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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/17 20:05:23」(JST)

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Aristolochic acids are a family of carcinogenic, mutagenic, and nephrotoxic compounds commonly found in the Aristolochiaceae family of plants, including Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine.^[1]^[2] Aristolochic acid I is the most abundant of the aristolochic acids and is found in almost all Aristolochia species.^[3] Aristolochic acids are often accompanied by aristolactams.^[4]

Aristolochic acids are slightly soluble in water, have a melting point between 281 and 286 degrees celsius,^[5] and have a bitter flavor.^[6]

Toxicity[edit]

Aristolochic acids are hypothesized to be causative agents in Balkan endemic nephropathy;^[7]^[8]^[9] and a related—possibly identical—condition known as "Chinese herbs nephropathy".^[10] Exposure to aristolochic acid is associated with a high incidence of uroepithelial tumorigenesis,^[11] and is linked to urothelial cancer.^[12]^[13]

In April 2001, the Food and Drug Administration issued a consumer health alert warning against consuming botanical products, sold as "traditional medicines" or as ingredients in dietary supplements, containing aristolochic acid.^[14] The agency warned that consumption of aristolochic acid-containing products was associated with "permanent kidney damage, sometimes resulting in kidney failure that has required kidney dialysis or kidney transplantation. In addition, some patients have developed certain types of cancers, most often occurring in the urinary tract."^[14]

In August 2013, two studies identified aristolochic acid mutational signature in upper urinary tract cancer patients from Taiwan.^[15]^[16] The carcinogenic effect is found to be the most potent found thus far, exceeding the amount of mutations in smoking-induced lung cancer and UV-exposed melanoma. Exposure to aristolochic acid may also cause certain types of liver cancer.^[15]

References[edit]

^ Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558.
^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3.
^ Wu, Tian-Shung et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2.
^ Wink, Michael & Schimmer, Oskar (1999). "Modes of action of defensive secondary metabolites". In Wink, Michael. Functions of plant secondary metabolites and their exploitation in biotechnology. CRC Press. p. 75. ISBN 978-0-8493-4086-4.
^ Barceloux, Donald G. (2008). "Aristolochic acid and Chinese Herb nephropathy". Medical toxicology of natural substances: foods, fungi, medicinal herbs, plants, and venomous animals. John Wiley & Sons. p. 384. ISBN 978-0-471-72761-3.
^ Offermanns, S. & Amara, Susan G., ed. (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 978-3-540-30384-8.
^ Gluhovschi G, Margineanu F, Velciov S, Gluhovschi C, Bob F, Petrica L, Bozdog G, Trandafirescu V, Modalca M (January 2011). "Fifty years of Balkan endemic nephropathy in Romania: some aspects of the endemic focus in the Mehedinti county". Clin. Nephrol. 75 (1): 34–48. PMID 21176749.
^ Geacintov, Nicholas E. & Broyde, Suse, ed. (2010). "Introduction and perspectives on the Chemistry and Biology of DNA Damage". The Chemical Biology of DNA Damage. Wiley-VCH. p. 7. ISBN 978-3-527-32295-4.
^ Wild, Chris et al., ed. (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 978-0-470-02743-1.
^ De Broe ME (March 2012). "Chinese herbs nephropathy and Balkan endemic nephropathy: toward a single entity, aristolochic acid nephropathy". Kidney Int. 81 (6): 513–5. doi:10.1038/ki.2011.428. PMID 22373701.
^ Ronco, Claudio et al., ed. (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 978-1-4160-4252-5.
^ Chen CH, Dickman KG, Moriya M, Zavadil J, Sidorenko VS, Edwards KL, Gnatenko DV, Wu L, Turesky RJ, Wu XR, Pu YS, Grollman AP (May 2012). "Aristolochic acid-associated urothelial cancer in Taiwan". Proc. Natl. Acad. Sci. U.S.A. 109 (21): 8241–6. doi:10.1073/pnas.1119920109. PMC 3361449. PMID 22493262.
^ Lai, M.-N.; Wang, S.-M.; Chen, P.-C.; Chen, Y.-Y.; Wang, J.-D. (2009). "Population-Based Case-Control Study of Chinese Herbal Products Containing Aristolochic Acid and Urinary Tract Cancer Risk". JNCI Journal of the National Cancer Institute 102 (3): 179. doi:10.1093/jnci/djp467.
^ ^a ^b FDA Warns Consumers to Discontinue Use of Botanical Products that Contain Aristolochic acid. April 11, 2001.
^ ^a ^b Poon, S. L.; Pang, S.-T.; McPherson, J. R.; Yu, W.; Huang, K. K.; Guan, P.; Weng, W.-H.; Siew, E. Y. et al. (2013). "Genome-Wide Mutational Signatures of Aristolochic Acid and Its Application as a Screening Tool". Science Translational Medicine 5 (197): 197ra101. doi:10.1126/scitranslmed.3006086. PMID 23926199. |displayauthors= suggested (help)
^ Hoang, M. L.; Chen, C.-H.; Sidorenko, V. S.; He, J.; Dickman, K. G.; Yun, B. H.; Moriya, M.; Niknafs, N. et al. (2013). "Mutational Signature of Aristolochic Acid Exposure as Revealed by Whole-Exome Sequencing". Science Translational Medicine 5 (197): 197ra102. doi:10.1126/scitranslmed.3006200. PMID 23926200. |displayauthors= suggested (help)

External links[edit]

Wikimedia Commons has media related to Aristolochic acid.

Complete list of warnings from the US Food and Drug Administration
FDA Concerned About Botanical Products, Including Dietary Supplements, Containing Aristolochic Acid May 2000.
Plants Containing Aristolochic Acid
Herbal medicines causing kidney failure, bladder cancer in India, Times of India, Mar 19, 2013

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ハーブ含有アリストロキン酸（AA）誘発性腎症 nephropathy induced by aristolochic acid aa containing herbs
2. 尿路上皮（移行上皮）膀胱癌の疫学および病因 epidemiology and etiology of urothelial transitional cell carcinoma of the bladder
3. バルカン流行性腎症 balkan endemic nephropathy
4. 鎮痛剤性腎症の臨床症状および診断 clinical manifestations and diagnosis of analgesic nephropathy

English Journal

Vitamin C attenuates the toxic effect of aristolochic acid on renal tubular cells via decreasing oxidative stress‑mediated cell death pathways.

Wu TK1, Wei CW2, Pan YR2, Cherng SH3, Chang WJ4, Wang HF2, Yu YL1.
Molecular medicine reports.Mol Med Rep.2015 Oct;12(4):6086-92. doi: 10.3892/mmr.2015.4167. Epub 2015 Aug 3.
Aristolochic acid (AA) is a component of Chinese medicinal herbs, including asarum and aristolochia and has been used in Traditional Chinese Medicine for a long time. Recent studies found that AA has a cytotoxic effect resulting in nephropathy. These studies indicated that AA‑induced cytotoxicity
PMID 26239057

Low-coverage exome sequencing screen in formalin-fixed paraffin-embedded tumors reveals evidence of exposure to carcinogenic aristolochic acid.

Castells X1, Karanović S2, Ardin M1, Tomić K3, Xylinas E4, Durand G5, Villar S6, Forey N7, Le Calvez-Kelm F8, Voegele C7, Karlović K3, Mišić M3, Dittrich D3, Dolgalev I9, McKay JD7, Shariat SF10, Sidorenko VS11, Fernandes A11, Heguy A12, Dickman KG11, Olivier M6, Grollman AP13, Jelaković B14, Zavadil J15.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.Cancer Epidemiol Biomarkers Prev.2015 Sep 17. pii: cebp.0553.2015. [Epub ahead of print]
BACKGROUND: Dietary exposure to cytotoxic and carcinogenic aristolochic acid (AA) causes severe nephropathy typically associated with urological cancers. Monitoring of AA exposure uses biomarkers such as aristolactam-DNA adducts, detected by mass spectrometry in the kidney cortex, or the somatic A&g
PMID 26383547

Case study of building of conservation coalitions to conserve ecological interactions.

Chen G1, Luo S2, Mei N3, Shen D4, Sun W1.
Conservation biology : the journal of the Society for Conservation Biology.Conserv Biol.2015 Sep 15. doi: 10.1111/cobi.12583. [Epub ahead of print]
We engaged experts in various fields of study (pollination ecology, chemical ecology, and ethnobotany), invited community participation, and provided environmental education in an effort to conserve an endangered birthwort (Aristolochia delavayi) and a vulnerable pipevine swallowtail (Byasa daemoniu
PMID 26372410

Japanese Journal

P4-006　慢性肉芽腫症モデルマウスにおいてアリストロキア酸誘導性尿細管壊死性腎炎が増悪するメカニズムの解析

日本臨床免疫学会会誌 38(4), 331b-331b, 2015
NAID 130005104639

S2-1 Mutational signature of aristolochic acid as a unique biomarker of human cancer(Keynote Lecture,Symposium 2 Examples of Genotoxic and/or Carcinogenic Risk Assessment Based on Mechanism of Action)

日本環境変異原学会大会プログラム・要旨集 (43), 69, 2014-10-31
NAID 110010012332

Uptake of Aristolochic Acid I into Caco-2 Cells by Monocarboxylic Acid Transporters

Biological and Pharmaceutical Bulletin 37(9), 1475-1479, 2014
NAID 130004684786

「アリストロキア酸」

Aristolochic acid I
	IUPAC name 8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
	Other names Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736
Identifiers
CAS number	313-67-7
PubChem	2236
ChemSpider	2149
KEGG	C08469
ChEMBL	CHEMBL93353
Jmol-3D images	Image 1
	SMILES [O-][N+](=O)c1cc4c(c2c1c(C(=O)O)cc3OCOc23)cccc4OC ;
	InChI InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20) ; Key: BBFQZRXNYIEMAW-UHFFFAOYSA-N InChI=1/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20); Key: BBFQZRXNYIEMAW-UHFFFAOYAG ;
Properties
Molecular formula	C17H11NO7
Molar mass	341.27 g mol−1
Melting point	260 - 265 °C
Solubility in water	Slightly soluble
Hazards
NFPA 704	1 2 0
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: aristolochic acid
関: アリストロキン酸

「アリストロキン酸」

　　[★]

英: aristolochic acid
関: アリストロキア酸

[1] Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558.

[2] Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3.

[3] Wu, Tian-Shung et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2.

[4] Wink, Michael & Schimmer, Oskar (1999). "Modes of action of defensive secondary metabolites". In Wink, Michael. Functions of plant secondary metabolites and their exploitation in biotechnology. CRC Press. p. 75. ISBN 978-0-8493-4086-4.

[5] Barceloux, Donald G. (2008). "Aristolochic acid and Chinese Herb nephropathy". Medical toxicology of natural substances: foods, fungi, medicinal herbs, plants, and venomous animals. John Wiley & Sons. p. 384. ISBN 978-0-471-72761-3.

[6] Offermanns, S. & Amara, Susan G., ed. (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 978-3-540-30384-8.

[7] Gluhovschi G, Margineanu F, Velciov S, Gluhovschi C, Bob F, Petrica L, Bozdog G, Trandafirescu V, Modalca M (January 2011). "Fifty years of Balkan endemic nephropathy in Romania: some aspects of the endemic focus in the Mehedinti county". Clin. Nephrol. 75 (1): 34–48. PMID 21176749.

[8] Geacintov, Nicholas E. & Broyde, Suse, ed. (2010). "Introduction and perspectives on the Chemistry and Biology of DNA Damage". The Chemical Biology of DNA Damage. Wiley-VCH. p. 7. ISBN 978-3-527-32295-4.

[9] Wild, Chris et al., ed. (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 978-0-470-02743-1.

[10] De Broe ME (March 2012). "Chinese herbs nephropathy and Balkan endemic nephropathy: toward a single entity, aristolochic acid nephropathy". Kidney Int. 81 (6): 513–5. doi:10.1038/ki.2011.428. PMID 22373701.

[11] Ronco, Claudio et al., ed. (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 978-1-4160-4252-5.

[12] Chen CH, Dickman KG, Moriya M, Zavadil J, Sidorenko VS, Edwards KL, Gnatenko DV, Wu L, Turesky RJ, Wu XR, Pu YS, Grollman AP (May 2012). "Aristolochic acid-associated urothelial cancer in Taiwan". Proc. Natl. Acad. Sci. U.S.A. 109 (21): 8241–6. doi:10.1073/pnas.1119920109. PMC 3361449. PMID 22493262.

[13] Lai, M.-N.; Wang, S.-M.; Chen, P.-C.; Chen, Y.-Y.; Wang, J.-D. (2009). "Population-Based Case-Control Study of Chinese Herbal Products Containing Aristolochic Acid and Urinary Tract Cancer Risk". JNCI Journal of the National Cancer Institute 102 (3): 179. doi:10.1093/jnci/djp467.

[2001FDA-14] FDA Warns Consumers to Discontinue Use of Botanical Products that Contain Aristolochic acid. April 11, 2001.

[Poon-15] Poon, S. L.; Pang, S.-T.; McPherson, J. R.; Yu, W.; Huang, K. K.; Guan, P.; Weng, W.-H.; Siew, E. Y. et al. (2013). "Genome-Wide Mutational Signatures of Aristolochic Acid and Its Application as a Screening Tool". Science Translational Medicine 5 (197): 197ra101. doi:10.1126/scitranslmed.3006086. PMID 23926199. |displayauthors= suggested (help)

[16] Hoang, M. L.; Chen, C.-H.; Sidorenko, V. S.; He, J.; Dickman, K. G.; Yun, B. H.; Moriya, M.; Niknafs, N. et al. (2013). "Mutational Signature of Aristolochic Acid Exposure as Revealed by Whole-Exome Sequencing". Science Translational Medicine 5 (197): 197ra102. doi:10.1126/scitranslmed.3006200. PMID 23926200. |displayauthors= suggested (help)

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aristolochic acid