, a new flavonolignan along with a known flavone and three known flavonolignans, tricin (1), salcolin A (2), salcolin B (3), and salcolin C (4), were isolated through repeated silica gel and ODS column chromatography. The chemical structure of the new flavonolignan was determined to be tricin-4'-O-[erythro-β-guaiacyl-(7″-O-methyl)-glyceryl] ether and was named salcolin D (5) based on physicochemical and spectroscopic data, including FT-NMR and ESI-MS. All compounds were isolated for the first time from this plant. Compounds 2-5, tricin derivatives, all exhibited higher anti-inflammatory and anti-allergy activities than tricin. In particular, salcolin D (5) was shown to have the strongest inhibitory activity against LPS-induced NO production in RAW 264.7 cells as well as β-hexosaminidase release in IgE-sensitized RBL-2H3 cells. These results suggest that the presence of tricin derivatives conveys allergy and inflammation treatment ability to Z. latifolia.

Study on secondary metabolites of endophytic fungi Penicillium dangeardii

Endophytic fungi Penicillium dangeardii, isolated from Lysidice rhodostegia Hance root, was fermented and the secondary metabolites were studied. By means of Sephadex LH-20 column chromatography, ODS column chromatography and PHPLC over the fermented culture, 5 compounds were isolated. By using ESI-MS and NMR, the structures of the compounds were determined as N-[9-(β- D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acid (1), 3-caffeoylquinic acid (2), 4-caffeoylquinic acid (3), and 5-caffeoylquinic acid (4), 3-hydroxy-benzoic acid-4-O-β-D-glucopyranoside (5).

Trichoketides A and B, two new protein tyrosine phosphatase 1B inhibitors from the marine-derived fungus Trichoderma sp.

Two new octaketides, trichoketides A (1) and B (2), were isolated from a culture broth of the seawater-derived fungus Trichoderma sp. TPU1237 together with two known analogs, trichodermaketones C (3) and D (4), by ODS column chromatography followed by preparative ODS and chiral HPLC. The structures of 1 and 2 were elucidated on the basis of their spectroscopic data, and absolute configurations were assigned by comparing their experimental electronic circular dichroism (ECD) spectra with the calculated ECD spectra. Compounds 1 and 2 were epimers at the C-8 position (α-position of dihydrofuran ring). The IC50 values of compounds 1-4 against protein tyrosine phosphatase 1B were 53.1, 65.1, 68.0 and 55.9 μM, respectively.

Structural elucidation of two new megastigmane glycosides from the leaves of AquiAquilaria sinensi

The present study was designed to determine the chemical constituents and identify new components of the leaves of Aquilaria sinensis (Lour.) Gilg. The compounds were isolated and purified by repeated silica gel, Sephadex LH-20, and ODS column chromatography and their structures were elucidated by NMR and HR-ESI-MS spectrometry. Eight megastigmane glycosides and two cucurbitacins were isolated and identified as (9S) megastigma-4,7-diene-2,3,9-triol 9-O-β-D-glucopyranoside (1), (9S) megastigma-4(13),7-diene-3,6,9-triol 9-O-β-D-glucopyranoside (2), macarangloside D (3), corchoionoside C (4), staphylionoside H (5), (+) 3-oxo-α-ionol-β-D-glucopyranoside (6), (−) 3-oxo-α-ionol-β-D-glucopyranoside (7), citroside B (8), 2-O-β-D-glucopyranosyl cucurbitacin I (9), bryoamaride (10). Compounds 1 and 2 were newly identified megstigmane glucosides and reported from this genus for the first time.

Studies on chemical constituents of Zhuang medicine Excoecaria venenata and their cytotoxic activity

Fourteen compounds were isolated from 95% ethanol extract by silica gel, MCI, and ODS column chromatography. These compounds were respectively identified as quercetin (1), kaempferol (2), (+)-catechin (3), fraxin (4), protocatechuic acid (5), gallic acid (6), methyl gallate (7), ethyl gallate (8), apocynol A (9), baccatin (10), cerevisterol (11), ellagic acid (12), 3, 3',4'-tri-0-methylellagic acid(13) and N-benzoyl-L-phenylalaninyl-N-benzoyl-L-phenylalaninate(14) by analyzing their spectral data and comparing with the previously reported literatures. Except for gallic acid (6), all other compounds were isolated from this plant for the first time. Compounds 1, 2 and 6 showed moderate anti-proliferation activities on tumor cells.

Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derivedPenicilliumsp. KCB12C078

Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (36) by chemical investigation. Compounds 1 6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.

Isolation and Identification of Adenosine and Phlomuroside from the Aerial Parts of Oryza sativa L.

벼 지상부를 MeOH 수용액으로 추출하고 이 추출물을 n-hexane, EtOAc, n-BuOH, 및 H2O 분획으로 나누었다. n-BuOH 분획에 대하여 silica gel, ODS 및 Sephadex LH-20 column chromatography 를 반복실시 하여 2종의 화합물을 분리하였다. NMR, IR 및 MS data를 해석하여 각각 adenosine (1)과 phlomuroside (2)로 구조동정 하였다. 이들 화합물들은 벼에서는 처음으로 분리되었다.

Study on steroidal saponins from Dioscorea zingiberensis and their platelet aggregation activities

Using the absorbent resin, silica gel and ODS column chromatography as well as semi-preparative HPLC, ten compounds were isolated from 70% ethanol extract of tubers of Dioscorea zingiberensis C. H. Wright, and their structures were elucidated as trigoneoside XIIIa (1), parvifloside (2), trigoneoside IVa (3), deltoside (4), protobioside (5), lilioglycoside k (6), zingiberensis newsaponin I (7), deltonin (8), prosapogenin A of dioscin (9), and trillin (10) on the basis of NMR and MS spectral data analysis. Among these compounds, 1, 3, 5 and 6 were isolated from this plant for the first time. In the screening test on platelet aggregation, compounds 7 and 8 exhibited induction effect on platelet aggregation, while compound 9 exhibited significant inhibitory effect on platelet aggregation in vitro.

Chemical constituents from Paris mairei

Twelve compounds were isolated from the rhizome of Paris mairei Lévl by silica gel, Sephadex LH-20 and ODS col-umn chromatographies. The structure elucidation was accomplished by ESI-MS and NMR methods. These compounds were identified as lupeol(1), lup-20(29) -ene-3β-yl octacosanoate(2), palmitic acid(3), glyceryl α-mono-palmitate(4), α-spinasterol(5), diosgenin (6), (25R) diosgenin-3-O-α-L-rhamnopyranosyl (1--> 4) -α-L-rhamnopyranosyl (1 --> 4) - [α-L-rhamnopyranosyl(1 --> 2)] -β-D-glucopyranoside(7), pennogenin(8), pennogenin-3-O-β-D-glucopyranosyl(1 -->3) - [α-L-rhamnopyranosyl(1 --> 2)] -β-D-glucopyranoside(9), flazin(10), calonysterone(11), and isorhamnetin-3-O-β-gentiobioside(12). Compounds 1-5,10-11 were isolated from the genus Paris for the first time, and all compounds were isolated from this plant for the first time.

Chemical constituents from Safflower injection and their bioactivity

The chemical constituents of Safflower injection were isolated and purified by polyamide, silica gel, Sephadex LH-20, ODS column chromatographies and preparative HPLC. As a result, sixteen compounds have been isolated. Based on the spectral data analysis, their structures were elucidated as scutellarin (1), kaempferol-3-O-β-rutinoside(2), hydroxysafflor yellow A(3), rutin (4), coumalic acid(5), adenosine(6), syringoside(7), (3E)-4-(4'-hydroxyphenyl)-3-buten-2-one(8), (8Z)-decaene-4, 6-diyne-1-Oβ-D-glucopyranoside(9), 4-hydroxybenzaldehyde (10), (2E, 8E) -tetradecadiene-4, 6-diyne-1, 12, 14-triol-1-O-β-D-glucopyranoside (11), kaem-pferol-3-O-β-sophorose (12), uridine (13), roseoside (14), cinnamic acid (15), and kaempferol (16). Compounds 1,2,7,9,11 and 12 were isolated from the Safflower injection for the first time. The anti-platelet aggregation activities of the isolated compounds were assayed. The results indicated all tested compounds exhibited potent activity except for 5, while 2, 3, 9 and 12 showed strong activity against platelet aggregation.

Lignans isolated from stems of Sambucus williamsii and their proliferation effects on UMR106 cells

The present study aims to investigate the lignan constituents from Sambucus williamsii and their proliferation effects on osteoblast-like UMR106 cells. Seven compounds were isolated and purified by macroporous resin D101, silica gel, Sephadex LH-20, Toyopearl HW-40, ODS column chromatographies and Preparative HPLC(C-18). Their structures were elucidated by spectroscopic methods as threo-guaiacylglycerol-beta-0-4'-conifery ether (1), lirioresinol A (2), 1-hydroxypinoresinol (3), 5-methoxybalanophonin (4), balanophonin (5), 5-methoxy-trans-dihydrodehydrodiconiferyl alcohol (6), and p-hydroxybenzaldehyde (7). Compounds 3-7 were obtained from this genus for the first time. The proliferation effects of all isolated compounds on osteoblast-like UMR106 cells were determined. Compounds 1-7 (1 x 10(-12)-1 x 10(-7) mol x L(-1)) increased UMR106 cell proliferation to some extent.

A new cytochalasin from endophytic Phomopsis sp. IFB-E060

AimTo study the chemical constituents of the solid culture of the endophyte Phomopsis sp. IFB-E060 in Vatica mangachapoi. MethodIsolation and purification were performed through silica gel column chromatography, gel filtration over Sephadex LH-20, ODS column chromatography, and HPLC. Structures of the isolated compounds were elucidated by a combination of spectroscopic analyses (UV, CD, IR, MS, 1D, and 2D NMR). The cytotoxicity of the isolates was evaluated in vitro by the MTT method against the human hepatocarcinoma cell line SMMC-7721. ResultsFive compounds were isolated from the solid culture of the endophyte Phomopsis sp. IFB-E060 and their structures were identified as 18-methoxy cytochalasin J (1), cytochalasin H (2), (22E, 24S)-cerevisterol (3), ergosterol (4), and nicotinic acid (5). Compound 1 had an inhibition rate of 24.4% at 10 μg·mL−1 and 2 had an IC50 value of 15.0 μg·mL−1, while a positive control 5-fluorouracil had an inhibition rate of 28.7% at 10 μg·mL−1. Conclusion18-Methoxy cytochalasin J (1), produced by endophytic Phomopsis sp. IFB-E060, is a new cytochalasin with weak cytotoxicity to the human hepatocarcinoma cell line SMMC-7721

Phenylpropanoids from red kohlrabi sprouts inhibits nitric oxide production in RAW 264.7 macrophage cells

The sprouts of red kohlrabi (Brassica oleracea var. gongylodes) were extracted with methanol, and the concentrated extracts were successively partitioned with ethyl acetate, n-butyl alcohol (n-BuOH), and H2O. From the n-BuOH fraction, four phenylpropanoids were isolated through repeated silica gel and ODS column chromatographies. On the basis of physico-chemical and spectroscopic data including NMR, MS, and IR, the isolated compounds were identified as 3-(3,4,5-trimethoxyphenyl)-2E-propenoic acid methyl ester (1), (E)-sinapic acid methyl ester (2), (E)-sinapoyl glucoside (3), and lawsoniaside B (4). Moreover, the compounds dose-dependently inhibited NO production in RAW 264.7 cells with IC50 values of 41.22 (1), 38.32 (3), and 22.65 (4) μM, respectively. With further studies, these compounds may be potentially useful in developing new anti-inflammatory agents.

Study on active constituents against Alzheimer's disease from Valeriana amurensis

In this study, the chemical constituentsfrom Valeriana amurensis AD-effective fraction were investigated based on the effect of Valeriana amurensis on Alzheimer's disease (AD) in previous study. Valeriana amurensis was extracted with 75% ethanol and the obtained extract were extracted and subjected to AB-8 macroporous resin column to obtain the AD-effective fraction of Valeriana amurensis. 9 compounds (1-9) were isolated with silica gel, ODS column chromatography and preparative HPLC. The structures of these compounds were determined as 6-hydroxy-7-(hydroxymethyl)-4-methylenehexahydrocyclopenta[c]-pyran-1(3H)-one (1), suspensolide F (2), loganin(3), α-morroniside(4), β-morronisid (5), partinovalerosidate (6), zansiumloside A (7), (-)-angelicoidenol-2-O-β-D-glucopyranoside (8), citroside A (9). Compounds 6-9 were isolated from the valerian genus for the first time and further investigated the anti-AD effect of compounds 1-9 in vitro found that compound 2 and 6 protected the PC12 cells from injury significantly.

Chemical constituents from Vaccinium bracteatum

The chemical constituents of Vaccinium bracteatum were studied by means of macroporous resin, ODS column chromatography and preparative HPLC. Eleven compounds were isolated from this plant. By using ESI-MS and NMR, the structures of the eleven compounds were determined as 10-O-trans-p-coumaroyl-6alpha-hydroxyl-dihydromonotropein (1), 10-O-cis-p-coumaroyl -6alpha-hydroxyl-dihydromonotropein (2), vaccinoside (3), 10-O-cis-p-coumaroyl monotropein (4), isolariciresinol-9-O-beta-D-xyloside (5), tectoridin (6), vicenin-3 (7), quercetin-3-O-alpha-L-rhamnoside (8), quercetin-3-O-alpha-L-arabinopyranoside (9), quercetin-3-O-beta-D-galactopyranoside (10), and quercetin-3-O-beta-D-glucuronide (11), respectively. Compounds 1 and 2 are new, and compounds 4, 6 and 7 are isolated from the genus Vaccinium for the first time.