Amaryllidaceae Alkaloids from Lycoris radiata

Abstract

A phytochemical investigation on bulbs of Lycoris radiata resulted in the isolation of three new Amaryllidaceae alkaloids, named 5,6-dehydrodihydrolycorine (1), 6b-acetoxycrinamine (2), and (þ)-8-O-acetylhomolycorine a-N-oxide (3), together with eleven known alkaloids, 4 -14. The structures of the new alkaloids were established by means of spectroscopic methods, and the known compounds were identified by comparison of their data with those in the literature. Compound 2 showed cytotoxicity against HL-60, A-549, and MCF-7 cells, with IC 50 values of 8.1, 24.3, and 15.0 mm, respectively.Introduction. -Amaryllidaceae alkaloids have for a long time attracted great interest of synthetic organic chemists because of their several biological activities and their potential diversity in pharmacology [1 -9]. So far, more than 100 alkaloids have been isolated from Amaryllidaceae plants [10], which exhibited diverse bioacitivities, such as antiviral, insect antifeedant, antineoplastic, and acetylcholinesterase inhibitory activities [10 -14]. As part of our search for novel and bioactive compounds, we isolated three new Amaryllidaceae alkaloids, 5,6-dehydrodihydrolycorine (1), 6b-acetoxycrinamine (2), and (þ)-8-O-acetylhomolycorine a-N-oxide (3), together with eleven known analogs from bulbs of Lycoris radiata, a Chinese folk medicine famous for the treatment of poliomyelitis [15]. The new structures were elucidated by means of spectroscopic methods, and the known compounds were identified as 6-hydroxycrinamine ( , and 5,6-dihydrobicolorine (14) [25]. In addition, compounds 1 -3 were evaluated for their cytotoxic activities against five human cancer cell lines.

Cytotoxicity Studies of Lycorine Alkaloids of the Amaryllidaceae

“…Feng and co-workers were the first for the year 2011 to investigate the cytotoxic effects of lycorine together with other alkaloid constituents isolated from Lycoris radiata [51]. Surprisingly, lycorine [52].…”

The study of chemical composition and pharmacological action of the alkaloid from plants of Lycoris Herb

“…It can be divided into seven types according to its molecular structure, including Lycorine, Crinine, Galanthamine, Tazettine, Narciclasine, Lycorenine, Homolycorine and Montanine [3] . [4][5][6] ; galanthine(5) and Caranine(6) isolated from L.haywardii [7] ; Ungminorine (7) isolated from L.haywardii [8][9][10] ; Ungminorine N-oxide (8) isolated from L.incanata [11] ; Hippadine(9) isolated from L.haywardii [14] ; Pseudolycorine(10) and Norpluviine(11) isolated from L.haywardii [12] ; lycoranineA (12) isolated from L.haywardii [11] ; (-)-amarbellisine (14) isolated from L.longituba [16] ; Pluviine (15) isolated from L.aurea [17] ; LT1 (16) and Incartine (17) isolated from L.incanata [18] .…”

“…It isolated 10 Crinine type or Hemanthamine alkaloids from Lycoris herb(figure 3), 6β-acetoxycrinamine (32) isolated from L.haywardii [6] ; Crinine(33)L.guangxiensis [10] and 6β-hydroxycrinamine(34) isolated from L.haywardii [6] ; 6α-hydroxycrinamine (35) and Macowine(39) isolated from L.longituba [19] ; 11-hydroxyvittatine(36) isolated from L.haywardii [6] ; Haemanthidine(37) isolated from L.haywardii [4,15] ; Vittatine(38) isolated from L.haywardii [4,18] ; O-demethylhaemanthamine(40) and haemanthamin(41) isolated from L.haywardii [19] . …”

Anti-TMV Effects of Amaryllidaceae Alkaloids Isolated from the Bulbs of Lycoris radiata and Lycoricidine Derivatives

“…Lycoris radiata, amaryllidaceae plant, is widely distributed in the South of China. It has been cultivated not only as ornamental plants for their colorful flowers, but also as folk herbal medicine against various diseases in many countries and areas, and their diverse activities have also been reported, such as anti-TMV [5, 13], antitumor, and acetylcholinesterase inhibitory activities ect [14]. …”