Likopen

Likopen
	ψ,ψ-karoten
Drugi nazivi	(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-oktametildotriakonta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridekaen
Identifikacija
CAS registarski broj	502-65-8
PubChem	446925
ChemSpider	394156
UNII	SB0N2N0WV6
EINECS broj	207-949-1
ChEBI	15948
ChEMBL	CHEMBL501174
Jmol-3D slike	Slika 1
SMILES
	C(\C=C\C=C(\CC/C=C(\C)C)C)(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(\C)CC\C=C(/C)C)C)C)C)C
InChI
	InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+ ; Kod: OAIJSZIZWZSQBC-GYZMGTAESA-N InChI=1/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+; Kod: OAIJSZIZWZSQBC-GYZMGTAEBZ
Svojstva
Molekulska formula	C40H56
Molarna masa	536.87 g mol−1
Agregatno stanje	Crvena čvrsta materija
Tačka topljenja	172–173 °C
Rastvorljivost u vodi	Nerastvoran
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Likopen je svetlo crveni karotenski i karotenoidni pigment i fitohemikalija koja je prisutna u paradajzu i drugom crvenom voću i povrću, kao što su crvene šargarepe, lubenice i papaje (mada nije prisutan u jagodama i trešnjama). Likopen je karoten koji ne deluje kao vitamin A.

Struktura i fizičke osobine

Skeletalna formula sve-trans likopena

Model sve-trans likopena

Likopen je simetrični tetraterpen formiran od 8 izoprenskih jedinica. On je član karotenoidne familije jedinjenja, te se u potpunosti sastoji od ugljenika i vodonika, poput karotena.^[5] Procedura za izolaciju likopena je privi put objavljena 1910, a struktura molekula je određena 1931. U svojoj prirodnoj, sve-trans formi, molekul je dug i prav, jer je ograničen svojim sistemom od jedanaest konjugovanih dvostrukih veza. Svako produženje ovog konjugovanog sistema umanjuje energiju neophodnu za prelaz elektrona na više energijske nivoe, što omogućava molekulu da apsorbuje vidljivu svetlost na progresivno dužim talasnim dužinama. Likopen apsorbuje svim sem najdužih talasnih dužina vidljive svetlosti, te poprima crvenu boju.^[6]

Biljke i fotosintetičke bakterije prirodno proizvode all-trans likopen. Ukupno je moguće formirati 72 geometrijska izomera ovog molekula.^[7] Pri izlaganju svetlosti ili toploti, likopen podleže izomerizaciji do bilo kog od tih cis-izomera, koji imaju povijen umesto linearnog oblika. Pokazano je da različiti izomeri imaju različite stabilnosti usled njihove molekulske energije (najviša stabilnost: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: najniža).^[8] U ljudskom krvotoku, razni cis-izomeri sačinjavaju više od 60% totalnog sadržaja likopena. Biološki efekti pojedinih izomera nisu istraženi.^[9]

Povezano

Reference

↑ 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
↑ 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
↑ Grossman et al. (2004) pp. 129
↑ Rao et al. (2007) pp. 210
↑ 1054 isomers are theoretically possible, but only 72 are possible due to steric hinderance. IARC Handbook, (1998) pp. 25
↑ Chasse et al. Journal of Molecular Structure: THEOCHEM, Volume 571, Number 1, 27 August 2001 , pp. 27-37(11)[1]
↑ Lycopene: Its role in human health and disease, Rao 'et al.', AGROFood industry hi-tech, July/August 2003 [2] Arhivirano 2012-02-16 na Wayback Machine-u

Literatura

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Basu A, Imrhan V (2007). „Tomatoes versus lycopene in oxidative stress and carcinogenesis: conclusions from clinical trials”. Eur J Clin Nutr 61 (3): 295–303. DOI:10.1038/sj.ejcn.1602510. PMID 16929242.
Berneburg M, Grether-Beck S, Kurten V, Ruzicka T, Briviba K, Sies H, Krutmann J (1999). „Singlet oxygen mediates the UVA-induced generation of the photoaging-associated mitochondrial common deletion”. The Journal of Biological Chemistry 274 (22): 15345-15349. DOI:10.1074/jbc.274.22.15345. PMID 10336420.
Britton, George; Synnove Liaaen-Jensen; Hanspeter Pfander; (1996). Carotenoids : Synthesis (Carotenoids). Boston: Birkhauser. ISBN 3-7643-5297-3.
Cunningham FX, Lee H, Gantt E (2007). „Carotenoid biosynthesis in the primitive red alga Cyanidioschyzon merolae”. Eukaryotic Cell 6 (3): 533–45. DOI:10.1128/EC.00265-06. PMC 1828917. PMID 17085635.
Di Mascio P, Kaiser S, Sies H (1989). „Lycopene as the most efficient biological carotenoid singlet oxygen quencher”. Arch. Biochem. Biophys. 274 (2): 532–8. DOI:10.1016/0003-9861(89)90467-0. PMID 2802626.
Gerster H (1997). „The potential role of lycopene for human health”. J Am Coll Nutr 16 (2): 109–26. PMID 9100211.
Giovannucci E, Ascherio A, Rimm EB, Stampfer MJ, Colditz GA, Willett WC (1995). „Intake of carotenoids and retinol in relation to risk of prostate cancer”. J. Natl. Cancer Inst. 87 (23): 1767–76. DOI:10.1093/jnci/87.23.1767. PMID 7473833.
Grossman AR, Lohr M, Im CS (2004). „Chlamydomonas reinhardtii in the landscape of pigments”. Annu. Rev. Genet. 38 (1): 119–73. DOI:10.1146/annurev.genet.38.072902.092328. PMID 15568974.
IARC Working Group on the Evaluation of Cancer Preventive Agents (1998). IARC Handbooks of Cancer Prevention: Volume 2: Carotenoids (IARC Handbooks of Cancer Prevention). Oxford University Press, USA. str. 25. ISBN 92-832-3002-7.
Khan N, Afaq F, Mukhtar H (2008). „Cancer chemoprevention through dietary antioxidants: progress and promise”. Antioxid. Redox Signal. 10 (3): 475–510. DOI:10.1089/ars.2007.1740. PMID 18154485.
Rao AV, Rao LG (March 2007). „Carotenoids and human health”. Pharmacol. Res. 55 (3): 207–16. DOI:10.1016/j.phrs.2007.01.012. PMID 17349800.
Stahl W, Sies H (1996). „Lycopene: a biologically important carotenoid for humans?”. Arch. Biochem. Biophys. 336 (1): 1–9. DOI:10.1006/abbi.1996.0525. PMID 8951028.
Giovannucci E, Willett WC, Stampfer MJ, Liu Y, Rimm EB (2002). „A prospective study of tomato products, lycopene, and prostate cancer risk”. J. Natl Cancer Inst 94 (5): 391–396.
Levy J, Sharoni Y, Danilenko M, Miinster A, Bosin E, Giat Y, Feldman B (1995). „Lycopene is a more potent inhibitor of human cancer cell proliferation than either alpha-carotene or beta-carotene”. Nutr Cancer 24 (3): 257–266. DOI:10.1080/01635589509514415. PMID 8610045.
Pollack A, Madar Z, Eisner Z, Nyska A, Oren,P (1997). „Inhibitory effect of lycopene on cataract development in galactosemic rats.”. Metab Pediatr Syst Ophthalmol 19 (20): 31–36.
Nahum A, Sharoni Y, Prall OW, Levy J, Hirsch K, Watts CK, Danilenko M (2001). „Lycopene inhibition of cell cycle progression in breast and endometrial cancer cells is associated with reduction in cyclin D levels and retention of p27(Kip1) in the cyclin E-cdk2 complexes”. Oncogene 20 (26): 3428–436. DOI:10.1038/sj.onc.1204452. PMID 11423993.
Narisawa T, Fukaura Y, Hasebe M, Ito M, Nishino H, Khachik F, Murakoshi M, Uemura S, Aizawa R (1996). „Ihibitory effects of natural carotenoids, alpha-carotene, beta-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in rats.”. Cancer Lett 107 (1): 137–142. DOI:10.1016/0304-3835(96)04354-6. PMID 8913278.

Spoljašnje veze

Portal Hemija

Likopen
Prehrambeni izvori likopena Arhivirano 2010-06-05 na Wayback Machine-u

[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] 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

[5] Grossman et al. (2004) pp. 129

[6] Rao et al. (2007) pp. 210

[7] 1054 isomers are theoretically possible, but only 72 are possible due to steric hinderance. IARC Handbook, (1998) pp. 25

[8] Chasse et al. Journal of Molecular Structure: THEOCHEM, Volume 571, Number 1, 27 August 2001 , pp. 27-37(11)[1]

[9] Lycopene: Its role in human health and disease, Rao 'et al.', AGROFood industry hi-tech, July/August 2003 [2] Arhivirano 2012-02-16 na Wayback Machine-u

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