CAS 20562-02-1: α-Solanine
Description:α-Solanine is a glycoalkaloid primarily found in species of the nightshade family, particularly in potatoes and tomatoes. It is a toxic compound that can cause gastrointestinal and neurological symptoms when ingested in significant amounts. Structurally, α-solanine consists of a steroidal alkaloid backbone with a sugar moiety, specifically a solanidine core linked to a carbohydrate component. This compound is known for its bitter taste and is part of the plant's defense mechanism against herbivores and pathogens. α-Solanine is soluble in water and organic solvents, which contributes to its bioavailability in biological systems. The toxicity of α-solanine is attributed to its ability to disrupt cell membranes and interfere with cholinergic signaling. While it has been studied for potential medicinal properties, such as anti-cancer effects, its toxic nature necessitates caution in consumption. Proper storage and preparation of nightshade vegetables can help minimize the risk of solanine poisoning, particularly in green or sprouted potatoes, where levels of this alkaloid can be elevated.
Formula:C45H73NO15
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
InChI key:InChIKey=ZGVSETXHNHBTRK-UDJLNJFBSA-N
SMILES:OCC1OC(OC2C(O)C(OC(OC3CC4=CCC5C(CCC6(C)C5CC7N8CC(C)CCC8C(C)C76)C4(C)CC3)C2OC9OC(C)C(O)C(O)C9O)CO)C(O)C(O)C1O
- Synonyms:
- (3beta)-solanid-5-en-3-yl 6-deoxy-beta-L-mannopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-galactopyranoside
- (3beta,22beta)-solanid-5-en-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-galactopyranoside
- (3β)-Solanid-5-en-3-yl O-6-deoxy-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl-(1→2)-O-[β-<smallcap>D</smallcap>-glucopyranosyl-(1→3)]-β-<smallcap>D</span>-galactopyranoside
- 1H-Naphth[2′,1′:4,5]indeno[1,2-b]indolizine, β-<span class="text-smallcaps">D</span>-galactopyranoside deriv.
- A-solanine from potato sprouts
- Solanidane, β-<span class="text-smallcaps">D</span>-galactopyranoside deriv.
- alpha-Solanine
- α-Solanin
- α-Solanine
- β-<span class="text-smallcaps">D</smallcap>-Galactopyranoside, (3β)-solanid-5-en-3-yl O-6-deoxy-α-<smallcap>L</smallcap>-mannopyranosyl-(1→2)-O-[β-<smallcap>D</span>-glucopyranosyl-(1→3)]-
- See more synonyms
- β-D-Galactopyranoside, (3β)-solanid-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-
- Solanidane, β-D-galactopyranoside deriv.
- (3β)-Solanid-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside
- 1H-Naphth[2′,1′:4,5]indeno[1,2-b]indolizine, β-D-galactopyranoside deriv.
