Solanine

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Contents

α-Solanine
Solanine.svg
Solanine 3d structure.png
Names
IUPAC name
Solanid-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside
Systematic IUPAC name
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5S,6R)-5-Hydroxy-6-(hydroxymethyl)-2-{[(2S,4aR,4bS,6aS,6bR,7S,7aR,10S,12aS,13aS,13bS)-4a,6a,7,10-tetramethyl-2,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-1H-naphtho[2′,1′:4,5]indeno[1,2-b]indolizin-2-yl]oxy}-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
Other names
α-Solanine; Solanin; Solatunine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.039.875 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 X mark.svgN
    Key: ZGVSETXHNHBTRK-OTYSSXIJSA-N X mark.svgN
  • 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-OTYSSXIJBP
  • C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C
Properties
C45H73NO15
Molar mass 868.06
Appearancewhite crystalline solid
Melting point 271 to 273 °C (520 to 523 °F; 544 to 546 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum , such as the potato (Solanum tuberosum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has 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] It belongs to the chemical family of saponins.

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, nightmares, headache, dizziness, itching, eczema, thyroid problems, and inflammation and pain in the joints. In more severe cases, hallucinations, loss of sensation, paralysis, fever, jaundice, dilated pupils, hypothermia, and death have been reported. [2] [3] [4]

Ingestion of solanine in moderate amounts can cause death. One study suggests that doses of 2 to 5 mg/kg of body weight can cause toxic symptoms, and doses of 3 to 6 mg/kg of body weight can be fatal. [5]

Symptoms usually occur 8 to 12 hours after ingestion, but may occur as rapidly as 10 minutes after eating high-solanine foods.[ citation needed ]

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 spina bifida in humans.[ citation needed ] However, other studies have shown no correlation between potato consumption and the incidence of birth defects. [6]

Livestock poisoning

Livestock can also be susceptible to glycoalkaloids. High concentrations of solanine are necessary to cause death to mammals. The gastrointestinal tract cannot efficiently absorb solanine, which helps decrease its strength to the mammal body. [7] Livestock can hydrolyze solanine and excrete its contents to diminish its presence in the body. [7]

Mechanism of action

There are several proposed mechanisms of how solanine causes toxicity in humans, but the true mechanism of action is not well understood. Solanum glycoalkaloids have been shown to inhibit cholinesterase, disrupt cell membranes, and cause birth defects. [8] 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, increasing their membrane potential. This, in turn, leads to Ca2+ being transported from the mitochondria into the cytoplasm, and this increased concentration of Ca2+ in the cytoplasm triggers cell damage and apoptosis. [9] Potato, tomato, and eggplant glycoalkaloids like solanine have also been shown to affect active transport of sodium across cell membranes. [10] This cell membrane disruption is likely the cause of many of the symptoms of solanine toxicity, including burning sensations in the mouth, nausea, vomiting, abdominal cramps, diarrhea, internal hemorrhaging, and stomach lesions. [11]

Biosynthesis

Biosynthesis of solanine From cholesterol CHM 275 Biosynthesis.png
Biosynthesis of solanine From cholesterol

Solanine is a glycoalkaloid poison created by various plants in the genus Solanum , such as the potato plant. When the plant's stem, tubers, or leaves are exposed to sunlight, it stimulates the biosynthesis of solanine and other glycoalkaloids as a defense mechanism so it is not eaten. [12] It is therefore considered to be a natural pesticide.[ citation needed ]

Though the structures of the intermediates in this biosynthetic pathway are shown, many of the specific enzymes involved in these chemical processes are not known. However, it is known that in the biosynthesis of solanine, cholesterol is first converted into the steroidal alkaloid solanidine. This is accomplished through a series of hydroxylation, transamination, oxidation, cyclization, dehydration, and reduction reactions. [13] Specifically, solanidine formation involves sequential hydroxylation, transamination, and cyclization reactions [1] .The solanidine is then converted into solanine through a series of glycosylation reactions catalyzed by specific glycosyltransferases. [12]

Plants like the potato and tomato constantly synthesize low levels of glycoalkaloids like solanine. However, under stress, such as the presence of a pest or herbivore, they increase the synthesis of compounds like solanine as a natural chemical defense. [14] This rapid increase in glycoalkaloid concentration gives the potatoes a bitter taste, and stressful stimuli like light also stimulate photosynthesis and the accumulation of chlorophyll. As a result, the potatoes turn green, and are thus unattractive to pests. [15] Other stressors that can stimulate increased solanine biosynthesis include mechanical damage, improper storage conditions, improper food processing, and sprouting. [16] The largest concentration of solanine in response to stress is on the surface in the peel, making it an even better defense mechanism against pests trying to consume it. [17]

Safety

Suggested limits on consumption of solanine

Toxicity typically occurs when people ingest potatoes containing high levels of solanine. The average consumption of potatoes in the U.S. is estimated to be about 167 g of potatoes per day per person. [11] There is variation in glycoalkaloid levels in different types of potatoes, but potato farmers aim to keep solanine levels below 0.2 mg/g. [18] Signs of solanine poisoning have been linked to eating potatoes with solanine concentrations of between 0.1 and 0.4 mg per gram of potato. [18] The average potato has 0.075 mg solanine/g potato, which is equal to about 0.18 mg/kg based on average daily potato consumption. [19]

Calculations have shown that 2 to 5 mg/kg of body weight is the likely toxic dose of glycoalkaloids like solanine in humans, with 3 to 6 mg/kg constituting the fatal dose. [20] Other studies have shown that symptoms of toxicity were observed with consumption of even 1 mg/kg. [11]

Storage of potatoes

Various storage conditions can have an impact on the level of solanine in potatoes. Glycoalkaloid levels increase when potatoes are exposed to light because light increases synthesis of glycoalkaloids like solanine. [18] Potatoes stored in a dark place avoid increased solanine synthesis. Potatoes that have turned green due to increased chlorophyll and photosynthesis are indicative of increased light exposure and are therefore associated with high levels of solanine. [20] Synthesis of solanine is also stimulated by mechanical injury because glycoalkaloids are synthesized at cut surfaces of potatoes. [18] Storage of potatoes for extended periods of time has also been associated with increased solanine content. [21] A study found that the solanine levels in Kurfi Jyoti and Kurfi Giriraj potatoes increase solanine levels by 0.232 mg/g and 0.252 mg/g respectively after being poorly stored in a heap. [22]

Effects of cooking on solanine levels

Most home processing methods like boiling, cooking, and frying potatoes have been shown to have minimal effects on solanine levels. For example, boiling potatoes reduces the α-chaconine and α-solanine levels by only 3.5% and 1.2% respectively, but microwaving potatoes reduces the alkaloid content by 15%. [23] Deep frying at 150 °C (302 °F) also does not result in any measurable change. Alkaloids like solanine have been shown to start decomposing and degrading at approximately 170 °C (338 °F), and deep-frying potatoes at 210 °C (410 °F) for 10 minutes causes a loss of ~40% of the solanine. [10] Freeze-drying and dehydrating potatoes has a very minimal effect on solanine content. [24] [25]

The majority (30–80%) of the solanine in potatoes is found in the outer layer of the potato. [25] Therefore, peeling potatoes before cooking them reduces the glycoalkaloid intake from potato consumption. Fried potato peels have been shown to have 1.4–1.5 mg solanine/g, which is seven times the recommended upper safety limit of 0.2 mg/g. [18] Chewing a small piece of the raw potato peel before cooking can help determine the level of solanine contained in the potato; bitterness indicates high glycoalkaloid content. [18] If the potato has more than 0.2 mg/g of solanine, an immediate burning sensation will develop in the mouth. [18]

Recorded human poisonings

Though fatalities from solanine poisoning are rare, there have been several notable cases of human solanine poisonings. Between 1865 and 1983, there were around 2000 documented human cases of solanine poisoning, with most recovering fully and 30 deaths. [26] Because the symptoms are similar to those of food poisoning, it is possible that there are many undiagnosed cases of solanine toxicity. [27]

In 1899, 56 German soldiers fell ill due to solanine poisoning after consuming cooked potatoes containing 0.24 mg of solanine per gram of potato. [28] There were no fatalities, but a few soldiers were left partially paralyzed and jaundiced. In 1918, there were 41 cases of solanine poisoning in people who had eaten a bad crop of potatoes with 0.43 mg solanine/g potato with no recorded fatalities. [25]

In Scotland in 1918, there were 61 cases of solanine poisoning after consumption of potatoes containing 0.41 mg of solanine per gram of potato, resulting in the death of a five-year old. [29]

A case report from 1925 reported that 7 family members who ate green potatoes fell ill from solanine poisoning two days later, resulting in the deaths of the 45-year-old mother and 16-year-old daughter. The other family members recovered fully. [19] In another case report from 1959, four members of a British family exhibited symptoms of solanine poisoning after eating jacket potatoes containing 0.5 mg of solanine per gram of potato.[ citation needed ]

There was a mass solanine poisoning incident in 1979 in the U.K., when 78 adolescent boys at a boarding school exhibited symptoms after eating potatoes that had been stored improperly over the summer. [30] Seventeen of them ended up hospitalized, but they all recovered. The potatoes were determined to have between 0.25 and 0.3 mg of solanine per gram of potato.[ citation needed ]

Another mass poisoning was reported in Canada in 1984, after 61 schoolchildren and teachers showed symptoms of solanine toxicity after consuming baked potatoes with 0.5 mg of solanine per gram of potato. [31]

In potatoes

Green potatoes usually have elevated levels of solanine and should not be eaten in large quantities. Groene aardappels 'Dore' (Solanum tuberosum 'Dore').jpg
Green potatoes usually have elevated levels of solanine and should not be eaten in large quantities.

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

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. In potato tubers, 30–80% of the solanine develops in and close to the skin, and some potato varieties have high levels of solanine.[ citation needed ]

Some potato diseases, such as late blight, can dramatically increase the levels of glycoalkaloids present in potatoes. Tubers damaged in harvesting and/or transport also produce increased levels of glycoalkaloids; this is believed to be a natural reaction of the plant in response to disease and damage.[ citation needed ]

Also, the tuber glycoalkaloids (such as solanine) can be affected by some chemical fertilization. For example, different studies have reported that glycoalkaloids content increases by increasing the concentration of nitrogen fertilizer. [32] [33]

Green colouring 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. [34]

The United States National Institutes of Health's information on solanine strongly advises against eating potatoes that are green below the skin. [3]

In other plants

Fatalities are also known from solanine poisoning from other plants in the nightshade family, such as the berries of Solanum dulcamara (woody nightshade). [35]

In tomatoes

Some, such as the California Poison Control Center, have claimed that unripe tomatoes and tomato leaves contain solanine. However, Mendel Friedman of the United States 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. [36]

Dorothy L. Sayers's short story "The Leopard Lady", in the 1939 collection In the Teeth of the Evidence , features a child poisoned by potato berries injected with solanine to increase their toxicity.[ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Potato</span> Starchy tuber used as a staple food

The potato is a starchy tuberous vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are underground tubers of the plant Solanum tuberosum, a perennial in the nightshade family Solanaceae.

<span class="mw-page-title-main">Aconitine</span> Toxic plant alkaloid

Aconitine is an alkaloid toxin produced by various plant species belonging to the genus Aconitum, commonly known by the names wolfsbane and monkshood. Aconitine is notorious for its toxic properties.

<span class="mw-page-title-main">Phytochemical</span> Chemical compounds produced by plants

Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes from Greek φυτόν (phyton) 'plant'. Some phytochemicals have been used as poisons and others as traditional medicine.

<span class="mw-page-title-main">Glycoalkaloid</span> Class of chemical compounds

Glycoalkaloids are a family of chemical compounds derived from alkaloids to which sugar groups are appended. Several are potentially toxic, most notably the poisons commonly found in the plant species Solanum dulcamara and other plants in the genus Solanum, including potato.

<i>Solanum americanum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum americanum, commonly known as American black nightshade, small-flowered nightshade or glossy nightshade, is a herbaceous flowering plant of wide though uncertain native range. The certain native range encompasses the tropics and subtropics of the Americas, Melanesia, New Guinea, and Australia.

<i>Solanum nigrum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum nigrum, the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the family Solanaceae, native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe berries and cooked leaves of edible strains are used as food in some locales, and plant parts are used as a traditional medicine. Some other species may also be referred to as "black nightshade".

<span class="mw-page-title-main">Epidemic dropsy</span> Medical condition

Epidemic dropsy is a form of edema of extremities due to poisoning by Argemone mexicana.

<span class="mw-page-title-main">Lupin bean</span> Yellow legume seeds used as food

Lupin are the yellow legume seeds of the genus Lupinus. They are traditionally eaten as a pickled snack food, primarily in the Mediterranean basin, Latin America and North Africa. The most ancient evidence of lupin is from ancient Egypt, dating back to the 22nd century BC. The bitter variety of the beans are high in alkaloids and are extremely bitter unless rinsed methodically. Low alkaloid cultivars called sweet lupins have been bred, and are increasingly planted.

<i>Solanum jamesii</i> Species of plant

Solanum jamesii is a species of nightshade. Its range includes the southern United States. All parts of the plant, and especially the fruit, are toxic, containing solanine when it matures. The tubers were/are eaten raw or cooked by several Native American tribes, but they require leaching and boiling in clay in order to be rendered edible. The tubers are small when compared to familiar varieties of S. tuberosum.

<span class="mw-page-title-main">Tomatine</span> Chemical compound

Tomatine is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.

<span class="mw-page-title-main">Senecionine</span> Chemical compound

Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris. It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.

<span class="mw-page-title-main">Solasodine</span> Chemical compound

Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.

<span class="mw-page-title-main">Solamargine</span> Chemical compound

Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine.

<span class="mw-page-title-main">Chaconine</span> Chemical compound

α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be a defensive allelochemical. Solanine, a related substance also found in potatoes, has similar properties.

<span class="mw-page-title-main">Solanidine</span> Chemical compound

Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the family Solanaceae, such as potato and Solanum americanum. The sugar portion of glycoalkaloids hydrolyses in the body, leaving the solanidine portion.

<span class="mw-page-title-main">Dioscorine</span> Chemical compound

Dioscorine is an alkaloid toxin isolated from the tubers of tropical yam on several continents. It has been used as a monkey poison in some African countries, and as an arrow poison to aid in hunting in several parts of Asia. It was first isolated from Dioscorea hirsute by Boorsma in 1894 and obtained in a crystalline form by Schutte in 1897, and has since been found in other Dioscorea species. Dioscorine is a neurotoxin that acts by blocking the nicotinic acetylcholine receptor. Dioscorine is generally isolated in tandem with other alkaloids such as dioscin but is usually the most potent toxin in the mixture. It is a convulsant, producing symptoms similar to picrotoxin, with which it shares a similar mechanism of action.

<span class="mw-page-title-main">Solanaceae</span> Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or the nightshades, is a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell, and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida (dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology.

Lenape (B5141-6) is a potato cultivar first released in 1967 and named after the Lenape Native American tribe, which had to be pulled from the market in 1970 after findings of its high glycoalkaloid content. It was bred by Wilford Mills of Pennsylvania State University in collaboration with the Wise Potato Chip Company. The Lenape potato was produced by crossing Delta Gold with a wild Peruvian potato known for its resistance to insects. It was selected for its high specific gravity and low sugar content which made it ideal for producing potato chips but it was also immune to potato virus A and resistant to common strains of late blight. It is of medium-late maturity and produces round, white tubers with shallow eyes.

<span class="mw-page-title-main">Potato fruit</span> Inedible fruit of the potato plant

The potato fruit is the part of the potato plant that, after flowering, produces a toxic, green cherry tomato-like fruit.

<span class="mw-page-title-main">Zygacine</span> Chemical compound

Zygacine is a steroidal alkaloid of the genera Toxicoscordion, Zigadenus, Stenanthium and Anticlea of the family Melanthiaceae. These plants are commonly known and generally referred to as death camas. Death camas is prevalent throughout North America and is frequently the source of poisoning for outdoor enthusiasts and livestock due to its resemblance to other edible plants such as the wild onion. Despite this resemblance, the death camas plant lacks the distinct onion odor and is bitter to taste.

References

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