Pyrrolizidine alkaloid
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. 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. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines.
Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disease and liver cancer. PAs are tumorigenic. Disease associated with consumption of PAs is known as pyrrolizidine alkaloidosis.
Of concern is the health risk associated with the use of medicinal herbs that contain PAs, notably borage leaf, comfrey and coltsfoot in the West, and some Chinese medicinal herbs.
Some ruminant animals, for example cattle, showed no change in liver enzyme activities or any clinical signs of poisoning when fed plants containing pyrrolizidine alkaloids. Yet Australian studies have demonstrated toxicity Sheep, goats and cattle are much more resistant and tolerate much higher PA dosages, thought to be due to thorough detoxification via PA-destroying rumen microbes. Males react more sensitively than females and fetuses and children.
PA is also used as a defense mechanism for 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.

This is an excerpt from the article Pyrrolizidine alkaloid from the Wikipedia free encyclopedia. A list of authors is available at Wikipedia.
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Pyrrolizidine alkaloid - Wikipedia, the free encyclopedia
Pyrrolizidine alkaloids (PAs; sometimes referred to as necine bases) are a group of naturally occurring alkaloids based on the structure of pyrrolizidine.
en.wikipedia.org/wiki/Pyrrolizidine_alkaloid
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BBB - Pyrrolizidine Alkaloids - Food and Drug Administration
Aug 5, 2013 ... Provides basic facts about Pyrrolizidine alkaloids. ... Pyrrolizidine alkaloid intoxication is caused by consumption of plant material containing ...
www.fda.gov/Food/FoodborneIllnessContaminants/CausesOfIllnessBadBugBook/ucm071047.htm
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Pyrrolizidine alkaloid plants, metabolism…
1. J Nat Toxins. 1999 Feb;8(1):95-116. Pyrrolizidine alkaloid plants, metabolism and toxicity. Stegelmeier BL, Edgar JA, Colegate SM, Gardner DR, Schoch TK, Coulombe ...
www.ncbi.nlm.nih.gov/pubmed/10091131
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Safety Issues Affecting Herbs:…
Pyrrolizidine alkaloidS. by Subhuti Dharmananda, Ph.D., Director, Institute for Traditional Medicine, Portland, Oregon. Pyrrolizidine alkaloids (see Figure 1) are ...
www.itmonline.org/arts/pas.htm
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Pyrrolizidine alkaloid sequestration - Wikipedia, the free encyclopedia
Pyrrolizidine alkaloid sequestration by insects is done for defense and mating purposes. Various species of insects have been known to utilize molecular ...
en.wikipedia.org/wiki/Pyrrolizidine_alkaloid_sequestration
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pyrrolizidine alkaloids in foods - Toxicology - Utah State University
group of compounds; more than 350 Pyrrolizidine alkaloids have been isolated ... cases of Pyrrolizidine alkaloid poisoning are probably only a small percentage.
toxicology.usu.edu/endnote/Pyrrolizidine-alkaloids-in-food.pdf
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Scientific Opinion on Pyrrolizidine alkaloids in food and feed
related to the presence of Pyrrolizidine alkaloids (PA) in food and feed. ... phytotoxins, including Pyrrolizidine alkaloids, no replies for PAs were received even by ...
www.efsa.europa.eu/en/efsajournal/doc/2406.pdf
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Frequently asked questions on Pyrrolizidine alkaloids in food - BfR
Jul 15, 2013 ... Updated BfR FAQ, 15. Juli 2013 Pyrrolizidine alkaloids are secondary metabolites that are produced by certain plants. Due to their potential ...
www.bfr.bund.de/en/frequently_asked_questions_on_pyrrolizidine_alkaloids_in_food-187360.html
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ARS Project: THE TOXICITY OF PYRROLIZIDINE ALKALOID ...
Aug 20, 2013 ... THE TOXICITY OF Pyrrolizidine alkaloid-CONTAINING PLANTS AND OTHER HEPATOTOXIC AND NEUROTOXIC PLANTS ...
www.ars.usda.gov/research/projects/projects.htm?accn_no=412851
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Pyrrolizidine Alkaloids—Genotoxicity, Metabolism ... - ResearchGate
Pyrrolizidine alkaloid-containing plants are widely distributed in the world and are ... mechanisms by which Pyrrolizidine alkaloids exert genotoxicity and ...
www.researchgate.net/publication/8630233_Pyrrolizidine_alkaloids--genotoxicity_metabolism_enzymes_metabolic_activation_and_mechanisms/file/79e4150933929c269c.pdf
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Pyrrolizidine alkaloid in science
Pyrrolizidine alkaloid - Wikipedia, the free encyclopedia
Skeletal formula of retronecine, a Pyrrolizidine alkaloid found in the Common groundsel (Senecio vulgaris) .... Stanford, California: Stanford University Press. pp.
Pyrrolizidine alkaloid-induced DNA-protein cross-links.
Department of Veterinary Sciences, Utah State University, Logan, 84322-4620, USA. Pyrrolizidine alkaloids (PAs) are potent carcinogenic and anti-mitotic ...
Toxicity of pyrrolizidine alkaloids - a serious health problem ...
Wiedenfeld, Helmut. 2011. Toxicity of Pyrrolizidine alkaloids - a serious health problem. Journal of Marmara University Institute of Health Sciences, 1 (2), 79-87.
[PDF]Analysis of pyrrolizidine alkaloids in Crotalaria - UPeTD - University ...
iii. University of Pretoria. Abstract. Analysis of Pyrrolizidine alkaloids in Crotalaria species by HPLC-MS/MS in order to evaluate related Food Health Risks.
[PDF]Pyrrolizidine Alkaloids from Symphytum sylvaticum Boiss. subsp ...
˙Istanbul University, TK-34452 ˙Istanbul-TURKEY. Received 16.03.2001. Pyrrolizidine alkaloid (Echimidine-N-oxide) was isolated from Symphytum sylvaticum ...
[PDF]PREPARATIVE ISOLATION OF PYRROLIZIDINE ALKALOIDS ...
PREPARATIVE ISOLATION OF Pyrrolizidine alkaloidS. DERIVED FROM SENECIO VULGARIS. H.J. Segall. University o f California. School o f ...
[PDF]Evaporative light scattering detection of pyrrolizidine alkaloids
of Mississippi, University, MS 38677 USA. Email: ikhan@olemiss.edu. Evaporative Light Scattering Detection of. Pyrrolizidine alkaloids. Brian T. Schaneberg,1 ...
[PDF]Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum ...
a Department of Pharmacognosy, Faculty of Pharmacy, Zagazig University, Egypt ... Echium rauwolfii, Echium horridum, Boraginaceae, Pyrrolizidine alkaloids, ...
[PDF]Variation in pyrrolizidine alkaloid patterns of Senecio ... - Xs4all
Variation in Pyrrolizidine alkaloid patterns of Senecio jacobaea. Mirka Macel*, Klaas Vrieling, Peter G.L. Klinkhamer. Leiden University, Institute for Biology, Plant ...
Comfrey | University of Maryland Medical Center
May 7, 2013 ... However, it has toxic substances called Pyrrolizidine alkaloids that damage the liver and can lead to death. Comfrey is no longer sold in the ...
Books on the term Pyrrolizidine alkaloid
Pyrrolizidine Alkaloids: Structure and Toxicity
Pyrrolizidine Alkaloids: Structure and Toxicity
2008
This book describes the incidence and the process of the intoxication as well as the possibilities to how the substances may reach the organism.
Pyrrolizidine Alkaloids: Environmental Health Criteria Series No. 80
Pyrrolizidine Alkaloids: Environmental Health Criteria Series No. 80
ILO, UNEP and World Health Organization, 1988
Alerts the medical and public health professions to the severe risks of morbidity and mortality posed by human consumption of plants, including cereals and herbal medicines, containing Pyrrolizidine alkaloids. Citing well over 500 published studies, the book draws together the evidence documenting acute and often fatal organ damage arising from bot...
Naturally Occurring Pyrrolizidine Alkaloids
Naturally Occurring Pyrrolizidine Alkaloids
A. M. Rizk, 1991
Tashkhodzhaev, B., Telezhenetskaya, M. V., and Yunusov, S. Yu., Crystal and molecular stnrcture of macrocyclic Pyrrolizidine alkaloid trichodesmine, Khim. Prir . Soedin., 368, 1979; C .A., 92, 111194, 1980. . Sussman, ,1. L. and Wodak, S. J.,  ...
Naturally Occurring Pyrrolizidine Alkaloids
Naturally Occurring Pyrrolizidine Alkaloids
Dr. Abdel-Fatta Rizk, 1990
Plants containing Pyrrolizidine alkaloids are so numerous and widespread that they can be expected to be present in most environments. About 200 Pyrrolizidine alkaloids have been isolated and identified from different plants. Interest in these alkaloids has increased in recent years due to their causative effects in the heavy loss of livestock in m...
Biosynthesis of the Unique Necic Acid Moiety in Lycopsamine ...
Biosynthesis of the Unique Necic Acid Moiety in Lycopsamine ...
Dorothee Langel, 2008
Hartmann, T. (1999) Chemical ecology of Pyrrolizidine alkaloids. Planta 206, 443 - 451 Hartmann, T. (2006) Plant Pyrrolizidine alkaloids (PAs) structures, toxicity, utilization by insects (Arctiids). Personal communications 31.03.2006, Inst. f.
A Field Guide to Medicinal Plants and Herbs: Of Eastern and Central North America (Peterson Field Guides)
A Field Guide to Medicinal Plants and Herbs: Of Eastern and Central North America (Peterson Field Guides)
Steven Foster, James A. Duke and Roger Tory Peterson, 1999
With more than 300 photos, this new edition shows how to identify more than 500 healing plants. Descriptive text includes information on where the plants are found, as well as their known medicinal uses. An index to medical topics, symbols next to plant descriptions, and organization of plants by colors all make this an essential guide to understan...
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Pyrrolizidine alkaloid
Tin Roof Teas » Blog Archive » Know Your Herbs – Pyrrolizidine Alkaloids Prt. 2:
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Molecules | Free Full-Text | Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization
The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten Pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1–9 were found in the aerial parts, 7 and 8 in the roots, and 6–10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1–10 were established based on spectroscopic studies (1H- and 13C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.
www.mdpi.com/1420-3049/18/9/10694
Village Herbalist: Pyrrolizidine Alkaloids in Healing Herbs
Borage ~ Borago officinalis Folks continue to ask about the safety of PA alkaloids (Pyrrolizidine alkaloids) that are found in many healing herbs such as borage, coltsfoot and comfrey. Point-by-point, here are things to consider: 1) No viable animal testing was done with any PA containing herbs on primates so there is no proof for fear of PA's in humans.
celticherbalist.blogspot.com/2013/08/borage-borago-officinalis-folks.html
"Pyrrolizidine Alkaloid– Containing Toxic Plants (Senecio, Crotala" by Bryan L. Stegelmeier
Many problematic Pyrrolizidine alkaloid (PA)-containing plants are foreign invasive weeds that invade pastures, fields, and ranges, and contaminate feeds and food. Others are native plants that may increase or expand on field edges or in disturbed areas. Most are unpalatable, only becoming a problem for livestock when alternative forages are unavailable, or when they are included in hay and other harvested feeds. Human poisoning is most often a result of contaminated grain or flour, although several poisonings have resulted from the use of PA-containing herbal preparations. Major PA plants and their specific health-related characteristics are discussed individually.
digitalcommons.unl.edu/usdaarsfacpub/877/
Levels of pyrrolizidine alkaloids in herbal teas and teas are too high - - The first non-representative results of a BfR research project show that efforts are required to minimise levels
The BfR is currently conducting a research project on “Determination of Pyrrolizidine alkaloids in Food and Feed”. Initially, various samples of off-the-shelf tea, herbal tea and medicinal tea wer ...
www.bionity.com/en/news/144040/
Smoothie Essentials: The Herbs of Smoothie Essentials: Borage Oil The Essential Herbs
Borage seed oil is derived from the seeds of the Borago officinalis (borage). Borage seed oil has one of the highest amounts of γ-linolenic acid (GLA) of seed oils — higher than blackcurrant seed oil or evening primrose oil, to which it is considered similar.
smoothieessentials.com/the-essential-herbs/the-herbs-of-smoothie-essentials-borage-oil/
Pyrrolizidine Alkaloids Found Six Thousand Different Plant Species Biology Essay
Pyrrolizidine alkaloids (PAs) can be found in 6,000 different plant species representing more than 3% of all flower plants throughout the world...
www.ukessays.com/essays/biology/pyrrolizidine-alkaloids-found-six-thousand-different-plant-species-biology-essay.php
The hard working bee | Focus on food safety
Bees are hard at work collecting pollen and nectar to feed themselves and their off-spring. When foraging for food they use the sun for direction, initially using a somewhat irregular path away from the hive to find a suitable source up to 10 km away. The bee will then fly a straight line back to…
focusonfoodsafety.wordpress.com/2013/02/28/pyrrolizidine-alkaloids/
Dr. Dach’s Corner – November 21, 2013 | Optimum Health Report
Arthritis and Nightshade Vegetables by Jeffrey Dach MD Susan, a Young Woman with Rheumatoid Arthritis Susan, a 46 year old female retired nurse arrived in my office with a chief complaint of joint pain, involving the hands. Susan was post menopausal, and had been taking prednisone (a synthetic steroid) for her diagnosis of rheumatoid arthritis.
optimumhealthreport.com/2013/11/dr-dachs-corner-november-21-2013/
Pyrrolizidine on my Mind | Eat The Weeds and other things, too
www.eattheweeds.com/pyrrolizidine-on-my-mind/
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