lycorine

リコリン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/08 23:25:20」(JST)

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Lycorine
IUPAC name 1,2,4,5,12b,12c-Hexahydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol
Other names Galanthidine, Amarylline, Narcissine, Licorine, Belamarine
Identifiers
CAS number	476-28-8 N
PubChem	72378
ChemSpider	65312 Y
ChEBI	CHEBI:6601 Y
ChEMBL	CHEMBL400092 Y
Jmol-3D images	Image 1
SMILES O1c2c(OC1)cc3c(c2)[C@H]4[C@@H]/5N(C3)CCC\5=C/[C@H](O)[C@H]4O
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 Y Key: XGVJWXAYKUHDOO-DANNLKNASA-N Y 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
Properties
Molecular formula	C16H17NO4
Molar mass	287.31 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N (verify) (what is: Y/N?)
Infobox references

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. Symptoms of lycorine toxicity are vomiting, diarrhea, and convulsions. Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

It inhibits protein synthesis, 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.

Daffodil bulbs are sometimes confused with onions, leading to accidental poisoning.

References

External links

• Hill, R. K.; Joule, J. A.; Loeffler, L. J. (1962). "Stereoselective Syntheses of d,l-α- and β-Lycoranes". Journal of the American Chemical Society 84 (24): 4951–4956. doi:10.1021/ja00883a064. 
• Wolfgang Oppolzer, Alan C. Spivey, and Christian G. Bochet (1994). "Suprafaciality of Thermal N-4-Alkenylhydroxylamine Cyclizations: Syntheses of (±)-α-Lycorane and (+)-Tianthine". J. Am. Chem. Soc. 116 (7): 3139–3140. doi:10.1021/ja00086a060. 

English Journal

• 5,10b-Ethanophenanthridine amaryllidaceae alkaloids inspire the discovery of novel bicyclic ring systems with activity against drug resistant cancer cells.

• Henry S1, Kidner R1, Reisenauer MR1, Magedov IV1, Kiss R2, Mathieu V2, Lefranc F3, Dasari R4, Evidente A5, Yu X6, Ma X6, Pertsemlidis A6, Cencic R7, Pelletier J7, Cavazos DA8, Brenner AJ8, Aksenov AV9, Rogelj S1, Kornienko A10, Frolova LV11.
• European journal of medicinal chemistry.Eur J Med Chem.2016 Sep 14;120:313-28. doi: 10.1016/j.ejmech.2016.05.004. Epub 2016 May 6.
• Plants of the Amaryllidaceae family produce a large variety of alkaloids and non-basic secondary metabolites, many of which are investigated for their promising anticancer activities. Of these, crinine-type alkaloids based on the 5,10b-ethanophenanthridine ring system were recently shown to be effec
• PMID 27218860

• Lycorine protects cartilage through suppressing the expression of matrix metalloprotenases in rat chondrocytes and in a mouse osteoarthritis model.

• Chen S1, Fang XQ1, Zhang JF1, Ma Y1, Tang XZ1, Zhou ZJ1, Wang JY1, Qin A2, Fan SW1.
• Molecular medicine reports.Mol Med Rep.2016 Aug 8. doi: 10.3892/mmr.2016.5594. [Epub ahead of print]
• Extracellular matrix (ECM) degrading enzymes, including matrix metalloproteinases (MMPs), are critical for cartilage destruction in the progression of osteoarthritis (OA). Thus, identifying novel drugs, which suppress the synthesis of MMPs may facilitate the treatment of OA. The cytotoxicity of lyco
• PMID 27509914

• [Antitumor activity of lycorine in renal cell carcinoma ACHN cell line and its mechanism].

• Huang YQ1, Zhang YM, Jin Z, Li XZ, Wang CS, Xu K, Huang P, Liu CX.
• Nan fang yi ke da xue xue bao = Journal of Southern Medical University.Nan Fang Yi Ke Da Xue Xue Bao.2016 Jun;36(6):857-62.
• OBJECTIVE: To investigate the antitumor effect of lycorine on renal cell carcinoma ACHN cells and explore the possible mechanism.METHODS: We used flow cytometry to examine the effect of lycorine on ACHN cell cycle and apoptosis. The cell proliferation, migration and invasion were assessed with MTS a
• PMID 27320892

Japanese Journal

• Inhibitory Effects of Herbal Alkaloids on the Tumor Necrosis Factor-.ALPHA. and Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW264 Macrophages

• Yamazaki Yoshimitsu,Kawano Yasuhiro
• Chemical and Pharmaceutical Bulletin 59(3), 388-391, 2011
• … A harmala alkaloid, harmine, an opium alkaloid, papaverine, and Lycoris alkaloids, lycorine and lycoricidinol, showed TNF-α suppressive activities stronger than or comparable to that of a reference polyphenol, butein, in RAW264 cells (IC50=4, 10, 2.1, 0.02, and 8 μM, respectively). …
• NAID 130000648951

• Trichomonas vaginalis nucleoside triphosphate diphosphohydrolase and ecto-5'-nucleotidase activities are inhibited by lycorine and candimine

• GIORDANI Raquel B.,WEIZENMANN Marina,ROSEMBERG Denis Broock,DE CARLI Geraldo Attilio,BOGO Mauricio Reis,ZUANAZZI Jose Angelo S.,TASCA Tiana
• Parasitology international : official journal of the Japanese Society of Parasitology 59(2), 226-231, 2010-06-01
• NAID 10029824230

• 36 有機リチウムの不斉タンデム型共役付加-閉環反応の開発とLycorine類の不斉全合成への展開(口頭発表の部)

• 山田 健一,山下 光明,西村 克己,福山 尚志,住吉 孝明,富岡 清
• 天然有機化合物討論会講演要旨集 (49), 211-216, 2007-08-24
• … We planned asymmetric synthesis of Amaryllidaceae alkaloids, lycorine (1) and related compounds using 4 as a key intermediate. … Formation of double bond followed by reduction gave 2-epi-lycorine diacetate (23) after acetylation of the resulting 2-epi-lycorine (22). …
• NAID 110006682766

Related Links

• Lycorine | definition of lycorine by Medical dictionary

lycorine a toxic alkaloid found commonly in the bulbs of plants of the family Amaryllidaceae. Causes salivation, vomiting and diarrhea; large doses cause ... By doing a chemical screen in large numbers of zebrafish embryos, the ...

• lycorineとは - コトバンク - コトバンク [ 時事問題、ニュースも ...

世界大百科事典 第2版 - lycorineの用語解説 - スイセン栽培の盛んな国はイギリス，アイルランド，オランダ，ニュージーランド，オーストラリア，アメリカである。鱗茎にはグルコマンナンやアルカロイドのリコリンlycorineを含有し ...

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lycorine

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石蒜アルカロイド bulbus lycoridis alkaloid

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