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Pyrrolizidine alkaloid

May 03, 2023

Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than 660 PAs and PA N-oxides have been identified in over 6,000 plants, and about half of them exhibit hepatotoxicity.[1] They are found frequently in plants in the Boraginaceae, Asteraceae, Orchidaceae and Fabaceae families; less frequently in the Convolvulaceae and Poaceae, and in at least one species in the Lamiaceae. It has been estimated that 3% of the world’s flowering plants contain pyrrolizidine alkaloids.[2] Honey can contain pyrrolizidine alkaloids,[3][4] as can grains, milk, offal and eggs.[5] To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines.[6][7]

Skeletal formula of retronecine, a pyrrolizidine alkaloid found in the common groundsel (Senecio vulgaris) and comfrey (Symphytum spp.)

Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver.[8][9] PAs also cause hepatic veno-occlusive disease and liver cancer.[10] PAs are tumorigenic.[11] Disease associated with consumption of PAs is known as pyrrolizidine alkaloidosis.

In humans, the use of medicinal herbs containing PAs, notably borage leaf, comfrey and coltsfoot in the West, and some Chinese medicinal herbs, has been shown to pose health risks.[11] The degree of toxicity can vary based on age and gender, with fetuses and neonates showing high sensitivity, including instances of death. [12]

Some ruminant animals, for example cattle, show no change in liver enzyme activities or any clinical signs of poisoning when fed low concentrations of plants containing pyrrolizidine alkaloids.[13] Yet, Australian studies have demonstrated toxicity.[14] Sheep and goats especially, and to a lesser degree cattle, are much more resistant and tolerate much higher PA dosages, thought to be due to thorough detoxification via PA-destroying rumen microbes. [12]

PA is also used as a defense mechanism by some organisms such as Utetheisa ornatrix. Utetheisa ornatrix caterpillars obtain these toxins from their food plants and use them as a deterrent for predators. PAs protect them from most of their natural enemies. The toxins stay in these organisms even when they metamorphose into adult moths, continuing to protect them throughout their adult stage.[15]

Ecology

Main article: Pyrrolizidine alkaloid sequestration

Many plants contain pyrrolizidine alkaloids, and in turn there are many insects which consume the plants and build up the alkaloids in their bodies.[16] For example, male queen butterflies utilize pyrrolizidine alkaloids to produce pheromones useful for mating.[17] The butterfly Danaus chrysippus is known to obtain pyrrolizidine alkaloids in their diet and store these chemicals, making them toxic and unpalatable to predators.[18] Greta oto, the glasswing butterfly, uses pyrrolizidine alkaloids for both toxicity in the adult moth and pheromone production in the male butterfly. The garden tiger moth also stores these compounds as a caterpillar, using them for larval (through the use of spines) and adult defense (in the form of a spray and bad taste).[19]

Plants species containing pyrrolizidine alkaloids

This is a dynamic list and may never be able to satisfy particular standards for completeness. You can help by adding missing items with reliable sources.

The effect of PAs in humans, that is PAILDs (Pyrrolizidine Alkaloid Induced Liver Diseases),[28] of epidemic proportions was recorded after a long field-level epidemiological investigation in the northern region of Ethiopia-Tigray.[29]

Classification

One classification is based on the substitution pattern of the pyrrolizidine ring. This part of the structure is normally referred to as necine bases. The three largest groups are based on the three necine bases platynecine, heliotridine and retronecine.

  •  

    Platynecine

  •  

    Heliotridine

  •  

    Retronecine

References

  1. ^ Radominska-Pandya, A (2010). "Invited Speakers". Drug Metabolism Reviews. 42 (S1): 1–2. doi:10.3109/03602532.2010.506057. PMID 20842800.
  2. ^ Smith, L. W.; Culvenor, C. C. J. (1981). "Plant sources of hepatotoxic pyrrolizidine alkaloids". J. Nat. Prod. 44 (2): 129–15. doi:10.1021/np50014a001. PMID 7017073.
  3. ^ Kempf, M; Reinhard, A; Beuerle, T (Jan 2010). "Pyrrolizidine alkaloids (PAs) in honey and pollen-legal regulation of PA levels in food and animal feed required". Mol Nutr Food Res. 54 (1): 158–68. doi:10.1002/mnfr.200900529. PMID 20013889.
  4. ^ Edgar, John A.; Roeder, Erhard; Molyneux, Russell J. (2002). "Honey from Plants Containing Pyrrolizidine Alkaloids: A Potential Threat to Health". J. Agric. Food Chem. 50 (10): 2719–2730. doi:10.1021/jf0114482. PMID 11982390.
  5. ^ (PDF). Archived from the original (PDF) on 2009-10-14.
  6. ^ Coulombe, Roger A. Jr (2003). "Pyrrolizidine alkaloids in foods". Advances in Food and Nutrition Research Volume 45. Advances in Food and Nutrition Research. Vol. 45. pp. 61–99. doi:10.1016/S1043-4526(03)45003-1. ISBN 9780120164455. PMID 12402679.
  7. ^ German Commission E monographs
  8. ^ "Foodborne Pathogenic Microorganisms and Natural Toxins Handbook: Pyrrolizidine Alkaloids". Bad Bug Book. United States Food and Drug Administration. Retrieved 2009-07-11.
  9. ^ Schoental, R.; Kelly, JS (April 1959). "Liver lesions in young rats suckled by mothers treated with the pyrrolizidine (Senecio) alkaloids, lasiocarpine and retrorsine". The Journal of Pathology and Bacteriology. 77 (2): 485–495. doi:10.1002/path.1700770220. PMID 13642195.
  10. ^ Schoental, R (1968). "Toxicology and Carcinogenic Action of Pyrrolizidine Alkaloids" (PDF). Cancer Research. 28 (11): 2237–2246. PMID 4302035.
  11. ^ a b Fu, P.P.; Yang, Y.C.; Xia, Q.; et al. (2002). "Pyrrolizidine alkaloids-tumorigenic components in Chinese herbal medicines and dietary supplements". {{cite journal}}: Cite journal requires |journal= (help)
  12. ^ a b Wiedenfeld, H.; Edgar, J. (2011). "Toxicity of pyrrolizidine alkaloids to humans and ruminants". Phytochemistry Reviews. 2010 (1): 1–15. Bibcode:2011PChRv..10..137W. doi:10.1007/s11101-010-9174-0. S2CID 36631492.
  13. ^ Skaanild, M.T.; Friis, C.; Brimer, L. (2001). "Interplant alkaloid variation and Senecio vernalis toxicity in cattle". Veterinary and Human Toxicology. 43 (3): 147–151. PMID 11383654.
  14. ^ Noble, J.W.; Crossley, J.; Hill, B.D.; et al. (1994). "Pyrrolizidine alkaloidosis of cattle associated with Senecio lautus". Australian Veterinary Journal. 71 (7): 196–200. doi:10.1111/j.1751-0813.1994.tb03400.x. PMID 7945096.
  15. ^ Conner, W.E. (2009). Tiger Moths and Woolly Bears: Behaviour, Ecology, and Evolution of the Arctiidae. New York: Oxford University Press. pp. 1–10. ISBN 9780195327373.
  16. ^ Nishida, R; Schulz, S; Kim, C. S; et al. (1996). "Male sex pheromone of a giant danaine butterfly,Idea leuconoe". Journal of Chemical Ecology. 22 (5): 949–72. doi:10.1007/BF02029947. PMID 24227617. S2CID 23449117.
  17. ^ Scott, James A. (1997). "Family Nymphalidae: Brush-Footed Butterflies". The Butterflies of North America: A Natural History and Field Guide. Stanford, California: Stanford University Press. pp. 228–232. ISBN 9780804720137.
  18. ^ Edgar, J. A.; Cockrum, P. A.; Frahn, J. L. (1976-12-01). "Pyrrolizidine alkaloids inDanaus plexippus L. and Danaus chrysippus L.". Experientia. 32 (12): 1535–1537. doi:10.1007/bf01924437. ISSN 0014-4754. S2CID 27664625.
  19. ^ Macel, Mirka (2011-03-01). "Attract and deter: a dual role for pyrrolizidine alkaloids in plant–insect interactions". Phytochemistry Reviews. 10 (1): 75–82. Bibcode:2011PChRv..10...75M. doi:10.1007/s11101-010-9181-1. ISSN 1568-7767. PMC 3047672. PMID 21475391.
  20. ^ Wiedenfeld, H; Andrade-Cetto, A (2001). "Pyrrolizidine alkaloids from Ageratum houstonianum Mill". Phytochemistry. 57 (8): 1269–71. Bibcode:2001PChem..57.1269W. CiteSeerX 10.1.1.576.4086. doi:10.1016/S0031-9422(01)00192-3. PMID 11454357.
  21. ^ Broch-Due, Å. I.; Aasen, A. J. (1980). "Alkaloids of Anchusa officinalis L. Identification of the Pyrrolizidine Alkaloid Lycopsamine". Acta Chem. Scand. B34: 75–77. doi:10.3891/acta.chem.scand.34b-0075.
  22. ^ a b c d e f g h . The Merck Veterinary Manual. Archived from the original on 2010-11-17.
  23. ^ Connor Yearsley. "American Herbal Pharmacopoeia Publishes Boneset Monograph and Therapeutic Compendium". HerbalGram. American Botanical Council. 125: 26–28.
  24. ^ Wood, Matthew. "The Book of Herbal Wisdom: Using Plants As Medicines." Berkeley CA. North Atlantic Books. 1997.
  25. ^ Kakar F, Akbarian Z, Leslie T, et al. (28 Jun 2010). "An outbreak of hepatic veno-occlusive disease in Western afghanistan associated with exposure to wheat flour contaminated with pyrrolizidine alkaloids". J Toxicol. 2010: 313280. doi:10.1155/2010/313280. PMC 2905904. PMID 20652038.
  26. ^ Rizk A. M. (1990). "The Pyrrolizidine Alkaloids: Plant Sources and Properties". Naturally Occurring Pyrrolizidine Alkaloids. CRC Press. p. 12. ISBN 0849346509.
  27. ^ Yeong M. L.; et al. (1990). "Hepatic veno-occlusive disease associated with comfrey ingestion". Journal of Gastroenterology and Hepatology. 5 (2): 211–214. doi:10.1111/j.1440-1746.1990.tb01827.x. PMID 2103401. S2CID 42511497.
  28. ^ "Pyrrolizidine Alkaloid Induced Liver Diseases", cited in Chiu, C; Buttke, D; Welde, G; et al. (2013). "Evaluation of the Pyrrolizidine Alkaloid Induced Liver Disease (PAILD) Active Surveillance System in Tigray, Ethiopia". Online Journal of Public Health Informatics. 5 (1): e167. doi:10.5210/ojphi.v5i1.4560. PMC 3692817.
  29. ^ "Investigating Liver disease in Ethiopia". National Center for Environmental Health. CDC. 30 Oct 2012.

External links

  • Subhuti Dharmananda. "Safety issues affecting herbs: pyrrolizidine alkaloids". Institute for Traditional Medicine, Portland, Oregon.
  • E. Röder (1995). "Medicinal plants in Europe containing pyrrolizidine alkaloids". Die Pharmazie. 50 (2): 83–98. PMID 7700976.
  • Retronecine at KEGG
  • msn.com/de News Report: Well-known brands affected: This is how much poison there is in these herbal and chamomile teas. 6 out of 13 brands of herbal tea available in Germany contain the poison.

May 03, 2023
pyrrolizidine, alkaloid, sometimes, referred, necine, bases, group, naturally, occurring, alkaloids, based, structure, pyrrolizidine, produced, plants, defense, mechanism, against, insect, herbivores, more, than, oxides, have, been, identified, over, plants, a. Pyrrolizidine alkaloids PAs sometimes referred to as necine bases are a group of naturally occurring alkaloids based on the structure of pyrrolizidine Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores More than 660 PAs and PA N oxides have been identified in over 6 000 plants and about half of them exhibit hepatotoxicity 1 They are found frequently in plants in the Boraginaceae Asteraceae Orchidaceae and Fabaceae families less frequently in the Convolvulaceae and Poaceae and in at least one species in the Lamiaceae It has been estimated that 3 of the world s flowering plants contain pyrrolizidine alkaloids 2 Honey can contain pyrrolizidine alkaloids 3 4 as can grains milk offal and eggs 5 To date 2011 there is no international regulation of PAs in food unlike those for herbs and medicines 6 7 Skeletal formula of retronecine a pyrrolizidine alkaloid found in the common groundsel Senecio vulgaris and comfrey Symphytum spp Unsaturated pyrrolizidine alkaloids are hepatotoxic that is damaging to the liver 8 9 PAs also cause hepatic veno occlusive disease and liver cancer 10 PAs are tumorigenic 11 Disease associated with consumption of PAs is known as pyrrolizidine alkaloidosis In humans the use of medicinal herbs containing PAs notably borage leaf comfrey and coltsfoot in the West and some Chinese medicinal herbs has been shown to pose health risks 11 The degree of toxicity can vary based on age and gender with fetuses and neonates showing high sensitivity including instances of death 12 Some ruminant animals for example cattle show no change in liver enzyme activities or any clinical signs of poisoning when fed low concentrations of plants containing pyrrolizidine alkaloids 13 Yet Australian studies have demonstrated toxicity 14 Sheep and goats especially and to a lesser degree cattle are much more resistant and tolerate much higher PA dosages thought to be due to thorough detoxification via PA destroying rumen microbes 12 PA is also used as a defense mechanism by some organisms such as Utetheisa ornatrix Utetheisa ornatrix caterpillars obtain these toxins from their food plants and use them as a deterrent for predators PAs protect them from most of their natural enemies The toxins stay in these organisms even when they metamorphose into adult moths continuing to protect them throughout their adult stage 15 Contents 1 Ecology 2 Plants species containing pyrrolizidine alkaloids 3 Classification 4 References 5 External linksEcology EditMain article Pyrrolizidine alkaloid sequestration Many plants contain pyrrolizidine alkaloids and in turn there are many insects which consume the plants and build up the alkaloids in their bodies 16 For example male queen butterflies utilize pyrrolizidine alkaloids to produce pheromones useful for mating 17 The butterfly Danaus chrysippus is known to obtain pyrrolizidine alkaloids in their diet and store these chemicals making them toxic and unpalatable to predators 18 Greta oto the glasswing butterfly uses pyrrolizidine alkaloids for both toxicity in the adult moth and pheromone production in the male butterfly The garden tiger moth also stores these compounds as a caterpillar using them for larval through the use of spines and adult defense in the form of a spray and bad taste 19 Plants species containing pyrrolizidine alkaloids EditThis is a dynamic list and may never be able to satisfy particular standards for completeness You can help by adding missing items with reliable sources Adenostyles alliariae Adenostyles glabra Ageratum conyzoides Ageratum houstonianum 20 Anchusa officinalis 21 Arnebia euchroma Borago officinalis lt 10 ppm non toxic Cacalia hastata Cacalia hupehensis Chromolaena odorata Cordia myxa Crassocephalum crepidioides Crotalaria albida Crotalaria assamica Crotalaria crispat Crotalaria dura Crotalaria globifera Crotalaria mucronata Crotalaria sesseliflora Crotalaria spectabilis Crotalaria tetragona Crotalaria retusa Cynoglossum amabile Cynoglossum lanceolatum Cynoglossum officinale Cynoglossum zeylanicum Echium plantagineum 22 Echium vulgare Emilia sonchifolia Eupatorium cannabinum Eupatorium chinense Eupatorium fortunei Eupatorium japonicum Eupatorium perfoliatum 23 Eupatorium purpureum 24 Farfugium japonicum Gynura bicolor Gynura divaricata Gynura segetum Heliotropium amplexicaule 22 Heliotropium europaeum 22 Heliotropium indicum Heliotropium popovii 25 Lappula intermedia Ligularia cymbulifera Ligularia dentata Ligularia duiformis Ligularia heterophylla Ligularia hodgsonii Ligularia intermedia Ligularia lapathifolia Ligularia lidjiangensis Ligularia platyglossa Ligularia tongolensis Ligularia tsanchanensis Ligularia vellerea Liparis nervosa Lithospermum erythrorhizon Neurolaena lobata Petasites japonicus Senecio alpinus Senecio argunensis Senecio brasiliensis 26 Senecio chrysanthemoides Senecio cineraria Senecio glabellus Senecio integrifolius var fauriri Senecio interggerrimus Senecio jacobaea 22 Senecio lautus 22 Senecio linearifolius 22 Senecio madagascariensis 22 Senecio nemorensis Senecio quadridentatus 22 Senecio riddelli Senecio scandens Senecio vulgaris Syneilesis aconitifolia Symphytum officinale 27 Tussilago farfara The effect of PAs in humans that is PAILDs Pyrrolizidine Alkaloid Induced Liver Diseases 28 of epidemic proportions was recorded after a long field level epidemiological investigation in the northern region of Ethiopia Tigray 29 Classification EditOne classification is based on the substitution pattern of the pyrrolizidine ring This part of the structure is normally referred to as necine bases The three largest groups are based on the three necine bases platynecine heliotridine and retronecine Platynecine Heliotridine RetronecineReferences Edit Radominska Pandya A 2010 Invited Speakers Drug Metabolism Reviews 42 S1 1 2 doi 10 3109 03602532 2010 506057 PMID 20842800 Smith L W Culvenor C C J 1981 Plant sources of hepatotoxic pyrrolizidine alkaloids J Nat Prod 44 2 129 15 doi 10 1021 np50014a001 PMID 7017073 Kempf M Reinhard A Beuerle T Jan 2010 Pyrrolizidine alkaloids PAs in honey and pollen legal regulation of PA levels in food and animal feed required Mol Nutr Food Res 54 1 158 68 doi 10 1002 mnfr 200900529 PMID 20013889 Edgar John A Roeder Erhard Molyneux Russell J 2002 Honey from Plants Containing Pyrrolizidine Alkaloids A Potential Threat to Health J Agric Food Chem 50 10 2719 2730 doi 10 1021 jf0114482 PMID 11982390 Pyrrolizidine alkaloids in Food PDF Archived from the original PDF on 2009 10 14 Coulombe Roger A Jr 2003 Pyrrolizidine alkaloids in foods Advances in Food and Nutrition Research Volume 45 Advances in Food and Nutrition Research Vol 45 pp 61 99 doi 10 1016 S1043 4526 03 45003 1 ISBN 9780120164455 PMID 12402679 German Commission E monographs Foodborne Pathogenic Microorganisms and Natural Toxins Handbook Pyrrolizidine Alkaloids Bad Bug Book United States Food and Drug Administration Retrieved 2009 07 11 Schoental R Kelly JS April 1959 Liver lesions in young rats suckled by mothers treated with the pyrrolizidine Senecio alkaloids lasiocarpine and retrorsine The Journal of Pathology and Bacteriology 77 2 485 495 doi 10 1002 path 1700770220 PMID 13642195 Schoental R 1968 Toxicology and Carcinogenic Action of Pyrrolizidine Alkaloids PDF Cancer Research 28 11 2237 2246 PMID 4302035 a b Fu P P Yang Y C Xia Q et al 2002 Pyrrolizidine alkaloids tumorigenic components in Chinese herbal medicines and dietary supplements a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help a b Wiedenfeld H Edgar J 2011 Toxicity of pyrrolizidine alkaloids to humans and ruminants Phytochemistry Reviews 2010 1 1 15 Bibcode 2011PChRv 10 137W doi 10 1007 s11101 010 9174 0 S2CID 36631492 Skaanild M T Friis C Brimer L 2001 Interplant alkaloid variation and Senecio vernalis toxicity in cattle Veterinary and Human Toxicology 43 3 147 151 PMID 11383654 Noble J W Crossley J Hill B D et al 1994 Pyrrolizidine alkaloidosis of cattle associated with Senecio lautus Australian Veterinary Journal 71 7 196 200 doi 10 1111 j 1751 0813 1994 tb03400 x PMID 7945096 Conner W E 2009 Tiger Moths and Woolly Bears Behaviour Ecology and Evolution of the Arctiidae New York Oxford University Press pp 1 10 ISBN 9780195327373 Nishida R Schulz S Kim C S et al 1996 Male sex pheromone of a giant danaine butterfly Idea leuconoe Journal of Chemical Ecology 22 5 949 72 doi 10 1007 BF02029947 PMID 24227617 S2CID 23449117 Scott James A 1997 Family Nymphalidae Brush Footed Butterflies The Butterflies of North America A Natural History and Field Guide Stanford California Stanford University Press pp 228 232 ISBN 9780804720137 Edgar J A Cockrum P A Frahn J L 1976 12 01 Pyrrolizidine alkaloids inDanaus plexippus L and Danaus chrysippus L Experientia 32 12 1535 1537 doi 10 1007 bf01924437 ISSN 0014 4754 S2CID 27664625 Macel Mirka 2011 03 01 Attract and deter a dual role for pyrrolizidine alkaloids in plant insect interactions Phytochemistry Reviews 10 1 75 82 Bibcode 2011PChRv 10 75M doi 10 1007 s11101 010 9181 1 ISSN 1568 7767 PMC 3047672 PMID 21475391 Wiedenfeld H Andrade Cetto A 2001 Pyrrolizidine alkaloids from Ageratum houstonianum Mill Phytochemistry 57 8 1269 71 Bibcode 2001PChem 57 1269W CiteSeerX 10 1 1 576 4086 doi 10 1016 S0031 9422 01 00192 3 PMID 11454357 Broch Due A I Aasen A J 1980 Alkaloids of Anchusa officinalis L Identification of the Pyrrolizidine Alkaloid Lycopsamine Acta Chem Scand B34 75 77 doi 10 3891 acta chem scand 34b 0075 a b c d e f g h TABLE 05 Important Poisonous Vascular Plants of Australia The Merck Veterinary Manual Archived from the original on 2010 11 17 Connor Yearsley American Herbal Pharmacopoeia Publishes Boneset Monograph and Therapeutic Compendium HerbalGram American Botanical Council 125 26 28 Wood Matthew The Book of Herbal Wisdom Using Plants As Medicines Berkeley CA North Atlantic Books 1997 Kakar F Akbarian Z Leslie T et al 28 Jun 2010 An outbreak of hepatic veno occlusive disease in Western afghanistan associated with exposure to wheat flour contaminated with pyrrolizidine alkaloids J Toxicol 2010 313280 doi 10 1155 2010 313280 PMC 2905904 PMID 20652038 Rizk A M 1990 The Pyrrolizidine Alkaloids Plant Sources and Properties Naturally Occurring Pyrrolizidine Alkaloids CRC Press p 12 ISBN 0849346509 Yeong M L et al 1990 Hepatic veno occlusive disease associated with comfrey ingestion Journal of Gastroenterology and Hepatology 5 2 211 214 doi 10 1111 j 1440 1746 1990 tb01827 x PMID 2103401 S2CID 42511497 Pyrrolizidine Alkaloid Induced Liver Diseases cited in Chiu C Buttke D Welde G et al 2013 Evaluation of the Pyrrolizidine Alkaloid Induced Liver Disease PAILD Active Surveillance System in Tigray Ethiopia Online Journal of Public Health Informatics 5 1 e167 doi 10 5210 ojphi v5i1 4560 PMC 3692817 Investigating Liver disease in Ethiopia National Center for Environmental Health CDC 30 Oct 2012 External links EditSubhuti Dharmananda Safety issues affecting herbs pyrrolizidine alkaloids Institute for Traditional Medicine Portland Oregon E Roder 1995 Medicinal plants in Europe containing pyrrolizidine alkaloids Die Pharmazie 50 2 83 98 PMID 7700976 Retronecine at KEGG msn com de News Report Well known brands affected This is how much poison there is in these herbal and chamomile teas 6 out of 13 brands of herbal tea available in Germany contain the poison Retrieved from https en wikipedia org w index php title Pyrrolizidine alkaloid amp oldid 1152904736, wikipedia, wiki, book, books, library,

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