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Glycoalkaloid

Glycoalkaloid

Overview
Glycoalkaloids are a family of poison
Poison
In the context of biology, poisons are substances that can cause disturbances to organisms, usually by chemical reaction or other activity on the molecular scale, when a sufficient quantity is absorbed by an organism...

s commonly found in the plant species Solanum dulcamara (nightshade). There are several glycoalkaloids (alkaloids + sugars) that are potentially toxic. A prototypical glycoalkaloid is called solanine
Solanine
Solanine is a glycoalkaloid poison found in species of the nightshade family , such as potatoes. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. It is very toxic even in small quantities. Solanine has both fungicidal and pesticidal properties, and it is one...

 (sugar [solanose] + alkaloid [solanidine] = solanine), which is found in potato
Potato
The potato is a starchy, tuberous crop from the perennial Solanum tuberosum of the Solanaceae family . The word potato may refer to the plant itself as well. In the region of the Andes, there are some other closely related cultivated potato species. Potatoes are the world's fourth largest food...

es. The alkaloidal portion of the glycoalkaloid is also generically referred to as an aglycone
Aglycone
An aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The spelling aglycon is sometimes encountered, but is incorrect.- References :...

.
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Encyclopedia
Glycoalkaloids are a family of poison
Poison
In the context of biology, poisons are substances that can cause disturbances to organisms, usually by chemical reaction or other activity on the molecular scale, when a sufficient quantity is absorbed by an organism...

s commonly found in the plant species Solanum dulcamara (nightshade). There are several glycoalkaloids (alkaloids + sugars) that are potentially toxic. A prototypical glycoalkaloid is called solanine
Solanine
Solanine is a glycoalkaloid poison found in species of the nightshade family , such as potatoes. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. It is very toxic even in small quantities. Solanine has both fungicidal and pesticidal properties, and it is one...

 (sugar [solanose] + alkaloid [solanidine] = solanine), which is found in potato
Potato
The potato is a starchy, tuberous crop from the perennial Solanum tuberosum of the Solanaceae family . The word potato may refer to the plant itself as well. In the region of the Andes, there are some other closely related cultivated potato species. Potatoes are the world's fourth largest food...

es. The alkaloidal portion of the glycoalkaloid is also generically referred to as an aglycone
Aglycone
An aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The spelling aglycon is sometimes encountered, but is incorrect.- References :...

. The intact glycoalkaloid is poorly absorbed from the GI tract but causes GI irritation. The aglycone is absorbed and is believed to be responsible for observed nervous system signs. Glycoalkaloids are bitter tasting, and produce a burning irritation in the back of the mouth
Mouth
The mouth, buccal cavity, or oral cavity is the first portion of the alimentary canal that receives food and begins digestion by mechanically breaking up the solid food particles into smaller pieces and mixing them with saliva...

 and side of the tongue
Tongue
The tongue is a muscle on the floor of the mouth that manipulates food for chewing and swallowing . It is the primary organ of taste, as much of the upper surface of the tongue is covered in papillae and taste buds. A secondary function of the tongue is speech, in which the organ assists...

 when eaten.

Laboratory diagnosis: although not routinely available, detection of alkaloids in tissues or urine is possible.

Sale of a glycoalkaloid-based treatment
Pharmacotherapy
Pharmacotherapy is that area of pharmacy practice that is responsible for ensuring the safe, appropriate, and economical use of drugs in patient care. A speciailist in pharmacotherapy has responsibility for direct patient care, often functions as a member of a multidisciplinary team and is...

 marketed by Lane Labs USA Inc. for prevention of skin cancer
Skin cancer
Skin cancer is a malignant growth on the skin which can have many causes. The most common skin cancers are basal cell cancer, squamous cell cancer, and melanoma. Skin cancer generally develops in the epidermis , so a tumor is usually clearly visible. This makes most skin cancers detectable in the...

 was banned by the FDA in 2004 as an unapproved drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...

. Similar glycoalkaloid gel
Gel
A gel is a solid, jelly-like material that can have properties ranging from soft and weak to hard and tough. Gels are defined as a substantially dilute crosslinked system, which exhibits no flow when in the steady-state...

s are now marketed as exfoliants.