Campesterol

Last updated
Campesterol
Campesterol Structural Formula V1.svg
Campesterol molecule ball.png
Names
IUPAC name
Campest-5-en-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,5R)-5,6-Dimethylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Other names
(24R)-Ergost-5-en-3β-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.806 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1 Yes check.svgY
    Key: SGNBVLSWZMBQTH-PODYLUTMSA-N Yes check.svgY
  • InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
    Key: SGNBVLSWZMBQTH-PODYLUTMBW
  • O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CC[C@@H](C)C(C)C)C)[C@@]3(C)CC4
Properties
C28H48O
Molar mass 400.691 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Campesterol is a phytosterol whose chemical structure is similar to that of cholesterol, and is one of the ingredients for E number E499.

Contents

Natural occurrences

Many vegetables, fruits, nuts, [1] and seeds contain campesterol, but in low concentrations. Banana, pomegranate, pepper, coffee, grapefruit, cucumber, onion, oat, potato, and lemon grass (citronella) are few examples of common sources containing campesterol at roughly 1–7 mg/100 g of the edible portion. In contrast, canola and corn oils contain as much as 16–100 mg/100 g. Levels are variable and are influenced by geography and growing environment. In addition, different strains have different levels of plant sterols. A number of new genetic strains are currently being engineered with the goal of producing varieties high in campesterol and other plant sterols. [2] It is also found in dandelion coffee.

It is so named because it was first isolated from the rapeseed (Brassica campestris). [3]

Precursor of anabolic steroid boldenone

Campesterol can serve as a precursor to a wide range of steroid hormones. This is because it has structural similarity to cholesterol. Anabolic steroids like testosterone and boldenone are among the compounds that can be biosynthesized from either cholesterol or phytosterols like campesterol through a process called steroidogenesis.

Boldenone undecylenate is commonly used in veterinary medicine to induce growth in cattle, but it is also one of the most commonly abused anabolic steroids in sports. This led to suspicions that some of the athletes that have tested positive on boldenone undecylenate did not actually abuse the hormone itself, but had increased levels because they consumed food rich in campesterol or similar phytosteroids. [4] [5] [6]

Effect on blood lipids

Plant sterols were first shown in the 1950s to lower LDLs and cholesterol. [7] Since then, numerous studies have reported the lipid-lowering effects of dietary phytosterols, including campesterol. [8]

In basic research, campesterol competes with cholesterol, thus reducing the absorption of cholesterol in the human intestine. [9] Plant sterols may also act directly on intestinal cells and affect transporter proteins. In addition, an effect on the synthesis of cholesterol-transporting proteins may occur in the liver cells through processes including cholesterol esterification and lipoprotein assembly, cholesterol synthesis, and apolipoprotein (apo) B100-containing lipoprotein removal. [10]

Serum levels of campesterol and the ratio of campesterol to cholesterol have been proposed as measures of cardiac risk. Some studies have suggested that higher levels predict lower cardiac risk. However, extremely high levels are thought to be indicative of higher risk, as indicated by genetic disorders, such as sitosterolemia. [11]

Study results of serum levels have been conflicting. A 2012 meta-analysis found that no clear relationship exists between campesterol or sitosterol blood levels and risk of cardiovascular disease, and that perhaps previous studies have been confounded by other factors. [12] For example, people who have a higher campesterol level related to a diet high in fruits and nuts may be consuming a Mediterranean-style diet, thus have lower risk because of other lipids or lifestyle factors. [13]

Adverse effects

Nutrient levels

Excessive supplementation with plant sterols may be associated with reductions in beta-carotene and lycopene levels. [14] Excessive long-term consumption of plant sterols may have a deleterious effect on vitamin E, possibly leading to vitamin E deficiency. [15]

Increased risk of disease

Excessive use of plant sterols has been associated with an increased risk of cardiovascular disease, [9] and genetic conditions that cause extremely elevated levels of some phytosterols, such as sitosterol, are associated with higher risks of cardiovascular disease. However, this is an active area of debate, and no data suggest that modestly elevated levels of campesterol have a negative cardiac impact. [16]

Related Research Articles

<span class="mw-page-title-main">Cholesterol</span> Sterol biosynthesized by all animal cells

Cholesterol is the principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are typically composed of 80–100 proteins per particle. HDL particles enlarge while circulating in the blood, aggregating more fat molecules and transporting up to hundreds of fat molecules per particle.

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

<span class="mw-page-title-main">Low-density lipoprotein</span> One of the five major groups of lipoprotein

Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons, very low-density lipoprotein (VLDL), intermediate-density lipoprotein (IDL), low-density lipoprotein (LDL) and high-density lipoprotein (HDL). LDL delivers fat molecules to cells. LDL is involved in atherosclerosis, a process in which it is oxidized within the walls of arteries.

<span class="mw-page-title-main">Atherosclerosis</span> Form of arteriosclerosis

Atherosclerosis is a pattern of the disease arteriosclerosis, characterized by development of abnormalities called lesions in walls of arteries. These lesions may lead to narrowing of the arteries' walls due to buildup of atheromatous plaques. At onset there are usually no symptoms, but if they develop, symptoms generally begin around middle age. In severe cases, it can result in coronary artery disease, stroke, peripheral artery disease, or kidney disorders, depending on which body parts(s) the affected arteries are located in the body.

<span class="mw-page-title-main">Hypercholesterolemia</span> High levels of cholesterol in the blood

Hypercholesterolemia, also called high cholesterol, is the presence of high levels of cholesterol in the blood. It is a form of hyperlipidemia, hyperlipoproteinemia, and dyslipidemia.

<span class="mw-page-title-main">Stanol ester</span> Class of chemical compounds

Stanol esters is a heterogeneous group of chemical compounds known to reduce the level of low-density lipoprotein (LDL) cholesterol in blood when ingested, though to a much lesser degree than prescription drugs such as statins. The starting material is phytosterols from plants. These are first hydrogenated to give a plant stanol which is then esterified with a mixture of fatty acids also derived from plants. Plant stanol esters are found naturally occurring in small quantities in fruits, vegetables, nuts, seeds, cereals, legumes, and vegetable oils.

<span class="mw-page-title-main">Sterol</span> Chemical compound

Sterol is an organic compound with formula C
17
H
28
O
, whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria. The most familiar type of animal sterol is cholesterol, which is vital to cell membrane structure, and functions as a precursor to fat-soluble vitamins and steroid hormones.

Hyperlipidemia is abnormally high levels of any or all lipids or lipoproteins in the blood. The term hyperlipidemia refers to the laboratory finding itself and is also used as an umbrella term covering any of various acquired or genetic disorders that result in that finding. Hyperlipidemia represents a subset of dyslipidemia and a superset of hypercholesterolemia. Hyperlipidemia is usually chronic and requires ongoing medication to control blood lipid levels.

<span class="mw-page-title-main">Phytosterol</span> Class of steroids derived from plants

Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanols. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.

Sterol esters are a heterogeneous group of chemical compounds. They are created when the hydroxyl group of a sterol and a fatty acid undergo an esterification reaction. They can be found in trace amounts in every cell type but are highly enriched in foam cells and are common components of human skin oil.

<span class="mw-page-title-main">Stigmasterol</span> Chemical compound

Stigmasterol – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.

<i>beta</i>-Sitosterol Chemical compound

β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

<span class="mw-page-title-main">Benecol</span> Brand of cholesterol-lowering food products

Benecol is a brand of cholesterol-lowering food products owned by the Finnish company Raisio Group, which owns the trademark.

<span class="mw-page-title-main">Sitosterolemia</span> Medical condition

Sitosterolemia is a rare autosomal recessively inherited lipid metabolic disorder. It is characterized by hyperabsorption and decreased biliary excretion of dietary sterols. Healthy persons absorb only about 5% of dietary plant sterols, but sitosterolemia patients absorb 15% to 60% of ingested sitosterol without excreting much into the bile. The phytosterol campesterol is more readily absorbed than sitosterol.

ABCG5 and ABCG8 genes encode for two proteins sterolin-1 and -2, respectively. Sterolin-1 and –2 are two ‘half’ adenosine triphosphate binding (ATP) cassette (ABC) transporters which found to be indispensable for the regulation of sterol absorption and excretion. Mutations in either genes result in a lipid disorder, sitosterolemia.

The lipid hypothesis is a medical theory postulating a link between blood cholesterol levels and the occurrence of cardiovascular disease. A summary from 1976 described it as: "measures used to lower the plasma lipids in patients with hyperlipidemia will lead to reductions in new events of coronary heart disease". It states, more concisely, that "decreasing blood cholesterol [...] significantly reduces coronary heart disease".

<span class="mw-page-title-main">Familial hypercholesterolemia</span> Genetic disorder characterized by high cholesterol levels

Familial hypercholesterolemia (FH) is a genetic disorder characterized by high cholesterol levels, specifically very high levels of low-density lipoprotein cholesterol, in the blood and early cardiovascular diseases. The most common mutations diminish the number of functional LDL receptors in the liver or produce abnormal LDL receptors that never go to the cell surface to function properly. Since the underlying body biochemistry is slightly different in individuals with FH, their high cholesterol levels are less responsive to the kinds of cholesterol control methods which are usually more effective in people without FH. Nevertheless, treatment is usually effective.

<span class="mw-page-title-main">PCSK9</span> Mammalian protein found in humans

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is an enzyme encoded by the PCSK9 gene in humans on chromosome 1. It is the 9th member of the proprotein convertase family of proteins that activate other proteins. Similar genes (orthologs) are found across many species. As with many proteins, PCSK9 is inactive when first synthesized, because a section of peptide chains blocks their activity; proprotein convertases remove that section to activate the enzyme. The PCSK9 gene also contains one of 27 loci associated with increased risk of coronary artery disease.

The chronic endothelial injury hypothesis is one of two major mechanisms postulated to explain the underlying cause of atherosclerosis and coronary heart disease (CHD), the other being the lipid hypothesis. Although an ongoing debate involving connection between dietary lipids and CHD sometimes portrays the two hypotheses as being opposed, they are in no way mutually exclusive. Moreover, since the discovery of the role of LDL cholesterol (LDL-C) in the pathogenesis of atherosclerosis, the two hypotheses have become tightly linked by a number of molecular and cellular processes.

References

  1. Segura, Ramon; Javierre, Casimiro; Lizarraga, M Antonia; Ros, Emilio (2007). "Other relevant components of nuts: Phytosterols, folate and minerals". British Journal of Nutrition. 96: S36–44. doi: 10.1017/BJN20061862 . PMID   17125532.
  2. Gül, Muhammet Kemal; Amar, Samija (2006). "Sterols and the phytosterol content in oilseed rape (Brassica napus L.)" (PDF). Journal of Cell and Molecular Biology. 5: 71–9. Archived from the original (PDF) on 2009-02-19. Retrieved 2012-03-02.
  3. Fernholz, Erhard; MacPhillamy, H. B. (1941). "Isolation of a New Phytosterol: Campesterol". Journal of the American Chemical Society. 63 (4): 1155. doi:10.1021/ja01849a079.
  4. Boldenone, Boldione, and Milk Replacers in the Diet of Veal Calves: The Effects of Phytosterol Content on the Urinary Excretion of Boldenone Metabolites, G. Gallina, G. Ferretti, R. Merlanti, C. Civitareale, F. Capolongo, R. Draisci and C. Montesissa, J. Agric. Food Chem., 2007, 55 (20), pp 8275–8283
  5. Food Addit Contam. 2007 Jul;24(7):679-84.;Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted; Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N.;National Institute for Public Health and the Environment (RIVM), the Netherlands.
  6. Excretion profile of boldenone in urine of veal calves fed two different milk replacers; R. Draisci, R. Merlanti, G. Ferretti, L. Fantozzi, C. Ferranti, F. Capolongo, S. Segato, C. Montesissa; Analytica Chimica Acta, Volume 586, Issues 1–2, 14 March 2007, Pages 171–176
  7. Farquhar, John W.; Sokolow, Maurice (1958). "Response of Serum Lipids and Lipoproteins of Man to Beta-Sitosterol and Safflower Oil". Circulation. 17 (5): 890–9. doi:10.1161/01.CIR.17.5.890. PMID   13537276. S2CID   5755751.
  8. Heggen, E.; Granlund, L.; Pedersen, J.I.; Holme, I.; Ceglarek, U.; Thiery, J.; Kirkhus, B.; Tonstad, S. (2010). "Plant sterols from rapeseed and tall oils: Effects on lipids, fat-soluble vitamins and plant sterol concentrations". Nutrition, Metabolism and Cardiovascular Diseases. 20 (4): 258–65. doi:10.1016/j.numecd.2009.04.001. hdl: 10852/55512 . PMID   19748247.
  9. 1 2 Choudhary, SP; Tran, LS (2011). "Phytosterols: Perspectives in human nutrition and clinical therapy". Current Medicinal Chemistry. 18 (29): 4557–67. doi:10.2174/092986711797287593. PMID   21864283.
  10. Calpe-Berdiel, Laura; Escolà-Gil, Joan Carles; Blanco-Vaca, Francisco (2009). "New insights into the molecular actions of plant sterols and stanols in cholesterol metabolism". Atherosclerosis. 203 (1): 18–31. doi:10.1016/j.atherosclerosis.2008.06.026. PMID   18692849.
  11. Tsubakio-Yamamoto, Kazumi; Nishida, Makoto; Nakagawa-Toyama, Yumiko; Masuda, Daisaku; Ohama, Tohru; Yamashita, Shizuya (2010). "Current Therapy for Patients with Sitosterolemia – Effect of Ezetimibe on Plant Sterol Metabolism". Journal of Atherosclerosis and Thrombosis. 17 (9): 891–900. doi: 10.5551/jat.4614 . PMID   20543520.
  12. Genser B, Silbernagel G, De Backer G, Bruckert E, Carmena R, Chapman MJ, Deanfield J, Descamps OS, Rietzschel ER, Dias KC, März W (February 2012). "Plant sterols and cardiovascular disease: a systematic review and meta-analysis". European Heart Journal. 33 (4): 444–51. doi:10.1093/eurheartj/ehr441. PMC   3279314 . PMID   22334625.
  13. Helgadottir, Anna; Thorleifsson, Gudmar; Alexandersson, Kristjan F.; et al. (2020-07-21). "Genetic variability in the absorption of dietary sterols affects the risk of coronary artery disease". European Heart Journal. 41 (28): 2618–2628. doi: 10.1093/eurheartj/ehaa531 . ISSN   0195-668X. PMC   7377579 . PMID   32702746.
  14. Richelle, Myriam; Enslen, Marc; Hager, Corinne; et al. (2004). "Both free and esterified plant sterols reduce cholesterol absorption and the bioavailability of β-carotene and α-tocopherol in normocholesterolemic humans". American Journal of Clinical Nutrition. 80 (1): 171–7. doi: 10.1093/ajcn/80.1.171 . PMID   15213045.
  15. Tuomilehto, J; Tikkanen, M J; Högström, P; et al. (2008). "Safety assessment of common foods enriched with natural nonesterified plant sterols". European Journal of Clinical Nutrition. 63 (5): 684–91. doi: 10.1038/ejcn.2008.11 . PMID   18270526.
  16. Calpe-Berdiel, L; Méndez-González, J; Blanco-Vaca, F; Carles Escolà-Gil, J (2009). "Increased plasma levels of plant sterols and atherosclerosis: A controversial issue". Current Atherosclerosis Reports. 11 (5): 391–8. doi:10.1007/s11883-009-0059-x. PMID   19664384. S2CID   3776406.