Resveratrol

Izvor: Wikipedia
Resveratrol
Chemical 9–69 structure of trans-resveratrol
Chemical structure of trans-resveratrol
Chemical structures of cis- and trans-resveratrols
Drugi nazivi trans-3,5,4'-Trihidroksistilben;
3,4',5-Stilbenetriol;
trans-Resveratrol;
(E)-5-(p-Hidroksistiril)resorcinol;
(E)-5-(4-hidroksistiril)benzen-1,3-diol
Identifikacija
CAS registarski broj 501-36-0 YesY
PubChem[1][2] 445154
ChemSpider[3] 392875 YesY
UNII Q369O8926L YesY
DrugBank DB02709
KEGG[4] C03582
ChEBI 45713
ChEMBL[5] CHEMBL165 YesY
RTECS registarski broj toksičnosti CZ8987000
Jmol-3D slike Slika 1
Svojstva
Molekulska formula C14H12O3
Molarna masa 228.24 g mol−1
Agregatno stanje Beli prah
Tačka topljenja

261 - 263 °C [6]

Rastvorljivost u voda 0,03 g/L
Rastvorljivost u DMSO 16 g/L
Rastvorljivost u etanol 50 g/L
λmax 304 nm (trans-resveratrol, u vodi)
286 nm (cis-resveratrol, u vodi)[7]
Opasnost
Podaci o bezbednosti prilikom rukovanja (MSDS) Fisher Scientific[6]
Sigma Aldrich[8]
R-oznake R36 (iritatant očiju)[8]
S-oznake S26 (u slučaju kontakta sa očima, odmah ih isprerite sa većom količinom vode i obratite se lekaru)[8]
LD50 23,2 µM (5,29 g)[9]

 YesY (šta je ovo?)   (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

Resveratrol (3,5,4'-trihidroksi-trans-stilben) je stilbenoid, tip prirodnog fenola, i fitoaleksin koji proizvodi više biljaka kad su napadnute patogenima kao što su bakterije ili gljive.

Efekti resveratrola su tema brojnih studija na životinjama i ljudima. Njegovi efekti na životni vek mnogih model organizama su kontroverzni.[10] U eksperimentima na miševima i pacovima, zapaženo je antikancerno i antiinflamatorno dejstvo, snižavanje nivoa krvnog šećera i drugi korisni kardiovaskularni efekti. Kod ljudi, su ti efekti generalno pozitivni, ali su izraženi u manjoj meri.[11] U jednom kliničkom ispitivanju, ekstremno visoke doze (3–5 g) resveratrola, u posebno dizajniranoj formulaciji kojom se povećava biodostupnost, su znatno snizili nivoe krvnog šećera.[12] Ta 28 dana duga studija faze 1b je sprovedena u Indiji, i objavljena 2008.[13] Mada postoje trvrdnje u štampi da resveratrol manifestuje antistarosno dejstvo,[14] one za sad nisu zasnovane na rigoroznim naučnim podacima. Istraživanja resveratrola su u svojoj ranoj fazi i dugotrajni efekti suplementacije kod ljudi nisu poznati.[15][16]

Reference[uredi - уреди]

  1. Li Q, Cheng T, Wang Y, Bryant SH (2010). "PubChem as a public resource for drug discovery.". Drug Discov Today 15 (23-24): 1052–7. doi:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). "Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities". Annual Reports in Computational Chemistry 4: 217–241. doi:10.1016/S1574-1400(08)00012-1. 
  3. Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). "Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining". J Cheminform 2 (1): 3. doi:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. Joanne Wixon, Douglas Kell (2000). "Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG". Yeast 17 (1): 48–55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
  5. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). "ChEMBL: a large-scale bioactivity database for drug discovery". Nucleic Acids Res 40 (Database issue): D1100–7. doi:10.1093/nar/gkr777. PMID 21948594.  edit
  6. 6.0 6.1 Resveratrol MSDS on Fisher Scientific website
  7. Camont L, Cottart CH, Rhayem Y, Nivet-Antoine V, Djelidi R, Collin F, Beaudeux JL, Bonnefont-Rousselot D (February 2009). "Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions". Anal. Chim. Acta 634 (1): 121–8. doi:10.1016/j.aca.2008.12.003. PMID 19154820. 
  8. 8.0 8.1 8.2 Resveratrol MSDS on www.sigmaaldrich.com
  9. Bechmann, LP; Zahn, D; Gieseler, RK; Fingas, CD; Marquitan, G; Jochum, C; Gerken, G; Friedman, SL et al. (2009). "Resveratrol amplifies profibrogenic effects of free fatty acids on human hepatic stellate cells". Hepatology research : the official journal of the Japan Society of Hepatology 39 (6): 601–8. doi:10.1111/j.1872-034X.2008.00485.x. PMC 2893585. PMID 19207580. 
  10. Bass TM, Weinkove D, Houthoofd K, Gems D, Partridge L (October 2007). "Effects of resveratrol on lifespan in Drosophila melanogaster and Caenorhabditis elegans". Mech. Ageing Dev. 128 (10): 546–52. doi:10.1016/j.mad.2007.07.007. PMID 17875315. 
  11. "Micronutrient Information Center: Resveratrol". Linus Pauling Institute at Oregon State University. http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol. pristupljeno 13. 01. 2012.. 
  12. Elliott PJ, Jirousek M (April 2008). "Sirtuins: novel targets for metabolic disease". Curr Opin Investig Drugs 9 (4): 371–8. PMID 18393104. 
  13. "Sirtris Announces Positive Results with Proprietary Version of Resveratrol, SRT501, in a Phase 1b Type 2 Diabetes Clinical Study - Drugs.com MedNews". Press Release. Drugs.com. 07. 01. 2008.. http://www.drugs.com/clinical_trials/sirtris-announces-positive-results-proprietary-version-resveratrol-srt501-phase-1b-type-2-diabetes-3127.html. pristupljeno 22. 02. 2012.. 
  14. "Pharma seeks genetic clues to healthy aging", Reuters, 6. 4. 2010..
  15. The Connecticut Post, "Selling resveratrol: Wonder drug or snake oil?," 08/04/2009, by Melissa Healy for the Los Angeles Times news service
  16. Gehm BD, McAndrews JM, Chien PY, Jameson JL (December 1997). "Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor". Proc. Natl. Acad. Sci. U.S.A. 94 (25): 14138–43. doi:10.1073/pnas.94.25.14138. PMC 28446. PMID 9391166. 

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