Aristolochic acid (original) (raw)
Aristolochic acids (English: /əˌrɪstəˈloʊkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering plant family Aristolochiaceae (birthworts). Aristolochic acid (AA) I is the most abundant one. The family Aristolochiaceae includes the genera Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine. Although these compounds are widely associated with kidney problems, liver and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. The FDA has issued warnings regarding consumption of AA-containing supplements.
| Property | Value |
|---|---|
| dbo:abstract | Aristolochic acids (English: /əˌrɪstəˈloʊkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering plant family Aristolochiaceae (birthworts). Aristolochic acid (AA) I is the most abundant one. The family Aristolochiaceae includes the genera Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine. Although these compounds are widely associated with kidney problems, liver and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. The FDA has issued warnings regarding consumption of AA-containing supplements. (en) Aristolochiasäuren sind sekundäre Pflanzenstoffe, die in einer Vielzahl von Arten der Gattungen Aristolochia (Pfeifenblumen), Asarum (Haselwurzen), Saruma und Thottea, alle zur Familie der Aristolochiaceae (Osterluzeigewächse) gehörig, nachgewiesen wurden. Biogenetisch leiten sie sich von Aporphin-Alkaloiden ab, wie an der Strukturähnlichkeit mit z. B. den Aporphin-Alkaloiden Apomorphin oder Bulbocapnin zu erkennen ist. Die bei Naturstoffen relativ seltene Nitrogruppe entsteht durch Oxidation des Stickstoffatoms im vormaligen Piperidinring. (de) La aristoloquina o ácido aristolóquico es un componente químico presente en muchas plantas. Debe su nombre a la alta cantidad del mismo que se presenta en las plantas de la familia Aristolochiaceae, más concretamente en la subfamilia Aristolochioideae, sobre todo presentes en el género Aristolochia. La aristoloquina es un derivado de los alcaloides del tipo de las aporfinas. Es nefrotóxica y carcinogénica. Su ingestión se ha asociado a un cuadro clínico caracterizado por fibrosis intersticial renal rápidamente progresiva que conduce de forma rápida a la insuficiencia renal crónica, junto con la aparición de tumores uroteliales del tracto urinario superior. * Datos: Q424210 * Multimedia: Aristolochic acid / Q424210 (es) L'acide aristolochique (C17H11NO7) est un acide carboxylique produit par plusieurs espèces d'aristoloche. La teneur en cet acide varie selon l'espèce, la partie de la plante et les individus. C'est un composé toxique pour les reins, qui peut provoquer des défaillances rénales nécessitant une transplantation de rein.Il est considéré comme carcinogène par l’Organisation mondiale de la santé (OMS).Il est pour ces raisons interdit dans plusieurs pays, comme l'Europe, l'Égypte, le Japon et le Venezuela (fr) Aristolochiazuur I is een van de twee bestanddelen van aristolochiazuur. (nl) Aristolochiazuur is een kankerverwekkende stof, die in planten van de pijpbloemfamilie, onder andere in sommige soorten uit het geslacht Asarum voorkomt. Aristolochiazuur is in wezen een mengsel dat bestaat uit gelijke delen aristolochiazuur I en aristolochiazuur II. Naast de kankerverwekkendheid is de stof ook sterk nefrotoxisch (nierbeschadigend). Ondanks deze goed gedocumenteerde gevaren wordt aristolochiazuur soms aangetroffen in afslankmiddelen. Aristolochiaplanten worden soms aangetroffen in Chinese kruidenmengsels. In 1992 werd de invoer van Aristolochia in Europa verboden en in 2002, werd in het Nederlandse bepaald dat planten met aristolochiazuur niet meer in kruidenmiddelen mogen worden gebruikt. Ook in België zijn dergelijke planten verboden. (nl) アリストロキア酸 (Aristolochic acid) は、ウマノスズクサ属 Aristolochia およびカンアオイ属 Asarum の植物などに含まれる、フェナントレン骨格を持つ芳香族カルボン酸。 アリストロキア酸 I (8-methoxy-6-nitro-phenanthro-(3,4-d)-1,3-dioxolo-5-carboxylic acid) と、アリストロキア酸 II (6-nitro-phenanthro-(3,4-d)-1,3-dioxolo-5-carboxylic acid) の 2 種類 が知られている。II 体は I 体のメトキシ基を水素原子に置換した構造をもつ。 (ja) 马兜铃酸（英語：Aristolochic acids，简称AAs）也被称为马兜铃总酸、增噬力酸或木通甲素，是一类具有強烈致癌性和的硝基菲羧酸。这类有机化合物天然存在于诸如马兜铃属（Aristolochia）及细辛属（Asarum）等马兜铃科植物中，而这些植物曾广泛地被用作中草药。此外，依靠吸食这类植物生存的蝴蝶体内也有马兜铃酸。马兜铃酸Ⅰ是最常见的一种马兜铃酸类化合物，它可在几乎所有马兜铃属植物中发现，并常与（aristolactams）共存。 利用热二甲基甲酰胺水溶液中萃取获得的马兜铃酸为有光泽的褐色片状结晶，利用甲醇萃取获得的马兜铃酸则为橘黄色棒状结晶。马兜铃酸类化合物味微苦，可溶于乙醇、氯仿、乙醚、丙酮、冰醋酸、苯胺或碱液，微溶于水，几乎不溶于苯或二硫化碳，熔点介于281-286℃之间（约于286℃分解）。 自然界含有马兜铃酸的植物达600余种，涉及木通属、木香属、广防己属、千金藤属、青藤属、铁线莲属、蝙蝠葛属、细辛属等约70种中草药，在中国有40余种药材含马兜铃酸：马兜铃、关木通、天仙藤、青木香、广防己、、细辛、、寻骨风、淮通、、三筒管、杜衡、管南香、南木香、、背蛇生、假大薯、蝴蝶暗消、逼血雷、白金果榄、金耳环、等。一些药材由于形态与上述药材相似，而有可能在采集、物流环节被混用、搀杂含马兜铃酸的药材，应考虑慎用：木通、苦木通、紫木通、白木通、川木通、、木防己、铁线莲、威灵仙、、白英、白毛藤、等。 (zh) |
| dbo:alternativeName | Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736 (en) |
| dbo:iupacName | 8-Methoxy-6-nitro-2H-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/Aristolochic_acid.png?width=300 |
| dbo:wikiPageExternalLink | https://archive.today/20130811144359/http:/www.timesofindia.indiatimes.com/home/science/Herbal-medicines-causing-kidney-failure-bladder-cancer-in-India/articleshow/19052908.cms https://books.google.com/books%3Fid=85M0N8UioCcC&pg=PA15%7Cauthor1=Mills, https://books.google.com/books%3Fid=ibxfK1l6oXoC&pg=PA55 https://www.fda.gov/Food/DietarySupplements/Alerts/ucm095272.htm https://www.fda.gov/Food/DietarySupplements/Alerts/ucm095302.htm http://monographs.iarc.fr/ENG/Monographs/vol100A/mono100A-23.pdf |
| dbo:wikiPageID | 359884 (xsd:integer) |
| dbo:wikiPageLength | 25448 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1108570842 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Norlaudanosoline dbr:Benzylisoquinoline dbr:Phase_I_metabolism dbr:Carcinogenic dbr:List_of_herbs_with_known_adverse_effects dbc:Benzodioxoles dbc:Nitro_compounds dbc:Phenanthrenes dbc:Phenol_ethers dbr:TP53 dbr:Aristolochia dbr:Aristolochia_clematitis dbr:Tumor_suppressor_gene dbr:Thymine dbr:Tumorigenesis dbr:Tyrosine dbr:DNA_adducts dbr:Adenine dbr:FDA dbr:Flowering_plant dbr:Food_and_Drug_Administration dbr:Balkan_endemic_nephropathy dbc:Benzoic_acids dbc:IARC_Group_1_carcinogens dbr:Tetrahydropapaveroline dbr:Aristolochiaceae dbc:Plant_toxins dbr:L-DOPA dbr:Dopamine dbr:3,4-dihydroxyphenylacetaldehyde dbr:Asarum dbr:Phytochemicals dbr:Piperolactam_A dbr:Afterbirth dbr:Nephrotoxic dbr:Traditional_medicine dbr:Science_Translational_Medicine dbr:Nephritis dbr:Transversion dbr:Mutagenic dbr:Nephropathy dbr:Uroepithelial dbr:Stephania_tetrandra dbr:Chinese_herbal_medicine dbr:Pictet-Spengler dbr:File:Aristolactams.svg dbr:File:Aristolochia_clematitis_002.JPG dbr:File:Aristolochic_acid_biosynthesis.png |
| dbp:date | September 2022 (en) |
| dbp:imagealt | Aristolochic acid molecule (en) |
| dbp:imagefile | Aristolochic acid.png (en) Aristolochic-acid-3D-spacefill.png (en) |
| dbp:imagename | C=black, H=white, O=red, N=blue (en) |
| dbp:imagesize | 160 (xsd:integer) 180 (xsd:integer) |
| dbp:name | Aristolochic acid I (en) |
| dbp:othernames | Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736 (en) |
| dbp:pin | 8 (xsd:integer) |
| dbp:reason | incidence is normally used only in the singular form, perhaps incidence or incidents was intended (en) |
| dbp:verifiedrevid | 412505426 (xsd:integer) |
| dbp:watchedfields | changed (en) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Cite_book dbt:Cite_journal dbt:Commons_category dbt:IPAc-en dbt:Reflist dbt:Cascite dbt:Chemboximage dbt:Chemspidercite dbt:Ebicite dbt:Fdacite dbt:Keggcite dbt:Stdinchicite dbt:Verify_spelling |
| dcterms:subject | dbc:Benzodioxoles dbc:Nitro_compounds dbc:Phenanthrenes dbc:Phenol_ethers dbc:Benzoic_acids dbc:IARC_Group_1_carcinogens dbc:Plant_toxins |
| gold:hypernym | dbr:Family |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 yago:WikicatAromaticCompounds yago:WikicatBenzoicAcids yago:WikicatCarboxylicAcids yago:WikicatMolecularFormulas yago:WikicatNitroCompounds yago:WikicatNitrobenzenes yago:Abstraction100002137 yago:Acid114607521 yago:AromaticCompound114610088 yago:AromaticHydrocarbon114767996 yago:BenzoicAcid114775321 yago:CarboxylicAcid114739360 yago:Chemical114806838 yago:Cognition100023271 yago:Communication100033020 yago:Compound105870180 yago:Compound114818238 yago:Concept105835747 yago:Content105809192 yago:Element114840755 yago:Formula106816935 yago:Hydrocarbon114911057 yago:Idea105833840 yago:Material114580897 yago:Matter100020827 yago:Message106598915 yago:MolecularFormula106817173 yago:Nitrobenzene114963486 yago:OrganicCompound114727670 yago:Part113809207 yago:PhysicalEntity100001930 yago:Phytochemical114983143 yago:PsychologicalFeature100023100 yago:Quintessence114847103 yago:Relation100031921 dbo:ChemicalCompound yago:Statement106722453 yago:Substance100019613 yago:Whole105869584 yago:WikicatPhenolEthers yago:WikicatPhytochemicals yago:WikicatPolycyclicAromaticHydrocarbons umbel-rc:ChemicalSubstanceType |
| rdfs:comment | Aristolochic acids (English: /əˌrɪstəˈloʊkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering plant family Aristolochiaceae (birthworts). Aristolochic acid (AA) I is the most abundant one. The family Aristolochiaceae includes the genera Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine. Although these compounds are widely associated with kidney problems, liver and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. The FDA has issued warnings regarding consumption of AA-containing supplements. (en) Aristolochiasäuren sind sekundäre Pflanzenstoffe, die in einer Vielzahl von Arten der Gattungen Aristolochia (Pfeifenblumen), Asarum (Haselwurzen), Saruma und Thottea, alle zur Familie der Aristolochiaceae (Osterluzeigewächse) gehörig, nachgewiesen wurden. Biogenetisch leiten sie sich von Aporphin-Alkaloiden ab, wie an der Strukturähnlichkeit mit z. B. den Aporphin-Alkaloiden Apomorphin oder Bulbocapnin zu erkennen ist. Die bei Naturstoffen relativ seltene Nitrogruppe entsteht durch Oxidation des Stickstoffatoms im vormaligen Piperidinring. (de) L'acide aristolochique (C17H11NO7) est un acide carboxylique produit par plusieurs espèces d'aristoloche. La teneur en cet acide varie selon l'espèce, la partie de la plante et les individus. C'est un composé toxique pour les reins, qui peut provoquer des défaillances rénales nécessitant une transplantation de rein.Il est considéré comme carcinogène par l’Organisation mondiale de la santé (OMS).Il est pour ces raisons interdit dans plusieurs pays, comme l'Europe, l'Égypte, le Japon et le Venezuela (fr) Aristolochiazuur I is een van de twee bestanddelen van aristolochiazuur. (nl) アリストロキア酸 (Aristolochic acid) は、ウマノスズクサ属 Aristolochia およびカンアオイ属 Asarum の植物などに含まれる、フェナントレン骨格を持つ芳香族カルボン酸。 アリストロキア酸 I (8-methoxy-6-nitro-phenanthro-(3,4-d)-1,3-dioxolo-5-carboxylic acid) と、アリストロキア酸 II (6-nitro-phenanthro-(3,4-d)-1,3-dioxolo-5-carboxylic acid) の 2 種類 が知られている。II 体は I 体のメトキシ基を水素原子に置換した構造をもつ。 (ja) La aristoloquina o ácido aristolóquico es un componente químico presente en muchas plantas. Debe su nombre a la alta cantidad del mismo que se presenta en las plantas de la familia Aristolochiaceae, más concretamente en la subfamilia Aristolochioideae, sobre todo presentes en el género Aristolochia. * Datos: Q424210 * Multimedia: Aristolochic acid / Q424210 (es) Aristolochiazuur is een kankerverwekkende stof, die in planten van de pijpbloemfamilie, onder andere in sommige soorten uit het geslacht Asarum voorkomt. Aristolochiazuur is in wezen een mengsel dat bestaat uit gelijke delen aristolochiazuur I en aristolochiazuur II. Naast de kankerverwekkendheid is de stof ook sterk nefrotoxisch (nierbeschadigend). Ondanks deze goed gedocumenteerde gevaren wordt aristolochiazuur soms aangetroffen in afslankmiddelen. Aristolochiaplanten worden soms aangetroffen in Chinese kruidenmengsels. (nl) 马兜铃酸（英語：Aristolochic acids，简称AAs）也被称为马兜铃总酸、增噬力酸或木通甲素，是一类具有強烈致癌性和的硝基菲羧酸。这类有机化合物天然存在于诸如马兜铃属（Aristolochia）及细辛属（Asarum）等马兜铃科植物中，而这些植物曾广泛地被用作中草药。此外，依靠吸食这类植物生存的蝴蝶体内也有马兜铃酸。马兜铃酸Ⅰ是最常见的一种马兜铃酸类化合物，它可在几乎所有马兜铃属植物中发现，并常与（aristolactams）共存。 利用热二甲基甲酰胺水溶液中萃取获得的马兜铃酸为有光泽的褐色片状结晶，利用甲醇萃取获得的马兜铃酸则为橘黄色棒状结晶。马兜铃酸类化合物味微苦，可溶于乙醇、氯仿、乙醚、丙酮、冰醋酸、苯胺或碱液，微溶于水，几乎不溶于苯或二硫化碳，熔点介于281-286℃之间（约于286℃分解）。 (zh) |
| rdfs:label | Aristolochiasäuren (de) Aristolochic acid (en) Aristoloquina (es) Acide aristolochique (fr) アリストロキア酸 (ja) Aristolochiazuur I (nl) Aristolochiazuur (nl) 马兜铃酸 (zh) |
| owl:sameAs | freebase:Aristolochic acid yago-res:Aristolochic acid wikidata:Aristolochic acid wikidata:Aristolochic acid dbpedia-de:Aristolochic acid dbpedia-es:Aristolochic acid dbpedia-fa:Aristolochic acid dbpedia-fr:Aristolochic acid dbpedia-ja:Aristolochic acid dbpedia-nl:Aristolochic acid dbpedia-nl:Aristolochic acid dbpedia-sh:Aristolochic acid dbpedia-sl:Aristolochic acid dbpedia-sr:Aristolochic acid http://ta.dbpedia.org/resource/அரிஸ்டோலோக்கிக்_அமிலம் dbpedia-vi:Aristolochic acid dbpedia-zh:Aristolochic acid https://global.dbpedia.org/id/zsEY |
| prov:wasDerivedFrom | wikipedia-en:Aristolochic_acid?oldid=1108570842&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Aristolactams.svg wiki-commons:Special:FilePath/Aristolochia_clematitis_002.jpg wiki-commons:Special:FilePath/Aristolochic-acid-3D-spacefill.png wiki-commons:Special:FilePath/Aristolochic_acid.png wiki-commons:Special:FilePath/Aristolochic_acid_biosynthesis.png |
| foaf:isPrimaryTopicOf | wikipedia-en:Aristolochic_acid |
| foaf:name | Aristolochic acid I (en) |
| is dbo:wikiPageRedirects of | dbr:Aristinic_acid dbr:Aristolochia_yellow dbr:Aristolochic_acid_A dbr:Aristolochic_acid_B dbr:Aristolochic_acid_I dbr:Aristolochic_acid_II dbr:Aristolochic_acids dbr:Aristolochin dbr:Aristolochine dbr:Isoaristolochic_acid dbr:TR_1736 dbr:Descresept dbr:C17H11NO7 dbr:Tardolyt |
| is dbo:wikiPageWikiLink of | dbr:Transitional_epithelium dbr:Birdwing dbr:Bladder_cancer dbr:List_of_traditional_Chinese_medicines dbr:Aristinic_acid dbr:Aristolochia_yellow dbr:Aristolochic_acid_A dbr:Aristolochic_acid_B dbr:Aristolochic_acid_I dbr:Aristolochic_acid_II dbr:Aristolochic_acids dbr:Aristolochin dbr:Aristolochine dbr:List_of_herbs_with_known_adverse_effects dbr:Isoaristolochic_acid dbr:Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons dbr:Opsin dbr:TR_1736 dbr:Aristolochia dbr:Aristolochia_californica dbr:Aristolochia_clematitis dbr:Aristolochia_didyma dbr:Aristolochia_grandiflora dbr:Aristolochia_indica dbr:Aristolochia_littoralis dbr:Aristolochia_paucinervis dbr:Aristolochia_rotunda dbr:Battus_philenor dbr:Battus_philenor_hirsuta dbr:Descresept dbr:C17H11NO7 dbr:Doctrine_of_signatures dbr:Drosophila_melanogaster dbr:Ginger dbr:Balkan_endemic_nephropathy dbr:Queen_Alexandra's_birdwing dbr:Aristolochia_chilensis dbr:Aristolochia_macrophylla dbr:Aristolochiaceae dbr:Swallowtail_butterfly dbr:Asarum dbr:Asarum_canadense dbr:Asarum_caudatum dbr:Piperolactam_A dbr:Methylglyoxal dbr:Ochratoxin_A dbr:Nephrotoxicity dbr:IARC_group_1 dbr:Phytochemical dbr:Transversion dbr:Uddanam_nephropathy dbr:Pachliopta_aristolochiae dbr:Pachliopta_hector dbr:Stephania_tetrandra dbr:Tardolyt |
| is foaf:primaryTopic of | wikipedia-en:Aristolochic_acid |
