Agaritin - Povijest promjena

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	~~<!--'''Agaritin'''-->~~{{Infookvir kemijski spoj		{{Infookvir kemijski spoj
	\| formula = <chem> C12H17N3O4 </chem>		\| formula = <chem> C12H17N3O4 </chem>
	\| slika = Agaritine.svg		\| slika = Agaritine.svg

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	'''Agaritin''' je [[otrov]]ni [[Kemijski spojevi\|kemijski spoj]] za koji se vjeruje da je [[kancerogen]], a nalazi se u [[Jestive gljive\|jestivim gljivama]] koje treba kuhati ili bar osušiti da bi se neutralizirao (pogotovo [[pečurke]] ili rod ''[[Agaricus]]''). <ref name="Missingor">{{cite journal \|pmid=2132000 \|year=1990 \|last1=Hashida \|first1=C \|last2=Hayashi \|first2=K \|last3=Jie \|first3=L \|last4=Haga \|first4=S \|last5=Sakurai \|first5=M \|last6=Shimizu \|first6=H \|title=[Quantities of agaritine in mushrooms (Agaricus bisporus) and the carcinogenicity of mushroom methanol extracts on the mouse bladder epithelium] \|volume=37 \|issue=6 \|pages=400–5 \|journal=[Nihon Koshu Eisei Zasshi] Japanese Journal of Public Health}}</ref> <ref>{{cite journal \|id= 17950755 \|doi=10.1248/cpb.54.922 \|pmid=16755074 \|title=Measurement of a Genotoxic Hydrazine, Agaritine, and Its Derivatives by HPLC with Fluorescence Derivatization in the Agaricus Mushroom and Its Products \|year=2006 \|last1=Nagaokaa \|first1=Megumi Hamano \|last2=Nagaoka \|first2=Hiroaki \|last3=Kondo \|first3=Kazunari \|last4=Akiyama \|first4=Hiroshi \|last5=Maitani \|first5=Tamio \|journal=Chemical & Pharmaceutical Bulletin \|volume=54 \|issue=6 \|pages=922–4\|doi-access=free }}</ref> Studije su pronašle značajnu (više od 1 000 mg/kg) agaritina u svježim uzorcima najmanje 24 vrste rodova ''Agaricus'', ''[[Turkinja\|Leucoagaricus]]'' i ''[[Velika sunčanica\|Macrolepiota]]''. <ref name=one>{{cite journal \|doi=10.1080/02652030802039903 \|title=Agaritine content of 53 ''Agaricus'' species collected from nature \|year=2009 \|last1=Schulzová \|first1=V. \|last2=Hajslova \|first2=J. \|last3=Peroutka \|first3=R. \|last4=Hlavasek \|first4=J. \|last5=Gry \|first5=J. \|last6=Andersson \|first6=H.C. \|journal=Food Additives & Contaminants: Part A \|volume=26 \|issue=1 \|pages=82–93 \|pmid=19680875\|s2cid=427230 \|url=https://hal.archives-ouvertes.fr/hal-00577390/file/PEER_stage2_10.1080%252F02652030802039903.pdf }}</ref> Gljive ovih vrsta nalaze se širom svijeta, pogotovo samo jedna vrsta - [[plemenita pečurka]] ili [[šampinjon]] (lat. ''Agaricus bisporus''), koja se uzgaja u preko 70 država i na svim kontinentima, osim na [[Antarktik]]u. <ref name=three>{{~~cite book~~ \|last1=Hayes \|first1=W. A. \|last2=Chang \|first2=S. T. \|title=The Biology and cultivation of edible mushrooms \|publisher=Academic Press \|year=1978 \|isbn=978-0-12-168050-3 \|url=http://www.sciencedirect.com/science/book/9780121680503}}<!-- {{page needed\|date=December 2013}} --></ref>		'''Agaritin''' je [[otrov]]ni [[Kemijski spojevi\|kemijski spoj]] za koji se vjeruje da je [[kancerogen]], a nalazi se u [[Jestive gljive\|jestivim gljivama]] koje treba kuhati ili bar osušiti da bi se neutralizirao (pogotovo [[pečurke]] ili rod ''[[Agaricus]]''). <ref name="Missingor">{{cite journal \|pmid=2132000 \|year=1990 \|last1=Hashida \|first1=C \|last2=Hayashi \|first2=K \|last3=Jie \|first3=L \|last4=Haga \|first4=S \|last5=Sakurai \|first5=M \|last6=Shimizu \|first6=H \|title=[Quantities of agaritine in mushrooms (Agaricus bisporus) and the carcinogenicity of mushroom methanol extracts on the mouse bladder epithelium] \|volume=37 \|issue=6 \|pages=400–5 \|journal=[Nihon Koshu Eisei Zasshi] Japanese Journal of Public Health}}</ref> <ref>{{cite journal \|id= 17950755 \|doi=10.1248/cpb.54.922 \|pmid=16755074 \|title=Measurement of a Genotoxic Hydrazine, Agaritine, and Its Derivatives by HPLC with Fluorescence Derivatization in the Agaricus Mushroom and Its Products \|year=2006 \|last1=Nagaokaa \|first1=Megumi Hamano \|last2=Nagaoka \|first2=Hiroaki \|last3=Kondo \|first3=Kazunari \|last4=Akiyama \|first4=Hiroshi \|last5=Maitani \|first5=Tamio \|journal=Chemical & Pharmaceutical Bulletin \|volume=54 \|issue=6 \|pages=922–4\|doi-access=free }}</ref> Studije su pronašle značajnu (više od 1 000 mg/kg) agaritina u svježim uzorcima najmanje 24 vrste rodova ''Agaricus'', ''[[Turkinja\|Leucoagaricus]]'' i ''[[Velika sunčanica\|Macrolepiota]]''. <ref name=one>{{cite journal \|doi=10.1080/02652030802039903 \|title=Agaritine content of 53 ''Agaricus'' species collected from nature \|year=2009 \|last1=Schulzová \|first1=V. \|last2=Hajslova \|first2=J. \|last3=Peroutka \|first3=R. \|last4=Hlavasek \|first4=J. \|last5=Gry \|first5=J. \|last6=Andersson \|first6=H.C. \|journal=Food Additives & Contaminants: Part A \|volume=26 \|issue=1 \|pages=82–93 \|pmid=19680875\|s2cid=427230 \|url=https://hal.archives-ouvertes.fr/hal-00577390/file/PEER_stage2_10.1080%252F02652030802039903.pdf }}</ref> Gljive ovih vrsta nalaze se širom svijeta, pogotovo samo jedna vrsta - [[plemenita pečurka]] ili [[šampinjon]] (lat. ''Agaricus bisporus''), koja se uzgaja u preko 70 država i na svim kontinentima, osim na [[Antarktik]]u. <ref name=three>{{Citiranje knjige \|last1=Hayes \|first1=W. A. \|last2=Chang \|first2=S. T. \|title=The Biology and cultivation of edible mushrooms \|publisher=Academic Press \|year=1978 \|isbn=978-0-12-168050-3 \|url=http://www.sciencedirect.com/science/book/9780121680503}}<!-- {{page needed\|date=December 2013}} --></ref>

	== Objašnjenje ==		== Objašnjenje ==

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2021-12-11T09:58:15Z

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{{Infookvir kemijski spoj
| formula = <chem> C12H17N3O4 </chem>
| slika = Agaritine.svg
| slika_opis = Kemijska struktura agaritina
| slika1 = Agaritine 3d structure.png
| slika_opis1 =
| IUPAC nomenklatura = 2-[4-(hidroksimetil)fenil]-glutamohidrazid
| ostala imena = Agaritin
| CAS = 2757-90-6
| EC =
| UN =
| RTECS = MA1284000
| molarna masa = 267,285 g·mol−1
| molekulska masa =
| izgled =
| gustoća =
| tališteK =
| tališteC = 203 °C
| vrelišteK =
| vrelišteC =
| tlak para =
| topljivost =
| dipolni moment =
| slika2 =
| slika_opis2 =
| oblik molekule =
| izvor znkops =
| znakovi opasnosti = Otrovan
| NFPA 704 =
}}

'''Agaritin''' je [[otrov]]ni [[Kemijski spojevi|kemijski spoj]] za koji se vjeruje da je [[kancerogen]], a nalazi se u [[Jestive gljive|jestivim gljivama]] koje treba kuhati ili bar osušiti da bi se neutralizirao (pogotovo [[pečurke]] ili rod ''[[Agaricus]]''). <ref name="Missingor">{{cite journal |pmid=2132000 |year=1990 |last1=Hashida |first1=C |last2=Hayashi |first2=K |last3=Jie |first3=L |last4=Haga |first4=S |last5=Sakurai |first5=M |last6=Shimizu |first6=H |title=[Quantities of agaritine in mushrooms (Agaricus bisporus) and the carcinogenicity of mushroom methanol extracts on the mouse bladder epithelium] |volume=37 |issue=6 |pages=400–5 |journal=[Nihon Koshu Eisei Zasshi] Japanese Journal of Public Health}}</ref> <ref>{{cite journal |id= 17950755 |doi=10.1248/cpb.54.922 |pmid=16755074 |title=Measurement of a Genotoxic Hydrazine, Agaritine, and Its Derivatives by HPLC with Fluorescence Derivatization in the Agaricus Mushroom and Its Products |year=2006 |last1=Nagaokaa |first1=Megumi Hamano |last2=Nagaoka |first2=Hiroaki |last3=Kondo |first3=Kazunari |last4=Akiyama |first4=Hiroshi |last5=Maitani |first5=Tamio |journal=Chemical & Pharmaceutical Bulletin |volume=54 |issue=6 |pages=922–4|doi-access=free }}</ref> Studije su pronašle značajnu (više od 1 000 mg/kg) agaritina u svježim uzorcima najmanje 24 vrste rodova ''Agaricus'', ''[[Turkinja|Leucoagaricus]]'' i ''[[Velika sunčanica|Macrolepiota]]''. <ref name=one>{{cite journal |doi=10.1080/02652030802039903 |title=Agaritine content of 53 ''Agaricus'' species collected from nature |year=2009 |last1=Schulzová |first1=V. |last2=Hajslova |first2=J. |last3=Peroutka |first3=R. |last4=Hlavasek |first4=J. |last5=Gry |first5=J. |last6=Andersson |first6=H.C. |journal=Food Additives & Contaminants: Part A |volume=26 |issue=1 |pages=82–93 |pmid=19680875|s2cid=427230 |url=https://hal.archives-ouvertes.fr/hal-00577390/file/PEER_stage2_10.1080%252F02652030802039903.pdf }}</ref> Gljive ovih vrsta nalaze se širom svijeta, pogotovo samo jedna vrsta - [[plemenita pečurka]] ili [[šampinjon]] (lat. ''Agaricus bisporus''), koja se uzgaja u preko 70 država i na svim kontinentima, osim na [[Antarktik]]u. <ref name=three>{{cite book |last1=Hayes |first1=W. A. |last2=Chang |first2=S. T. |title=The Biology and cultivation of edible mushrooms |publisher=Academic Press |year=1978 |isbn=978-0-12-168050-3 |url=http://www.sciencedirect.com/science/book/9780121680503}}</ref>

== Objašnjenje ==
Sadržaj agaritina se razlikuje između pojedinih [[gljive|gljiva]] i među vrstama. Sadržaj agaritina (% svježe mase) u sirovom ''[[Agaricus bisporus]]'', na primjer, kreće se od 0,033% do 0,173%, s prosjekom od 0,088%. <ref name=four>{{cite journal |doi=10.1111/j.1365-2621.1982.tb04978.x |title=Agaritine Content of Fresh and Processed Mushrooms [''Agaricus bisporus'' (Lange) Imbach] |year=1982 |last1=Liu |first1=J.-W. |last2=Beelman |first2=R. B. |last3=Lineback |first3=D. R. |last4=Speroni |first4=J. J. |journal=Journal of Food Science |volume=47 |issue=5 |pages=1542–4}}</ref> Najveća količina agaritina nalazi se u [[Klobuk (gljiva)|klobuku]] i listićima ispod, a najmanja u [[Stručak (mikologija)|stručku]]. <ref name=five>{{cite journal |doi=10.1016/S0015-6264(82)80226-5 |title=Occurrence, stability and decomposition of ''β''-''n''[''γ''-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom ''Agaricus bisporus'' |year=1982 |last1=Ross |first1=A.E. |last2=Nagel |first2=D.L. |last3=Toth |first3=B. |journal=Food and Chemical Toxicology |volume=20 |issue=6 |pages=903–7 |pmid=6131022}}</ref> Agaritin brzo [[oksidacija|oksidira]] nakon skladištenja, a nakon 48 sati potpuno se razgrađuje u [[voda|vodenoj]] [[otopina|otopini]] uz izlaganje [[zrak]]u. <ref name=six>{{cite journal |doi=10.1080/02652030210157691 |title=Stability of agaritine - a natural toxicant ofAgaricusmushrooms |year=2002 |last1=Hajšlová |first1=J. |last2=Hájková |first2=L. |last3=Schulzová |first3=V. |last4=Frandsen |first4=H. |last5=Gry |first5=J. |last6=Andersson |first6=H. C. |journal=Food Additives and Contaminants |volume=19 |issue=11 |pages=1028–33 |pmid=12456273|s2cid=19357429 }}</ref> Također se pokazalo da se lako razgrađuje nakon [[Kuhanje|kuhanja]] (smanjenje do 90%), kao i zamrzavanjem (smanjenje do 75%). <ref name=seven>{{cite journal |doi=10.1080/02652030210156340 |title=Influence of storage and household processing on the agaritine content of the cultivatedAgaricusmushroom |year=2002 |last1=Schulzová |first1=V. |last2=Hajslová |first2=J. |last3=Peroutka |first3=R. |last4=Gry |first4=J. |last5=Andersson |first5=H. C. |journal=Food Additives and Contaminants |volume=19 |issue=9 |pages=853–62 |pmid=12396396|s2cid=23953741 }}</ref>
Dokazano je da agaritin potiče stvaranje [[adenom]]e ([[benigan|benigni]] ili blagi [[tumor]] žljezdanog tkiva, na primjer dojke, prostate; može se pretvoriti u [[Rak (bolest)|maligni]]) i adeno[[karcinom]]e u plućima miševa kada se daju putem vode za piće. <ref>{{cite journal |pmid=563287 |year=1978 |last1=Toth |first1=Bela |last2=Nagel |first2=Donald |last3=Patil |first3=Kashinath |last4=Erickson |first4=James |last5=Antonson |first5=Kenneth |title=Tumor induction with the N'-acetyl derivative of 4-hydroxymethyl-phenylhydrazine, a metabolite of agaritine of Agaricus bisporus |volume=38 |issue=1 |pages=177–80 |journal=Cancer Research |url=http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=563287}}</ref> Također se pokazalo da uzrokuje rak mokraćnog mjehura kod miševa. Tvrdi se da je agaritin slabo karcinogen, s procjenom kumulativnog životnog rizika od konzumacije gljiva na približno 1 na 10 000. <ref>{{cite journal |doi=10.1016/0278-6915(94)00142-B |title=Genotoxicity of agaritine in the lacI transgenic mouse mutation assay: Evaluation of the health risk of mushroom consumption |year=1995 |last1=Shephard |first1=S.E. |last2=Gunz |first2=D. |last3=Schlatter |first3=C. |journal=Food and Chemical Toxicology |volume=33 |issue=4 |pages=257–64 |pmid=7737599}}</ref> Međutim, ova je tvrdnja slabo podržana, s malo dostupnih podataka o otrovnosti i bez objavljenog LD50 (smrtna doza). <ref>{{cite journal |pmid=7201775 |year=1981 |last1=Toth |first1=B |last2=Raha |first2=CR |last3=Wallcave |first3=L |last4=Nagel |first4=D |title=Attempted tumor induction with agaritine in mice |volume=1 |issue=5 |pages=255–8 |journal=Anticancer Research}}</ref>

Pokazalo se da agaritin ima pozitivan test kao [[Mutacija|mutagen]] u [[Amesov test|Amesovom testu]] i mutagenizira [[DNA]] u [[bakterija|bakteriji]] ''[[Salmonella]] typhimurium''. <ref name="Walton, K. 1997">{{cite journal |doi=10.1093/carcin/18.8.1603 |title=Bioactivation of the mushroom hydrazine, agaritine, to intermediates that bind covalently to proteins and induce mutations in the Ames test |year=1997 |last1=Walton |first1=K |journal=Carcinogenesis |volume=18 |issue=8 |pages=1603–8 |pmid=9276636 |last2=Coombs |first2=MM |last3=Catterall |first3=FS |last4=Walker |first4=R |last5=Ioannides |first5=C|doi-access=free }}</ref> Također se pokazalo da se [[Kovalentna veza|kovalentno veže]] za DNA ''in vivo''. <ref>{{cite journal |doi=10.1016/0165-1218(82)90104-5 |pmid=6757742 |title=Microbial mutagenicity of selected hydrazines |year=1982 |last1=Rogan |first1=Eleanor G. |last2=Walker |first2=Betty A. |last3=Gingell |first3=Ralph |last4=Nagel |first4=Donald L. |last5=Toth |first5=Bela |journal=Mutation Research/Genetic Toxicology |volume=102 |issue=4 |pages=413–24}}</ref> It has also been shown to covalently bind to DNA ''in vivo''.<ref>{{cite journal |doi=10.1016/S0278-6915(98)00076-3 |title=Covalent Binding of Agaritine to DNA in Vivo |year=1998 |last1=Shephard |first1=S.E |last2=Schlatter |first2=C |journal=Food and Chemical Toxicology |volume=36 |issue=11 |pages=971–4 |pmid=9771560}}</ref> Pokazalo se da [[enzim]]i u [[Bubreg|bubrezima]] životinja agaritin razgrađuju u otrovne [[metabolizam|metabolite]] 4-(hidroksimetil)fenilhidrazin i 4-(hidroksimetil)benzendiazonijeve ione. Pokazalo se da ti metaboliti uzrokuju rak želuca kod miševa <ref>{{cite journal |doi=10.1038/bjc.1982.218 |title=Gastric tumorigenesis by a single dose of 4-(hydroxymethyl)benzenediazonium ion of Agaricus bisporus |year=1982 |last1=Toth |first1=B |last2=Nagel |first2=D |last3=Ross |first3=A |journal=British Journal of Cancer |volume=46 |issue=3 |pages=417–22 |pmid=6889885 |pmc=2011129}}</ref> i uzrokuju trajno oštećenje DNA nakon jedne doze kod miševa. <ref>{{cite journal |doi=10.1016/j.fct.2007.10.022 |title=The metabolisms of agaritine, a mushroom hydrazine in mice |year=2008 |last1=Kondo |first1=Kazunari |last2=Watanabe |first2=Asako |last3=Akiyama |first3=Hiroshi |last4=Maitani |first4=Tamio |journal=Food and Chemical Toxicology |volume=46 |issue=3 |pages=854–62 |pmid=18061328}}</ref> Mutagena aktivnost [[Diazo-spojevi|diazonijevog]] [[ion]]a posljedica je njegove reakcije s [[kisik]]om pri čemu nastaje [[vodikov peroksid]], koji zatim kovalentno modificira DNA putem radikalnog mehanizma. <ref name=twelve>{{cite journal |doi=10.1016/0027-5107(68)90004-3 |pmid=5727268 |title=DNA damage caused by antidepressant hydrazines and related drugs |year=1968 |last1=Freese |first1=Ernst |last2=Sklarow |first2=Stephen |last3=Freese |first3=Elisabeth Bautz |journal=Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis |volume=5 |issue=3 |pages=343–8}}</ref>

Ekstrakti [[gljive|gljiva]] iz roda ''[[Agaricus]]'' generacijama se koriste kao tradicionalni [[kina|kineski]] biljni [[lijek]]ovi. <ref>{{cite journal |doi=10.2174/156802608786786633 |title=Drug Candidates from Traditional Chinese Medicines |year=2008 |last1=Wang |first1=Jing-Fang |last2=Wei |first2=Dong-Qing |last3=Chou |first3=Kuo-Chen |journal=Current Topics in Medicinal Chemistry |volume=8 |issue=18 |pages=1656–65 |pmid=19075772}}</ref> Pokazalo se da neki od ovih ekstrakata posjeduju anti[[virus]]na svojstva, a istražitelji su identificirali agaritin kao istaknuti spoj u ekstraktima. <ref>{{cite journal |doi=10.2174/157341208783497551 |title=Agaricus blazei Water Extracts as Alternative Medicines |year=2008 |last1=Sorimachi |first1=Kenji |last2=Koge |first2=Takashi |journal=Current Pharmaceutical Analysis |volume=4 |pages=39–43}}</ref> To je vodilo istraživače da istraže potencijalna antivirusna svojstva agaritina, a testovi pristajanja pokazali su da je molekula snažan inhibitor HIV proteaze. Istraživanje računalnog modeliranja provedeno je u pokušaju optimizacije vezanja za potencijalnu upotrebu kao lijek protiv [[HIV]]-a.

== Diazo-spojevi ==
{{glavni|Diazo-spojevi}}

'''Diazo-spojevi''' (di: dva + azo-, od [[Francuski jezik|franc]]. ''azote'': dušik) su [[organski spojevi]] u kojima je skupina –N2 vezana jednim [[dušik]]ovim [[atom]]om na [[ugljik]]ov atom, a dušikovi su atomi međusobno povezani dvostrukom ili trostrukom [[Kemijska veza|kemijskom vezom]]. Vrlo su [[Kemijska reakcija|reaktivni]] i služe za pripravu [[tehnika|tehnički]] važnih [[Kemijski spojevi|kemijskih spojeva]]. Najjednostavniji je alifatski diazo-spoj diazometan, CH2N2, žut, [[eksploziv]]an i [[otrov]]an [[plin]] neugodna [[miris]]a, čest [[reagens]] u [[Organska kemija|organskoj kemiji]], a najčešće se upotrebljava u [[Eteri|eterskoj]] [[otopina|otopini]]. Među aromatskim diazo-spojevima ističu se [[diazonijeve soli]], važne u proizvodnji [[azo-bojila]]. <ref> '''diazo-spojevi''', [http://www.enciklopedija.hr/Natuknica.aspx?ID=14958] "Hrvatska enciklopedija", mrežno izdanje, Leksikografski zavod Miroslav Krleža, www.enciklopedija.hr, pristupljeno 18. 7. 2020. </ref>

== Izvori ==
{{izvori}}

[[Kategorija:Organska kemija]]
[[Kategorija:Jestive gljive]]