MiMeDB: Showing metabocard for beta-Sitosterol (MMDBc0052894)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:08:21 UTC

Update Date

2022-09-01 02:19:34 UTC

MiMeDB ID

MMDBc0052894

Metabolite Identification

Common Name

beta-Sitosterol

Description

beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445 , 11432711 ). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381 ). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀O

Average Molecular Weight

414.718

Monoisotopic Molecular Weight

414.38616623

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Fibroblasts
Intestine
Kidney
Liver
Prostate
Testis
Urine

Tissue Locations

Fibroblasts
Intestine
Kidney
Liver
Prostate
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x00007f092014b268>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Short bowel syndrome		This associated disease is originally imported from HMDB metabolite HMDB0000852 concentration id 17515	Association	Human Blood		15896428	details
Sitosterolemia	Increased	This associated disease is originally imported from HMDB metabolite HMDB0000852 concentration id 59564	Association	Human Urine		17613052	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites
Fungi	Basidiomycota	9	Human Feces
Fungi	Blastocladiomycota	1
Fungi	Ascomycota	8	Human Feces
Fungi	Mucoromycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	14.1	10.6	Adult (>18 years old)	Both	Short bowel syndrome	HMDB	15896428	details
Human	Detected and Quantified	0.0021		Adult (>18 years old)	Female	Sitosterolemia	HMDB	17613052	details
Human	Detected and Quantified	0.00017	0.000095	Adult (>18 years old)	Female	Normal	HMDB	17613052	details
Human	Detected and Quantified	0.902	0.089	Adult (>18 years old)	Both	Normal	HMDB	20671299	details
Human	Detected and Quantified	22.8	6.7	Adult (>18 years old)	Both	Normal	HMDB	15896428	details
Human	Detected and Quantified	5.53	0.021	Adult (>18 years old)	Both	Normal	HMDB	20671299	details
Human	Detected and Quantified	8.222	4.340	Adult (>18 years old)	Female	Normal	HMDB	11432711	details
Human Fibroblasts	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Intestine	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Kidney	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Liver	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Prostate	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Testis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Feces	Detected but not Quantified			Infant (0-1 year old)	NULL	Normal	HMDB	24628373	details
Human Feces	Detected but not Quantified			Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373	details
Human Feces	Detected but not Quantified			Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373	details
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	25037050	details
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	29808030	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. doi: 10.1016/0005-2760(79)90093-6. [PubMed:573140 ]
Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. doi: 10.1016/0009-8981(92)90077-4. [PubMed:1499139 ]
Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. doi: 10.1016/0024-3205(95)00263-6. [PubMed:7596226 ]
Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9. doi: 10.1016/0026-0495(94)90266-6. [PubMed:8028508 ]
Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13. doi: 10.1016/0016-5085(93)91079-w. [PubMed:8253356 ]
Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9. [PubMed:8429265 ]
Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. doi: 10.1046/j.1464-410x.1999.00026.x. [PubMed:10368239 ]
Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9. doi: 10.1067/mlc.2000.104459. [PubMed:10695663 ]
Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91. doi: 10.1016/s0735-1097(00)00527-1. [PubMed:10758959 ]
Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4. [PubMed:10810360 ]
Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6. doi: 10.1046/j.1365-2796.2001.00788.x. [PubMed:11240845 ]
Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. doi: 10.1097/00008469-200106000-00007. [PubMed:11432711 ]
Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. [PubMed:12579296 ]
Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. doi: 10.1079/bjn2003956. [PubMed:13129445 ]
Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73. doi: 10.1016/j.toxlet.2003.09.001. [PubMed:14615068 ]
Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. doi: 10.1093/jn/133.12.4252. [PubMed:14652381 ]
Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20. doi: 10.1007/s00120-005-0778-8. [PubMed:15726313 ]
Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8. doi: 10.1042/CS20050030. [PubMed:15816807 ]
Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. doi: 10.1007/s00280-004-0914-y. Epub 2005 Apr 12. [PubMed:15824923 ]
Fernandez ML, Vega-Lopez S: Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev. 2005 Spring;23(1):57-70. doi: 10.1111/j.1527-3466.2005.tb00157.x. [PubMed:15867948 ]
Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. doi: 10.1016/j.fitote.2005.03.011. [PubMed:15893885 ]
Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801. doi: 10.1016/j.jacc.2005.02.063. [PubMed:15936608 ]
Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. doi: 10.1016/j.atherosclerosis.2004.11.025. Epub 2005 Feb 12. [PubMed:15939057 ]
Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63. doi: 10.1258/0004563054255605. [PubMed:15989725 ]
Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. doi: 10.1097/01.tp.0000189173.46727.18. [PubMed:16477216 ]

Showing metabocard for beta-Sitosterol (MMDBc0052894)

MOL for #<Metabolite:0x000055b76dca36e8>

3D MOL for #<Metabolite:0x000055b76dca36e8>

3D SDF for #<Metabolite:0x000055b76dca36e8>

3D-SDF for #<Metabolite:0x000055b76dca36e8>

PDB for #<Metabolite:0x000055b76dca36e8>

3D PDB for #<Metabolite:0x000055b76dca36e8>

SMILES for #<Metabolite:0x000055b76dca36e8>

INCHI for #<Metabolite:0x000055b76dca36e8>

Structure for #<Metabolite:0x000055b76dca36e8>

3D Structure for #<Metabolite:0x000055b76dca36e8>