Droplet Counter-current Chromatography Research Articles

Calmodulin inhibitors from the bitter mushroom Naematoloma fasciculare (Fr.) Karst. (Strophariaceae) and absolute configuration of fasciculols.

Calmodulin inhibitors were found in the bitter poisonous mushroom Naematoloma fasciculare (Fr.) KARST. (Strophariaceae). The active compounds, fasciculols B, C, and F, were isolated by droplet counter-current chromatography and identified on the basis of various physical and spectral data. Application of the dibenzoate chirality method to a p-bromobenzoate derivative of fasciculol C allowed the absolute configurations at the C-2 and C-3 positions to be determined as (R) and (S), respectively.

Short‐chain phorbol ester constituents of croton oil

AbstractFive phorbol diesters, three 4‐deoxy‐4α‐phorbol diesters, two phorbol monoesters, and one 4‐deoxy‐4α‐phorbol monoester were isolated from a commercial sample of croton oil and characterized spectroscopically. Their purification was achieved using combinations of droplet countercurrent chromatography, low‐pressure column chromatography over phase‐bonded silica gel, and preparative thin layer chromatography. All of these isolates were shown to possess short‐chain ester functionalities, with 12‐O‐tiglylphorbol‐13‐isobutyrate, 12‐O‐(2‐methyl)butyrylphorbol‐13‐isobutyrate, 12‐O‐(2‐methyl)butyrylphorbol‐13‐acetate, 12‐O‐tiglyl‐4‐deoxy‐4α‐phorbol‐13‐isobutyrate, 12‐O‐tiglyl‐4‐deoxy‐4α‐phorbol‐13‐acetate, 12‐O‐(2‐methyl)butyryl‐4‐deoxy‐4α‐phorbol‐13‐acetate, phorbol‐12‐tiglate and 4‐deoxy‐4α‐phorbol‐13‐acetate being new compounds.

Flavonoid glycosides and a bitter principle from lomatogonium carinthiacum

Three flavone glycosides, including the novel 6-hydroxyluteolin 7- O-gentiobioside, and a bitter secoiridoid glycoside, swertiamarin, have been identified in the aerial parts of Lomatogonium carinthiacum. Four minor xanthone glycosides were also detected. Separations were made with droplet counter-current chromatography (DCCC) in combination with column chromatography. Structure elucidation was achieved by UV, 1H and 13C NMR, FDMS and D/CIMS spectra.

Droplet Countercurrent Chromatography - New Applications in Natural Products Chemistry

Abstract Droplet counter-current chromatography (DCCC) has found wide application for preparative separation of plant constituents and other natural products. It is particularly indicated for the isolation of polar compounds. The use of non-aqueous solvent systems allows the separation of weakly polar substances. Large-bore columns can be employed without decreasing the resolution when the flow-rate is increased. New fields of applications include essential oils, triterpenoids and steroids, plant growth regulators (gibberellins), antibiotics.

Isolation of natural products by droplet counter-current chromatography and related methods

Isolation of natural products by droplet counter-current chromatography and related methods

Complete resolution of dl-isoleucine by droplet counter-current chromatography

Les phases stationnaire et mobile, utilisees sont les phases organiques et aqueuses preparees par mise en equilibre de volumes egaux de solution tampon acetate contenant de l'acetate de Cu(II) et de n-butanol contenant de la N-n-dodecyl proline

Efficient isolation of a large amount of 20-hydroxyecdysone from Vitex madiensis (Verbenaceae) by droplet counter-current chromatography.

Efficient isolation of a large amount of 20-hydroxyecdysone from Vitex madiensis (Verbenaceae) by droplet counter-current chromatography.

Method of Cleanup by Droplet Counter-Current Chromatography (DCC) for Food Contamination Monitoring by GC/MS

Method of Cleanup by Droplet Counter-Current Chromatography (DCC) for Food Contamination Monitoring by GC/MS

Separation of veratrine using high-performance liquid chromatography or droplet countercurrent chromatography

Separation of veratrine using high-performance liquid chromatography or droplet countercurrent chromatography

Droplet counter-current chromatography of anthocyanins

Droplet counter-current chromatography of anthocyanins

The dermatitis-producing constituents of Euphorbia hermentiana latex.

Five ingenane derivatives, 3-O-n-(deca-2,4,6-trienoyl)-16-O-[(Z)-2-methyl-2-butenoyl]-16-hydroxyingenol (1), 3-O-[(Z)-2-methyl-2-butenoyl]-5,16,20-O-triacetyl-16-hydroxyingenol (2), 3-O-[(Z)-2-methyl-2-butenoyl]-16,20-O-diacetyl-16-hydroxyingenol (3), 3-O-[(Z)-2-methyl-2-butenoyl]-20-O-acetylingenol (4), and 3-O-[(Z)-2-methyl-2-butenoyl]-16-O-acetyl-20-deoxy-16-hydroxyingenol (5) were isolated with a new procedure that uses droplet counter-current chromatography, from a dermatitis-producing fraction of the latex of Euphorbia hermentiana Lem. The structures of the new compounds 2,3, and 5 were established by the interpretation of their spectroscopic data and those of their hydrolytic and acetylated derivatives.

Efficient isolation of phytoecdysones from Ajuga plants by high-performance liquid chromatography and droplet counter-current chromatography

Efficient isolation of phytoecdysones from Ajuga plants by high-performance liquid chromatography and droplet counter-current chromatography

Two Bitter Biphenyl Glucosides from Swertia japonica1

From the whole plants of Swertia japonica Makino a mixture of two new bitter biphenyl glucosides biphenosides A and B, was isolated along with three known secoiridoid glucosides by the application of droplet countercurrent chromatography (DCCC). The structure of the biphenyl glucoside was established by chemical degradation and spectroscopic methods.

8-methoxyingol esters from the latex of Euphorbia hermentiana

Two new ingol esters, 3,12- O-diacetyl-7- O-benzoyl-8-methoxyingol and 3,12- O-diacetyl-7- O-tigloyl-8-methoxyingol, were isolated from an acetone-soluble fraction of the latex of Euphorbia hermentiana. These macrocyclic diterpenes were identified on the basis of their spectroscopic parameters, as well as those of their hydrolytic derivatives. A third methoxylated ingol ester and a fourth new compound were tentatively identified as 3,12- O-diacetyl-7- O-angeloyl-8-methoxyingol and 3,7,12- O-triacetyl-8- O-benzoyl-18-hydroxyingol, respectively. All four new compounds, and three further ingol ester constituents of known structure, were found to be easily separable using a newly developed isolation procedure involving droplet counter-current chromatography.

Droplet counter-current chromatography with non-aqueous solvent systems

Droplet counter-current chromatography with non-aqueous solvent systems

Potential sweetening agents of plant origin: I. Purification of Stevia rebaudiana sweet constituents by droplet counter-current chromatography

Potential sweetening agents of plant origin: I. Purification of Stevia rebaudiana sweet constituents by droplet counter-current chromatography

Water-free solvent system for droplet counter-current chromatography and its suitability for the separation of non-polar substances

Water-free solvent system for droplet counter-current chromatography and its suitability for the separation of non-polar substances

Novel dammarane triterpenoid glycosides from the leaves of Hovenia dulcis. X-Ray crystal structure of hovenolactone monohydrate

Saponin E, isolated from the leaves of Hoevenia dulcis, afforded a new dammarane triterpene aglycone, hovenolactone, on treatment with naringinase. The structure of hovenolactone, including the relative configurations at C-17, C-20, and C-23, was established by chemical and spectroscopic investigations as well as by X-ray analysis. Saponins E and H were separated by droplet counter-current chromatography. The complete molecular configurations of both glycosides were determined to be 3-O-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)hovenolactone and 3-O-β-D-glucopyranosylhovenolactone, respectively, by 13C n.m.r. spectroscopy.

The application of droplet counter-current chromatography (DCC) for the separation of acidic glycolipids.

Droplet counter-current chromatography (DCC) a novel liquid-liquid partition technique, is a useful method for the separation of glycolipids. After a series of investigations on suitable experimental conditions for DDC, mouse brain chloroform-methanol-0.5% CaCl2-n-propanol (50:60:40:6) by the ascending method with 500 standard columns. GM1 and cerebroside sulfuric ester (CSE) from whale brain glycolipid fraction were separated by DCC into two peaks and three peaks, respectively, with chloroform-methanol-water-n-propanol (50:60:40:2) and 500 standard columns. The occurrence of two peaks of GM1 was due to the differences of sphingenine and fatty acid compositions. In the former peak of GM1, the majority of long chain base and fatty acid were 18:1 sphingenine and stearic acid, respectively, while the latter contained 18:1 (32%), 20:1 (68%) sphingenine and 16:0 (14.5%), 18:0 (61.4%), and 20:0 (21.0%) fatty acids. The three peaks of CSE were due to the difference of carbon chain length and to the presence or absence of a hydroxyl group in fatty acids. The first polar fraction (CSE-I) had hydroxy 23:0 (34%) and 24.1 (53.4%) fatty acids and the second fraction (CSE-II) contained hydroxy 24:0 (70.5%) and 25:1 (12.8%) fatty acids, while the third fraction (CSE-III) had normal 23:0 (11.9%), 24:1 (56.4%), hydroxy 25:0 (11.4%) and 26:1 (9.7%) fatty acids. Preparative DCC was also applied to the glycolipid fraction from Tay-Sachs' brain to give 242 mg of practically pure GM2 from 700 mg of crude brain extract without any preliminary purification.

Separation and Determination of Phenol Glycosides with anti-Pseudomonas Activity from Poplar leaves by Droplet Counter Current Chromatography (DCCC)

Separation and Determination of Phenol Glycosides with anti-Pseudomonas Activity from Poplar leaves by Droplet Counter Current Chromatography (DCCC)