Lycorine

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Lycorine
Lycorine.svg
Names
IUPAC name
3,12-Didehydro-2′H-[1,3]dioxolo[4′,5′:9,10]galanthan-1α,2β-diol
Systematic IUPAC name
(1S,2S,3a1S,12bS)-2,3a1,4,5,7,12b-Hexahydro-1H,10H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol
Other names
Galanthidine, Amarylline, Narcissine, Licorine, Belamarine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.822 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1 Yes check.svgY
    Key: XGVJWXAYKUHDOO-DANNLKNASA-N Yes check.svgY
  • InChI=1/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
    Key: XGVJWXAYKUHDOO-DANNLKNABD
  • O1c2c(OC1)cc3c(c2)[C@H]4[C@@H]/5N(C3)CCC\5=C/[C@H](O)[C@H]4O
Properties
C16H17NO4
Molar mass 287.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily ( Clivia miniata ), surprise lilies ( Lycoris ), and daffodils ( Narcissus ). It may be highly poisonous, or even lethal, when ingested in certain quantities. [1] Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

Contents

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. [2]

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. [3]

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 dogs. [4]

Lycorine inhibits protein synthesis, [5] and may inhibit ascorbic acid biosynthesis, although studies on the latter are controversial and inconclusive. Presently, it serves some interest in the study of certain yeasts, the principal organism on which lycorine is tested. [6]

It is known that lycorine weakly inhibits acetylcholinesterase (AChE) and ascorbic acid biosynthesis. [7] The IC50 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. [8]

Lycorine exhibits cytostatic effects by targeting the actin cytoskeleton rather than by inducing apoptosis in cancer cells, though lycorine has been found to induce apoptosis or arrest the cell cycle at different points in various cell lines. [9]

Toxicity

Poisoning by lycorine most often occurs through the ingestion of daffodil bulbs. Daffodil bulbs are sometimes confused with onions, leading to accidental poisoning. [10]

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 in the dogs was seen to be 2.0 mg/kg and lasted no longer than 2.5 hours after administration. [11]

Symptoms

Symptoms of lycorine toxicity are nausea, [12] vomiting, diarrhea, and convulsions. [13]

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. [14] 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. [15]

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. [16]

Related Research Articles

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

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

<i>Narcissus</i> (plant) Genus of plants in the Amaryllis (Amaryllidaceae)

Narcissus is a genus of predominantly spring flowering perennial plants of the amaryllis family, Amaryllidaceae. Various common names including daffodil, narcissus and jonquil, are used to describe all or some members of the genus. Narcissus has conspicuous flowers with six petal-like tepals surmounted by a cup- or trumpet-shaped corona. The flowers are generally white and yellow, with either uniform or contrasting coloured tepals and corona.

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

Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

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

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species. Bufotalin can be extracted from the skin parotoid glands of several types of toad.

Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.

<i>Zephyranthes robusta</i> Species of plant

Zephyranthes robusta, synonym Habranthus robustus, commonly known as the Brazilian copperlily, pink fairy lily or the pink rain lily, is a species of herbaceous flowering bulb. It is native to Brazil, Argentina and Uruguay, but is now naturalized in Florida, Colombia, South Africa, and Mauritius.

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

Nuciferine is an alkaloid found within the plants Nymphaea caerulea and Nelumbo nucifera.

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

Pancratistatin (PST) is a natural compound initially extracted from spider lily, a Hawaiian native plant of the family Amaryllidaceae (AMD).

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

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.

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

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian vine Menispermum dauricum, commonly known as Asian moonseed, and the North American vine Menispermum canadense, commonly known as Canadian moonseed. Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so. Dauricine has been studied in vitro for its potential to inhibit cancer cell growth and to block cardiac transmembrane Na+, K+, and Ca2+ ion currents.

<i>Lycoris radiata</i> Species of plant

Lycoris radiata, known as the red spider lily, red magic lily, corpse flower, or equinox flower, is a plant in the amaryllis family, Amaryllidaceae, subfamily Amaryllidoideae. Originally from China, Japan, Korea and Nepal and from there to the United States and elsewhere. It is considered naturalized in Seychelles and in the Ryukyu Islands. It flowers in the late summer or autumn, often in response to heavy rainfall. The common name hurricane lily refers to this characteristic, as do other common names, such as resurrection lily; these may be used for the genus as a whole.

<i>Narcissus asturiensis</i> Species of daffodil

Narcissus asturiensis, the pygmy daffodil, is a perennial bulbous plant native to the mountains of North Portugal and Spain, where it grows at altitudes up to 2000 m (6000 ft). As of March 2022, Kew sources consider the correct name to be Narcissus cuneiflorus.

α-Neurotoxin Group of neurotoxic peptides found in the venom of snakes

α-Neurotoxins are a group of neurotoxic peptides found in the venom of snakes in the families Elapidae and Hydrophiidae. They can cause paralysis, respiratory failure, and death. Members of the three-finger toxin protein family, they are antagonists of post-synaptic nicotinic acetylcholine receptors (nAChRs) in the neuromuscular synapse that bind competitively and irreversibly, preventing synaptic acetylcholine (ACh) from opening the ion channel. Over 100 α-neurotoxins have been identified and sequenced.

Ichthyotoxins are compounds which are either toxic to fish, or are toxins produced by fish. The former include the algae-produced euglenophycin and prymnesins, which can cause large-scale fish deaths. The latter includes ostracitoxin, produced by boxfish. Many toxin-producing algal species can be found both in marine and fresh water environments when the algae are in bloom. Ichthyotoxic poisoning in humans can cause symptoms ranging in severity dependent on how much toxin was consumed. The symptoms of an ichthyotoxin poisoning from fish venoms can include headache, vomiting, diarrhea, dizziness, and drop in blood pressure.

<i>Leucojum vernum</i> Species of flowering plant in the family Amaryllidaceae

Leucojum vernum, called the spring snowflake, is a species of flowering plant in the family Amaryllidaceae. It is native to central and southern Europe from Belgium to Ukraine. It is considered naturalized in north-western Europe, including Great Britain and parts of Scandinavia, and in the US states of Georgia and Florida. This spring flowering bulbous herbaceous perennial is cultivated as an ornamental for a sunny position. The plant multiplies in favourable conditions to form clumps. Each plant bears a single white flower with greenish marks near the tip of the tepal, on a stem about 10–20 cm (3.9–7.9 in) tall, occasionally more.

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

Homolycorine is one of a number of toxic alkaloids found in various Amaryllidaceae species such as daffodils (Narcissus).

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

Lunamarine (punarnavine) is a quinolone alkaloid present in Boerhavia diffusa (punarnava).

<i>Crinum macowanii</i> Species of flowering plant

Crinum macowanii is a species of flowering plant in the Amaryllidaceae family. It is a deciduous bulbous plant species native to Africa that has been used in traditional medicine throughout southern Africa.

Bolesatine is a glycoprotein isolated from the Rubroboletus satanas mushroom which has a lectin function that is specific to the sugar binding site of D-galactose. It is a monomeric protein with a compact globular structure and is thermostable. One tryptophan can be found in its primary sequence along with one disulfide bridge.

<span class="mw-page-title-main">19,20-Dihydroervahanine A</span> Chemical compound

19,20-Dihydroervahanine A is an alkaloid, a natural product which is found in the root of the South-East Asian plant Tabernaemontana divaricata. It inhibits acetylcholinesterase more potently than galantamine in vitro.

References

  1. ↑ "T3DB: Lycorine". www.t3db.ca. Retrieved 2018-11-12.
  2. ↑ Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe (2012). "Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models". Analytica Chimica Acta. 756 (756): 60–72. doi:10.1016/j.aca.2012.10.042. PMID   23176740 . Retrieved 25 April 2017.
  3. ↑ Berkov, Strahil; Martinez-Frances, Vanessa; Bastida, Jaume; Codina, Carles; Rios, Sequndo (2014). "Evolution of alkaloid biosynthesis in the genus Narcissus". Phytochemistry. 99 (99): 95–106. doi:10.1016/j.phytochem.2013.11.002. PMID   24461780.
  4. ↑ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. doi:10.1016/j.toxicon.2010.10.012. PMID   21055413 . Retrieved 25 April 2017.
  5. ↑ Vrijsen R, Vanden Berghe DA, Vlietinck AJ, Boeyé A (1986). "Lycorine: a eukaryotic termination inhibitor?". J. Biol. Chem. 261 (2): 505–7. doi: 10.1016/S0021-9258(17)36118-5 . PMID   3001065.
  6. ↑ Garuccio I, Arrigoni O (1989). "[Various sensitivities of yeasts to lycorine]". Boll. Soc. Ital. Biol. Sper. (in Italian). 65 (6): 501–8. PMID   2611011.
  7. ↑ Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe (2012). "Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models". Analytica Chimica Acta. 756 (756): 60–72. doi:10.1016/j.aca.2012.10.042. PMID   23176740 . Retrieved 25 April 2017.
  8. ↑ Elisha, I.L.; Elgorashi, E.E.; Hussein, A.A.; Duncan, G.; Eloff, J.N. (2013). "Acetlycholinesterase inhibitory effects of the bulb of Ammocharis coranica (Amaryllidaceae) and its active constituent lycorine". South African Journal of Botany. 85 (85): 44–47. doi: 10.1016/j.sajb.2012.11.008 .
  9. ↑ Wang, Peng; Yuan, Hui-Hui; Zhang, Xue; Li, Yun-Ping; Shang, Lu-Qing; Yin, Zheng (21 February 2014). "Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation". Molecules. 19 (2): 2469–2480. doi: 10.3390/molecules19022469 . PMC   6271160 . PMID   24566315.
  10. ↑ Pupils ill after bulb put in soup, BBC News, 3 May 2009
  11. ↑ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. doi:10.1016/j.toxicon.2010.10.012. PMID   21055413 . Retrieved 25 April 2017.
  12. ↑ Kretzing, Sascha; Abraham, Getu; Seiwert, Bettina; Ungemach, Fritz Rupert; Krugel, Ute; Regenthal, Ralf (2011). "Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs". Toxicon. 57 (57): 117–124. doi:10.1016/j.toxicon.2010.10.012. PMID   21055413 . Retrieved 25 April 2017.
  13. ↑ Lycorine, definition at mercksource.com
  14. ↑ Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe (2012). "Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models". Analytica Chimica Acta. 756 (756): 60–72. doi:10.1016/j.aca.2012.10.042. PMID   23176740 . Retrieved 25 April 2017.
  15. ↑ Wang, Peng; Yuan, Hui-Hui; Zhang, Xue; Li, Yun-Ping; Shang, Lu-Qing; Yin, Zheng (21 February 2014). "Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation". Molecules. 19 (2): 2469–2480. doi: 10.3390/molecules19022469 . PMC   6271160 . PMID   24566315.
  16. ↑ Cao, Zhifei; Yu, Di; Fu, Shilong; Zhang, Gaochuan; Pan, Yanyan; Bao, Meimei; Tu, Jian; Shang, Bingxue; Guo, Pengda; Yang, Ping; Zhou, Quansheng (2013). "Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity". Toxicology Letters. 218 (2): 174–185. doi:10.1016/j.toxlet.2013.01.018. PMID   23376478 . Retrieved 25 April 2017.
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