Resveratrol

Resveratrol
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
PubChem	445154
ChemSpider	392875
UNII	Q369O8926L
DrugBank	DB02709
KEGG	C03582
ChEBI	45713
ChEMBL	CHEMBL165
RTECS registarski broj toksičnosti	CZ8987000
Jmol-3D slike	Slika 1
SMILES
	Oc2ccc(C=Cc1cc(O)cc(O)c1)cc2
InChI
	InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+ ; Kod: LUKBXSAWLPMMSZ-OWOJBTEDSA-N InChI=1/C14H12O3/c15-; 12-5-3-10(4-6-12); 1-2-11-7-13(16)9-; 14(17)8-11/h1-9,15-; 17H/b2-1+
Svojstva
Molekulska formula	C14H12O3
Molarna masa	228.24 g mol−1
Agregatno stanje	Beli prah
Tačka topljenja	261 - 263 °C
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)
Opasnost
Podaci o bezbednosti prilikom rukovanja (MSDS)	Fisher Scientific; Sigma Aldrich
R-oznake	R36 (iritatant očiju)
S-oznake	S26 (u slučaju kontakta sa očima, odmah ih isprerite sa većom količinom vode i obratite se lekaru)
LD50	23,2 µM (5,29 g)
	(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

↑ 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
↑ 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.
↑ 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
↑ 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.
↑ 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
↑ ^6,0 ^6,1 „Resveratrol MSDS on Fisher Scientific website”. Arhivirano iz originala na datum 2012-11-03. Pristupljeno 2014-04-11.
↑ 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.
↑ ^8,0 ^8,1 ^8,2 Resveratrol MSDS on www.sigmaaldrich.com
↑ Bechmann, LP; Zahn, D; Gieseler, RK; Fingas, CD; Marquitan, G; Jochum, C; Gerken, G; Friedman, SL i dr.. (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.
↑ 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.
↑ „Micronutrient Information Center: Resveratrol”. Linus Pauling Institute at Oregon State University. Pristupljeno 13. 01. 2012.
↑ Elliott PJ, Jirousek M (April 2008). „Sirtuins: novel targets for metabolic disease”. Curr Opin Investig Drugs 9 (4): 371–8. PMID 18393104.
↑ „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.. Arhivirano iz originala na datum 2012-02-05. Pristupljeno 22. 02. 2012.
↑ „Pharma seeks genetic clues to healthy aging”. Reuters. 6. 4. 2010..
↑ The Connecticut Post, "Selling resveratrol: Wonder drug or snake oil?," 08/04/2009, by Melissa Healy for the Los Angeles Times news service
↑ 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.

Vidi još uredi

Spoljašnje veze uredi

Portal Hemija

Félicien Breton (2008). „Resveratrol and polyphenols in wines”. Arhivirano iz originala na datum 2013-04-14. Pristupljeno 2014-04-11.
CTD's Resveratrol page Arhivirano 2012-05-22 na Wayback Machine-u from the Comparative Toxicogenomics Database
U.S. National Library of Medicine: Drug Information Portal – Resveratrol
Detailed Micro-Nutrient information on Resveratrol from the Linus Pauling Institute
Resveratrol: Don't Buy the Hype
Stay young on red wine drugs? Think again
Zalet – a site that specializes in Resveratrol information

}{-}}

[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

[FisherScientificMSDS-6] 6,0 ^6,1 „Resveratrol MSDS on Fisher Scientific website”. Arhivirano iz originala na datum 2012-11-03. Pristupljeno 2014-04-11.

[Camont-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.

[SigmaAldrichMSDS-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 i dr.. (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.

[Bass2007-10] 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.

[urlLinus_Pauling_Institute_at_Oregon_State_University-11] „Micronutrient Information Center: Resveratrol”. Linus Pauling Institute at Oregon State University. Pristupljeno 13. 01. 2012.

[pmid18393104-12] Elliott PJ, Jirousek M (April 2008). „Sirtuins: novel targets for metabolic disease”. Curr Opin Investig Drugs 9 (4): 371–8. PMID 18393104.

[url_Sirtris_SRT501-13] „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.. Arhivirano iz originala na datum 2012-02-05. Pristupljeno 22. 02. 2012.

[14] „Pharma seeks genetic clues to healthy aging”. Reuters. 6. 4. 2010..

[The_Connecticut_Post_2009-15] The Connecticut Post, "Selling resveratrol: Wonder drug or snake oil?," 08/04/2009, by Melissa Healy for the Los Angeles Times news service

[Gehm_BD,_McAndrews_JM,_Chien_PY,_Jameson_JL_1997_14138–43-16] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]