Discovery, Isolation and Physicochemical Properties of Narciclasine, a New Antimitotic of Vegetable Origin

Abstract

A crystalline substance with marked antimitotic activity on several biological systems (mitoses of ascites S 180, of the megaloblasts of chick embryo, of the tips of wheat radicles) has been isolated from the bulbs of several varieties of Narcissus and named Narciclasine. After reference to the tests that led to its discovery and isolation and to the work of others in the same field, the method of isolation is described together with the physical and chemical properties of the substance (identification, chromatographic behavior, UV, IR and fluorescence). The structural formula, established on the basis of work reported elsewhere, is given.

(2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one hemihydrate

“…Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Since his first isolation from Narcissus bulbs by Ceriotti in 1967(Ceriotti, 1967aCeriotti, 1967b;Ceriotti et al, 1967), narciclasine has been extensively studied from chemical and biological standpoints (Kornienko & Evidente, 2008). It exhibits a broad range of biological activities and thus has various potential practical applications, for example, in the treatment of brain cancers, such as glioblastoma multiforme.…”

“…For general background to narciclasine, see: Ceriotti (1967a,b); Ceriotti et al (1967); Kornienko & Evidente (2008). For the crystal structures of related compounds, see: Savona et al (1970); Immirzi & Fuganti (1972); Bi et al (1998); McNulty et al (2011).…”

Discovery of new anticancer agents from higher plants

“…Two isocarbostyril alkaloids, narciclasine ( 32 ) and pancratistatin ( 33 ), first isolated from bulbs of a Narcissus species (97) and from Hymenocallis littoralis Salisb. (formerly known as Pancratium littorale Jacq.)…”

Discovery of new anticancer agents from higher plants

“…Two isocarbostyril alkaloids, narciclasine (32) and pancratistatin (33), first isolated from bulbs of a Narcissus species (97) and from Hymenocallis littoralis Salisb. (formerly known as Pancratium littorale Jacq.)…”