Soybean Sterols Research Articles

Microbial Degradation of Steroids to Hexahydroindanone Derivatives

A Mutated strain of Nocardia corallina IFO 3338 accumulated following substances as cholesterol degradation products, 3aα-H-4α-[3′-propionic acid]-5α-hydroxy-7aβ-methylhexahydro-1-indanone-δ-Iactone (VIII), 3aα-H-4α-[3′-trans acrylic acid]-5α-hydroxy-7aβ-methylhexahydro-1-indanone (IX) and 3aα-H-4α-acetyl-5α-hydroxy-7aβ-methylhexahydro-1-indanone (X). Substance X is a new compound in the microbial degradation of sterols. These substances were also produced from steroid other than cholesterol, such as β-cholestanol, β-sitosterol, soy bean sterol (mixture), cholest-4-en-3-one, lithocholic acid, cholic acid and progesterone. A degradation pathway has been proposed for steroids by Nocardia corallina: cholesterol or other sterols - - - → 3aα-H-4α-[3′-propionic acid]-7aβ-methylhexahydro-1,5-indanedione or compound VIII — →3aα-H-4α-[3′-trans acrylic acid]-7aβ-methylhexahydro-1,5-indanedione or compound IX— → 3aα-H-4α-acetyl-7aβ-methylhexahydro-1,5-indanedione or compound X - - - → CO2 + H2O.

Microbial degradation of steroids to hexahydroindanone derivatives.

A Mutated strain of Nocardia corallina IFO 3338 accumulated following substances as cholesterol degradation products, 3aα-H-4α-[3′-propionic acid]-5α-hydroxy-7aβ-methylhexahydro-1-indanone-δ-Iactone (VIII), 3aα-H-4α-[3′-trans acrylic acid]-5α-hydroxy-7aβ-methylhexahydro-1-indanone (IX) and 3aα-H-4α-acetyl-5α-hydroxy-7aβ-methylhexahydro-1-indanone (X). Substance X is a new compound in the microbial degradation of sterols.These substances were also produced from steroid other than cholesterol, such as β-cholestanol, β-sitosterol, soy bean sterol (mixture), cholest-4-en-3-one, lithocholic acid, cholic acid and progesterone.A degradation pathway has been proposed for steroids by Nocardia corallina: cholesterol or other sterols - - - → 3aα-H-4α-[3′-propionic acid]-7aβ-methylhexahydro-1,5-indanedione or compound VIII — →3aα-H-4α-[3′-trans acrylic acid]-7aβ-methylhexahydro-1,5-indanedione or compound IX— → 3aα-H-4α-acetyl-7aβ-methylhexahydro-1,5-indanedione or compound X - - - → CO2 + H2O.

Microbial conversion of tall oil sterols to C19 steroids.

Mycobacterium sp. NRRL B-3683 converted tall oil sterols to C(19) steroids as efficiently as it converted soybean sterols.

Fractional Analyses of Soybean Sterols in Four Classes

Journal Article Fractional Analyses of Soybean Sterols in Four Classes Get access Takako Hirota, Takako Hirota Department of Agricultural Chemistry, University of Tokyo, Bunkyo-ku, Tokyo 113 Present address: Habaramae, Sakura-mura, Nii-hari-gun, Ibaraki 300–31. Search for other works by this author on: Oxford Academic Google Scholar Shigemi Gotȏ, Shigemi Gotȏ Department of Agricultural Chemistry, University of Tokyo, Bunkyo-ku, Tokyo 113 Present address: Department of Food and Nutrition, Ochanomizu University, Bunkyo-ku, Tokyo 112. Search for other works by this author on: Oxford Academic Google Scholar Masayuki Katayama, Masayuki Katayama Department of Agricultural Chemistry, University of Tokyo, Bunkyo-ku, Tokyo 113 Present address: Department of Agricultural Chemistry, University of Osaka Prefecture, Sakai, Osaka 591. Search for other works by this author on: Oxford Academic Google Scholar Saburo Funahashi Saburo Funahashi Department of Agricultural Chemistry, University of Tokyo, Bunkyo-ku, Tokyo 113 Present address: Shizuoka Eiwa-Jogakuin Junior College, Ikeda, Shizuoka 420. Search for other works by this author on: Oxford Academic Google Scholar Agricultural and Biological Chemistry, Volume 38, Issue 8, 1 August 1974, Pages 1539–1540, https://doi.org/10.1080/00021369.1974.10861370 Published: 01 August 1974 Article history Received: 29 March 1974 Published: 01 August 1974

Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol and campestanol.

AbstractCampesterol ([24R]‐24‐methyl‐5‐cholesten‐3β‐ol) was isolated from a soybean sterol mixture and purified on a small scale by column chromatography and on a large scale by crystallization from acetone to 97% purity. From this, 7‐dehydrocampesterol ([24R]‐24‐methyl‐5,7‐cholestadien‐3β‐ol) and campestanol ([24R]‐24‐methyl‐cholestan‐3β‐ol) were prepared. The acetates and benzoates of all four compounds also were obtained and compared to the corresponding members of the ergostane series.

A method for fractional determination of soybean sterols in four classes by florisil column chromatography.

A procedure for fractional determination of soybean sterols is presented. Sterols in lipid extracts were fractionated into four classes, fatty acid esters, the free form, acylated glucosides and non-acylated glucosides, by Florisil column chromatography. Sterol contents in the four classes were determined colorimetrically with ferric chloride-perchloric acid reagent. Before the colorimetry, the fatty acid ester fraction was hydrolyzed with ethanolic KOH, and the sterol was isolated as tomatinide. The free sterol fraction was directly treated with tomatine solution. The tomatinides were dissociated with dimethyl sulfoxide. To avoid the contamination of pigments from the acylated glucoside fraction, the second Florisil column was rinsed with diethyl ether between the elution with the first solvent (0 to 50% diethyl ether in n-hexane) and that with the second solvent (0 to 30% methanol in diethyl ether).

Fractional Analyses of Soybean Sterols in Four Classes

Fractional Analyses of Soybean Sterols in Four Classes

Soybean sterols during maturation of seeds I. Accumulation of sterols in the free form, fatty acid esters, acylated glucosides and non-acylated glucosides

Soybean sterols during maturation of seeds I. Accumulation of sterols in the free form, fatty acid esters, acylated glucosides and non-acylated glucosides

Separation of Soybean Sterols by Florisil Chromatography and Characterization of Acylated Steryl Glucoside

Florisil column chromatography was demonstrated to be effective in differentiation between different forms of sterols. Sterols of ground soybeans are in four forms, free, ester, and free and acylated glucosides, as analyzed on acetone extracts. In soybean oil foots, steryl ester is present in negligibly small amount. The acylated steryl glucosides were isolated from oil foots in a crystalline state. A chemical structure, steryl 6-acyl d-glucoside, was assigned to the compound, and its probable identity with the glucosides reported by Lepage is discussed. The acylated glucoside preparation was shown to be heterogeneous in composition, carrying palmitic, stearic, oleic, linoleic and linolenic acids as the main acyl moieties and campesterol, stigmasterol and β-sitosterol as steryl moieties. The presence of the three sterols is common to three other forms of sterols.

Separation of Soybean Sterols by Florisil Chromatography and Characterization of Acylated Steryl Glucoside

Florisil column chromatography was demonstrated to be effective in differentiation between different forms of sterols. Sterols of ground soybeans are in four forms, free, ester, and free and acylated glucosides, as analyzed on acetone extracts. In soybean oil foots, steryl ester is present in negligibly small amount. The acylated steryl glucosides were isolated from oil foots in a crystalline state. A chemical structure, steryl 6-acyl d-glucoside, was assigned to the compound, and its probable identity with the glucosides reported by Lepage is discussed. The acylated glucoside preparation was shown to be heterogeneous in composition, carrying palmitic, stearic, oleic, linoleic and linolenic acids as the main acyl moieties and campesterol, stigmasterol and β-sitosterol as steryl moieties. The presence of the three sterols is common to three other forms of sterols.

Feeding on filter paper by larvae of the silkworm, Bombyx mori L.

Larvae of the silkworm, Bombyx mori L., were found to feed on filter paper which had previously been heated to approximately 200°C for 15 hr. Feeding on filter paper was largely accelerated when the paper had been impregnated with sucrose. β-Sitosterol and soybean sterol, previously demonstrated to stimulate feeding of the silkworm on agar-diets, showed rather little stimulating action on paper-feeding.

Effects of sterols on feeding and nutrition of the silkworm, Bombyx mori L.

The feeding responses of the silkworm, Bombyx mori L., as tested on agar-diets showed that β-sitosterol, isolated from mulberry leaves and identified by gas-chromatographic analysis, stimulates feeding. A commercial sample of β-sitosterol was entirely inactive but showed a stimulating activity after recrystallization from an organic solvent. Gas-phase chromatography of recrystallized commercial β-sitosterol showed three peaks, namely, β-sitosterol, stigmasterol, and probably campesterol. Pure stigmasterol also stimulated feeding. Campesterol of either 90 or 93 per cent purity, the only impurity of which was β-sitosterol, showed a positive stimulation. Soybean sterol, rape-seed sterol, and pulp (waste liquor) sterol, all of them mixtures of sterols, also stimulated feeding. On the other hand, cholesterol lacked stimulatory activity, as had been shown previously. Nutritional studies with these sterols were also carried out by the use of semi-defined diets. The results confirmed previous results that the silkworm requires dietary sterol for normal growth and development. In these nutritional tests the various sterols, except cholesterol, had almost equally high value, irrespective of their stimulatory action on the feeding. Even cholesterol improved the efficiency of diets. It therefore appears that dietary sterols are primarily nutritional but also play a minor part as phagostimulants. It is also evident that β-sitosterol does not explain the unique relation of the silkworm to mulberry leaves. Further, a triterpenoid, C 30H 50O, was isolated from mulberry leaves and shown to elicit feeding.

Determination of Stigmasterol in Soybean Sterol Mixtures by Infrared Method

Determination of Stigmasterol in Soybean Sterol Mixtures by Infrared Method

The Separation of Stigmasterol from Soybean Sterols1

The Separation of Stigmasterol from Soybean Sterols¹

Modification of abnormal serum lipid patterns in atherosclerosis by administration of sitosterol.

Excerpt The reports by Peterson that the addition of soybean sterols to experimental diets of chicks appeared to inhibit the absorption of cholesterol1and to effect a decreased incidence of atheros...

The Hypocholesterolizing Effects of Drugs

The hypocholesterolizing effect on serum and tissue cholesterol of α-phenylbutyramide (PB) is evident in the cholesterol-fed fowl. PB and Gallogen (the diethanolamine salt of the mono-(+)-camphoric acid ester of α,4-dimethylbenzyl alcohol) are mutually antagonistic with respect to this effect, while PB and soybean sterols are additive. The latter combination is approximately as effective as a Gallogen-soybean sterol combination, but has distinct toxic effects that are not observed with the Gallogen-soybean sterol combination.

Effect of dihydrocholesterol and soybean sterols on cholesterol metabolism in rabbit and rat.

Summary1. Dietary dihydrocholesterol and soybean sterols were absorbed by rabbits, and soy sterols produced atherosclerosis in these animals. 2. Livers of rabbits and rats fed dihydrocholesterol and of rabbits fed soybean sterols had an impaired ability to incorporate C14-labeled-acetate into cholesterol. 3. Rats fed a 3% soybean sterols diet did not absorb significant amounts of these sterols. Soy sterols failed to produce a lowering of total liver sterol levels in rats.

The hypocholesterolizing effect of gallogen and its potentiation by soybean sterols.

Gallogen (the diethanolamine salt of the mono-(+)-camphoric acid ester of α,4-dimethylbenzyl alcohol) and soybean sterols have been tested for their effect, singly and in combination, on hypercholesterolemia and aortic cholesterol in cholesterol-fed cockerels. Gallogen alone was found to impede the rise of serum and aortic cholesterol, and also to potentiate these effects of soybean sterols.

Effect of soybean sterols on liver deposition of cholesterol-C14.

1. The effect of soybean sterols A on liver deposition and fecal excretion of cholesterol-C14 following a single feeding of I the labeled material has been studied using cholesterol-fed rats. Average recoveries of J labeled cholesterol in liver (measured as radioactivity recovered from liver non-saponifiable fraction) were 6.61% in a cholesterol-fed group, 1.80% in a cholesterol-fed group receiving one g of soy sterol immediately after cholesterol-C14 administration and 0.47% in a group fed both cholesterol and soybean sterol for 120 days. 3. Average recoveries of radioactivity in the non-saponifiable fraction of feces were 20.14%, 25.13%, and 27.76%, respectively, for the 3 groups described above.

Effect of dihydrocholesterol and soy bean sterols on elevated tissue cholesterol.

Summary1. Feeding a diet containing dihydrocholesterol to mice with elevated liver cholesterol did not result in an increased rate of liver cholesterol mobilization. 2. Rabbits with elevated blood cholesterol levels were treated with dietary soy bean sterols. The rate of fall of plasma cholesterol was not increased above that observed in a control group.