Lycorine is a

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...

line

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

found in various

Amaryllidaceae The Amaryllidaceae are a family of herbaceous, mainly perennial and bulbous (rarely rhizomatous) flowering plants in the monocot order Asparagales. The family takes its name from the genus '' Amaryllis'' and is commonly known as the amaryl ...

species, such as the cultivated bush lily (''

Clivia miniata ''Clivia'' is a genus of monocot flowering plants native to southern Africa. They are from the family Amaryllidaceae, subfamily Amaryllidoideae. Common names are Natal lily or bush lily. They are herbaceous or evergreen perennial plants, with ...

''), surprise lilies ('' Lycoris''), and daffodils ('' Narcissus''). It may be highly poisonous, or even lethal, when ingested in certain quantities. Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular ''Clivia miniata''.

Source

Lycorine is found in different species of Amaryllidaceae which include flowers and bulbs of daffodil, snowdrop (''Galanthus'') or spider lily (''Lycoris''). Lycorine is the most frequent alkaloid of Amaryllidaceae. The earliest diversification of Amaryllidaceae was most likely in North Africa and the Iberian peninsula and that lycorine is one of the oldest in the Amaryllidaceae alkaloid biosynthetic pathway.

Mechanism of action

There is currently very little known about the mechanism of action of lycorine, although there have been some tentative hypotheses advanced concerning the metabolism of the alkaloid, based on experiments carried out upon

beagle The Beagle is a small breed of scent hound, similar in appearance to the much larger foxhound. The beagle was developed primarily for hunting rabbit or hare, known as beagling. Possessing a great sense of smell and superior tracking inst ...

dogs. Lycorine inhibits

protein synthesis Protein biosynthesis, or protein synthesis, is a core biological process, occurring inside cells, balancing the loss of cellular proteins (via degradation or export) through the production of new proteins. Proteins perform a number of critica ...

, and may inhibit

ascorbic acid Ascorbic acid is an organic compound with formula , originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent. Asco ...

biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...

, although studies on the latter are controversial and inconclusive. Presently, it serves some interest in the study of certain

yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom (biology), kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are est ...

s, the principal organism on which lycorine is tested. It is known that lycorine weakly inhibits

acetylcholinesterase Acetylcholinesterase (HUGO Gene Nomenclature Committee, HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme th ...

(AChE) and ascorbic acid biosynthesis. The

IC50 Half maximal inhibitory concentration (IC50) is a measure of the potency of a substance in inhibiting a specific biological or biochemical function. IC50 is a quantitative measure that indicates how much of a particular inhibitory substance (e. ...

of lycorine was found to vary between the different species it can be found in, but a common deduction from the experiments on lycorine was that it had some effect on inhibiting AChE. Lycorine exhibits

cytostatic Cytostasis (cyto – cell; stasis – stoppage) is the inhibition of cell growth and multiplication. Cytostatic refers to a cellular component or medicine that inhibits cell division and induce cell death. Cytostasis is an important prerequisite ...

effects by targeting the

actin Actin is a family of globular multi-functional proteins that form microfilaments in the cytoskeleton, and the thin filaments in muscle fibrils. It is found in essentially all eukaryotic cells, where it may be present at a concentration of ...

cytoskeleton The cytoskeleton is a complex, dynamic network of interlinking protein filaments present in the cytoplasm of all cells, including those of bacteria and archaea. In eukaryotes, it extends from the cell nucleus to the cell membrane and is compos ...

rather than by inducing

apoptosis Apoptosis (from ) is a form of programmed cell death that occurs in multicellular organisms and in some eukaryotic, single-celled microorganisms such as yeast. Biochemistry, Biochemical events lead to characteristic cell changes (Morphology (biol ...

in cancer cells, though lycorine has been found to induce apoptosis or arrest the cell cycle at different points in various cell lines.

Toxicity

Poisoning by lycorine most often occurs through the ingestion of daffodil bulbs. Daffodil bulbs are sometimes confused with

onions An onion (''Allium cepa'' , from Latin ), also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus ''Allium''. The shallot is a botanical variety of the onion which was classified ...

, leading to accidental poisoning. In a study of dosage used on beagle dogs, the first sign of nausea was observed at as little of a dose of 0.5 mg/kg and occurred within a 2.5 hour span. The effective dose to induce

emesis Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pregna ...

in the dogs was seen to be 2.0 mg/kg and lasted no longer than 2.5 hours after administration.

Symptoms

Symptoms of lycorine toxicity are

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...

, and

convulsion A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is often used as a synony ...

Current research

Lycorine has been seen to have promising biological and pharmacological activities such as antibacterial, antiviral, or anti-inflammatory effects and may have anticancer properties. It has displayed various inhibitory properties towards multiple cancer cell lines that include, lymphoma, carcinoma, multiple myeloma, melanoma, leukemia, human A549 non-small-cell lung cancer, human OE21 esophageal cancer and more. Lycorine has many derivatives used for anti-cancer research such as lycorine hydrochloride (LH) which is a novel anti-ovarian cancer agent, and data has shown that LH effectively inhibited mitotic proliferation of Hey1B cells with very low toxicity. This drug could be used for effective anti-ovarian cancer therapy in the future.

References

External links

* * {{Acetylcholine metabolism and transport modulators Quinoline alkaloids Diols Phenanthridines Plant toxins Acetylcholinesterase inhibitors Protein synthesis inhibitors Heterocyclic compounds with 5 rings Methylenedioxyphenethylamines Tetrahydroisoquinoline alkaloids