Chemical and Biochemical Features of Spinasterol and Schottenol.
Phytosterols
Schottenol
Seed oils
Spinasterol
Δ7-sterols
Journal
Advances in experimental medicine and biology
ISSN: 0065-2598
Titre abrégé: Adv Exp Med Biol
Pays: United States
ID NLM: 0121103
Informations de publication
Date de publication:
2024
2024
Historique:
medline:
4
12
2023
pubmed:
1
12
2023
entrez:
30
11
2023
Statut:
ppublish
Résumé
Phytosterols, which are produced in plants, are structurally similar to cholesterol. Their basic structures consist of a cyclo pentano-perhydrophenanthrene nucleus composed of 3 hexane rings and of a pentane ring with an alkyl side chain. There are around more than 250 phytosterols and related compounds that have been identified in natural resources. Among them, spinasterol and schottenol, its dihydro analog, are often found in seeds, and consequently in seed oils, and in other botanical parts of some plant families such as Sapotaceae, Cactaceae, and Cucurbitaceae. Spinasterol and/or schottenol has been identified in dietary and cosmetic argan oil, milk thistle seed oil, nigella seed oil, and pumkin seed oil. These phytosterols that have several bioactive properties make them potentially attractive molecules in pharmacology. Their chemical and biochemical features are summarized and the analytical methods used to characterize and analyze these compounds are presented.
Identifiants
pubmed: 38036874
doi: 10.1007/978-3-031-43883-7_3
doi:
Substances chimiques
Nigella sativa oil
CS4U38E731
stigmast-7-enol
6869-99-4
spinasterol
0LG993QX1A
milk-thistle extract
U946SH95EE
Plant Oils
0
Phytosterols
0
Fatty Acids
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
45-55Informations de copyright
© 2024. The Author(s), under exclusive license to Springer Nature Switzerland AG.
Références
Abidi SL (2001) Chromatographic analysis of plant sterols in foods and vegetable oils. J Chromatogr A 935:173–201
pubmed: 11762774
doi: 10.1016/S0021-9673(01)00946-3
Ajagbe BO, Othman RA, Myrie SB (2015) Plant sterols, stanols, and sitosterolemia. J AOAC Int 98:716–723
pubmed: 25941971
doi: 10.5740/jaoacint.SGEAjagbe
Aljohani OS (2022) Phytochemical evaluation of Cucumis Prophetarum: protective effects against carrageenan-induced prostatitis in rats. Drug Chem Toxicol 45:1461–1469
pubmed: 33092416
doi: 10.1080/01480545.2020.1838538
Arisawa M, Kinghorn AD, Cordell GA, Phoebe CH, Fansworth NR (1985) Plant anticancer agents. Xxxvi schottenol glucoside from baccharis coridifolia and ipomopsis aggregata. Planta Med:544–545
Azmir J, Zaidul ISM, Rahman MM, Sharif KM, Mohamed A, Sahena F, Jahurul MHA, Ghafoor K, Norulaini NAN, Omar AKM (2013) Techniques for extraction of bioactive compounds from plant materials: a review. J Food Eng 117:426–436
doi: 10.1016/j.jfoodeng.2013.01.014
Badreddine A, Karym El M, Zarrouk A, Nury T, El Kharrassi Y, Nasser B, Cherkaoui Malki M, Lizard G, Samadi M (2015) An expeditious synthesis of Spinasterol and Schottenol, two phytosterols present in Argan oil and in cactus pear seed oil, and evaluation of their biological activities on cells of the central nervous system. Steroids 99:119–124
pubmed: 25595450
doi: 10.1016/j.steroids.2015.01.005
Balme S, Gülaçar FO (2012) Rapid screening of phytosterols in Orange juice by solid-phase microextraction on polyacrylate fibre derivatisation and gas chromatographic-mass spectrometric. Food Chem 132:613–618
pubmed: 26434339
doi: 10.1016/j.foodchem.2011.10.097
Barton DHR, Cox JD (1948) The application of the method of molecular rotation differences to steroids. Part V. Olefinic unsaturation at the 7: 8-position. J Chem Soc (Resumed):1354–1357
Beveridge TH, Li TS, Drover JC (2002) Phytosterol content in American ginseng seed oil. J Agric Food Chem 50:744–750
pubmed: 11829639
doi: 10.1021/jf010701v
Breinhölder P, Mosca L, Lindner W (2002) Concept of sequential analysis of free and conjugated phytosterols in different plant matrices. J Chromatogr B Analyt Technol Biomed Life Sci 777:67–82
pubmed: 12270201
doi: 10.1016/S1570-0232(02)00093-4
Brooks CJ, Cole WJ, Mcintyre HB, Smith AG (1980) Selective reactions in the analysis and characterization of steroids by gas chromatography-mass spectrometry. Lipids 15:745–755
pubmed: 7421429
doi: 10.1007/BF02534028
Ceylan FD, Adrar N, Bolling BW, Capanoglu E (2022) Valorisation of hazelnut by-products: current applications and future potential. Biotechnol Genet Eng Rev:1–36
Chen Y, She Y, Kaur R, Guo N, Zhang X, Zhang R, Gou X (2019) Is plant sterols a good strategy to lower cholesterol? J Oleo Sci 68:811–816
pubmed: 31413246
doi: 10.5650/jos.ess19116
Choudhary SP, Tran LS (2011) Phytosterols: perspectives in human nutrition and clinical therapy. Curr Med Chem 18:4557–4567
pubmed: 21864283
doi: 10.2174/092986711797287593
Da Silva Araújo JR, Silva Morais JG, Santos CM, Araújo Rocha KC, Rios Fagundes A, Fa ESF, Martins FA, De Almeida PM (2021) Phytochemical prospecting, isolation, and protective effect of the Ethanolic extract of the leaves of Jatropha Mollissima (Pohl) Baill. J Toxicol Environ Health A 84:743–760
pubmed: 34120581
doi: 10.1080/15287394.2021.1938767
De Araújo FF, De Paulo Farias D, Neri-Numa IA, Pastore GM (2021) Underutilized plants of the Cactaceae family: nutritional aspects and technological applications. Food Chem 362:130196
pubmed: 34091165
doi: 10.1016/j.foodchem.2021.130196
De Figueiredo LC, Bonafe EG, Martins JG, Martins AF, Maruyama SA, De Oliveira Santos Junior O, Biondo PBF, Matsushita M, Visentainer JV (2018) Development of an ultrasound assisted method for determination of phytosterols in vegetable oil. Food Chem 240:441–447
pubmed: 28946296
doi: 10.1016/j.foodchem.2017.07.140
Dragoun M, Klausová K, Šimicová P, Honzíková T, Stejskal J, Navrátilová K, Hajšlová J, Bárta J, Bártová V, Jarošová M, Bjelková M, Filip V, Kyselka J (2022) Formation of previously undescribed Δ(7)-Phytosterol oxidation products and Tocopherylquinone adducts in pumpkin seed oil during roasting, screw-pressing, and simulated culinary processing at elevated temperatures. J Agric Food Chem 70:11689–11703
pubmed: 36094395
doi: 10.1021/acs.jafc.2c03292
El Kharrassi Y, Samadi M, Lopez T, Nury T, El Kebbaj R, Andreoletti P, El Hajj HI, Vamecq J, Moustaid K, Latruffe N, El Kebbaj MS, Masson D, Lizard G, Nasser B, Cherkaoui-Malki M (2014) Biological activities of Schottenol and Spinasterol, two natural Phytosterols present in Argan oil and in cactus pear seed oil, on murine Miroglial Bv2 cells. Biochem Biophys Res Commun 446:798–804
pubmed: 24582563
doi: 10.1016/j.bbrc.2014.02.074
Esche R, Scholz B, Engel KH (2013) Online Lc-Gc analysis of free sterols/Stanols and intact Steryl/Stanyl esters in cereals. J Agric Food Chem 61:10932–10939
pubmed: 24117337
doi: 10.1021/jf403046z
Farag MA, Bahaa Eldin A, Khalifa I (2022) Valorization and extraction optimization of Prunus seeds for food and functional food applications: a review with further perspectives. Food Chem 388:132955
pubmed: 35462219
doi: 10.1016/j.foodchem.2022.132955
Fernández-Cuesta A, Jan CC, Fernández-Martínez JM, Velasco L (2014) Variability for seed phytosterols in sunflower germplasm. Crop Sci 54:190–197
doi: 10.2135/cropsci2013.05.0285
Francavilla M, Colaianna M, Zotti M, Morgese MG, Trotta P, Tucci P, Schiavone S, Cuomo V, Trabace L (2012) Extraction, characterization and in vivo neuromodulatory activity of phytosterols from microalga Dunaliella Tertiolecta. Curr Med Chem 19:3058–3067
pubmed: 22519401
doi: 10.2174/092986712800672021
Freire CS, Coelho DS, Santos NM, Silvestre AJ, Pascoal Neto C (2005) Identification of Delta7 phytosterols and phytosteryl glucosides in the wood and bark of several acacia species. Lipids 40:317–322
pubmed: 15957259
doi: 10.1007/s11745-005-1388-y
Freitas CS, Baggio CH, Dos Santos AC, Mayer B, Twardowschy A, Luiz AP, Marcon R, Soldi C, Pizzolatti MG, Dos Santos EP, Marques MC, Santos AR (2009) Antinociceptive properties of the hydroalcoholic extract, fractions and compounds obtained from the aerial parts of Baccharis Illinita Dc in mice. Basic Clin Pharmacol Toxicol 104:285–292
pubmed: 19281601
doi: 10.1111/j.1742-7843.2008.00367.x
Garg VK, Nes WR (1984) Studies on the C-24 configurations of Δ7-sterols in Theseeds of Cucurbita maxima. Phytochemistry 23:2919–2923
doi: 10.1016/0031-9422(84)83042-3
Ghzaiel I, Zarrouk A, Nury T, Libergoli M, Florio F, Hammouda S, Ménétrier F, Avoscan L, Yammine A, Samadi M, Latruffe N, Biressi S, Levy D, Bydlowski SP, Hammami S, Vejux A, Hammami M, Lizard G (2021) Antioxidant properties and cytoprotective effect of Pistacia Lentiscus L. seed oil against 7β-hydroxycholesterol-induced toxicity in C2c12 myoblasts: reduction in oxidative stress, mitochondrial and peroxisomal dysfunctions and attenuation of cell death. Antioxidants (Basel) 10
Grille S, Zaslawski A, Thiele S, Plat J, Warnecke D (2010) The functions of steryl glycosides come to those who wait: recent advances in plants, fungi, bacteria and animals. Prog Lipid Res 49:262–288
pubmed: 20138912
doi: 10.1016/j.plipres.2010.02.001
Hartmann M-A, Benveniste P (1987) Plant membrane sterols: isolation, identification, and biosynthesis. Methods in enzymology. Academic Press
Harvey DJ, Vouros P (2020) Mass spectrometric fragmentation of trimethylsilyl and related alkylsilyl derivatives. Mass Spectrom Rev 39:105–211
pubmed: 31808199
doi: 10.1002/mas.21590
Jun X (2013) High-pressure processing as emergent technology for the extraction of bioactive ingredients from plant materials. Crit Rev Food Sci Nutr 53:837–852
pubmed: 23768146
doi: 10.1080/10408398.2011.561380
Junker J, Chong I, Kamp F, Steiner H, Giera M, Müller C, Bracher F (2019) Comparison of strategies for the determination of sterol sulfates via Gc-Ms leading to a novel deconjugation-derivatization protocol. Molecules 24
Kamal-Eldin A, Määttä K, Toivo J, Lampi AM, Piironen V (1998) Acid-catalyzed isomerization of fucosterol and Delta5-avenasterol. Lipids 33:1073–1077
pubmed: 9870901
doi: 10.1007/s11745-998-0307-6
Khallouki F, Younos C, Soulimani R, Oster T, Charrouf Z, Spiegelhalder B, Bartsch H, Owen RW (2003) Consumption of Argan oil (Morocco) with its unique profile of fatty acids, tocopherols, squalene, sterols and phenolic compounds should confer valuable cancer chemopreventive effects. Eur J Cancer Prev 12:67–75
pubmed: 12548113
doi: 10.1097/00008469-200302000-00011
Kojima H, Sato N, Hatano A, Ogura H (1990) Sterol glucosides from Prunella Vulgaris. Phytochemistry 29:2351–2355
doi: 10.1016/0031-9422(90)83073-A
Kovacheva E, Ganchev G, Neicheva A, Ivanova I, Konoushlieva M, Andreev V (1990) Gas chromatographic determination of sterols in fat-soluble concentrates obtained from plant materials. J Chromatogr A 509:79–84
doi: 10.1016/S0021-9673(01)93239-X
Lam DT, Le VTT, Quan PM, Minh PTH, Thuy TTT, Anh NTN, Tai BH, Kiem PV (2021) Two new terpenoids from the leaves of Callicarpa Macrophylla. Nat Prod Res 35:1107–1114
pubmed: 31303054
doi: 10.1080/14786419.2019.1639180
Levasseur W, Perré P, Pozzobon V (2020) A review of high value-added molecules production by microalgae in light of the classification. Biotechnol Adv 41:107545
pubmed: 32272160
doi: 10.1016/j.biotechadv.2020.107545
Lizard G (2008) Phytosterols: to be or not to be toxic; that is the question. Br J Nutr 100:1150–1151
pubmed: 18466650
doi: 10.1017/S0007114508986888
Määttä K, Lampi A-M, Petterson J, Fogelfors BM, Piironen V, Kamal-Eldin A (1999) Phytosterol content in seven oat cultivars grown at three locations in Sweden. J Sci Food Agric 79:1021–1027
doi: 10.1002/(SICI)1097-0010(19990515)79:7<1021::AID-JSFA316>3.0.CO;2-E
Makhmudova U, Schulze PC, Lütjohann D, Weingärtner O (2021) Phytosterols and cardiovascular disease. Curr Atheroscler Rep 23:68
pubmed: 34468867
pmcid: 8410723
doi: 10.1007/s11883-021-00964-x
Meddeb W, Rezig L, Zarrouk A, Nury T, Vejux A, Prost M, Bretillon L, Mejri M, Lizard G (2018) Cytoprotective activities of Milk thistle seed oil used in traditional Tunisian medicine on 7-Ketocholesterol and 24s-hydroxycholesterol-induced toxicity on 158n murine oligodendrocytes. Antioxidants (Basel) 7
Mohamed HMA, Awatif II (1998) The use of sesame oil unsaponifiable matter as a natural antioxidant. Food Chem 62:269–276
doi: 10.1016/S0308-8146(97)00193-3
Montesano D, Blasi F, Simonetti MS, Santini A, Cossignani L (2018) Chemical and nutritional characterization of seed oil from Cucurbita Maxima L. (Var. Berrettina) pumpkin. Foods 7
Moreau RA, Whitaker BD, Hicks KB (2002) Phytosterols, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses. Prog Lipid Res 41:457–500
pubmed: 12169300
doi: 10.1016/S0163-7827(02)00006-1
Moreau RA, Powell MJ, Singh V (2003) Pressurized liquid extraction of polar and nonpolar lipids in corn and oats with hexane, methylene chloride, isopropanol, and ethanol. J Am Oil Chem Soc 80:1063–1067
doi: 10.1007/s11746-003-0821-y
Moreau RA, Nyström L, Whitaker BD, Winkler-Moser JK, Baer DJ, Gebauer SK, Hicks KB (2018) Phytosterols and their derivatives: structural diversity, distribution, metabolism, analysis, and health-promoting uses. Prog Lipid Res 70:35–61
pubmed: 29627611
doi: 10.1016/j.plipres.2018.04.001
Münger LH, Nyström L (2014) Enzymatic hydrolysis of steryl glycosides for their analysis in foods. Food Chem 163:202–211
pubmed: 24912717
doi: 10.1016/j.foodchem.2014.04.082
Münger LH, Boulos S, Nyström L (2018) Uplc-Ms/Ms based identification of dietary Steryl glucosides by investigation of corresponding free sterols. Front Chem 6:342
pubmed: 30186828
pmcid: 6113793
doi: 10.3389/fchem.2018.00342
Nes WD (2011) Biosynthesis of cholesterol and other sterols. Chem Rev 111:6423–6451
pubmed: 21902244
pmcid: 3191736
doi: 10.1021/cr200021m
Nyström L, Schär A, Lampi A-M (2012) Steryl glycosides and acylated steryl glycosides in plant foods reflect unique sterol patterns. Eur J Lipid Sci Technol 114:656–669
doi: 10.1002/ejlt.201200033
Oliveira L, Freire CSR, Silvestre AJD, Cordeiro N, Torres IC, Evtuguin D (2005) Steryl glucosides from Banana plant Musa Acuminata Colla Var Cavendish. Ind Crop Prod 22:187–192
doi: 10.1016/j.indcrop.2004.10.001
Phillips KM, Ruggio DM, Ashraf-Khorassani M (2005) Analysis of steryl glucosides in foods and dietary supplements by solid-phase extraction and gas chromatography. J Food Lipids 12:124–140
doi: 10.1111/j.1745-4522.2005.00011.x
Plat J, Baumgartner S, Mensink RP (2015) Mechanisms underlying the health benefits of plant sterol and Stanol ester consumption. J AOAC Int 98:697–700
pubmed: 25942754
doi: 10.5740/jaoacint.SGEPlat
Plat J, Baumgartner S, Vanmierlo T, Lütjohann D, Calkins KL, Burrin DG, Guthrie G, Thijs C, Te Velde AA, Vreugdenhil ACE, Sverdlov R, Garssen J, Wouters K, Trautwein EA, Wolfs TG, Van Gorp C, Mulder MT, Riksen NP, Groen AK, Mensink RP (2019) Plant-based sterols and Stanols in health & disease: “Consequences Of Human Development In A Plant-Based Environment?”. Prog Lipid Res 74:87–102
pubmed: 30822462
doi: 10.1016/j.plipres.2019.02.003
Rezig L, Martine L, Nury T, Msaada K, Mahfoudhi N, Ghzaiel I, Prost-Camus E, Durand P, Midaoui AE, Acar N, Latruffe N, Vejux A, Lizard G (2022) Profiles of fatty acids, polyphenols, sterols, and tocopherols and scavenging property of Mediterranean oils: new sources of dietary nutrients for the prevention of age-related diseases. J Oleo Sci 71:1117–1133
pubmed: 35922928
doi: 10.5650/jos.ess22110
Rodriguez JB, Gros EG, Bertoni MH, Cattaneo P (1996) The sterols of Cucurbita Moschata (“Calabacita”) seed oil. Lipids 31:1205–1208
pubmed: 8934454
doi: 10.1007/BF02524296
Roiaini M, Seyed H, Jinap S, Norhayati H (2016) Effect of extraction methods on yield, oxidative value, phytosterols and antioxidant content of cocoa butter. Int Food Res J 23:47–54
Rozentsvet OA, Kotlova ER, Bogdanova ES, Nesterov VN, Senik SV, Shavarda AL (2022) Balance of Δ(5)-and Δ(7)-sterols and Stanols in halophytes in connection with salinity tolerance. Phytochemistry 198:113156
pubmed: 35248579
doi: 10.1016/j.phytochem.2022.113156
Schlag S, Götz S, Rüttler F, Schmöckel SM, Vetter W (2022) Quantitation of 20 phytosterols in 34 different accessions of quinoa (Chenopodium Quinoa). J Agric Food Chem 70:9856–9864
pubmed: 35926102
doi: 10.1021/acs.jafc.2c03374
Strobl M (2004) Delta-7-sterole und delta-7-sterolglykoside Aus Samen Von Cucurbita Pepo L.
Thotathil V, Rizk HH, Fakrooh A, Sreerama L (2022) Phytochemical analysis of Acaciaehrenbergiana (Hayne) grown in Qatar: identification of active ingredients and their biological activities. Molecules 27
Uddin MS, Sarker MZ, Ferdosh S, Akanda MJ, Easmin MS, Bt Shamsudin SH, Bin Yunus K (2015) Phytosterols and their extraction from various plant matrices using supercritical carbon dioxide: a review. J Sci Food Agric 95:1385–1394
pubmed: 25048690
doi: 10.1002/jsfa.6833
Vejux A, Montange T, Martine L, Zarrouk A, Riedinger JM, Lizard G (2012) Absence of oxysterol-like side effects in human monocytic cells treated with phytosterols and oxyphytosterols. J Agric Food Chem 60:4060–4066
pubmed: 22490085
doi: 10.1021/jf300487r
Wang GK, Wang Z, Yu Y, Zhang N, Zhou ZY, Wang G, Liu JS (2018) A new sesquiterpene from Kalimeris Integrifolia. Nat Prod Res 32:1004–1009
pubmed: 28927288
doi: 10.1080/14786419.2017.1375917
Winkler JK, Rennick KA, Eller FJ, Vaughn SF (2007) Phytosterol and tocopherol components in extracts of corn Distiller’s dried grain. J Agric Food Chem 55:6482–6486
pubmed: 17636937
doi: 10.1021/jf070594q
Xiao X-H, Yuan Z-Q, Li G-K (2013) Preparation of phytosterols and phytol from edible marine algae by microwave-assisted extraction and high-speed counter-current chromatography. Sep Purif Technol 104:284–289
doi: 10.1016/j.seppur.2012.11.032
Yang Y, Lai Q, Wang C, Zhou G (2022) Protective effects of Herba Houttuyniae aqueous extract against ova-induced airway Hyperresponsiveness and inflammation in asthmatic mice. Evid Based Complement Alternat Med 2022:7609785
pubmed: 36408342
pmcid: 9674414
doi: 10.1155/2022/7609785
Zarrouk A, Martine L, Grégoire S, Nury T, Meddeb W, Camus E, Badreddine A, Durand P, Namsi A, Yammine A, Nasser B, Mejri M, Bretillon L, Mackrill JJ, Cherkaoui-Malki M, Hammami M, Lizard G (2019) Profile of fatty acids, tocopherols, Phytosterols and polyphenols in Mediterranean oils (Argan oils, olive oils, Milk thistle seed oils and nigella seed oil) and evaluation of their antioxidant and cytoprotective activities. Curr Pharm Des 25:1791–1805
pubmed: 31298157
doi: 10.2174/1381612825666190705192902
Zhang X, Cambrai A, Miesch M, Roussi S, Raul F, Aoude-Werner D, Marchioni E (2006) Separation of Δ5- and Δ7-phytosterols by adsorption chromatography and semipreparative reversed phase high-performance liquid chromatography for quantitative analysis of phytosterols in foods. J Agric Food Chem 54:1196–1202
pubmed: 16478236
doi: 10.1021/jf052761x