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Pyrrolizidine Alkaloids

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Definition: A group of ALKALOIDS, characterized by a nitrogen-containing necine, occurring mainly in plants of the BORAGINACEAE; COMPOSITAE; and LEGUMINOSAE plant families. They can be activated in the liver by hydrolysis of the ester and desaturation of the necine base to reactive electrophilic pyrrolic CYTOTOXINS.     
Examples Monocrotaline 		Other names Alkaloids, Senecio; Alkaloids, Pyrrolizidine; Senecio Alkaloids
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
acetylnorloline  0   *Pyrrolizidine Alkaloids. Org Lett. 2011 Mar 4;13(5):1246-9
osyrisine  0   *Pyrrolizidine Alkaloids. J Asian Nat Prod Res. 2010 Sep;12(9):814-20
penicinoline  0   *Pyrrolizidine Alkaloids *Quinolones. Bioorg Med Chem Lett 2010 Jun 1;20(11):3284-6
hyacinthacine A3  0   *Pyrrolizidine Alkaloids. Org Biomol Chem 2010 May 7;8(9):2085-91
N-(2-(2-methoxy-6H-dipyrido(2,3-a-3,2-e)pyrrolizin-11-yl)ethyl)-2-furamide  0   *Pyridines *Pyrrolizidine Alkaloids NAD(P)H Dehydrogenase (Quinone)/antagonists & inhibitors. Chem Biol Interact 2010 Jul 30;186(2):103-9
hyacinthacine B7  0   *Pyrrolizidine Alkaloids. Chem Commun (Camb). 2010 Feb 7;46(5):713-5
hyacinthacine B3  0   *Pyrrolizidine Alkaloids. Chem Commun (Camb). 2010 Feb 7;46(5):713-5
5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidine  0   *Pyrrolizidine Alkaloids Acetylglucosaminidase/antagonists & inhibitors. Bioorg Med Chem 2009 Oct 15;17(20):7248-53
adonifoline  0   *Lactones *Pyrrolizidine Alkaloids. J Pharm Biomed Anal 2009 Dec 5;50(5):1070-4
xenovenine  0   *Pyrrolizidine Alkaloids. J Org Chem. 2009 Sep 4;74(17):6784-91
bistellettazine C  0   *Amides *Pyrrolizidine Alkaloids. Org Lett 2008 Oct 2;10(19):4247-50
bistellettazine B  0   *Amides *Pyrrolizidine Alkaloids. Org Lett 2008 Oct 2;10(19):4247-50
bistellettazine A  0   *Amides *Pyrrolizidine Alkaloids. Org Lett 2008 Oct 2;10(19):4247-50
thesinine-O-4'-alpha-rhamnoside  0   *Monosaccharides *Pyrrolizidine Alkaloids. Phytochemistry. 2008 Jun;69(9):1927-32
deacetylclivorine  0   *Pyrrolizidine Alkaloids. Drug Metab Dispos 2007 Apr;35(4):607-13
heliotridane  0   *Pyrrolizidine Alkaloids. Org Lett 2006 May 25;8(11):2249-52
5-chlorobohemamine C  0   *Pyrrolizidine Alkaloids. J Nat Prod 2006 Nov;69(11):1626-8
bohemamine C  0   *Pyrrolizidine Alkaloids. J Nat Prod 2006 Nov;69(11):1626-8
bohemamine B  0   *Pyrrolizidine Alkaloids. J Nat Prod 2006 Nov;69(11):1626-8
amphorogynine D  0   *Pyrrolizidine Alkaloids. J Org Chem 2005 Oct 14;70(21):8352-63
hexahydro-1H-pyrrolizin-1-ylmethyl 1-methyl-1H-indole-3-carboxylate  0   *Indoles *Pyrrolizidine Alkaloids Receptors, Serotonin, 5-HT4/antagonists & inhibitors. J Med Chem 2006 Feb 9;49(3):1125-39
hyacinthacine A1  0   *Pyrrolizidine Alkaloids Stereoisomerism. Org Lett 2005 Jun 23;7(13):2587-90
danaidone  0   *Pyrrolizidine Alkaloids. J Chem Ecol. 2005 Apr;31(4):959-64
cremastrine  0   *Pyrrolizidine Alkaloids. J Nat Prod 2005 Apr;68(4):572-3
hyacinthacine A2  0   *Pyrrolizidine Alkaloids. J Org Chem. 2005 Feb 18;70(4):1459-62
3-hydroxy-cis-nemorensic acid  0   *Furans *Pyrrolizidine Alkaloids. Chem Commun (Camb). 2004 Apr 7;(7):822-3
1-aminopyrrolizidine  0   *Pyrrolizidine Alkaloids. J Org Chem. 2004 Oct 15;69(21):7303-8
isoline  0   *Pyrrolizidine Alkaloids. J Anal Toxicol 2004 Jan-Feb;28(1):11-5
3-(3,4-dihydroxyphenyl)-8H-thieno(2,3-b)pyrrolizin-8-one  0   *Pyrrolizidine Alkaloids. J Med Chem 2004 Mar 11;47(6):1448-64
3-(3-hydroxy-4-methoxyphenyl)-8H-thieno(2,3-b)pyrrolizin-8-one  0   *Pyrrolizidine Alkaloids. J Med Chem 2004 Mar 11;47(6):1448-64
NP 25302  0   *Pyrrolizidine Alkaloids. J Antibiot (Tokyo) 2003 Aug;56(8):673-81
amphorogynine A  0   *Pyrrolizidine Alkaloids. Org Lett. 2003 May 15;5(10):1741-4
UCS1025B  0   *Pyrrolizidine Alkaloids. Org Lett 2002 Dec 12;4(25);4387-90
latifoline  0   *Pyrrolizidine Alkaloids. J Org Chem 2001 Oct 19;66(21):7025-9
9-angeloylhastanecine  0   *Pyrrolizidine Alkaloids. Fitoterapia 2002 Apr;73(2):171-3
erucifoline  0   *Pyrrolizidine Alkaloids. Fitoterapia 2002 Apr;73(2):171-3
nemorensic acid  0   *Furans *Pyrrolizidine Alkaloids. Org Lett 2002 May 16;4(10):1809-11
4-hydroxy-nemorensic acid  0   *Furans *Pyrrolizidine Alkaloids. Org Lett 2002 May 16;4(10):1809-11
turneforcidine  0   *Pyrrolizidine Alkaloids. J Org Chem 2001 Dec 14;66(25):8513-7
chestnutamide  0   *Pyrrolizidine Alkaloids *Indole Alkaloids. J Asian Nat Prod Res 2001;3(2):89-93
symlandine  0   *Pyrrolizidine Alkaloids. J Nat Prod 2001 Feb;64(2):251-3
otosenine  0   *Pyrrolizidine Alkaloids. Fitoterapia 2000 Sep;71(5):615-20
hastanecine  0   *Pyrrolizidine Alkaloids. Org Lett 2001 May 3;3(9):1367-9
rosmarinecine  0   *Pyrrolizidine Alkaloids. Org Lett 2001 May 3;3(9):1367-9
croalbinecine  0   *Pyrrolizidine Alkaloids. J Org Chem 2000 Dec 29;65(26):9249-51
pyrrolam A  0   *Pyrrolizidine Alkaloids. Yakugaku Zasshi 2000 Oct;120(10):1035-50
otonecine  0   *Pyrrolizidine Alkaloids. J Nat Prod 2000 Jun;63(6):857-60
epiaustraline  0   *Pyrrolizidine Alkaloids Stereoisomerism. J Org Chem 2000 May 19;65(10):2887-96
UCS 1025A  0   *Pyrrolizidine Alkaloids. J Antibiot (Tokyo) 2000 Mar;53(3):294-6
BE 54238B  0   *Pyrrolizidine Alkaloids. J Antibiot (Tokyo) 2000 Jan;53(1):26-32
BE 54238A  0   *Pyrrolizidine Alkaloids. J Antibiot (Tokyo) 2000 Jan;53(1):26-32
(hexahydro-5-oxo-1H-pyrrolizinyl-1-yl)acetic acid  0   *Acetic Acids *Pyrrolizidine Alkaloids. Acta Crystallogr C 1999 Jan 15;55( Pt 1):84-7
megalanthonine  0   *Pyrrolizidine Alkaloids. J Nat Prod 1998 Nov;61(11):1418-20
spiropyrrolizidine oxime 222  0   *Pyrrolizidine Alkaloids. Biochem Pharmacol 1996 Sep 27;52(6):933-9
spiropyrrolizidine oxime 236  0   *Pyrrolizidine Alkaloids. Biochem Pharmacol 1996 Sep 27;52(6):933-9
talarotoxin  0   *Pyrrolizidine Alkaloids Mycotoxins. Appl Environ Microbiol 1995 Mar;61(3):941-3
PF 1018  131256-42-3   *Pyrrolizidine Alkaloids. J Antibiot (Tokyo) 1994 May;47(5):571-80
glutathione-jacobine conjugate  0   *Pyrrolizidine Alkaloids Glutathione/*analogs & derivatives. Biochem Biophys Res Commun 1994 Jan 28;198(2):516-22
acetylanonamine  138079-62-6 4,8-Secosenecionan-8,11,16-trione, 21-(acetyloxy)-12-hydroxy-4-methyl-, (15E)  *Pyrrolizidine Alkaloids. J Nat Prod 1991 Sep-Oct;54(5):1425-6
hydroxydanaidal  34199-35-4   *Pyrrolizidine Alkaloids Moths. Proc Natl Acad Sci U S A 1991;88(20):9224
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
Warning: the drugs or drug combinations referred to here may be similar or related, but are not be the same ones and may not have the same pharmacological action as other substances described on the same page or in the same row. Please refer to product monograph or to your doctor
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