Free and bound sterols in seedlings of Cucumis sativus

Кинтя, П. К.; Wojciechowski, Zdzisław A.

doi:10.1016/0031-9422(74)85034-x

Cited by 30 publications

(11 citation statements)

References 7 publications

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“…The mass spectrum of this component gave major peaks at m/e (relative intensity}: 410 (M § 15), 300 (10), 273 {12}, 272 {26}, 271 (100), 255 (24), 253 (9), 246 110), 231 (14), 229 (12), 213 (17) and 211 (7). This fragmentation pattern was consistent with a 24~-ethyl-5a-cholesta-7,22,25(27)-trien-3/3-ol structure (8,9,13). The final confirmation of this structure and of the configuration at C-24 was provided by 1H-NMR data {Table 4).…”

Section: Characterization Of the A~-sterols In Mature Plantssupporting

confidence: 70%

“…An important peculiarity is the presence of a AT-bond replacing-the more commonly encountered AS-unsaturation (1)(2)(3)(4)(5)(6). Only a few investigators have reported the presence of A%terols in plants of this family, and in most cases only trace amounts were found (7)(8)(9). It was, therefore, of considerable interest when we found a substantial amount (ca.…”

Section: Changes In a S-and Ht-sterols During Germination And Seedlinmentioning

confidence: 99%

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Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Garg

Nes

1985

Lipids

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While seeds of Cucurbita maxima contain both A s-and AT-sterols, the former, which have been described earlier, now have been found to disappear during germination. This suggests that a hmction exists for the AS-compounds only in the early part of the life cycle of C maxima, unlike most of the other higher plants studied. In contrast to the AS-sterols, the level of AT-sterols increased during germination as well as during seedling development and maturation. The period ol i~rm~i~ion between germination and seedling development appeared to be of special importance in terms of sterol changes. This period represented a surge of sterol biosynthesis with an ontogenetic shift in sterol composition from approximately equal amounts of 24a-and 24/~-ethyl stereochemistry to a predominance of the former. The sterol composition of the mature plants included only about 5% of the 24/~-ethylstorols. The configurational relationships were demonstrated by high resolution IH-NMR. The sterols of the mature plants were: 25(27Fdehydrochondrillasterol, 24~ethyl-25{27)dehydrolathosterol, avenasterol, spinasterol, 22-dihydrospinasterol and 24~-methyUathosterol. Based on the changes which occurred in the relative amounts of the AT-sterols, it did not appear that the AS-components were being converted to their AT-analogs. Lipids 20: 876-883, 1985.

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Section: Characterization Of the A~-sterols In Mature Plantssupporting

confidence: 70%

Section: Changes In a S-and Ht-sterols During Germination And Seedlinmentioning

confidence: 99%

Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Garg

Nes

1985

Lipids

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“…It is apparent that the sterol fraction from pumpkin seed oil consists mainly of A^-sterols with small proportions of A5-sterols, in spite that the sterol fractions of most vegetable oils consist mainly of As-sterols while A^-sterols are present in small proportions (27,28,29). The sterol fraction of pumpkin seed oil predominated mainly by A7.22,25-stigmastatrien-3(3-ol, a-spinasterol, A^-ss-stigmastadienol and A^-avenasterol, followed by stigmasterol, 24-methylcholest-7-enol and A^-stigmastenol in proportions varying from 3,5 to 4,5% (Table III).…”

Section: Grasas Y Aceitesmentioning

confidence: 99%

“…As a result sterols present in trace or minor amounts in crude oil were not detected in purified oil (Table III). Furthermore, it should be pointed out that p-sitosterol, present in most vegetable oils in high proportions, is absent from pumpkin seed oil as well as from the oils of other Cucurbitaceae (27,28,29,30). Regarding the main components of the sterolic fraction, it could be concluded that there was practically no difference in composition between pumpkin seed oils of different origin.…”

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confidence: 98%

Characterization of crude and purified pumpkin seed oil.

1997

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RESUMENCaracterización de aceite de semilla de calabaza crudo y purificado.Aceite de semillas de calabaza descascarada (Cucúrbita pepo y Cucúrbita maxima) fue extraído con éter de petróleo caliente, y luego desgomado, neutralizado y decolorado consecutivamente. Las características físicas y químicas de aceites crudo y purificado fueron determinadas. La densidad, el índice de refracción, la viscosidad y el índice de peróxido no se afectaron por la purificación, mientras que se observó una disminución en la acidez, color, insaponificable, E1% ^cm 232, y estabilidad oxidativa, y un aumento en el punto de humo y de E1% -i cm 270. La purificación no afectó los perfiles de ácidos grasos y esteróles. El análisis CGL para la composición de ácidos grasos del aceite de semilla mostró que los insaturados predominantes fueron linoleico (42%) y oleico (38%), mientras que los saturados mayoritarios fueron palmítico (12,7%) y esteárico (6%). Sólo el a-tocoferol fue detectado a nivel de 126mg/kg, el cual se redujo a 78mg/kg después de la purificación. Los principales esteróles de la materia insaponificable del aceite de semilla de algodón fueron A7-22,25 -stigmastatr¡en-3(3-ol, a-spinasterol, A7.25-stigmastadienol y A^ -avenasterol, seguidos por el stigmasterol, 24-metilcolest-7-enol y A''-stigmastenol, y también se encontraron trazas de componentes menores de colesterol, brasicasterol, campesterol, sitostanol, A^-avenasterol, eritrodiol y uvaol. PALABRAS-CLAVE: Aceite de semilia de calabazaCaracterística física -Característica química -Refinación. SUMMARY Characterization of crude and purified pumpkin seed oil.Oil from hulled pumpkin seeds (Cucúrbita pepo and Cucúrbita maxima) was extracted with hot petroleum ether, and then it was degummed, neutralized and bleached, consecutively Physical and chemical characteristics of crude and purified oils were determined. Density, refractive index, viscosity and peroxide value were not affected by purification, while decreases in acidity, colour, unsaponifiable, £1% ^cm 232, and oxidative stability, and increases in smoke point and E1% icm 270 were observed. Purification did not affect the fatty acid and sterol profiles. GLC analysis for the fatty acid composition of the seed oil showed that the predominant unsaturates were linoleic (42%) and oleic (38%), while the major saturates were palmitic (12,7%) and stearic (6%). Only a-tocopherol was detected at a level of 126 mg/kg, which reduced to 78 mg/kg after purification. The main sterols of pumpkin seed oil unsaponifiable were A7.22,25^ -stigmastatrien-3(3-ol, a-spinasterol, A7,25_stigmastadienol and A^-avenasterol, followed by stigmasterol, 24-methylcholest-7-enol and A^-stigmastenol, and also trace to minor amounts of cholesterol, brassicasterol, campesterol, sitostanol, A^-avenasterol, erythrodiol and uvaol were found. KEY-WORDS:Ctiemical ctiaracteristic -Physical characteristic -Pumpkin seed oil -Refining.

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“…Glycoside 26 is rather widely distributed in higher plants [6,34,108,110,111,113,114,116,117,[119][120][121][122][123][124][125][147][148][149][150][151][152][153]. This compound is usually found in a difficultly separated mixture with [3-sitosterol 3-O-[~-D-glucopyranoside (1) and campesterol 3-O-13-D-glucopyranoside (27).…”

Section: Ho" (~1-i 27mentioning

confidence: 99%

Sterol glycosides and acylglycosides

Ковганко¹,

Kashkan²

1999

Chem Nat Compd

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The stntctlo'e, properties, distribution in nature, and biological activity of sterol glycosides and acylglycosides are reviewed.Sterols are one of the most widely distributed natural substances [1][2][3]. They exist in animals and plants in the free state and as derivatives. Glycoside and acylglycoside derivatives of sterols have been known for a long time. In the plant world, these compounds are found in higher plants [2,[4][5][6], algae [7], fungi [8][9][10], and bacteria [11][12][13][14][15][16]. In the animal kingdom, these substances have been identified in soft coral [17], holothuriae [18-20[, amphibians [211, snakes [21, 22], and birds [21,23]: Such a wide distribution in nature suggests that sterol glycosides and acylglycosides possess important physiological functions. Therefore, these compounds are constantly under intense scientific scrutiny. Sterol glycosides and acylglycosides are usually isolated from natural sources as very complicated mixtures that cannot always be separated into, the pure components. However, several physicochemical methods have recently been proposed for separating, analyzing, and identifying them [23][24][25][26][27][28][29][30][31][32][33][34]. Use of these methods greatly facilitates the investigation of glycosides and acylglycosides.Owing to the wide distribution in nature and the variety of physiological functions for glycosides and acylglycosides, research articles about them are published in a wide range of scientific literature. However, this subject has not yet been reviewed. The present work is intended to fill that gap. It should be noted that we pay the most attention to discreet natural compounds that can be isolated pure and for which the structures are reliably proved since this is where our interest lies. Substances that have been isolated as mixtures and are insufficiently characterized are examined in less detail.Some of the most widely distributed sterol glycosides are ~sitosterol 3-O-~D-glucopyranoside (1). This compound was isolated from higher plants early in the 20th century under various names: ipuranol, citrullol, trifolianol, etc. [35,36]. Later glycoside 1 was prepared by chemical synthesis via glycosylation of I~-sitosterol [37]. Direct comparision with this synthesized compound provided final structural proof tbr various natural samples of I [36]. Glycoside 1 is the most typical sterol glycoside of higher plants and is usually observed in preliminary phytochemical analysis of them. Hydrolysis of glycoside 1 by sulfuric acid in ethanol with boiling lbr 22 h yields [~-sitosterol and D-glucose [41]. The same result is obtained by hydrolysis in 6% HCI with heating lbr 50 min [46]. Hydrolysis of compound 1 to give ~sitosterol

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Free and bound sterols in seedlings of Cucumis sativus

Cited by 30 publications

References 7 publications

Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Characterization of crude and purified pumpkin seed oil.

Sterol glycosides and acylglycosides

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Free and bound sterols in seedlings of Cucumis sativus

Cited by 30 publications

References 7 publications

Changes in Δ5‐ and Δ7‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Changes in Δ5‐ and Δ7‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Characterization of crude and purified pumpkin seed oil.

Sterol glycosides and acylglycosides

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Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima

Changes in Δ⁵‐ and Δ⁷‐sterols during germination and seedling development ofCucurbita maximaduring germination and seedling development ofCucurbita maxima