Phytosterols and their derivatives: Structural diversity, distribution, metabolism, analysis, and health-promoting uses

Moreau, Robert A.; Nyström, Laura; Whitaker, Bruce D.; Winkler‐Moser, Jill K.; Baer, David J.; Gebauer, Sarah K; Hicks, Kevin B.

doi:10.1016/j.plipres.2018.04.001

Cited by 341 publications

(236 citation statements)

References 270 publications

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“…The essential fatty acids, tocopherols, tocotrienols, phytosterols, and carotenoids belong to a group of beneficial compounds with a lipophilic nature. Consumption of plant products rich in polyunsaturated fatty acids (PUFA) omega‐3 decreases the blood pressure in hypertensive patients (Colussi et al, ); carotenoids can contribute to the inhibition of cardiovascular disease development (Kulczyński et al, ); phytosterols very effectively reduce low‐density lipoprotein (LDL) cholesterol in some individuals but have very little effect in others (Moreau et al, ); while tocotrienols are promising analogs of vitamin E for cancer therapeutics (Sailo et al, ). In turn, phenolic compounds belong to the group of beneficial compounds with a hydrophilic nature.…”

Section: Introductionmentioning

confidence: 99%

Profiling of the Beneficial and Potentially Harmful Components of Trichodesma indicum Seed and Seed Oil Obtained by Ultrasound‐Assisted Extraction

Górnaś

Picron

Pērkons

et al. 2019

J Americ Oil Chem Soc

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The beneficial and potentially harmful bioactive components in the seeds and seed oil of Trichodesma indicum L. (Boraginaceae) were investigated in the present study. The T. indicum seeds were rich in oil (29.0%), phenolic compounds (PC, 1881.2 mg per 100 g), and pyrrolizidine alkaloids (PA, 2,702,338 ng g −1 ). Seven PC were identified in T. indicum seeds by liquid chromatographyquadrupole-time-of-flight mass spectrometry system (LC-Q-TOF-MS). Rosmarinic acid (67%) and isomers of salvianolic acid B/E/L (26%) were the main phenolics, while melitric acid A and sebestenoid C/D constituted 6% and 1%, respectively. Only a minor part of the total PC and PA was transferred from the seeds into the oil fraction during the extraction procedure (<0.03%). The T. indicum seed oil was predominated by the following polyunsaturated fatty acids (PUFA):linoleic (23.2%), γ-linolenic (6.0%), α-linolenic (26.8%), and stearidonic (5.9%). High levels were also observed for oleic (26.7%) and palmitic (7.4%) acids. Additionally, notable amounts of γ-tocopherol (92% of total tocochromanols) and β-sitosterol (53% of total sterols) were found in T. indicum seed oil. The total content of tocochromanols, sterols, and carotenoids in T. indicum seed oil was 102.7, 236.0, and 0.6 mg per 100 g oil, respectively. Among 10 detected hepatotoxic PA in T. indicum seeds, intermedine/lycopsamine/indicine (90.9%), intermedine N-oxide (4.9%), and lycopsamine N-oxide (4.1%) consisted 99.9% of the total PA concentration. The T. indicum seeds should be used carefully due to the presence of PA.

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Section: Introductionmentioning

confidence: 99%

Profiling of the Beneficial and Potentially Harmful Components of Trichodesma indicum Seed and Seed Oil Obtained by Ultrasound‐Assisted Extraction

Górnaś

Picron

Pērkons

et al. 2019

J Americ Oil Chem Soc

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“…In the plant species, there were identified more than 200 various kinds of phytosterols [6]. The most abundant sterols are β-sitosterol, campesterol, and stigmasterol, which represent up to 98% of total sterols [7]. Further minor sterols, divided according to number of carbons, are C30 sterols-lanosterol, amyrin, lupeol, C29 sterols-fucosterols, avenasterols, β-sitosterol, and sitostanol, C28 sterols-brassicasterol, crinosterol, campesterol, stigmasterol, as well as C27 sterols-cholesterol, lathosterol and desmosterol [3,6,8].…”

Section: Introductionmentioning

confidence: 99%

“…Further minor sterols, divided according to number of carbons, are C30 sterols-lanosterol, amyrin, lupeol, C29 sterols-fucosterols, avenasterols, β-sitosterol, and sitostanol, C28 sterols-brassicasterol, crinosterol, campesterol, stigmasterol, as well as C27 sterols-cholesterol, lathosterol and desmosterol [3,6,8]. Their content differs in connection with their location [7]. Phytosterols are present in plants as esters, free alcohols, or glycosides [7].…”

Section: Introductionmentioning

confidence: 99%

“…Their content differs in connection with their location [7]. Phytosterols are present in plants as esters, free alcohols, or glycosides [7].…”

Section: Introductionmentioning

confidence: 99%

“…In the plant cell membranes, the role of phytosterols is analogous to that of cholesterol in animals [9]. Sterols play an essential role in fluidity and permeability of membrane, even in the synthesis of steroid hormones [7]. Phytosterols also serve as substrates for brassinolids which protect plants from both pathogen and oxidative stress [10].…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive sterol and fatty acid analysis in nineteen nuts, seeds, and kernel

et al. 2019

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Consumption of nuts and seeds is considered to have many beneficial health effects, as lowering cholesterol, incidence of cancer, or enhancement of immunity system. Among the most important lipid constituents of oils present in nuts and seeds are fatty acyls in lipid classes and phytosterols. The aim of the study was to quantify wide profile of fatty acids and phytosterols in 19 nuts, seeds, and kernel commonly available in the Czech Republic. Samples were extracted by the modified Folch procedure. Fatty acid analyses were conducted by gas chromatography. The sterols were derivatized and subsequently measured by HPLC-MS/MS procedure allowing for the separation of isobaric compounds including sterol Δ5-Δ7 isomers. Nuts and seeds contained predominantly oleic (18:1n-9) and linoleic (18:2n-6) acids, rich sources of α-linoleic acid (18:3n-3) were linseed, chestnut, walnuts and hempseed, the last being the best source of stearidonic acid (18:4n-3). The phytosterol analyses revealed majority of β-sitosterol and campesterol with the exception of pumpkin and melon seeds, rich in Δ7 sterols, which were separable from Δ5 isomers. Correlation of sterols and fatty acids content revealed positive correlation between monounsaturated/saturated fatty acids (16:1n-9, 18:1n-9, 20:1n-9, 20:0) and stigmasterol and negative correlation between fatty acids (16:1n-9, 18:1n-9) and sitostanols. In summary, our study revealed the wide profile of fatty acids and phytosterols between different nuts and seeds. Further studies are needed to confirm the positive effect of each nut and seeds for health.

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Plant Steroids: Occurrence, Biological Significance, and Their Analysis

Gunaherath¹,

Gunatilaka²

2020

Encyclopedia of Analytical Chemistry

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Plant steroids constitute a diverse group of natural products. Biosynthetically, they are derived from S ‐squalene‐2,3‐epoxide via acetate‐mevalonate pathway. Among the plant steroids, phytosterols are ubiquitous in the plant kingdom and some of them are reported to possess hypocholesterolemic activity. Withanolides are a large group of steroidal lactones with various biological activities. Brassinosteroids are a small group of plant steroids classified as plant growth hormones. Phytoecdysteroids are polyhydroxylated plant steroids, many of which are known to exhibit anabolic effects with no undesirable side effects. Steroidal alkaloids are nitrogen‐containing plant steroids with an array of biological activities. It is noteworthy that trace amounts of cholesterol and mammalian steroidal hormones including progesterone have been detected in some plants. Analyses of plant steroids mainly utilize chromatographic methods such as thin‐layer chromatography ( TLC ), high‐performance liquid chromatography ( HPLC ), ultra‐high‐performance liquid chromatography ( UHPLC ), and gas‐liquid chromatography ( GLC ). In general, photodiode array ( PDA ), evaporative light scattering ( ELS ), and fluorescence ( FL ) detectors and mass spectrometry ( MS ) are commonly used for detection, quantification, and identification of plant steroids. UHPLC hyphenated with tandem mass spectrometry ( MS/MS ) has recently become the state‐of‐the‐art method of choice for the analysis of plant steroids, especially for the ones that are present in minor quantities such as brassinosteroids and phytoecdysteroids. Some less common techniques employed for the analyses of plant steroids are immunoassays and biological assays.

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Phytosterols and their derivatives: Structural diversity, distribution, metabolism, analysis, and health-promoting uses

Cited by 341 publications

References 270 publications

Profiling of the Beneficial and Potentially Harmful Components of Trichodesma indicum Seed and Seed Oil Obtained by Ultrasound‐Assisted Extraction

Profiling of the Beneficial and Potentially Harmful Components of Trichodesma indicum Seed and Seed Oil Obtained by Ultrasound‐Assisted Extraction

Comprehensive sterol and fatty acid analysis in nineteen nuts, seeds, and kernel

Plant Steroids: Occurrence, Biological Significance, and Their Analysis

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