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{{Short description|Chemical compound}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 389527396 |
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| Watchedfields = changed |
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| ImageFile = Chaconine.svg |
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| verifiedrevid = 437977784 |
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| ImageSize = |
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| ImageFile = Chaconine.svg |
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| IUPACName =beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))- |
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| OtherNames = |
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| ImageSize = |
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| ImageFile2 = File:Chaconine1.png |
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| Section1 = {{Chembox Identifiers |
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| ImageCaption2 = 3D model of chaconine using MolView |
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| CASNo =20562-03-2 |
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| IUPACName = Solanid-5-en-3β-yl α-{{small|L}}-rhamnopyranosyl-(1→2)--β-{{small|D}}-glucopyranoside |
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| PubChem =104750 |
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| SystematicName = (2''S'',2′''S'',3''R'',3′''R'',4''R'',4′''R'',5''R'',5′''R'',6''S'',6′''S'')-2,2′-<nowiki/>{indenoindolizin-2-yl]oxy}oxane-3,5-diyl]bis(oxy)}bis(6-methyloxane-3,4,5-triol) |
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| Beilstein = 77396 |
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| OtherNames = α-Chaconine, Chaconine |
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| SMILES = C1CC2(3(N2C1)C43(CC54CC=C65(CC(C6)O7((((O7)CO)O8((((O8)C)O)O)O)O)O9((((O9)C)O)O)O)C)C)C}} |
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| Section2 = {{Chembox Properties |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Formula = |C=45|H=73|N=1|O=14| |
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| CASNo = 20562-03-2 |
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| Beilstein = 77396 |
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| PubChem = 442971 |
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| ChEBI = 10219 |
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| ChEMBL2 = 2288884 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 391274 |
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| KEGG = C10796 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5QOL0LIM81 |
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| SMILES = O(8(O4C/C3=C/C25C1N6((C)15(C)CC23(C)CC4)CC(C)C6)O(CO)(O7O(C)(O)(O)7O)8O)9O((O)(O)9O)C |
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| SMILES2 = C1CC2(3(N2C1)C43(CC54CC=C65(CC(C6)O7((((O7)CO)O8((((O8)C)O)O)O)O)O9((((O9)C)O)O)O)C)C)C |
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| InChI = 1/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1 |
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| InChIKey = TYNQWWGVEGFKRU-AJDPQWBVBS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = TYNQWWGVEGFKRU-AJDPQWBVSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = | C=45 | H=73 | N=1 | O=14 |
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| MolarMass =<!-- calculated --> |
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| MolarMass =<!-- calculated --> |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = 243°C |
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| MeltingPtC = 243 |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=alpha-Chaconine |url=https://pubchem.ncbi.nlm.nih.gov/compound/442971#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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| GHSPictograms = {{GHS08}} {{GHS skull and crossbones}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|361}} |
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| PPhrases = {{P-phrases|203|280|318|405|501}} |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''α-Chaconine''' is a ] ] ] ] that occurs in plants of the ] family. It is a natural toxicant produced in green ] and gives the potato a bitter taste.<ref name=toxin>Kuiper-Goodman, T. and Nawrot, P.S. "" IPCS, INCHEM</ref> Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties.<ref name=toxin/> |
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'''α-Chaconine''' is a ] ] that occurs in plants of the family ]. It is a natural ] produced in green ] and gives the potato a bitter taste.<ref name="toxin">{{cite web |author1=Kuiper-Goodman, T. |author2=Nawrot, P.S. |url=http://www.inchem.org/documents/jecfa/jecmono/v30je19.htm |title=Toxin profile: Solanine and Chaconine IPCS, INCHEM |url-status=live |access-date=2021-03-15|archive-url=https://web.archive.org/web/20010225195252/http://www.inchem.org:80/documents/jecfa/jecmono/v30je19.htm |archive-date=2001-02-25 }}</ref> ] produce this glycoalkaloid in response to stress, providing the plant with ] and ] properties.<ref name="toxin" /> It belongs to the chemical family of ]s. Since it causes physiological effects on individual organism, chaconine is considered to be a defensive ].<ref>{{cite book |title=Saponins used in traditional and modern medicine |date=1996 |publisher=Springer |location=Boston, MA |isbn=978-1-4899-1369-2 |pages=277–295}}</ref> ], a related substance also found in potatoes, has similar properties. |
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== Symptoms and treatment == |
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Symptoms resemble those seen following solanine ingestion including abdominal pain, diarrhea, and headache.<ref name="potato effect">{{cite journal |last1=McKenzie |first1=Marian |last2=Corrigan |first2=Virginia |title=Chapter 12 - Potato Flavor |journal=Advances in Potato Chemistry and Technology (Second Edition) |date=1 January 2016 |pages=339–368 |doi=10.1016/B978-0-12-800002-1.00012-1|isbn=9780128000021 }}</ref> |
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There is currently no ] for detoxification but if it is just after consumption, taking laxatives or gastric lavage could be effective. The symptoms could last several days. |
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== Toxicity == |
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The presence of more than 20 mg/100g tuber glycoalkaloids is toxic for humans.<ref name="old potato">{{cite book |title=Potato Flavor and Texture |chapter=Potato Flavour and Texture |year=2007 |doi=10.1016/B978-044451018-1/50066-X |chapter-url=https://doi.org/10.1016/B978-044451018-1/50066-X |last1=Taylor |first1=Mark A. |last2=McDougall |first2=Gordon J. |last3=Stewart |first3=Derek |pages=525–540 |isbn=9780444510181 }}</ref> |
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There have been instances of fatal poisoning cases from potatoes with high glycoalkaloid content.<ref name="old potato2">{{cite journal |title=a-Chaconine and a-Solanine Content of Potato Products and Their Stability during Several Modes of Cooking |volume=29| doi=10.1021/jf00106a033|journal=Journal of Agricultural and Food Chemistry |date=July 1981 |issue=4 |pages=814–817 |last1=Bushway |first1=Rodney J. |last2=Ponnampalam |first2=Rathy }}</ref> However, such cases are rare.<ref>{{cite web |title=Potato plant poisoning - green tubers and sprouts |url=https://medlineplus.gov/ency/article/002875.htm}}</ref> |
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Some research shows teratogenic effects on humans, but epidemiological investigations have produced conflicting research, as well.<ref name="old potato2" /> |
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Levels of glycoalkaloids most likely differ by cultivar, storage conditions (especially exposure to sunlight), and processing techniques.<ref name="old potato2" /> |
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== Difference between chaconine and solanine == |
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=== Structural difference === |
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Although α-chaconine and α-solanine are both derived from ], the difference appears in 3 groups attached to the terminal oxygen in solanidine. For α-chaconine, these groups are one ] and two ] whereas in α-solanine, they are ], ], and ]. |
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=== Difference in toxicity === |
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In an experiment demonstrating the feeding-inhibition effect of solanine and chaconine on snails, chaconine had a greater effect than solanine. However, a mixture of chaconine and solanine had a synergistic effect. The mixture had a significantly higher effect of deterred feeding than using solanine and chaconine on their own.<ref>{{cite journal |last1=Smith |first1=David B. |last2=Roddick |first2=James G. |last3=Jones |first3=J.Leighton |title=Synergism between the potato glycoalkaloids α-chaconine and α-solanine in inhibition of snail feeding |journal=Phytochemistry |date=May 2001 |volume=57 |issue=2 |pages=229–234 |doi=10.1016/S0031-9422(01)00034-6|pmid=11382238 |bibcode=2001PChem..57..229S }}</ref> |
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=== Ratio of ɑ-chaconine to ɑ-solanine in potato === |
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On average, it is between 1.2 and 2.6 to 1, meaning the amount of ɑ-chaconine is greater than ɑ-solanine.<ref name="potato size">{{cite journal |last1=Friedman |first1=Mendel |last2=Levin |first2=Carol E. |title=Analysis and Biological Activities of Potato Glycoalkaloids, Calystegine Alkaloids, Phenolic Compounds, and Anthocyanins |journal=Advances in Potato Chemistry and Technology |date=2009 |pages=127–161 |doi=10.1016/B978-0-12-374349-7.00006-4|isbn=9780123743497 }}</ref> However, the average ratio for the peel was 2.0 whereas that for the flesh was nearly 1.5. Also, the ratio was not consistent and depended on cultivar, growth condition, and method of storage.<ref name="potato size" /><ref name="potato effect" /> |
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== Research on glycoalkaloids == |
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=== Controlling the amount of steroidal glycoalkaloids in Potato === |
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In 2014, a research group in Japan from the ] (or RIKEN) found ] for ] that are involved in the synthesis of ], cycloartanol, and related steroidal glycoalkaloids (SGAs), SSR2. Since SGAs are biosynthesized from cholesterol, restricting those enzymes could reduce the amount of the SGAs in potato.<ref>{{cite journal |last1=Sawai |first1=S. |last2=Ohyama |first2=K. |last3=Yasumoto |first3=S. |last4=Seki |first4=H. |last5=Sakuma |first5=T. |last6=Yamamoto |first6=T. |last7=Takebayashi |first7=Y. |last8=Kojima |first8=M. |last9=Sakakibara |first9=H. |last10=Aoki |first10=T. |last11=Muranaka |first11=T. |last12=Saito |first12=K. |last13=Umemoto |first13=N. |title=Sterol Side Chain Reductase 2 Is a Key Enzyme in the Biosynthesis of Cholesterol, the Common Precursor of Toxic Steroidal Glycoalkaloids in Potato |journal=The Plant Cell |date=1 September 2014 |volume=26 |issue=9 |pages=3763–3774 |doi=10.1105/tpc.114.130096 |pmid=25217510 |pmc=4213163 |doi-access=free}}</ref> |
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=== Level of glycoalkaloids === |
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The research studied the effects of different cooking techniques on the amount of glycoalkaloids (containing more than 90% of both solanine and chaconine). The techniques studied were boiling, baking, frying, and microwaving. The research found that fried peel has the largest amount of glycoalkaloids (139–145 mg/100g of product), whereas potatoes prepared with other methods contained an average amount of 3 mg/100g product.<ref name="old potato2" /> |
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Another research found the amount of SGAs is unaffected by baking, boiling, and frying.<ref>{{cite journal |doi=10.1016/j.foodchem.2005.08.046 |title=Balance between nutrients and anti-nutrients in nine Italian potato cultivars |year=2006 |last1=Finotti |first1=Enrico |last2=Bertone |first2=Aldo |last3=Vivanti |first3=Vittorio |journal=Food Chemistry |volume=99 |issue=4 |pages=698–701 }}</ref> This research also showed very high level of SGAs with non-peeled potato tubers (200 mg kg^-1 FM). |
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In 2004, one study that investigated the change in the amount of α-chaconine and α-solanine over 90 days. The result showed how the amount of both α-chaconine and α-solanine did not change significantly if it is kept in a cold and dark place. While the amount varied slightly, the research concluded that it is due to the cultivar.<ref>{{cite journal |title=Contents and its Change during Storage of a-Solanine and a-Chaconine in Potatoes |date=2004 |doi=10.3358/shokueishi.45.277 |pmid=15678944 |doi-access=free |last1=Shindo |first1=T. |last2=Ushiyama |first2=H. |last3=Kan |first3=K. |last4=Yasuda |first4=K. |last5=Saito |first5=K. |journal=Shokuhin Eiseigaku Zasshi. Journal of the Food Hygienic Society of Japan |volume=45 |issue=5 |pages=277–282 }}</ref> |
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=== Treating poisons in potato === |
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Peels and sprouts usually contain high level of SGAs. Relatively larger amounts can be found if the tuber is exposed to sunlight. If tubers are not matured enough, those might contain high level of chaconine and solanine. Thus, sprouts on potato and peels should be removed and if there are green parts inside the potato, it should be removed as well. |
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It should be preserved in a dark and cold place, but it does not have to be in the fridge. It is likely to germinate or degrade when the surrounding is above 20°C. Heating might not be very effective towards SGAs, therefore, those contain high level of SGAs should be carefully removed.<ref>{{cite web |title=Review of Toxicological Literature |url=https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/chaconinesolanine_508.pdf |url-status=live |access-date=2021-03-15|archive-url=https://web.archive.org/web/20131107133518/http://ntp.niehs.nih.gov:80/ntp/htdocs/Chem_Background/ExSumPdf/ChaconineSolanine_508.pdf |archive-date=2013-11-07 }}</ref><ref name="toxin" /> |
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Also, if potatoes are kept in a fridge, it increases the amount of sugar. When cooked, such as frying or baking, ] can form. |
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When cooking potatoes, if it is fried at 210°C for 10 minutes, the amount of solanine and chaconine is reduced to 60% of the original amount. If it is fried at 170°C for 5 minutes, there was no significant change in the amount of solanine and chaconine. However, if it is fried for 15 minutes at the same temperature, solanine decreased to 76.1% and chaconine decreased to 81.5%. Thus, the break down of solanine and chaconine are considered to start around 170°C.<ref name="japa pot">{{cite journal |date=1990 |pages=67–73 |doi=10.3358/shokueishi.31.67 |url=https://ci.nii.ac.jp/naid/130003692956 |access-date=2021-03-15|doi-access=free |title=Effect of Cooking on the Contents of α-Chaconine and α-Solanine in Potatoes |last1=Takagi |first1=Kayoko |last2=Toyoda |first2=Masatake |last3=Fujiyama |first3=Yuki |last4=Saito |first4=Yukio |journal=Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) |volume=31 }}</ref> In another study, a solution containing α-solanine and α-chaconine is put into boiling water for 150 minutes. The study found no significant decrease in the amount of solanine and chaconine. Therefore, it can be considered that boiling potato is not effective to reduce the amount of solanine and chaconine.<ref name="japa pot" /> |
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Also, since glycoalkaloids are soluble in water, soaking potatoes in water may cause SGAs to dissolve into the water.<ref>{{cite journal |title=Changes in the Levels of Glycoalkaloids and Nitrates After the Dehydration of Cooked Potatoes |doi=10.1007/s12230-012-9273-0 |journal=American Journal of Potato Research |year=2012 |doi-access=free |last1=Rytel |first1=Elżbieta |volume=89 |issue=6 |pages=501–507 }}</ref> |
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=== Attempts to make toxin-free potato === |
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Research was launched in 2015 attempting to make potatoes with no glycoalkaloids by ]. Because glycoalkaloids heavily affects human health it is necessary to test for the amount present in potatoes, an expense that would be saved if a glycoalkaloid free potato were available, in addition to being a more healthy food. |
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Part of the research involves trying to determine what advantage potatoes achieve from producing glycoalkaloids. Research has been published suggesting that potatoes benefit little from the production of glycoalkaloids, though other research have questioned that conclusion.<ref>{{cite web |last1=Umemoto |first1=Naoyuki |title=Is It Possible to Breed Toxin-Free Potato?: Identification and Application of Glycoalkaloid Biosynthetic Genes |url=https://katosei.jsbba.or.jp/view_html.php?aid=491}}</ref><ref>{{cite journal |title=Leptine Glycoalkaloids and Resistance to the Colorado Potato Beetle (Coleoptera: Chrysomelidae) in Solanum chacoense | volume=15|doi=10.1093/ee/15.5.1057 |url=https://doi.org/10.1093/ee/15.5.1057 |journal=Environmental Entomology | year=1986|access-date=2021-03-15| last1=Sinden| first1=Stephen L.| last2=Sanford| first2=Lind L.| last3=Cantelo| first3=William W.| last4=Deahl| first4=Kenneth L.| issue=5| pages=1057–1062}}</ref> |
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== See also == |
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== See also == |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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==External links== |
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{{biochem-stub}} |
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*{{Commons category-inline}} |
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