Annonacin

Annonacin
Mga pangalan
	Pangalang IUPAC (5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13- [(2R,5R)-5-[(1R)-1- hydroxytridecyl]-2-tetrahydrofuranyl] tridecyl]-5H-furan-2-one
Mga pangkilala
Bilang ng CAS	111035-65-5;
Modelong 3D (JSmol)	Interactive image; Interactive image;
ChemSpider	314587 ;
PubChem CID	354398;
Dashboard ng CompTox (EPA)	DTXSID20892989 ;
	InChI InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1 Key: XNODZYPOIPVPRF-CGWDHHCXSA-N ; InChI=1/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1 Key: XNODZYPOIPVPRF-CGWDHHCXBQ;
	SMILES CCCCCCCCCCCCC(C1CCC(O1)C(CCCCC(CCCCCC(CC2=CC(OC2=O)C)O)O)O)O; O=C\1O[C@H](/C=C/1C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCC)CC2)C;
Mga pag-aaring katangian
Pormulang kemikal	C35H64O7
Bigat ng molar	596.88 g/mol
	Maliban kung saan nabanggit, binigay ang datos para sa mga materyales sa kanilang estadong pamantayan (sa 25 °C [77 °F], 100 kPa). patunayan (ano ang ?) Mga sanggunian ng Infobox

Ang annocin ay isang kemikal na natatagpuan sa ilang mga prutas gaya ng guyabano gayundin sa iba pang mga prutas mula sa pamilya Annonaceae. Ang isang pagsasaliksik na isinagawa sa Caribbean ay nagmungkahi ng koneksiyon sa pagitan ng pagkain ng guyabano at atipikal(hindi karaniwan) na mga anyo ng sakit na Parkinson sanhi ng sobrang taas na konsentrasyon ng annonacin. ^[1]^[2]^[3]^[4] Ang mga pagsasaliksik ay nagpakitang ang araw araw na konsumpsiyon(pagkain) sa mga daga(3.8 at 7.6 mg kada kg kada araw sa loob ng 28 araw) ng guyabano ay nagsanhi ng mga lesyon sa utak ng mga ito na konsistente sa sakit na Parkinson.^[5] ^[6]

Kasama ng ilang mga acetogenin, ang annonacin ay iniulat na humaharang ng mitochondrial complex I (NADH-dehydrogenase) na responsable sa konbersiyon ng NADH sa NAD⁺ at sa pagpuno ng proton gradient sa ibabaw ng panloob na membrano ng mitochondria(mitochondrial inner membrane). Ito ay epektibong nagsasara ng kakayahan ng isang selula na lumikha ng ATP sa pamamagitan ng landas oxidatibo na sa huli ay pumupwersa sa isang selula sa isang apoptosis(natural na kamatayan ng selula) o necrosis(kamatayan sanhi ng panlabas na paktor).^[7]

Sanggunian

↑ Lannuzel, A; atbp. (2003-10-06). "The mitochondrial complex i inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism". Neuroscience. International Brain Research Organization. 121 (2): 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988. {{cite journal}}: Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)
↑ Champy, Pierre; atbp. (2005-08-02). "Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe". Movement Disorders. 20 (12): 1629–1633. doi:10.1002/mds.20632. PMID 16078200. {{cite journal}}: Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)
↑ Lannuzel A, Höglinger GU, Champy P, Michel PP, Hirsch EC, Ruberg M. (2006). "Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae?". J Neural Transm Suppl. Journal of Neural Transmission. Supplementa. 70 (70): 153–7. doi:10.1007/978-3-211-45295-0_24. ISBN 978-3-211-28927-3. PMID 17017523.{{cite journal}}: CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)
↑ Caparros-Lefebvre D, Elbaz A. (1999-07-24). "Possible relation of atypical parkinsonism in the French West Indies with consumption of tropical plants: a case-control study". Lancet. 354 (9175): 281–6. doi:10.1016/S0140-6736(98)10166-6. PMID 10440304.{{cite journal}}: CS1 maint: date auto-translated (link)
↑ Lannuzel, A; atbp. (6 Oktubre 2003). "The mitochondrial complex i inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism". Neuroscience. International Brain Research Organization. 121 (2): 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988. {{cite journal}}: |access-date= requires |url= (tulong); Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)
↑ Champy, Pierre; Hoeglinger, Guenter U.; Feger, Jean; Gleye, Christophe; Hocquemiller, Reynald; Laurens, Alain; Guerineau, Vincent; Laprevote, Olivier; Medja, Fadia; Lombes, Anne; Michel, Patrick P.; Lannuzel, Annie; Hirsch, Etienne C.; Ruberg, Merle (2004). "Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: Possible relevance for atypical parkinsonism in Guadeloupe". Journal of Neurochemistry. 88 (1): 63–69. doi:10.1046/j.1471-4159.2003.02138.x. PMID 14675150.{{cite journal}}: CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)
↑ McLaughlin, J.L. Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products. J. Nat. Prod. 2008, 71, 1311-1321 and references cited

[health_parkinsons1-1] Lannuzel, A; atbp. (2003-10-06). "The mitochondrial complex i inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism". Neuroscience. International Brain Research Organization. 121 (2): 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988. {{cite journal}}: Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)

[2] Champy, Pierre; atbp. (2005-08-02). "Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe". Movement Disorders. 20 (12): 1629–1633. doi:10.1002/mds.20632. PMID 16078200. {{cite journal}}: Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)

[3] Lannuzel A, Höglinger GU, Champy P, Michel PP, Hirsch EC, Ruberg M. (2006). "Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae?". J Neural Transm Suppl. Journal of Neural Transmission. Supplementa. 70 (70): 153–7. doi:10.1007/978-3-211-45295-0_24. ISBN 978-3-211-28927-3. PMID 17017523.{{cite journal}}: CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)

[4] Caparros-Lefebvre D, Elbaz A. (1999-07-24). "Possible relation of atypical parkinsonism in the French West Indies with consumption of tropical plants: a case-control study". Lancet. 354 (9175): 281–6. doi:10.1016/S0140-6736(98)10166-6. PMID 10440304.{{cite journal}}: CS1 maint: date auto-translated (link)

[health_parkinsons2-5] Lannuzel, A; atbp. (6 Oktubre 2003). "The mitochondrial complex i inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism". Neuroscience. International Brain Research Organization. 121 (2): 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988. {{cite journal}}: |access-date= requires |url= (tulong); Explicit use of et al. in: |author2= (tulong)CS1 maint: date auto-translated (link)

[6] Champy, Pierre; Hoeglinger, Guenter U.; Feger, Jean; Gleye, Christophe; Hocquemiller, Reynald; Laurens, Alain; Guerineau, Vincent; Laprevote, Olivier; Medja, Fadia; Lombes, Anne; Michel, Patrick P.; Lannuzel, Annie; Hirsch, Etienne C.; Ruberg, Merle (2004). "Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: Possible relevance for atypical parkinsonism in Guadeloupe". Journal of Neurochemistry. 88 (1): 63–69. doi:10.1046/j.1471-4159.2003.02138.x. PMID 14675150.{{cite journal}}: CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)

[7] McLaughlin, J.L. Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products. J. Nat. Prod. 2008, 71, 1311-1321 and references cited

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