Campesterol
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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
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| Other names
Campestanol; (24R)-Ergost-5-en-3β-ol
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3D model (Jmol)
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| ECHA InfoCard | 100.006.806 |
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PubChem CID
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| Properties | |
| C28H48O | |
| Molar mass | 400.69 g·mol−1 |
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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.
Many vegetables, fruits, nuts, 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. It is also found in dandelion coffee.
It is so named because it was first isolated from the rapeseed (Brassica campestris). 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.
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.
Plant sterols were first shown in the 1950s to be beneficial in lowering LDLs and cholesterol. Since then, numerous studies have also reported the beneficial effects of the dietary intake of phytosterols, including campesterol.
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Wikipedia