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Lycorin

Lycorine

HCID 72378
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Grundinformationen

CAS
476-28-8
Standard-SMILES
O[C@H]1[C@H]2c3cc4c(cc3CN3CCC(=C[C@@H]1O)[C@H]23)OCO4
InChIKey
XGVJWXAYKUHDOO-DANNLKNASA-N
Summenformel
C16H17NO4
Durchschnittliche Molmasse
287,315 g/mol
Monoisotopische Masse
287,11575802

Namen und Bezeichner

Bevorzugter Name
Lycorine
IUPAC
(1S,2S,12bS,12cS)-2,4,5,7,12b,12c-Hexahydro-1H,10H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol
Lokaler Name
Lycorin
Englischer Name
LYCORINE
Summenformel
C16H17NO4
Molmasse
287.31

Namen und Synonyme

amaryllineLYCORINLYCORINELicorineAmarylineBelamarinenarcissineNSC 401360NSC 683873galanthidine

Datenbank-Bezeichner

CAS
476-28-8
PubChem CID
72378
DTXSID
DTXSID60197208
ChEMBL
CHEMBL400092
ChEBI
CHEBI:6601
UNII
I9Q105R5BU
EC Number
207-503-6
Nikkaji
J5.973K

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
253 · 253-255℃ (dec.)
Siedepunkt
429.61 °C · 429.61°C (rough estimate)
Dichte
1.53 · 1.53
Brechungsindex
1.55 · 1.5500 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Aggregatzustand
powder
pka
13.55 · 13.55±0.40(Predicted)
Farbe
White to off-white
InChI
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
InChIKey
XGVJWXAYKUHDOO-KDMZPGMDSA-N
SMILES
[C@H]1(O)[C@]2([H])C3N(CCC3=C[C@@H]1O)CC1C2=CC2OCOC=2C=1

Sicherheit und Regulatorisches

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Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1/PG 3
risk_code
25
hazard_code
T
safety_code
45

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungLycoris radiate, a traditional Chinese medicine (TCM), is the bulb of the amaryllidaceous Lycoris radiata herb. It has been applied for clinical purposes for centuries. It is firstly recorded in Tujing Bencao and mainly used for the pyogenic infections. According to A Supplement to Compendium of Materia Medica, lycoris radiate may be used for treating acute throat trouble, phlegm node, baihuodan, and pulmonary abscess.There are about 20 Lycoris species in the world, which are widely distributed in China and Japan. Lycoris radiate is an amazing horticultural plant with a graceful shape and a bright color. In TCM, it is acrid in taste and neutral in nature, with functions of detoxication, easy expectoration, and diuresis and emesis promotion. According to the modern medicine, lycoris radiate is considered to be in favor of the central nervous system and cardiovascular system.The main active ingredients extracted from the lycoris herbs are about 40 alkaloids with various contents. Pharmacological tests indicate that galanthamine, lycorine, lycoramine, lycorenine, and crinine are the major effective medicinal ingredients. Lycorine may be used to treat amebic dysentery and against cancer. Moreover, galanthamine, dihydrogalanthamine, and lycoramine may be used to treat infantile paralysis and restore nerve functions and against traumatic paraplegia, etc. Lycoris radiate is famous because galanthamine has been approved by FDA as an anti-Alzheimer disease drug. Lycoris radiate is the only natural source for galanthamine with extremely low content (

HistoryIn 1895, Morishima successfully extracted lycorine from the bulb of Lycoris radiata. However, its structure was unidentified until in 1935. In 1959, its stereochemical structure was dissected by monocrystal.The solvent extraction method, chromatographic separation, and resin absorption are commonly used for lycorine extraction. However, lycorine obtained from these techniques is not pure enough and often mixed with other alkaloids. The great differences in the efficacies of different alkaloids prevent such blending from being directly used. Furthermore, the separation and purification process so required has an adverse effect on and limits the development and utilization of the medicinal value of lycorine.

VerwendenLycorine is an analgesic, more so than aspirin, and a hypotensive, as are caranine and galanthine . The analgesic activity exhibited by the Amaryllidaceae alkaloids is attributed to their resemblance to the morphine and codeine skeletons. Lycorine also has antiarrhythmic action, and lycorine hydrochloride is a strong broncholytic. In fact, lycorine shows a relaxant effect on an isolated epinephrine-precontracted pulmonary artery and increases contractility and the rate of an isolated perfused heart. These effects are mediated by stimulation of b-adrenergic receptors.Lycorine also has a strong inhibitory effect on parasite (Encephalitozoon intestinalis) development and antifungal activity against Candida albicans. Additionally, lycorine has antifeedant, antimalarial, emetic, anti-inflammatory, antiplatelet , as well as antifertility activities. Galanthine, in turn, shows mild in vitro activity against Tripanosoma brucei rhodesiense and Plasmodium falciparum.

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: An indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it has been shown to exhibit antimalarial activit .