Zephgrabetaine (1), a new betaine type Amaryllidaceae alkaloid, along with seven known alkaloids, lycorine, galanthine, lycoramine, hamayne, haemanthamine, tortuosine, and ungeremine were isolated from the bulbs of Zephyranthes grandiflora and their structures elucidated by spectroscopic data analysis. The isolated alkaloids were tested for in vitro cytotoxic activities against two cell lines, C-6 (rat glioma cells) and CHO-K1 (Chinese hamster ovary cells). A dose dependent cytotoxic effect was exhibited by all the alkaloids on these two cancer cell lines with prominent activity of lycorine and haemanthamine.
KornienkoA, EvidenteA., (2008) Chemistry, biology and medicinal potential of narciclasine and its congeners. Chemical Reviews, 108, 1982–2014.
2.
BastidaJ, LavillaR, ViladomatF., (2006) Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids, Vol. 63, CordellGA. (Ed.), Elsevier Scientific Publishing: Amsterdam, The Netherlands. 87–179.
3.
EvidenteA, KireevAS, JenkinsAR, RomeroAE, SteelantWFA, Van slambrouckS, KornienkoA., (2009) Biological evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives: Discovery of novel leads for anticancer drug design. PlantaMedica, 75, 501–507.
4.
EvidenteA, GoietsenovenGV, AndolfiA, LallemandB, CimminoA, Lamoral-TheysD, GrasT, Abou-DoniaA, DuboisJ, LefrancF, MathieuV, KornienkoA, KissR., (2010) Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells. Journal of Natural Products, 73, 1223–1227.
LopezS, BastidaJ, ViladomatF, CodinaC., (2002) Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sciences, 71, 2521–2529;
8.
CahlíkováL, KulhánkováA, UrbanováK, ValterovaI, MacákováK, KunešJ. (2010) Analysis of Amaryllidaceae alkaloids from Zephyranthes robusta by GC-MS and their cholinesterase activity. Natural Product Communications, 5, 1201–1204;
9.
CahlíkováL, MacákováK, ZavadilS, JirošP, OpletalL, UrbanováK, JahodářL. (2011) Analysis of Amaryllidaceae alkaloids from Chlidanthus fragrans by GC-MS and their cholinesterase activity. Natural Product Communications, 6, 603–606;
10.
CahlíkováL, BenešováN, MacákováK, UrbanováK, OpletalL. (2011) GC/MS analysis of three Amaryllidaceae species and their cholinesterase activity. Natural Product Communications, 6, 1255–1258;
11.
CahlíkováL, ZavadilS, MacákováK, ValterovaI, KulhánkováA, Hošt’álkováA, KunešJ, OpletalL. (2011) Isolation and cholinesterase activity of Amaryllidaceae alkaloids from Nerine bowdenii. Natural Product Communications, 6, 1827–1830;
12.
CahlíkováL, BenešováN, MacákováK, KučeraR, HrstkaV, KlimešJ, JahodářL, OpletalL. (2012) Alkaloids from some Amaryllidaceae species and their cholinesterase activity. Natural Product Communications, >7, 571–574;
13.
NairJJ, van StadenJ. (2012) Acetylcholinesterase inhibition within the lycorine series of Amaryllidaceae alkaloids. Natural Product Communications, 7, 959–962.
14.
SenerB, OrhanI, SatayavivadJ., (2003) Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae. Phytotherapy Research, 17, 1220–1223.
15.
ÇitoğluG, TankerM, GümüşelB. (1998) Antiinflammatory effects of lycorine and haemanthidine. Phytotherapy Research, 12, 205–206.
16.
AkitoN, MotohM, KeisukeK, KeiichiroH, HajimeM, TomohikoO, YukioO., (2000) Unusual behavior of the NMR spectra of the alkaloids from Mexican medicinal plant, Zephyranthes carinata. Symposium on the chemistry of natural products, 42, 433–438.
17.
CahlíkováL, ValterovaI, MacakovaK, OpletalL., (2011) Analysis of Amaryllidaceae alkaloids from Zephyranthes grandiflora by GC/MS and their cholinesterase activity. Revista Brasileira de Farmacognosia, 21, 575–580.
18.
KojimaK, MutsugaM, InoueM, OgiharaY., (1998) Two alkaloids from Zephyranthes carinata. Phytochemistry, 48, 1199–1202.
KatochD, KumarS, KumarN, SinghB., (2010) Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC- DAD/ESI-MS/MS. Journal of Pharmaceutical and Biomedical Analysis, 71, 187–92.
21.
SharmaU, BalaM, KumarN, SinghB, MunshiRK, BhaleraoS., (2012) Immunomodulatory active compounds from Tinospora cordifolia. Journal of Ethnopharmacology, 141, 918–926.
22.
SharmaU, KumarN, SinghB., (2012) Furostanol saponin and diphenylpentendiol from the roots of Asparagus racemosus. Natural Product Communications, 7, 995–998.
23.
WaliaM, MannT, KumarD, AgnihotriVK, SinghB., (2012) Chemical composition and in-vitro cytotoxic activity of essential oil of leaves of Malus domestica growing in western Himalaya (India). Evidence Based Complementary and Alternative Medicine, 649727, 6 pages.
24.
BastidaJ, CodinaC, ViladomatF, RubiraltaM, QuirionJC, WenigerB, (1992) Narcissus alkaloids, XIV. (+)-8-O-Acetylhomolycorine and vasconine, two novel alkaloids from Narcissus vasconicus. Journal of Natural Products, 55, 122–125.
25.
StarkLM, LinXF, FlippinLA. (2000) Total synthesis of Amaryllidaceae pyrrolophenanthridinium alkaloids via the Ziegler-Ullmann reaction: tortuosine, criasbetaine, and ungeremine. Journal of Organic Chemistry, 65, 3227–3230.
Abou-DoniaAH, AbibA, El DinAS, EvidenteA, GaberM, ScopaA., (1992) Two betaine type alkaloids from Egyptian Pancratium maritimum. Phytochemistry, 31, 2139–2141.
SchmidtA. (2003) Heterocyclic mesomeric betaines and analogs in natural product chemistry, Betainic alkaloids and nucleobases, In Advances in Heterocyclic Chemistry, Vol. 85, KatritzkyAR (Ed.), Elsevier Science Publishers, The Netherland. 67–156.
30.
BastidaJ, ViladomatF, CodinaC., (1998) Narcissus alkaloids, In Studies in Natural Products Chemistry. Vol. 20, RahmanAU. (Ed.). Elsevier Science, The Netherland. 323–406.
31.
Lamoral-TheysD, DecaesteckerC, MathieuV, DuboisJ, KornienkoA, KissR, EvidenteA, PottierL., (2010) Lycorine and its derivatives for anticancer drug design. Mini Reviews in Medicinal Chemistry, 10, 41–50.
