sitostanol (BioDeep_00000183842)

Main id: BioDeep_00000000630

 

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs


代谢物信息卡片


17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C29H52O (416.4017942)
中文名称: β-谷甾烷醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CC[C@H](C(C)C)CC)C)C)C)O
InChI: InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3

描述信息

Constituent of pot marigold (Calendula officinalis), sweet corn (Zea mays) and Carolina allspice (Calycanthus floridus). Stigmastanol is found in many foods, some of which are corn, fats and oils, pepper (spice), and soy bean.
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents
C1907 - Drug, Natural Product > C28178 - Phytosterol > C68422 - Saturated Phytosterol
D009676 - Noxae > D000963 - Antimetabolites
Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].
Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].

同义名列表

34 个代谢物同义名

17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; 17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; 14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol; 24 alpha-ethyl-5 beta-cholestan-3 alpha-ol; 24 alpha-ethyl-5 alpha-cholestan-3 beta-ol; stigmastanol, (3beta,5beta,24S)-isomer; (3β,5α)-Stigmastan-3-ol; 4a-Methyl-5a,14a-lumistan-3b-ol; (3beta,5alpha)-Stigmastan-3-ol; 5α-Stigmastan-3β-ol; 5,6-Dihydro-β-sitosterol; 24-α-Ethylcholestanol; β-dihydro-Sitosterol; Dihydro-β-sitosterol; (3β)-Stigmastan-3-ol; 5,6-dihydro-b-Sitosterol; 24alpha-Ethylcholestanol; Stigmastane-3-β-ol; dihydro-b-Sitosterol; 4a-Methylcampestanol; 24a-Ethylcholestanol; (3b)-Stigmastan-3-ol; 24α-ethylcholestanol; 5a-Stigmastan-3b-ol; dihydrositosterol; Dihydrositosterin; β-Sitostanol; beta-sitostanol; Stigmastan-3-ol; Stigmastanol; b-Sitostanol; Spinastanol; sitostanol; Fucostanol



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

46 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • María Molina-Gutiérrez, Leonor Rodríguez-Sánchez, Carmen Doñoro, M Jesús Martínez, Alicia Prieto. Sustainable and Green Synthesis of Stanol Esters from Oil Wastes. Journal of agricultural and food chemistry. 2021 Jan; 69(1):286-293. doi: 10.1021/acs.jafc.0c06581. [PMID: 33375783]
  • Emmani B M Nascimento, Maurice Konings, Gert Schaart, Albert K Groen, Dieter Lütjohann, Wouter D van Marken Lichtenbelt, Patrick Schrauwen, Jogchum Plat. In vitro effects of sitosterol and sitostanol on mitochondrial respiration in human brown adipocytes, myotubes and hepatocytes. European journal of nutrition. 2020 Aug; 59(5):2039-2045. doi: 10.1007/s00394-019-02052-y. [PMID: 31317217]
  • Moacir Guimarães de Melo, Brina Aguiar da Silva, Gilcllys de Souza Costa, João Cândido André da Silva Neto, Patrícia Kaori Soares, Adalberto Luis Val, Jamal da Silva Chaar, Hector Henrique Ferreira Koolen, Giovana Anceski Bataglion. Sewage contamination of Amazon streams crossing Manaus (Brazil) by sterol biomarkers. Environmental pollution (Barking, Essex : 1987). 2019 Jan; 244(?):818-826. doi: 10.1016/j.envpol.2018.10.055. [PMID: 30390455]
  • Jogchum Plat, Sabine Baumgartner, Tom Houben, Anita C E Vreugdenhil, Ronald P Mensink, Dieter Lütjohann, Ronit Shiri-Sverdlov. Comment on Tauriainen et al.: Serum, liver and bile sitosterol and sitostanol in obese patients with and without NAFLD. Bioscience reports. 2018 10; 38(5):. doi: 10.1042/bsr20180505. [PMID: 30287500]
  • Hans-Frieder Schött, Sabrina Krautbauer, Marcus Höring, Gerhard Liebisch, Silke Matysik. A Validated, Fast Method for Quantification of Sterols and Gut Microbiome Derived 5α/β-Stanols in Human Feces by Isotope Dilution LC-High-Resolution MS. Analytical chemistry. 2018 07; 90(14):8487-8494. doi: 10.1021/acs.analchem.8b01278. [PMID: 29920210]
  • Milla-Maria Tauriainen, Ville Männistö, Dorota Kaminska, Maija Vaittinen, Vesa Kärjä, Pirjo Käkelä, Sari Venesmaa, Helena Gylling, Jussi Pihlajamäki. Serum, liver and bile sitosterol and sitostanol in obese patients with and without NAFLD. Bioscience reports. 2018 04; 38(2):. doi: 10.1042/bsr20171274. [PMID: 29540533]
  • Rgia A Othman, Semone B Myrie, David Mymin, Jean-Baptiste Roullet, Andrea E DeBarber, Robert D Steiner, Peter J H Jones. Thyroid Hormone Status in Sitosterolemia Is Modified by Ezetimibe. The Journal of pediatrics. 2017 09; 188(?):198-204.e1. doi: 10.1016/j.jpeds.2017.05.049. [PMID: 28625503]
  • Islam J A Hamdan, Lorena Claumarchirant, Guadalupe Garcia-Llatas, Amparo Alegría, María Jesús Lagarda. Sterols in infant formulas: validation of a gas chromatographic method. International journal of food sciences and nutrition. 2017 Sep; 68(6):695-703. doi: 10.1080/09637486.2017.1287883. [PMID: 28276904]
  • Silvia Vaghini, Antonio Cilla, Guadalupe Garcia-Llatas, María Jesús Lagarda. Bioaccessibility study of plant sterol-enriched fermented milks. Food & function. 2016 Jan; 7(1):110-7. doi: 10.1039/c5fo00458f. [PMID: 26447847]
  • Piia Simonen, Jaakko Lommi, Maarit Hallikainen, Satu Helske-Suihko, Kalervo Werkkala, Markku Kupari, Petri T Kovanen, Helena Gylling. Dietary plant stanols or sterols neither accumulate in stenotic aortic valves nor influence their structure or inflammatory status. Clinical nutrition (Edinburgh, Scotland). 2015 Dec; 34(6):1251-7. doi: 10.1016/j.clnu.2015.01.001. [PMID: 25614126]
  • Loïc Harrault, Emilie Jardé, Laurent Jeanneau, Patrice Petitjean. Are fecal stanols suitable to record and identify a pulse of human fecal contamination in short-term exposed shellfish? A microcosm study. Marine pollution bulletin. 2014 Dec; 89(1-2):40-48. doi: 10.1016/j.marpolbul.2014.10.037. [PMID: 25455370]
  • Jaleh Varshosaz, Abbas Jafarian, Golnaz Salehi, Behzad Zolfaghari. Comparing different sterol containing solid lipid nanoparticles for targeted delivery of quercetin in hepatocellular carcinoma. Journal of liposome research. 2014 Sep; 24(3):191-203. doi: 10.3109/08982104.2013.868476. [PMID: 24354715]
  • Loïc Harrault, Emilie Jardé, Laurent Jeanneau, Patrice Petitjean. Development of the analysis of fecal stanols in the oyster Crassostrea gigas and identification of fecal contamination in shellfish harvesting areas. Lipids. 2014 Jun; 49(6):597-607. doi: 10.1007/s11745-014-3908-5. [PMID: 24771549]
  • T J Tse, G Codling, P D Jones, K Thoms, K Liber, J P Giesy, H Wheater, L E Doig. Reconstructing long-term trends in municipal sewage discharge into a small lake in northern Manitoba, Canada. Chemosphere. 2014 May; 103(?):299-305. doi: 10.1016/j.chemosphere.2013.12.019. [PMID: 24405965]
  • Ainara Sistiaga, Carolina Mallol, Bertila Galván, Roger Everett Summons. The Neanderthal meal: a new perspective using faecal biomarkers. PloS one. 2014; 9(6):e101045. doi: 10.1371/journal.pone.0101045. [PMID: 24963925]
  • Moufida Oueslati Arfaoui, Justin Renaud, Hanen Ghazghazi, Sadok Boukhchina, Paul Mayer. Variation in oil content, fatty acid and phytosterols profile of Onopordum acanthium L. during seed development. Natural product research. 2014; 28(24):2293-300. doi: 10.1080/14786419.2014.940944. [PMID: 25103576]
  • Laura Kells Cusack, Maria Luz Fernandez, Jeff S Volek. The food matrix and sterol characteristics affect the plasma cholesterol lowering of phytosterol/phytostanol. Advances in nutrition (Bethesda, Md.). 2013 Nov; 4(6):633-43. doi: 10.3945/an.113.004507. [PMID: 24228192]
  • Wen-Sen He, Mei-Gui Wang, Xiao-Xia Pan, Jing-Jing Li, Cheng-Sheng Jia, Xiao-Ming Zhang, Biao Feng. Role of plant stanol derivatives in the modulation of cholesterol metabolism and liver gene expression in mice. Food chemistry. 2013 Sep; 140(1-2):9-16. doi: 10.1016/j.foodchem.2013.02.062. [PMID: 23578608]
  • M S Valerio, H Minderman, T Mace, A B Awad. β-Sitosterol modulates TLR4 receptor expression and intracellular MyD88-dependent pathway activation in J774A.1 murine macrophages. Cellular immunology. 2013 Sep; 285(1-2):76-83. doi: 10.1016/j.cellimm.2013.08.007. [PMID: 24121260]
  • Maija Marttinen, Essi Päivärinta, Markus Storvik, Laura Huikko, Heli Luoma-Halkola, Vieno Piironen, Anne-Maria Pajari, Marja Mutanen. Plant stanols induce intestinal tumor formation by up-regulating Wnt and EGFR signaling in Apc Min mice. The Journal of nutritional biochemistry. 2013 Jan; 24(1):343-52. doi: 10.1016/j.jnutbio.2012.07.002. [PMID: 22981369]
  • Anna Szakiel, Cezary Pączkowski, Satu Huttunen. Triterpenoid content of berries and leaves of bilberry Vaccinium myrtillus from Finland and Poland. Journal of agricultural and food chemistry. 2012 Dec; 60(48):11839-49. doi: 10.1021/jf3046895. [PMID: 23157739]
  • Jinying Zhao, Pavel Gershkovich, Kishor M Wasan. Evaluation of the effect of plant sterols on the intestinal processing of cholesterol using an in vitro lipolysis model. International journal of pharmaceutics. 2012 Oct; 436(1-2):707-10. doi: 10.1016/j.ijpharm.2012.07.040. [PMID: 22850295]
  • M Derrien, E Jardé, G Gruau, A M Pourcher, M Gourmelon, A Jadas-Hécart, A C Pierson Wickmann. Origin of fecal contamination in waters from contrasted areas: stanols as Microbial Source Tracking markers. Water research. 2012 Sep; 46(13):4009-16. doi: 10.1016/j.watres.2012.05.003. [PMID: 22673347]
  • H Gylling, M Hallikainen, P Simonen, H E Miettinen, M J Nissinen, T A Miettinen. Serum and lipoprotein sitostanol and non-cholesterol sterols after an acute dose of plant stanol ester on its long-term consumption. European journal of nutrition. 2012 Aug; 51(5):615-22. doi: 10.1007/s00394-011-0249-5. [PMID: 21947207]
  • Florence Brüll, Ronald P Mensink, Mandy F Steinbusch, Constanze Husche, Dieter Lütjohann, Geert-Jan Wesseling, Jogchum Plat. Beneficial effects of sitostanol on the attenuated immune function in asthma patients: results of an in vitro approach. PloS one. 2012; 7(10):e46895. doi: 10.1371/journal.pone.0046895. [PMID: 23091602]
  • Katarzyna Hąc-Wydro, Michał Flasiński, Marcin Broniatowski, Patrycja Dynarowicz-Łątka, Jarosław Majewski. Properties of β-sitostanol/DPPC monolayers studied with Grazing Incidence X-ray Diffraction (GIXD) and Brewster Angle Microscopy. Journal of colloid and interface science. 2011 Dec; 364(1):133-9. doi: 10.1016/j.jcis.2011.08.030. [PMID: 21903220]
  • Kazumi Tsubakio-Yamamoto, Makoto Nishida, Yumiko Nakagawa-Toyama, Daisaku Masuda, Tohru Ohama, Shizuya Yamashita. Current therapy for patients with sitosterolemia--effect of ezetimibe on plant sterol metabolism. Journal of atherosclerosis and thrombosis. 2010 Sep; 17(9):891-900. doi: 10.5551/jat.4614. [PMID: 20543520]
  • Wissem Zarrouk, Alegría Carrasco-Pancorbo, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez, Mokhtar Zarrouk. Exploratory characterization of the unsaponifiable fraction of tunisian virgin olive oils by a global approach with HPLC-APCI-IT MS/MS analysis. Journal of agricultural and food chemistry. 2010 May; 58(10):6418-26. doi: 10.1021/jf100024c. [PMID: 20438134]
  • Florence Brüll, Ronald P Mensink, Karin van den Hurk, Adriaan Duijvestijn, Jogchum Plat. TLR2 activation is essential to induce a Th1 shift in human peripheral blood mononuclear cells by plant stanols and plant sterols. The Journal of biological chemistry. 2010 Jan; 285(5):2951-8. doi: 10.1074/jbc.m109.036343. [PMID: 19948716]
  • Malene Schrøder, Christiane Fricke, Kirsten Pilegaard, Morten Poulsen, Ingmar Wester, Dieter Lütjohann, Alicja Mortensen. Effect of rapeseed oil-derived plant sterol and stanol esters on atherosclerosis parameters in cholesterol-challenged heterozygous Watanabe heritable hyperlipidaemic rabbits. The British journal of nutrition. 2009 Dec; 102(12):1740-51. doi: 10.1017/s0007114509991206. [PMID: 19772679]
  • Norashikin Saim, Rozita Osman, Dayang Ratena Sari Abg Spian, Mohd Zuli Jaafar, Hafizan Juahir, Md Pauzi Abdullah, Fuzziawati Ab Ghani. Chemometric approach to validating faecal sterols as source tracer for faecal contamination in water. Water research. 2009 Dec; 43(20):5023-30. doi: 10.1016/j.watres.2009.08.052. [PMID: 19896157]
  • Jun-hua Han, Yan-ping Li, Jian-hua Men, Wen-tao Yu, Yue-xin Yang. [Comparison of the dietary phytosterols intake and serum lipids content in elderly women from three cities of China]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2009 Dec; 43(12):1060-3. doi: NULL. [PMID: 20193499]
  • Trevor J Daly, S Aisling Aherne, Tom P O'Connor, Nora M O'Brien. Lack of genoprotective effect of phytosterols and conjugated linoleic acids on Caco-2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Aug; 47(8):1791-6. doi: 10.1016/j.fct.2009.04.031. [PMID: 19406198]
  • Pavel Gershkovich, Jerry Darlington, Olena Sivak, Panayiotis P Constantinides, Kishor M Wasan. Inhibition of intestinal absorption of cholesterol by surface-modified nanostructured aluminosilicate compounds. Journal of pharmaceutical sciences. 2009 Jul; 98(7):2390-400. doi: 10.1002/jps.21616. [PMID: 19090562]
  • K Laitinen, E Isolauri, L Kaipiainen, H Gylling, T A Miettinen. Plant stanol ester spreads as components of a balanced diet for pregnant and breast-feeding women: evaluation of clinical safety. The British journal of nutrition. 2009 Jun; 101(12):1797-804. doi: 10.1017/s0007114508133608. [PMID: 19017423]
  • Junhua Han, Mei He, Shengsheng Zhou, Guodong Wang. [Analysis of phytosterol contents in food plant materials and Chinese traditional medicines]. Wei sheng yan jiu = Journal of hygiene research. 2009 Mar; 38(2):188-91. doi: ". [PMID: 19408663]
  • Qixuan Chen, Heidi Gruber, Catherine Pakenham, Walisundera M N Ratnayake, Kylie A Scoggan. Dietary phytosterols and phytostanols alter the expression of sterol-regulatory genes in SHRSP and WKY inbred rats. Annals of nutrition & metabolism. 2009; 55(4):341-50. doi: 10.1159/000252350. [PMID: 19851062]
  • Ariënne de Jong, Jogchum Plat, Dieter Lütjohann, Ronald P Mensink. Effects of long-term plant sterol or stanol ester consumption on lipid and lipoprotein metabolism in subjects on statin treatment. The British journal of nutrition. 2008 Nov; 100(5):937-41. doi: 10.1017/s0007114508966113. [PMID: 18846701]
  • Xiaoming Jia, Yanfeng Chen, Jeffrey Zidichouski, Junzeng Zhang, Changhao Sun, Yanwen Wang. Co-administration of berberine and plant stanols synergistically reduces plasma cholesterol in rats. Atherosclerosis. 2008 Nov; 201(1):101-7. doi: 10.1016/j.atherosclerosis.2008.03.008. [PMID: 18430428]
  • Zhao-Tang Ma, Xiu-Wei Yang. [Studies on ethyl acetate soluble constituents of Huanglian Jiedutang]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Sep; 33(18):2080-6. doi: . [PMID: 19160789]
  • Keisuke Matsuoka, Tomomi Nakazawa, Ai Nakamura, Chikako Honda, Kazutoyo Endo, Masamichi Tsukada. Study of thermodynamic parameters for solubilization of plant sterol and stanol in bile salt micelles. Chemistry and physics of lipids. 2008 Aug; 154(2):87-93. doi: 10.1016/j.chemphyslip.2008.05.002. [PMID: 18544343]
  • Ephraim Sehayek, Stanley L Hazen. Cholesterol absorption from the intestine is a major determinant of reverse cholesterol transport from peripheral tissue macrophages. Arteriosclerosis, thrombosis, and vascular biology. 2008 Jul; 28(7):1296-7. doi: 10.1161/atvbaha.108.165803. [PMID: 18420997]
  • S Aisling Aherne, Nora M O'Brien. Modulation of cytokine production by plant sterols in stimulated human Jurkat T cells. Molecular nutrition & food research. 2008 Jun; 52(6):664-73. doi: 10.1002/mnfr.200700385. [PMID: 18465778]
  • Deepak Jain, Naoyuki Ebine, Xiaoming Jia, Amira Kassis, Christopher Marinangeli, Marc Fortin, Robin Beech, Kevin B Hicks, Robert A Moreau, Stan Kubow, Peter J H Jones. Corn fiber oil and sitostanol decrease cholesterol absorption independently of intestinal sterol transporters in hamsters. The Journal of nutritional biochemistry. 2008 Apr; 19(4):229-36. doi: 10.1016/j.jnutbio.2007.02.012. [PMID: 17601722]
  • Klaus Fassbender, Dieter Lütjohann, Miranda G Dik, Marijke Bremmer, Jochem König, Silke Walter, Yang Liu, Maryse Letièmbre, Klaus von Bergmann, Cees Jonker. Moderately elevated plant sterol levels are associated with reduced cardiovascular risk--the LASA study. Atherosclerosis. 2008 Jan; 196(1):283-288. doi: 10.1016/j.atherosclerosis.2006.10.032. [PMID: 17137582]
  • Ruijie Liu, Jahangir Iqbal, Calvin Yeang, David Q-H Wang, M Mahmood Hussain, Xian-Cheng Jiang. Phospholipid transfer protein-deficient mice absorb less cholesterol. Arteriosclerosis, thrombosis, and vascular biology. 2007 Sep; 27(9):2014-21. doi: 10.1161/atvbaha.107.149914. [PMID: 17641249]
  • Sara Hoet, Luc Pieters, Giulio G Muccioli, Jean-Louis Habib-Jiwan, Fred R Opperdoes, Joëlle Quetin-Leclercq. Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds. Journal of natural products. 2007 Aug; 70(8):1360-3. doi: 10.1021/np070038q. [PMID: 17637068]
  • Junhua Han, Yuexin Yang, Meiyuan Feng, Guodong Wang. [Analysis of phytosterol contents in Chinese plant food and primary estimation of its intake of people]. Wei sheng yan jiu = Journal of hygiene research. 2007 May; 36(3):301-5. doi: ". [PMID: 17712945]
  • Jogchum Plat, Jason A Nichols, Ronald P Mensink. Plant sterols and stanols: effects on mixed micellar composition and LXR (target gene) activation. Journal of lipid research. 2005 Nov; 46(11):2468-76. doi: 10.1194/jlr.m500272-jlr200. [PMID: 16150823]
  • S C Thuluva, M Igel, U Giesa, D Lütjohann, T Sudhop, K von Bergmann. Ratio of lathosterol to campesterol in serum predicts the cholesterol-lowering effect of sitostanol-supplemented margarine. International journal of clinical pharmacology and therapeutics. 2005 Jul; 43(7):305-10. doi: 10.5414/cpp43305. [PMID: 16035372]
  • Laura Soupas, Laura Juntunen, Anna-Maija Lampi, Vieno Piironen. Effects of sterol structure, temperature, and lipid medium on phytosterol oxidation. Journal of agricultural and food chemistry. 2004 Oct; 52(21):6485-91. doi: 10.1021/jf049168k. [PMID: 15479011]
  • Li-Ping Duan, Helen H Wang, David Q-H Wang. Cholesterol absorption is mainly regulated by the jejunal and ileal ATP-binding cassette sterol efflux transporters Abcg5 and Abcg8 in mice. Journal of lipid research. 2004 Jul; 45(7):1312-23. doi: 10.1194/jlr.m400030-jlr200. [PMID: 15102882]
  • Sergey M Mel'nikov, Jack W M Seijen ten Hoorn, Astrid P A M Eijkelenboom. Effect of phytosterols and phytostanols on the solubilization of cholesterol by dietary mixed micelles: an in vitro study. Chemistry and physics of lipids. 2004 Feb; 127(2):121-41. doi: 10.1016/j.chemphyslip.2003.09.015. [PMID: 14725996]
  • Sergey M Mel'nikov, Jack W M Seijen ten Hoorn, Benoit Bertrand. Can cholesterol absorption be reduced by phytosterols and phytostanols via a cocrystallization mechanism?. Chemistry and physics of lipids. 2004 Jan; 127(1):15-33. doi: 10.1016/j.chemphyslip.2003.08.007. [PMID: 14706738]
  • David Kritchevsky, Shirley A Tepper, Susanne K Czarnecki, Brian Wolfe, Kenneth D R Setchell. Serum and aortic levels of phytosterols in rabbits fed sitosterol or sitostanol ester preparations. Lipids. 2003 Nov; 38(11):1115-8. doi: 10.1007/s11745-003-1168-8. [PMID: 14733355]
  • Igor Mezine, Huizhen Zhang, Carlos Macku, Robert Lijana. Analysis of plant sterol and stanol esters in cholesterol-lowering spreads and beverages using high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectroscopy. Journal of agricultural and food chemistry. 2003 Sep; 51(19):5639-46. doi: 10.1021/jf030030w. [PMID: 12952413]
  • David Q-H Wang, Martin C Carey. Measurement of intestinal cholesterol absorption by plasma and fecal dual-isotope ratio, mass balance, and lymph fistula methods in the mouse: an analysis of direct versus indirect methodologies. Journal of lipid research. 2003 May; 44(5):1042-59. doi: 10.1194/jlr.d200041-jlr200. [PMID: 12588946]
  • Michael Igel, Uwe Giesa, Dieter Lutjohann, Klaus von Bergmann. Comparison of the intestinal uptake of cholesterol, plant sterols, and stanols in mice. Journal of lipid research. 2003 Mar; 44(3):533-8. doi: 10.1194/jlr.m200393-jlr200. [PMID: 12562824]
  • Tatu A Miettinen, Helena Gylling. Non-nutritive bioactive constituents of plants: phytosterols. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2003 Mar; 73(2):127-34. doi: 10.1024/0300-9831.73.2.127. [PMID: 12747220]
  • Thomas Sudhop, Dieter Lütjohann, Mohamed Agna, Claudia von Ameln, Wolfgang Prange, Klaus von Bergmann. Comparison of the effects of sitostanol, sitostanol acetate, and sitostanol oleate on the inhibition of cholesterol absorption in normolipemic healthy male volunteers. A placebo controlled randomized cross-over study. Arzneimittel-Forschung. 2003; 53(10):708-13. doi: 10.1055/s-0031-1299816. [PMID: 14650363]
  • Liqing Yu, Robert E Hammer, Jia Li-Hawkins, Klaus Von Bergmann, Dieter Lutjohann, Jonathan C Cohen, Helen H Hobbs. Disruption of Abcg5 and Abcg8 in mice reveals their crucial role in biliary cholesterol secretion. Proceedings of the National Academy of Sciences of the United States of America. 2002 Dec; 99(25):16237-42. doi: 10.1073/pnas.252582399. [PMID: 12444248]
  • Jacqueline De Graaf, Pernette R W De Sauvage Nolting, Marjel Van Dam, Elizabeth M Belsey, John J P Kastelein, P Haydn Pritchard, Anton F H Stalenhoef. Consumption of tall oil-derived phytosterols in a chocolate matrix significantly decreases plasma total and low-density lipoprotein-cholesterol levels. The British journal of nutrition. 2002 Nov; 88(5):479-88. doi: 10.1079/bjn2002690. [PMID: 12425728]
  • Jogchum Plat, Ronald P Mensink. Increased intestinal ABCA1 expression contributes to the decrease in cholesterol absorption after plant stanol consumption. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2002 Aug; 16(10):1248-53. doi: 10.1096/fj.01-0718hyp. [PMID: 12153993]
  • G Xu, G Salen, S Shefer, G S Tint, L B Nguyen, A K Batta, M Pcolinsky. Plant stanol fatty acid esters inhibit cholesterol absorption and hepatic hydroxymethyl glutaryl coenzyme A reductase activity to reduce plasma levels in rabbits. Metabolism: clinical and experimental. 2001 Sep; 50(9):1106-12. doi: 10.1053/meta.2001.25664. [PMID: 11555847]
  • A L Normén, H A Brants, L E Voorrips, H A Andersson, P A van den Brandt, R A Goldbohm. Plant sterol intakes and colorectal cancer risk in the Netherlands Cohort Study on Diet and Cancer. The American journal of clinical nutrition. 2001 Jul; 74(1):141-8. doi: 10.1093/ajcn/74.1.141. [PMID: 11451730]
  • T Akihisa, J Ogihara, J Kato, K Yasukawa, M Ukiya, S Yamanouchi, K Oishi. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids. 2001 May; 36(5):507-12. doi: 10.1007/s11745-001-0750-4. [PMID: 11432464]
  • J Plat, R P Mensink. Effects of diets enriched with two different plant stanol ester mixtures on plasma ubiquinol-10 and fat-soluble antioxidant concentrations. Metabolism: clinical and experimental. 2001 May; 50(5):520-9. doi: 10.1053/meta.2001.22509. [PMID: 11319712]
  • J Plat, R P Mensink. Effects of plant sterols and stanols on lipid metabolism and cardiovascular risk. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2001 Feb; 11(1):31-40. doi: . [PMID: 11383323]
  • T Ramjiganesh, S Roy, J C McIntyre, M Luz Fernandez. The hypocholesterolaemic effects of sitostanol in the guinea pig are in part related to changes in hepatic lipids and lipoprotein composition. The British journal of nutrition. 2001 Feb; 85(2):165-72. doi: 10.1079/bjn2000246. [PMID: 11242484]
  • N Weber, P Weitkamp, K D Mukherjee. Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. Journal of agricultural and food chemistry. 2001 Jan; 49(1):67-71. doi: 10.1021/jf000830w. [PMID: 11170561]
  • K M Wasan, L Holtorf, R Subramanian, S M Cassidy, P H Pritchard, D J Stewart, E Novak, M H Moghadasian. Assessing plasma pharmacokinetics of cholesterol following oral coadministration with a novel vegetable stanol mixture to fasting rats. Journal of pharmaceutical sciences. 2001 Jan; 90(1):23-8. doi: 10.1002/1520-6017(200101)90:1<23::aid-jps3>3.0.co;2-p. [PMID: 11064375]
  • G Salen, G Xu, G S Tint, A K Batta, S Shefer. Hyperabsorption and retention of campestanol in a sitosterolemic homozygote: comparison with her mother and three control subjects. Journal of lipid research. 2000 Nov; 41(11):1883-9. doi: . [PMID: 11060358]
  • M A Hallikainen, E S Sarkkinen, H Gylling, A T Erkkilä, M I Uusitupa. Comparison of the effects of plant sterol ester and plant stanol ester-enriched margarines in lowering serum cholesterol concentrations in hypercholesterolaemic subjects on a low-fat diet. European journal of clinical nutrition. 2000 Sep; 54(9):715-25. doi: 10.1038/sj.ejcn.1601083. [PMID: 11002384]
  • J Plat, E N van Onselen, M M van Heugten, R P Mensink. Effects on serum lipids, lipoproteins and fat soluble antioxidant concentrations of consumption frequency of margarines and shortenings enriched with plant stanol esters. European journal of clinical nutrition. 2000 Sep; 54(9):671-7. doi: 10.1038/sj.ejcn.1601071. [PMID: 11002377]
  • D J Sanders, H J Minter, D Howes, P A Hepburn. The safety evaluation of phytosterol esters. Part 6. The comparative absorption and tissue distribution of phytosterols in the rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2000 Jun; 38(6):485-91. doi: 10.1016/s0278-6915(00)00021-1. [PMID: 10828500]
  • L Normén, P Dutta, A Lia, H Andersson. Soy sterol esters and beta-sitostanol ester as inhibitors of cholesterol absorption in human small bowel. The American journal of clinical nutrition. 2000 Apr; 71(4):908-13. doi: 10.1093/ajcn/71.4.908. [PMID: 10731496]
  • M A Hallikainen, E S Sarkkinen, M I Uusitupa. Plant stanol esters affect serum cholesterol concentrations of hypercholesterolemic men and women in a dose-dependent manner. The Journal of nutrition. 2000 Apr; 130(4):767-76. doi: 10.1093/jn/130.4.767. [PMID: 10736328]
  • J Plat, R P Mensink. Vegetable oil based versus wood based stanol ester mixtures: effects on serum lipids and hemostatic factors in non-hypercholesterolemic subjects. Atherosclerosis. 2000 Jan; 148(1):101-12. doi: 10.1016/s0021-9150(99)00261-0. [PMID: 10580176]
  • T T Nguyen, L C Dale, K von Bergmann, I T Croghan. Cholesterol-lowering effect of stanol ester in a US population of mildly hypercholesterolemic men and women: a randomized controlled trial. Mayo Clinic proceedings. 1999 Dec; 74(12):1198-206. doi: 10.4065/74.12.1198. [PMID: 10593347]
  • R E Ostlund, C A Spilburg, W F Stenson. Sitostanol administered in lecithin micelles potently reduces cholesterol absorption in humans. The American journal of clinical nutrition. 1999 Nov; 70(5):826-31. doi: 10.1093/ajcn/70.5.826. [PMID: 10539742]
  • G R Thompson. Plant lipids that lower serum cholesterol. European heart journal. 1999 Nov; 20(21):1527-9. doi: 10.1053/euhj.1999.1824. [PMID: 10529318]
  • P L Cerrato. Using designer margarines to control lipid levels. RN. 1999 Oct; 62(10):67-8. doi: ". [PMID: 10578956]
  • K M Phillips, D M Ruggio, J A Bailey. Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. Journal of chromatography. B, Biomedical sciences and applications. 1999 Sep; 732(1):17-29. doi: 10.1016/s0378-4347(99)00257-1. [PMID: 10517218]
  • H Gylling, P Puska, E Vartiainen, T A Miettinen. Retinol, vitamin D, carotenes and alpha-tocopherol in serum of a moderately hypercholesterolemic population consuming sitostanol ester margarine. Atherosclerosis. 1999 Aug; 145(2):279-85. doi: 10.1016/s0021-9150(99)00078-7. [PMID: 10488954]
  • P J Jones, F Y Ntanios, M Raeini-Sarjaz, C A Vanstone. Cholesterol-lowering efficacy of a sitostanol-containing phytosterol mixture with a prudent diet in hyperlipidemic men. The American journal of clinical nutrition. 1999 Jun; 69(6):1144-50. doi: 10.1093/ajcn/69.6.1144. [PMID: 10357732]
  • H Gylling, T A Miettinen. Cholesterol reduction by different plant stanol mixtures and with variable fat intake. Metabolism: clinical and experimental. 1999 May; 48(5):575-80. doi: 10.1016/s0026-0495(99)90053-7. [PMID: 10337856]
  • S J Robins, J M Fasulo. Delineation of a novel hepatic route for the selective transfer of unesterified sterols from high-density lipoproteins to bile: studies using the perfused rat liver. Hepatology (Baltimore, Md.). 1999 May; 29(5):1541-8. doi: 10.1002/hep.510290518. [PMID: 10216140]
  • F Y Ntanios, P J Jones. Dietary sitostanol reciprocally influences cholesterol absorption and biosynthesis in hamsters and rabbits. Atherosclerosis. 1999 Apr; 143(2):341-51. doi: 10.1016/s0021-9150(98)00321-9. [PMID: 10217363]
  • H Gylling, P Puska, E Vartiainen, T A Miettinen. Serum sterols during stanol ester feeding in a mildly hypercholesterolemic population. Journal of lipid research. 1999 Apr; 40(4):593-600. doi: 10.1016/s0022-2275(20)32138-6. [PMID: 10191283]
  • M A Hallikainen, M I Uusitupa. Effects of 2 low-fat stanol ester-containing margarines on serum cholesterol concentrations as part of a low-fat diet in hypercholesterolemic subjects. The American journal of clinical nutrition. 1999 Mar; 69(3):403-10. doi: 10.1093/ajcn/69.3.403. [PMID: 10075323]
  • G Xu, G Salen, G S Tint, A K Batta, S Shefer. Campestanol (24-methyl-5alpha-cholestan-3beta-ol) absorption and distribution in New Zealand White rabbits: effect of dietary sitostanol. Metabolism: clinical and experimental. 1999 Mar; 48(3):363-8. doi: 10.1016/s0026-0495(99)90086-0. [PMID: 10094114]
  • F Y Ntanios, D E MacDougall, P J Jones. Gender effects of tall oil versus soybean phytosterols as cholesterol-lowering agents in hamsters. Canadian journal of physiology and pharmacology. 1998 Jul; 76(7-8):780-7. doi: 10.1139/cjpp-76-7-8-780. [PMID: 10030459]
  • F Y Ntanios, P J Jones, J J Frohlich. Dietary sitostanol reduces plaque formation but not lecithin cholesterol acyl transferase activity in rabbits. Atherosclerosis. 1998 May; 138(1):101-10. doi: 10.1016/s0021-9150(98)00008-2. [PMID: 9678775]
  • J A Weststrate, G W Meijer. Plant sterol-enriched margarines and reduction of plasma total- and LDL-cholesterol concentrations in normocholesterolaemic and mildly hypercholesterolaemic subjects. European journal of clinical nutrition. 1998 May; 52(5):334-43. doi: 10.1038/sj.ejcn.1600559. [PMID: 9630383]
  • F Y Ntanios, P J Jones. Effects of variable dietary sitostanol concentrations on plasma lipid profile and phytosterol metabolism in hamsters. Biochimica et biophysica acta. 1998 Feb; 1390(3):237-44. doi: 10.1016/s0005-2760(97)00196-3. [PMID: 9487145]
  • H Gylling, R Radhakrishnan, T A Miettinen. Reduction of serum cholesterol in postmenopausal women with previous myocardial infarction and cholesterol malabsorption induced by dietary sitostanol ester margarine: women and dietary sitostanol. Circulation. 1997 Dec; 96(12):4226-31. doi: 10.1161/01.cir.96.12.4226. [PMID: 9416886]
  • H Gylling, T A Miettinen. Treatment of lipid disorders in non-insulin-dependent diabetes mellitus. Current opinion in lipidology. 1997 Dec; 8(6):342-7. doi: 10.1097/00041433-199712000-00004. [PMID: 9412774]
  • S J Robins, J M Fasulo. High density lipoproteins, but not other lipoproteins, provide a vehicle for sterol transport to bile. The Journal of clinical investigation. 1997 Feb; 99(3):380-4. doi: 10.1172/jci119170. [PMID: 9022069]
  • H Gylling, T A Miettinen. Effects of inhibiting cholesterol absorption and synthesis on cholesterol and lipoprotein metabolism in hypercholesterolemic non-insulin-dependent diabetic men. Journal of lipid research. 1996 Aug; 37(8):1776-85. doi: . [PMID: 8864962]