Reversed-phase high-performance liquid chromatography

Rittich, Bohuslav; Polster, M; Králík, Oldřich

doi:10.1016/s0021-9673(00)80534-8

Cited by 39 publications

(3 citation statements)

References 21 publications

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“…The k'-values for a C-18 reverse phase HPLC system (Lichrosorp, 250 x 8mm, 7 [Sm) with pure water as an eluent were extrapolated from the k-values measured in eluents containing methanol and aqueous acetic acid (0.5%) in the ratios 10: 1, 7:1,5:1, and 9:2 (10).…”

Section: Synthesis Of Nortrilobolide (3)mentioning

confidence: 99%

Nortrilobolide, a New Potent Guaianolide Secretagogue fromThapsi garganica

Smitt¹,

Christensen²

1991

Planta Med

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only difference between 3 and 4 is the presence of an amethyl group in the 8-O-acyl group in 4. This makes us suggest the name nortrilobolide for 3. Based on a previously published structureactivity relationship for the thapsigargins as histamine secretagogues (9), the new guaianolide 3 was expected to induce a potent histamine release from peritoneal rat mast cells. Incubation of mast cells purified by centrifugation over Ficoll with 3 in a calcium ion containing medium provoked a concentration dependent histamine release as depicted in Fig. 1.

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Section: Synthesis Of Nortrilobolide (3)mentioning

confidence: 99%

Nortrilobolide, a New Potent Guaianolide Secretagogue fromThapsi garganica

Smitt¹,

Christensen²

1991

Planta Med

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“…Trilobolide monoacetate (16 and 17) and diacetate (15) Trilobolide (12) (28 mg, 54 smol) was aeetylated as described above for thapsigargin (1). The crude residue (30 mg) was purified by column chromatography [silica gel 40 g, eluent: toluene-ethyl acetate (9: 1) to which increasing amounts of ethyl acetate were added] to give the diacetate 15 (10 mg (6)].…”

Section: The Lactols 20mentioning

confidence: 99%

“…The k'-values for a C-18 reverse phase HPLC system with pure water as an eluent were extrapolated from the k'-values measured in system A, B, C, and D (15).…”

Section: Determination Of K-valuesmentioning

confidence: 99%

The Potencies of Thapsigargin and Analogues as Activators of Rat Peritoneal Mast Cells

Norup¹,

Smitt²,

Christensen³

1986

Planta Med

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A number of naturally occurring polyacylated guaianolides, structurally related to thapsigargin (1), are demonstrated to be potent activators of rat peritoneal mast cells. In order to characterize the structural requirements necessary for possessing this effect, a number of analogues are prepared and the activities are tested. The potencies of the natural products were positively correlated with their k'-values, as established by reverse-phase HPLC. The positive correlation could be expanded to partly hydrolyzed or partly hydrogenated derivatives. In contrast, derivatives not possessing the vicinal trans-dihydroxy moiety found in thapsigargin (1) have lost the structural requirements necessary for potently inducing a histamine release. Thus, lipophilicity is only one of the factors of importance for potency, another is the presence of the vicinal trans-dihydroxy moiety. The potency of one of the naturally occurring guaianolides, thapsigargicin (2), was only poorly predicted by the correlation.The structure of thapsivillosin F, previously isolated from Thapsia villosa, was established by spectroscopy and partial synthesis.

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Prediction of retention time of phenols in liquid chromatography

Hanai

Hubert

1983

J. High Resol. Chromatogr.

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The chromatographic behavior of phenols in reversed‐phase mode liquid chromatography differs from that of non‐ionic compounds such as alkyl alcohols, alkylbenzenes, halogenated benzenes, polyaromatic hydrocarbons, and aromatic acids. Therefore, the retention times of 61 phenols were measured in a system of an octadecyl bonded silica gel and acetonitrile/water mixtures. The logarithm of the capacity ratio (log k') was found to be a linear function of the hydrophobicity (log P) in acidic acetonitrile/water mixtures. This result was applied to a different octadecyl bonded silica gel. Eight phenols were selected as standard compounds, and their log k' values were measured in 0.05 M phosphoric acid in 10 to 90% acetonitrile/water mixtures. An empirical polynomial relation was obtained between the concentration of acetonitrile and the slope of the log k' vs log P curve. Finally the capacity ratio of all phenols were calculated in given eluents by the equations derived from the measurements of standard compounds and the calculated log P values. The difference between predicted capacity ratios and measured ones was within 10%.

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Reversed-phase high-performance liquid chromatography

Cited by 39 publications

References 21 publications

Nortrilobolide, a New Potent Guaianolide Secretagogue fromThapsi garganica

Nortrilobolide, a New Potent Guaianolide Secretagogue fromThapsi garganica

The Potencies of Thapsigargin and Analogues as Activators of Rat Peritoneal Mast Cells

Prediction of retention time of phenols in liquid chromatography

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