Methods for the isolation and characterization of constituents of natural products

Schwartz, Daniel P.; Shamey, Jennie; Brewington, C.R.; Parks, O.W.

doi:10.1016/0026-265x(68)90107-0

Cited by 36 publications

(13 citation statements)

References 11 publications

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“…Each peak from the saturated fractions obtained in step 6 was streaked across a 20 x 8 in. TLPC plate and developed in the hexane system described by Schwartz, et al (21). The bands were scraped from the plate, the color eluted with benzene, and any contaminating bands were pooled with the appropriate subsequent fraction.…”

Section: Step 7-thin Layer Partition Chromatography (Tlpc) Of Saturatmentioning

confidence: 99%

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Trace constituents in milk fat: Isolation and identification of oxofatty acids

Weihrauch

Brewington

Schwartz

1974

Lipids

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Ca. 1% of the glycerides of milk fat contain oxofatty acids. The isolation, fractionation, and characterization of oxofatty acids were accomplished using the following sequence of steps: (A) transmethylation, (B) conversion into 2,4‐dinitrophenylhydrazones, (C) adsorption of the 2,4‐dinitrophenylhydrazones on magnesium oxide to eliminate the colorless lipid, (D) fractionation of the 2,4‐dinitrophenylhydrazones into non‐oxofatty acid and oxofatty acid fractions on alumina, (E) separation of the oxofatty acid 2,4‐dinitrophenylhydrazones into saturated and unsaturated classes by argentation column chromatography, (F) separation of these classes by chain length using liquid‐liquid column and thin layer partition chromatography, (G) resolution of positional isomers by thin layer chromatography, (H) regeneration of the positional isomer 2,4‐dinitrophenylhydrazones, and (I) analysis of the parent oxofatty acids by gas liquid chromatographymass spectrometry. In this manner, 36 saturated and 11 unsaturated oxofatty acids were identified tentatively or positively. The saturated oxofatty acids ranged in chain length from C10–C24, predominantly C18 and C16, and generally contained an even number of carbon atoms. The unsaturated oxofatty acids ranged from C14–C18, with C18 predominating.

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Section: Step 7-thin Layer Partition Chromatography (Tlpc) Of Saturatmentioning

confidence: 99%

“…Each band obtained in steps 7 and 8 was streaked across the origin of a 20 x 8 in. alkaline TLPC plate (21) and developed in hexane and hexane:benzene (65:35). This system afforded further separation according to chain length which was not attained on either the partition column or on the neutral TLPC plates.…”

Section: Step 9--tlpc On Alkaline Platesmentioning

confidence: 99%

Trace constituents in milk fat: Isolation and identification of oxofatty acids

Weihrauch

Brewington

Schwartz

1974

Lipids

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“…The procedures for derivatizing, isolating and recovering the carbonyl compounds as their 2,4-DNPH's are reported elsewhere (11) and are similar to the procedures developed by Schwartz et al (14,15). The procedures used are outlined in Figure 1.…”

Section: Isolation Of Carbonyl Compoundsmentioning

confidence: 99%

Concentrations of some aliphatic aldehydes and ketones found in raw and roasted spanish and runner peanuts

Brown

Senn

Dollear

et al. 1973

J Americ Oil Chem Soc

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Carbonyl compounds in oil cold-pressed from raw and roasted peanuts were isolated and quantitated as their 2,4-dinitrophenylhydrazones. Quantitative data were obtained for more than 40 compounds and compared to the flavor threshold values of the compounds in oil. In general, concentrations of aldehydes and ketones in Spanish peanuts were higher than in runner peanuts. Hexanal and octanal and possibly nonanal, 2-octenal and 2-nonenal may contribute to the "green-beany" flavor of raw peanuts. Concentrations of 2-methylpropanal, 2-methylbutanal and 3-methylbutanal vastly exceeded their flavor thresholds and probably contribute significantly to the harsh note of freshly roasted peanuts. Other compounds that could contribute to the flavor and aroma of roasted peanuts are: hexanal, heptanal, octanal, nonanal, dodecanal, 2-heptenal, 2-octenal, 2-nonenal, 2-decenal and 2,4-decadienal.

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“…Growing cultures of Penicillium roqueforti oxidize fatty acids into their corresponding methyl ketones with one less carbon atom (Franke and Heinen, 1958;Hammer and Bryant, 1937;Lawrence, 1966;Starkle, 1924;Stokoe, 1928). Gehrig and Knight (1958) reported that only the spores of P. roqueforti oxidize fatty acids; however, Rolinson (1954), Vinze and Ghosh (1962), and Lawrence and Hawke (1968) demonstrated the oxidation of fatty acids into methyl ketones by the mycelium of P. roqueforti.…”

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confidence: 99%

“…However, a number of investigators showed that P. roqueforti oxidizes fatty acids via (3-oxidation (Gehrig and Knight, 1963;Hammer and Bryant, 1937;Katz and Chaikoff, 1955;Lawrence, 1966;Lawrence and Hawke, 1968;Starkle, 1924). However, a number of investigators showed that P. roqueforti oxidizes fatty acids via (3-oxidation (Gehrig and Knight, 1963;Hammer and Bryant, 1937;Katz and Chaikoff, 1955;Lawrence, 1966;Lawrence and Hawke, 1968;Starkle, 1924).…”

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confidence: 99%

Oxidation of sodium palmitate-U-carbon-14 into carbonyl compounds by Penicillium roqueforti spores

Dartey¹,

Kinsella²

1973

J. Agric. Food Chem.

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Spore suspensions of P. roqueforti metabolized sodium palmitate into carbon dioxide and a variety of carbonyl compounds, including a homologous series of methyl ketones. Both D-glucose and L-proline suppressed the catabolism of palmitate to COS but stimulated the rate of formation of carbonyl compounds, including methyl ketones. Spore concentrations of 6.3 X lo8 spores/ml produced the optimum yield of (32.4%) carbonyl compounds from the incubation of 5 m M of palmitate in the presence of 20 m M of D-glucose under optimum conditions of pH and tempera-ture; i,e., pH 6.5 (0.1 M phosphate buffer) and 30". Analyses of carbonyl compounds formed from [U-14C]palmitate revealed that a homologous series of labeled methyl ketones, C3 to C15 inclusive, was produced. Pentadecanone contained the highest radioactivity, followed by tridecanone and undecanone, with the lower methyl ketones containing varying amounts of radioactivity. Appreciable amounts of carbonyl compounds other than methyl ketones (Le., labeled, saturated, and unsaturated aldehydes) were also produced from [14C]palmitic acid.

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Methods for the isolation and characterization of constituents of natural products

Cited by 36 publications

References 11 publications

Trace constituents in milk fat: Isolation and identification of oxofatty acids

Trace constituents in milk fat: Isolation and identification of oxofatty acids

Concentrations of some aliphatic aldehydes and ketones found in raw and roasted spanish and runner peanuts

Oxidation of sodium palmitate-U-carbon-14 into carbonyl compounds by Penicillium roqueforti spores

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