Campesterol

Campesterol
Ball-and-stick model of campesterol
Names
IUPAC name
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names
Campestanol; (24R)-Ergost-5-en-3β-ol
Identifiers
474-62-4 YesY
ChEBI CHEBI:28623 YesY
ChEMBL ChEMBL520535 YesY
ChemSpider 151215 YesY
Jmol interactive 3D Image
PubChem 173183
UNII 5L5O665639 YesY
Properties
C28H48O
Molar mass 400.69 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Campesterol is a phytosterol whose chemical structure is similar to that of cholesterol.

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 ~1–7 mg/100 g of the edible portion. In contrast canola and corn oil 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] It is thought to have anti-inflammatory effects. It was demonstrated that it inhibits several pro-inflammatory and matrix degradation mediators typically involved in osteoarthritis-induced cartilage degradation.[4]

Precursor of anabolic steroid boldenone

Being a steroid, campesterol is a precursor of anabolic steroid boldenone. 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 suspicion that some athletes testing positive on boldenone undecylenate did not actually abuse the hormone itself but consumed food rich in campesterol or similar phytosteroids.[5][6][7]

Cardiovascular disease

It was first shown in the 1950s that plant sterols are beneficial in lowering LDLs and cholesterol.[8] Since then, numerous studies have also reported the beneficial effects of the dietary intake of phytosterols, including campesterol.[9]

It is thought that the campesterol molecules compete with cholesterol and thus reduces the absorption of cholesterol in the human intestine.[10] Plant sterols may also act directly on intestinal cells and affect transporter proteins. In addition, there may be an effect on the synthesis of cholesterol transporting proteins in the liver cells through processes including cholesterol esterification and lipoprotein assembly, cholesterol synthesis, and apolipoprotein (apo) B100-containing lipoprotein removal.[11]

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.[12] Study results of serum levels have been conflicting. A recent meta-analysis suggests that there is no clear relationship, and that perhaps previous studies have been confounded by other factors. 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 and thus have lower risk because of other lipids or lifestyle factors. Intestinal absorption of cholesterol varies between individuals, and it is possible that a higher absorption of plant sterols is related to a higher absorption of LDL.[13]

Although studies in humans have shown that consumption of phytosterols may reduce LDL levels, there is insufficient evidence to recommend them as a treatment for hypercholesterolemia. Larger trials are needed to provide such evidence, and are underway.[14] Animal studies have shown that campesterol and other phytosterols can reduce the size of atherogenic plaques, but there is no data yet to shown that consumption of phytosterols result in any clinical benefit such as a reduction in atherosclerosis, heart disease, cardiac events, or mortality.[15]

Adverse effects

Reduction in beta-carotene levels

Excessive supplementation with plant sterols may be associated with reductions in beta-carotene levels.[15][16]

Reduction in lycopene levels

Excessive supplementation with plant sterols may be associated with reductions in lycopene levels.[15][16]

Reduction in vitamin E levels

One small study showed no significant side effects after 15 weeks other than a slight reduction in vitamin E levels, which was not significant after LDL cholesterol levels were taken into consideration. However, the authors concluded that excessive long term consumption of plant sterols might have a deleterious effect on vitamin E.[17]

Increased risk of atherogenesis and cardiovascular disease

Excessive use of plant sterols has been associated with an increased risk of cardiovascular disease,[10] 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 there is no data to suggest that modestly elevated levels of campestrol have a negative cardiac impact.[18]

Hematological

Rare cases of hemolytic anemia have been reported.[19]

Other treatment

A recent trial with dalcetrapid, a cholesteryl esterase transport protein (CETP) inhibitor, (a new class of cholesterol lowering medications currently in development) showed that this agent may have the potential to increase levels of campesterol through increasing intestinal absorption.[20]

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.
  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. ↑ Gabay, O.; Sanchez, C.; Salvat, C.; Chevy, F.; Breton, M.; Nourissat, G.; Wolf, C.; Jacques, C.; Berenbaum, F. (2010). "Stigmasterol: A phytosterol with potential anti-osteoarthritic properties". Osteoarthritis and Cartilage 18 (1): 106–16. doi:10.1016/j.joca.2009.08.019. PMID 19786147.
  5. ↑ 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 Department of Public Health Comparative Pathology and Veterinary Hygiene, University of Padua, Viale dell’Università 16, 35020 Legnaro (PD), Italy, and Department of Food Safety and Veterinary Public Health, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Roma, Italy J. Agric. Food Chem., 2007, 55 (20), pp 8275–8283
  6. ↑ 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.
  7. ↑ 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
  8. ↑ 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.
  9. ↑ 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. PMID 19748247.
  10. 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ Genser, B.; Silbernagel, G.; De Backer, G.; Bruckert, E.; Carmena, R.; Chapman, M. J.; Deanfield, J.; Descamps, O. S.; et al. (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.
  14. ↑ Párraga, Ignacio; López-Torres, Jesús; Andrés, Fernando; Navarro, Beatriz; Del Campo, José M; García-Reyes, Mercedes; Galdón, María P; Lloret, Ángeles; Precioso, Juan C; Rabanales, Joseba (2011). "Effect of plant sterols on the lipid profile of patients with hypercholesterolaemia. Randomised, experimental study". BMC Complementary and Alternative Medicine 11: 73. doi:10.1186/1472-6882-11-73. PMC 3180270. PMID 21910898.
  15. 1 2 3 Clifton, Peter (2009). "Lowering cholesterol – A review on the role of plant sterols". Australian Family Physician 38 (4): 218–21. PMID 19350071.
  16. 1 2 Richelle, Myriam; Enslen, Marc; Hager, Corinne; Groux, Michel; Tavazzi, Isabelle; Godin, Jean-Philippe; Berger, Alvin; Métairon, Sylviane; et al. (2004). "Both free and esterified plant sterols reduce cholesterol absorption and the bioavailability of ß-carotene and α-tocopherol in normocholesterolemic humans". American Journal of Clinical Nutrition 80 (1): 171–7. PMID 15213045.
  17. ↑ Tuomilehto, J; Tikkanen, M J; Högström, P; Keinänen-Kiukaanniemi, S; Piironen, V; Toivo, J; Salonen, J T; Nyyssönen, K; 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.
  18. ↑ 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.
  19. ↑ Abdulkadyrov, KM; Bessmel'Tsev, SS (1990). "Immunological and rheological parallels in patients with autoimmune thrombocytopenic purpura treated with antilymphocyte globulin". Klinicheskaia meditsina 68 (6): 49–53. PMID 2214639.
  20. ↑ Niesor, Eric J.; Chaput, Evelyne; Staempfli, Andreas; Blum, Denise; Derks, Michael; Kallend, David (2011). "Effect of dalcetrapib, a CETP modulator, on non-cholesterol sterol markers of cholesterol homeostasis in healthy subjects". Atherosclerosis 219 (2): 761–7. doi:10.1016/j.atherosclerosis.2011.09.017. PMID 21982411.

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