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Not to be confused with Solanin.

Solanine is a glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the Potato (Solanum tuberosum) and the Tomato (Solanum lycopersicum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has fungicidal and pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named.^[1]

Solanine poisoning

Symptoms

Solanine poisoning is primarily displayed by gastrointestinal and neurological disorders. Symptoms include nausea, diarrhea, vomiting, stomach cramps, burning of the throat, cardiac dysrhythmia, headache and dizziness. In more severe cases, hallucinations, loss of sensation, paralysis, fever, jaundice, dilated pupils, hypothermia and death have been reported.

In large quantities, solanine poisoning can cause death. One study suggests that doses of 2 to 5 mg per kilogram of body weight can cause toxic symptoms, and doses of 3 to 6 mg per kilogram of body weight can be fatal.^[2]

Symptoms usually occur 8 to 12 hours after ingestion, but may occur as rapidly as 30 minutes after eating high-solanine foods.

The lowest dose to cause symptoms of nausea is about 25 mg solanine for adults, a life-threatening dose for a regular-weight adult ranges about 400 mg solanine.^{[citation needed]}

Mechanism of action

One study suggests that the toxic mechanism of solanine is caused by the chemical's interaction with mitochondrial membranes. Experiments show that solanine exposure opens the potassium channels of mitochondria, decreasing their membrane potential. This in turn leads to Ca²⁺ being transported from the mitochondria into the cytoplasm, and it is this increased concentration of Ca²⁺ in the cytoplasm that triggers cell damage and apoptosis.^[3]

Correlation with birth defects

Some studies show a correlation between the consumption of potatoes suffering from late blight (which increases solanine and other glycoalkaloid levels) and the incidence of congenital spina bifida in humans.^{[citation needed]} However, other studies have shown no correlation between potato consumption and the incidence of birth defects.^[4]

Solanine in potatoes

Green potatoes have solanine.

Solanine occurs naturally in many species of the genus Solanum, including the potato (Solanum tuberosum), tomato (Solanum lycopersicum), eggplant (Solanum melongena), and bittersweet nightshade (Solanum dulcamara).

Potatoes naturally produce solanine and chaconine, a related glycoalkaloid, as a defense mechanism against insects, disease, and predators. Potato leaves, stems and shoots are naturally high in glycoalkaloids.

When potato tubers are exposed to light, they turn green and increase glycoalkaloid production. This is a natural defense to help prevent the uncovered tuber from being eaten. The green colour is from chlorophyll, and is itself harmless. However, it is an indication that increased level of solanine and chaconine may be present.

Some diseases, such as late blight, can dramatically increase the levels of glycoalkaloids present in potatoes. Mechanically damaged potatoes also produce increased levels of glycoalkaloids. This is believed to be a natural reaction of the plant in response to disease and damage.

In potato tubers, 30–80% of the solanine develops in and close to the skin.

In the 70s, Solanine poisoning affected 78 school boys in Britain. Due to immediate and effective treatments, no one died.^[5]

Showing green under the skin strongly suggests solanine build-up in potatoes, although each process can occur without the other. A bitter taste in a potato is another, potentially more reliable indicator of toxicity. Because of the bitter taste and appearance of such potatoes, solanine poisoning is rare outside conditions of food shortage. The symptoms are mainly vomiting and diarrhea, and the condition may be misdiagnosed as gastroenteritis. Most potato poisoning victims recover fully, although fatalities are known, especially when victims are undernourished or do not receive suitable treatment.^[6] Fatalities are also known from solanine poisoning from other plants in the nightshade family, such as the berries of Solanum dulcamara (woody nightshade).^[7]

The United States National Institutes of Health's information on solanine says to never eat potatoes that are green below the skin.

Deep frying potatoes at 170°C (306°F) is known to effectively lower glycoalkaloid levels (because they move into the frying fat), whereas microwaving is only somewhat effective, freeze drying or dehydration has little effect, and boiling has no effect.^[8]

Solanine in tomatoes

Some, such as the California Poison Control System, have claimed that tomatoes and tomato leaves contain solanine. However, Dr. Mendel Friedman of the federal Department of Agriculture contradicts this claim stating that tomatine, a relatively benign alkaloid, is the tomato alkaloid while solanine is found in potatoes. Food science writer Harold McGee has found scant evidence for tomato toxicity in the medical and veterinary literature.^[9]

Other uses of solanine

Solanine has fungicidal and pesticidal properties, and solanine hydrochloride (a salt of solanine) has been used as a commercial pesticide, but never on a large scale.^{[citation needed]}

Solanine has sedative and anticonvulsant properties, and has been used as a treatment for asthma, as well as for cough and cold medicines. However, its effectiveness for either use is questionable.^{[citation needed]}

References

^ Desfosses, M. (1820): Extrait d'une lettre à M. Robiquet. In: J. de Pharmacie. Bd. 6, S. 374–376.
^ Executive Summary of Chaconine & Solanine
^ Gao SY, Wang QJ, Ji YB (June 2006). "Effect of solanine on the membrane potential of mitochondria in HepG2 cells and (Ca2+)i in the cells". World Journal of Gastroenterology 12 (21): 3359–67. PMID 16733852. http://www.wjgnet.com/1007-9327/12/3359.asp. Retrieved 2009-05-31.
^ "SOLANINE AND CHACONINE". http://www.inchem.org/documents/jecfa/jecmono/v30je19.htm. Retrieved 31 May 2009.
^ "Solanine Poisoning". Article. British Medical Journal. http://www.bmj.com/content/2/6203/1458.2. Retrieved 6 December 2012.
^ "Solanine poisoning". Br Med J. 2 (6203): 1458–1459. 1979-12-08. doi:10.1136/bmj.2.6203.1458-a. PMC 1597169. PMID 526812. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1597169/.
^ R. F. Alexander, G. B. Forbes, and E. S. Hawkins (1948-09-11). "A Fatal Case of Solanine Poisoning". Br Med J. 2 (4575): 518. doi:10.1136/bmj.2.4575.518. PMC 2091497. PMID 18881287. //www.ncbi.nlm.nih.gov/pmc/articles/PMC2091497/.
^ "Review of Toxicological Literature prepared for Errol Zeiger, Ph.D, National Institute of Environmental Health Sciences, Submitted by Raymond Tice". Testing Status of Agents at NTP (National Toxicology Program). February 1998. http://ntp.niehs.nih.gov/go/15334.
^ McGee, Harold (2009-07-29). "Accused, Yes, but Probably Not a Killer". The New York Times. http://www.nytimes.com/2009/07/29/dining/29curi.html. Retrieved 2010-05-23.

External links

a-Chaconine and a-Solanine, Review of Toxicological Literature
MedlinePlus Encyclopedia 002875 - "Green tubers and sprouts"

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. 小児での潜在的に毒性を持つ植物の摂取による臨床症状および評価 clinical manifestations and evaluation of potentially toxic plant ingestions in children
2. 有機食品と小児 organic foods and children

English Journal

Structural effects of the Solanum steroids solasodine, diosgenin and solanine on human erythrocytes and molecular models of eukaryotic membranes.

Manrique-Moreno M, Londoño-Londoño J, Jemioła-Rzemińska M, Strzałka K, Villena F, Avello M, Suwalsky M.Author information Faculty of Exact and Natural Sciences, University of Antioquia, A.A. 1226, Medellin, Colombia.AbstractThis report presents evidence that the following Solanum steroids: solasodine, diosgenin and solanine interact with human erythrocytes and molecular models of their membranes as follows: a) X-ray diffraction studies showed that the compounds at low molar ratios (0.1-10.0mol%) induced increasing structural perturbation to dimyristoylphosphatidylcholine bilayers and to a considerable lower extent to those of dimyristoylphosphatidylethanolamine; b) differential scanning calorimetry data showed that the compounds were able to alter the cooperativity of dimyristoylphosphatidylcholine, dimyristoylphosphatidylethanolamine and dimyristoylphosphatidylserine phase transitions in a concentration-dependent manner; c) in the presence of steroids, the fluorescence of Merocyanine 540 incorporated to the membranes decreased suggesting a fluidization of the lipid system; d) scanning electron microscopy observations showed that all steroids altered the normal shape of human erythrocytes inducing mainly echinocytosis, characterized by the formation of blebs in their surfaces, an indication that their molecules are located into the outer monolayer of the erythrocyte membrane.
Biochimica et biophysica acta.Biochim Biophys Acta.2014 Jan;1838(1):266-77. doi: 10.1016/j.bbamem.2013.08.003. Epub 2013 Aug 14.
This report presents evidence that the following Solanum steroids: solasodine, diosgenin and solanine interact with human erythrocytes and molecular models of their membranes as follows: a) X-ray diffraction studies showed that the compounds at low molar ratios (0.1-10.0mol%) induced increasing stru
PMID 23954587

Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation.

Petersson EV1, Nahar N1, Dahlin P2, Broberg A3, Tröger R4, Dutta PC5, Jonsson L2, Sitbon F1.Author information 1Department of Plant Biology and Forest Genetics, Uppsala BioCenter, Swedish University of Agricultural Sciences and Linnean Centre for Plant Biology, Uppsala, Sweden.2Department of Ecology, Environment and Plant Sciences, Stockholm University, Stockholm, Sweden.3Department of Chemistry, Uppsala BioCenter, Swedish University of Agricultural Sciences, Uppsala, Sweden.4Chemistry Division 1, Science Department, National Food Agency, Uppsala, Sweden.5Department of Food Science, Uppsala BioCenter, Swedish University of Agricultural Sciences, Uppsala, Sweden.AbstractSteroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investigate the steroidal origin of SGA biosynthesis, cut potato shoots were fed cholesterol labelled with deuterium (D) in the sterol ring structure (D5- or D6-labelled), or side chain (D7-labelled), and analysed after three or five weeks. The labelled cholesterol and presence of D-labelled SGA were analysed by GC-MS and LC-MS/MS, respectively. When feeding D-labelled cholesterol solubilised in Tween-80, labelled cholesterol in free form became present in both leaves and stems, although the major part was recovered as steryl esters. Minor amounts of D-labelled SGA (α-solanine and α-chaconine) were identified in cholesterol-treated shoots, but not in blank controls, or in shoots fed D6-27-hydroxycholesterol. Solubilising the labelled cholesterol in methyl-β-cyclodextrin instead of Tween-80 increased the levels of labelled SGA up to 100-fold, and about 1 mole% of the labelled cholesterol was recovered as labelled SGA in potato leaves. Both side chain and ring structure D labels were retained in SGA, showing that the entire cholesterol molecule is converted to SGA. However, feeding side chain D7-labelled cholesterol resulted in D5-labelled SGA, indicating that two hydrogen atoms were released during formation of the SGA nitrogen-containing ring system. Feeding with D7-sitosterol did not produce any labelled SGA, indicating that cholesterol is a specific SGA precursor. In conclusion, we have demonstrated a superior performance of methyl-β-cyclodextrin for delivery of cholesterol in plant tissue feeding experiments, and given firm evidence for cholesterol as a specific sterol precursor of SGA in potato.
PloS one.PLoS One.2013 Dec 9;8(12):e82955. doi: 10.1371/journal.pone.0082955.
Steroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investigate the steroidal origin of SGA biosynthesis, cut potato shoots were fed cholesterol labelled with
PMID 24349406

Electrochemical determination of glycoalkaloids using a carbon nanotubes-phenylboronic acid modified glassy carbon electrode.

Wang H, Liu M, Hu X, Li M, Xiong X.Author information College of Horticulture and Landscape, Hunan Agriculture University, Changsha 410128, China. xiongxingyao@caas.cn.AbstractA versatile strategy for electrochemical determination of glycoalkaloids (GAs) was developed by using a carbon nanotubes-phenylboronic acid (CNTs-PBA) modified glassy carbon electrode. PBA reacts with α-solanine and α-chaconine to form a cyclic ester, which could be utilized to detect GAs. This method allowed GA detection from 1 μM to 28 μM and the detection limit was 0.3 μM. Affinity interaction of GAs and immobilized PBA caused an essential change of the peak current. The CNT-PBA modified electrodes were sensitive for detection of GAs, and the peak current values were in quite good agreement with those measured by the sensors.
Sensors (Basel, Switzerland).Sensors (Basel).2013 Nov 27;13(12):16234-44. doi: 10.3390/s131216234.
A versatile strategy for electrochemical determination of glycoalkaloids (GAs) was developed by using a carbon nanotubes-phenylboronic acid (CNTs-PBA) modified glassy carbon electrode. PBA reacts with α-solanine and α-chaconine to form a cyclic ester, which could be utilized to detect GAs. This me
PMID 24287539

Japanese Journal

学校行事等で起きた食中毒について

櫻井秀樹
鈴鹿短期大学紀要 33, 57-68, 2013-03-01
… Distinctive food poisoning that occurs in schools, natural toxins -those natural vegetable poisons are the substances causing food poisoning, which are a type of Solanine poisoning that occurs from eating potatoes grown at school. …
NAID 110009613761

化学物質及び自然毒による食中毒等事件例(平成22年)

下井俊子,田口信夫,観公子 [他]
東京都健康安全研究センター研究年報 -(62) (-), 205-208, 2011
NAID 40019236280

.ALPHA.-Solanine Inhibits Human Melanoma Cell Migration and Invasion by Reducing Matrix Metalloproteinase-2/9 Activities

Lu Ming-Kun,Shih Yuan-Wei,Chang Chien Tzu-Tsung [他],Fang Li-Heng,Huang Hsiang-Ching,Chen Pin-Shern
Biological and Pharmaceutical Bulletin 33(10), 1685-1691, 2010
… α-Solanine, a naturally occurring steroidal glycoalkaloid in potato sprouts, was found to possess anti-carcinogenic properties, such as inhibiting proliferation and inducing apoptosis of tumor cells. … However, the effect of α-solanine on cancer metastasis remains unclear. … In the present study, we examined the effect of α-solanine on metastasis in vitro. …
NAID 130000402362

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リンク元

「ソラニン」

α-Solanine
Identifiers
CAS number	20562-02-1
PubChem	6537493
ChemSpider	5020632
UNII	3FYV8328OK
	InChI InChI=1S/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3/t19-,20+,21-,23?,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39-,40+,41+,42-,43+,44-,45-/m0/s1 ; Key: ZGVSETXHNHBTRK-WWELWOLRSA-N InChI=1/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3/t19-,20+,21-,23?,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39-,40+,41+,42-,43+,44-,45-/m0/s1; Key: ZGVSETXHNHBTRK-WWELWOLRBD ;
Properties
Molecular formula	C45H73NO15
Molar mass	868.06
Appearance	white crystalline solid
Melting point	271 - 273 °C
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: solanine
関: ジャガイモ

ジャガイモ芽の毒

[1] Desfosses, M. (1820): Extrait d'une lettre à M. Robiquet. In: J. de Pharmacie. Bd. 6, S. 374–376.

[2] Executive Summary of Chaconine & Solanine

[pmid16733852-3] Gao SY, Wang QJ, Ji YB (June 2006). "Effect of solanine on the membrane potential of mitochondria in HepG2 cells and (Ca2+)i in the cells". World Journal of Gastroenterology 12 (21): 3359–67. PMID 16733852. http://www.wjgnet.com/1007-9327/12/3359.asp. Retrieved 2009-05-31.

[v30je19-4] "SOLANINE AND CHACONINE". http://www.inchem.org/documents/jecfa/jecmono/v30je19.htm. Retrieved 31 May 2009.

[5] "Solanine Poisoning". Article. British Medical Journal. http://www.bmj.com/content/2/6203/1458.2. Retrieved 6 December 2012.

[6] "Solanine poisoning". Br Med J. 2 (6203): 1458–1459. 1979-12-08. doi:10.1136/bmj.2.6203.1458-a. PMC 1597169. PMID 526812. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1597169/.

[7] R. F. Alexander, G. B. Forbes, and E. S. Hawkins (1948-09-11). "A Fatal Case of Solanine Poisoning". Br Med J. 2 (4575): 518. doi:10.1136/bmj.2.4575.518. PMC 2091497. PMID 18881287. //www.ncbi.nlm.nih.gov/pmc/articles/PMC2091497/.

[8] "Review of Toxicological Literature prepared for Errol Zeiger, Ph.D, National Institute of Environmental Health Sciences, Submitted by Raymond Tice". Testing Status of Agents at NTP (National Toxicology Program). February 1998. http://ntp.niehs.nih.gov/go/15334.

[9] McGee, Harold (2009-07-29). "Accused, Yes, but Probably Not a Killer". The New York Times. http://www.nytimes.com/2009/07/29/dining/29curi.html. Retrieved 2010-05-23.

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solanine