Narcissus Narciclasine

The following Narcissus plants contain the lactams narciclasine and lyeoricidine, Narcissus pseudonarcissus L., King Alfred, Flower Carpet, Rembrandt, Mount Hood, President Lebrun, Golden Harvest. 

Amaryllidaceae Alkaloids.—Narciclasine (73) occurs in Narcissus plants along with the Amaryllidaceae alkaloids haemanthamine (70), lycorine (71), and nor-pluviine (72). The three alkaloids (70), (71), and (72) are derived41,42 from O-methylnorbelladine (68) following pathways outlined in Scheme 10. In path a phenol coupling of (68) in the para-para direction leads ultimately to haemanthamine (70) ortho-para coupling as in path b leads to lycorine (71) and nor-pluviine (72). 

Narcissus alkaloid structures. Narciclasine and Montanine types. 

Narciclasine, an alkaloid isolated from the bulbs of narcissus, possesses antimitotic activity against S-180 in ascites form suggesting thereby that it acts essentially as a metaphasic or preprophasic poison. 

Two neutral substances, narciclasine and narciprimine, have been isolated from Narcissus incomparabilis. The former, C14H13NO7 (mp 232°-234° decomp.) has strong antimitotic activity. It contains four... 

Narciclasine (68) is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+ )-pancratistatin (see Section IV) and to conduct a series of structure-activity relationship studies 77,78). Bicolorine (71), another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an V-methyl group 79). 

Narcissus Alkaloid Structures. Narciclasine and Montanine Types. 

N. poeticus and N. pseudonarcissus for this purpose. It is now known that N. poeticus contains 0.012% of the antineoplastic agent narciclasine (68) in the fresh bulb (14,101). Arabian, North African, and Chinese medical practitioners of the Middle Ages continued using Narcissus oil in cancer treatment (389). For example, bulbs of N. tazetta L. var. chinensis, cultivated in China as a decorative plant, were used topically for the treatment of tumors in folk medicine. In this case, pretazettine (64) was established to be one of the antitumor active compounds (133,390). The bulbs of N. tazetta continue to be used in Turkey as a home remedy for the treatment of abscesses because of their antiphlogistic and analgesic properties (391). 

Narciclasine para- para Narcissus spp. Leucojum aestivum Lycoris radiata, Pancratium maritimum Hymenocallis expansa cytotoxic [3,4]... 

The Amaryllidaceae alkaloids are restricted to the monocot family that coined their name. They are derived from one molecule of tyrosine and protocatechuic aldehyde, which originates from phenylalanine. The central intermediate of their biosynthetic pathway is norbelladine. Nearly 500 structures of Amaryllidaceae alkaloids are known, and some of them possess significant pharmacological activities (Jin, 2007) (Fig. 10). For example, the isocarbostyrils pancratistatin from the spider lily Hymenocallis littoralis) and narciclasine from Narcissus species show promising antineoplastic properties (Dumont et al., 2007 McLachlan et al, 2005). Lycorine that occurs, e.g., in Clivia, Crinum and Galanthus... 

Extracts of Narcissus bulbs have been used in the past for the treatment of cancers [127], Recent investigations have resulted in the isolation of a new alkaloid, narciclasine, having antimitotic activity against S 180 in ascites form at 0-5 mg/kg. Narciclasine has been found in other members of the family Amaryllidaceae, and is identical with the alkaloid lycoricidinol from Lycoris radiata [128]. 

Banwell, M. G. Cowden, C. J. Mackay, M. F. 1994. Concise synthetic ronte to both enantiomeric forms of 2,3,4,4a-tetrahydro[l,3]dioxolo[4,5-j]phenanthridin-6(5H)-one. Tetracyclic skeleton associated with the narcissus alkaloids lycoricidine and narciclasine. J. Chem. Soc. Chem. Commun. 61-62. 

This section is devoted to the discussion of selected syntheses of biologically intriguing Amaryllidaceae constituents—a more comprehensive overview of Amaryllidaceae alkaloids can be obtained from recent review articles [44, 45, 48, 170]. Narciclasine (55) is one of the major secondary metabolites of various Narcissus species. 

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