Campesterine

from Wikipedia, the free encyclopedia
Structural formula
Campesterol Structural Formula V1.svg
General
Surname Campesterine
other names
  • (3 S , 8 S , 9 S , 10 R , 13 R , 14 S , 17 R ) -17 - [(2 R , 5 R ) -5,6-dimethylheptan-2-yl] -10,13-dimethyl -2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1 H -cyclopenta [ a ] phenanthren-3-ol
  • Campestanol
  • (24 R ) -Ergost-5-en-3 β -ol
Molecular formula C 28 H 48 O
External identifiers / databases
CAS number 474-62-4
EC number 207-484-4
ECHA InfoCard 100.006.806
PubChem 173183
Wikidata Q2756479
properties
Molar mass 400.68 g mol −1
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-312-315-319-332-335
P: 261-280-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Campesterine , also campesterol, is a substance from the group of phytosterols ( i.e. plant sterols ) with the chemical formula C 28 H 48 O, which got its name because it was first isolated from the plant Brassica campestris .

Occurrence

The substance occurs in different plants and plant parts, whereby the proportion in which it occurs depends not only on the plant species, but also on its location (due to climatic conditions, soil properties, etc.). Campesterine occurs in fruit (e.g. grapefruit , pomegranate ), as well as vegetables (e.g. onions , cucumbers ) and grains ( canola , oats , corn ). It's also found in dandelions and in spices like cardamom, pepper, and lemongrass . In geochemistry , along with other sterols, it serves as a biomarker in various sediments .

Analytics

For a reliable qualitative and quantitative determination of campesterol sterol or its esters is dependent on the matrix, sample preparation , the HPLC-MS or coupling of the gas chromatography with the use of capillary columns with the mass spectrometry used. These methods are also suitable for the detection of adulteration of fat or oil.

effect

Campesterine has an anabolic effect on the organism as it is a steroid-like precursor of various growth hormones . Like most phytosterols, it is able to lower LDL and total cholesterol . Studies have not clearly shown whether this can reduce the cardiovascular risk. The studies that are available on this are questioned because there are counter studies and the assumption is that people who eat campesterine-rich foods eat more health-consciously overall ( Mediterranean diet , high proportion of vegetables, etc.), so that one isolated The effect of campesterine cannot be clearly demonstrated. Campesterol may have an inhibiting effect on the absorption of cholesterol in the intestine. It also inhibits the synthesis of cholesterol and apolipoproteins .

Like other phytosterols, campesterol can also contribute to the deposition of phytosterol-containing plaques in the blood vessels in the presence of a rare metabolic disorder, phytosterinaemia .

Campesterine is a precursor of the anabolic boldenone , which is why taking it can lead to positive doping test results.

The intake of Dalcetrapid , a CETP -Hemmstoff, increases the absorption of campesterol in the gut.

Effect on other nutrients

It is assumed that campesterine lowers the levels of various micronutrients , namely vitamin E , the vitamin precursor β-carotene and the secondary plant substance lycopene . It should certainly be questioned to what extent these effects are dose-dependent and whether they occur with a diet rich in phytosterols or only when the isolated substance is taken. Especially since some of the foods that contain campesterine also contain vitamin E (cardamom, pomegranate) or β-carotene.

Individual evidence

  1. ↑ a b Campesterol data sheet from Sigma-Aldrich , accessed on October 10, 2012 ( PDF ).
  2. ^ WG Jing, ZM Wang, Y. Zhao, J. Fu, XL Zhao, A. Liu: Chemical constituents from seeds of Brassica campestris. In: Zhongguo Zhong Yao Za Zhi. 39 (13), Jul 2014, pp. 2521-2525. Chinese. PMID 25276975
  3. ↑ GA Bataglion, E. Meurer, AC de Albergaria-Barbosa, MC Bícego, RR Weber, MN Eberlin: Determination of Geochemically Important Sterols and Triterpenols in Sediments Using Ultrahigh-Performance Liquid Chromatography Tandem Mass Spectrometry (UHPLC-MS / MS). In: Anal Chem. 87 (15), Aug 4, 2015, pp. 7771-7778. PMID 26132310 .
  4. ↑ B. Scholz, N. Menzel, V. Lander, KH Engel: An approach based on ultrahigh performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry allowing the quantification of both individual phytosteryl and phytostanyl fatty acid esters in complex mixtures. In: J Chromatogr A. 1429, Jan 15, 2016, pp. 218-229. PMID 26718186
  5. ↑ H. Zhao, Y. Wang, X. Xu, H. Ren, L. Li, L. Xiang, W. Zhong: Detection of Adulterated Vegetable Oils Containing Waste Cooking Oils Based on the Contents and Ratios of Cholesterol, β-Sitosterol , and Campesterol by Gas Chromatography / Mass Spectrometry. In: J AOAC Int. 98 (6), Dec 2015, pp. 1645–1654. PMID 26651578
  6. ↑ John W. Farquhar, Maurice Sokolow: Response of Serum Lipids and Lipoproteins of Man to Beta-Sitosterol and Safflower Oil . In: Circulation . tape 17 , no. 5 , 1958, pp. 890-899 , doi : 10.1161 / 01.CIR.17.5.890 , PMID 13537276 .
  7. ↑ E. Heggen, L. Granlund, JI Pedersen, I. Holme, U. Ceglarek, J. Thiery, B. Kirkhus, S. Tonstad: Plant sterols from rapeseed and tall oils: Effects on lipids, fat-soluble vitamins and plants sterol concentrations . In: Nutrition, Metabolism and Cardiovascular Diseases . tape 20 , no. 4 , 2010, p. 258-265 , doi : 10.1016 / j.numecd.2009.04.001 , PMID 19748247 .
  8. ↑ SP Choudhary, LS Tran: Phytosterols: Perspectives in human nutrition and clinical therapy . In: Current Medicinal Chemistry . tape 18 , no. 29 , 2011, p. 4557-4567 , doi : 10.2174 / 092986711797287593 , PMID 21864283 .
  9. ↑ Laura Calpe-Berdiel, Joan Carles Escolà-Gil, Francisco Blanco-Vaca: New insights into the molecular actions of plant sterols and stanols in cholesterol metabolism . In: Atherosclerosis . tape 203 , no. 1 , 2009, p. 18-31 , doi : 10.1016 / j.atherosclerosis.2008.06.026 , PMID 18692849 .
  10. ↑ G. Gallina, G. Ferretti, R. Merlanti, C. Civitareale, F. Capolongo, R. Draisci, C. Montesissa: Boldenone, Boldione, and Milk Replacers in the Diet of Veal Calves: The Effects of Phytosterol Content on the Urinary Excretion of Boldenone Metabolites. In: J. Agric. Food Chem. 55 (20), 2007, pp. 8275-8283.
  11. ↑ MM Ros, SS Sterk, H. Verhagen, AF Stalenhoef, N. de Jong: Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted. In: Food Addit Contam. 24 (7), Jul 2007, pp. 679-684.
  12. ↑ R. Draisci, R. Merlanti, G. Ferretti, L. Fantozzi, C. Ferranti, F. Longo Capo, S. Segato, C. Montesissa: Excretion profile of boldenone in urine of veal calves fed two different milk replacers. In: Analytica Chimica Acta. Volume 586, Issues 1-2, March 14, 2007, pp. 171-176.
  13. ↑ EJ Niesor, E. Chaput, A. Staempfli, D. Blum, M. Derks, D. Kallend: Effect of dalcetrapib, a CETP modulator, on non-cholesterol sterol markers of cholesterol homeostasis in healthy subjects. In: Atherosclerosis. Volume 219, Number 2, December 2011, ISSN  1879-1484 , pp. 761-767, doi: 10.1016 / j.atherosclerosis.2011.09.017 . PMID 21982411 .
  14. ↑ J. Tuomilehto, MJ Tikkanen, P. Högström, S. Keinänen-Kiukaanniemi, V. Piironen, J. Toivo, JT Salonen, K. Nyyssönen, UH Stenman, H. Alfthan, H. Karppanen: Safety assessment of common foods enriched with natural nonesterified plant sterols. In: European Journal of Clinical Nutrition. Volume 63, number 5, May 2009, ISSN  1476-5640 , pp. 684-691, doi: 10.1038 / ejcn.2008.11 . PMID 18270526 .
  15. ↑ Peter Clifton: Lowering cholesterol - A review on the role of plant sterols . In: Australian Family Physician . tape 38 , no. 4 , 2009, p. 218-221 , PMID 19350071 .
  16. ↑ M. Richelle, M. Enslen, C. Hager, M. Groux, I. Tavazzi, JP Godin, A. Berger, S. Métairon, S. Quaile, C. Piguet-Welsch, L. Sagalowicz, H. Green, LB Fay: Both free and esterified plant sterols reduce cholesterol absorption and the bioavailability of beta-carotene and alpha-tocopherol in normocholesterolemic humans. In: The American journal of clinical nutrition. Volume 80, Number 1, July 2004, ISSN  0002-9165 , pp. 171-177. PMID 15213045 .