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Solanine information


α-Solanine
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
CAS Number
  • 20562-02-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9188 ☒N
ChemSpider
  • 28033 ☒N
ECHA InfoCard 100.039.875 Edit this at Wikidata
PubChem CID
  • 6537493
UNII
  • 3FYV8328OK checkY
CompTox Dashboard (EPA)
  • DTXSID9030707 Edit this at Wikidata
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 ☒N
    Key: ZGVSETXHNHBTRK-OTYSSXIJSA-N ☒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-OTYSSXIJBP
SMILES
  • 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
Chemical formula
C45H73NO15
Molar mass 868.06
Appearance white 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).
☒N verify (what is checkY☒N ?)
Infobox references

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum), the tomato (Solanum lycopersicum), and the eggplant (Solanum melongena). 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.

  1. ^ Desfosses (1820). "Extrait d'une lettre de M. Desfosses, pharmacien, à Besançon, à M. Robiquet" [Extract of a letter from Mr. Desfosses, pharmacist in Besançon, to Mr. Robiquet]. Journal de Pharmacie. 2nd series (in French). 6: 374–376.

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Solanine

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Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum), the tomato...

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Potato fruit

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parts of the plant except the tubers, the fruit contain the toxic alkaloid solanine and are therefore unsuitable for consumption. All new potato varieties...

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Hilling

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below the surface, and can produce chlorophyll and solanine if exposed to light (green potatoes). Solanine is toxic in large doses, and can result in nausea...

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Solanum nigrum

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sarrachoides, S. scabrum, and S. villosum. Solanine levels in S. nigrum have been tested, and the plant is rarely fatal. Solanine poisoning symptoms may occur when...

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Potato

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in the genus Solanum; the aerial parts of the potato contain the toxin solanine. Normal potato tubers that have been grown and stored properly produce...

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Chaconine

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defensive allelochemical. Solanine is a related substance that has similar properties. These are similar to symptoms from ingesting solanine. There are a wide...

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Cestrum nocturnum

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All members of the family Solanaceae contain an alkaloid toxin called solanine, though some members of the family are routinely eaten without ill-effect...

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Solanum dulcamara

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bittersweet. The poison in this species is believed to be solanine. The alkaloids, solanine (from unripe fruits), solasodine (from flowers) and beta-solamarine...

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Solanum jamesii

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All parts of the plant, and especially the fruit, are toxic, containing solanine when it matures.[citation needed] The tubers were/are eaten raw or cooked...

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Tomato

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contain small amounts of solanine, a toxic alkaloid found in potato leaves and other plants in the nightshade family. However, solanine concentrations in foliage...

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Tomatine

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temperature and pressure. Tomatine is sometimes confused with the glycoalkaloid solanine. Tomatoes were brought to Europe in the early 1500s. The English botanist...

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Glycoalkaloid

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in the genus Solanum, including potato. A prototypical glycoalkaloid is solanine (composed of the sugar solanose and the alkaloid solanidine), which is...

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Baba ghanoush

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oxalate content may pose risks for those prone to kidney stones, and its solanine content could worsen inflammation in specific individuals.[citation needed]...

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Solanaceae

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autumnalis), tobacco, and others. Some of the main types of alkaloids are: Solanine: A toxic glycoalkaloid with a bitter taste, it has the formula C45H73NO15...

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Physalis angulata

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raw. Unripe raw fruits, flowers, leaves, and stems of the plant contain solanine and solanidine alkaloids that may cause poisoning if ingested by humans...

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Physalis pruinosa

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While most parts of the plant are toxic to humans due to the presence of solanine and solanidine, the fruit becomes edible (and sweet) once it has ripened...

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Macrobiotic diet

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practitioners also discourage the use of nightshades because of the alkaloid solanine which is thought to affect calcium balance. Some proponents of a macrobiotic...

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Solanum americanum

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somewhat with ripening. This is via high levels of the glycoalkaloids, solanine and solamargine. Other toxins present in the plant include chaconine, solasonine...

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Solanum carolinense

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tomato-like fruit, contain toxins in varying degrees due to the presence of solanine glycoalkaloids which is a toxic alkaloid and one of the plant's natural...

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Microgreen

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plant sprouts are poisonous. These sprouts contain toxic alkaloids such as solanine and tropanes, which can cause adverse symptoms in the digestive and nervous...

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Physalis peruviana

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stage. Unripe raw fruits, flowers, leaves, and stems of the plant contain solanine and solanidine alkaloids that may cause poisoning if ingested by humans...

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Vegetable

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antinutrients which interfere with the absorption of nutrients. These include α-solanine, α-chaconine, enzyme inhibitors (of cholinesterase, protease, amylase,...

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Fish

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Pseudaconitine Retronecine Resiniferatoxin Scopolamine Solamargine Solanidine Solanine Solasodamine Solasodine Solasonine Solauricidine Solauricine Strychnine...

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Solanum

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foliage and egg-shaped red berries are poisonous, the active principle being solanine, which can cause convulsions and death if taken in large doses. Black nightshade...

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List of poisonous plants

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ISBN 978-1-879906-54-9. Barceloux DG (June 2009). "Potatoes, Tomatoes, and Solanine Toxicity (Solanum tuberosum L., Solanum lycopersicum L.)". Disease-a-Month...

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Median lethal dose

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Archived from the original (PDF) on 2018-06-13. Retrieved 2016-12-26. "Solanine – National Library of Medicine HSDB Database". toxnet.nlm.nih.gov. Archived...

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Bush tomato

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of Australia. A number of Solanum species contain significant levels of solanine and as such are highly poisonous. It is strongly recommended that people...

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Solanum pseudocapsicum

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solanocapsine, which is similar to other alkaloids found in their genus, such as solanine. Although the toxin is poisonous, it is generally not life-threatening...

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Selective breeding

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resistance which was attributed to their high levels of toxic glycoalkaloid solanine which are usually present only in small amounts in potatoes fit for human...

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Ricin

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Pseudaconitine Retronecine Resiniferatoxin Scopolamine Solamargine Solanidine Solanine Solasodamine Solasodine Solasonine Solauricidine Solauricine Strychnine...

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