Studies on the Chemical Constituents and Pharmacological Activities of Zephyranthes Candida (Lindl.) Herb
|School||Nanjing Agricultural College|
|Keywords||Zephyranthes candida(Lindl.)Herb chemical constituents ceramides alkaloids pharmacological activity biosynthesis pathway|
Zephyranthes candida (Lindl.) Herb belongs to the genus Zephyranthes Herb and family Amaryllideceae, and it is a common perennial plant and used as a horticultural and traditional medicinal plant with its bulbs in many countries. The genus Zephyranthes Herb is a big genus containing about60species, mainly distributes in the warm temperate regions of west global, especially in the countries of South America.Only two species of the genus Zephyranthes Herb, Zephyranthes candida and Zephyranthes carinata grow in China, and they were early introduced from South America only for horticultural purpose, and have not being occupied an important place in the Chinese traditional medicines from then on. At present, Zephyranthes candida is widely planted in many areas in Chinese cities, mainly the South area of Yangtse River for horticultural or ornamental utilization. Both the previous investigations and the present works on chemical constituents of the plants from the genus Zephyranthes Herb mainly focused on some alkaloids and a few flavans in foreign countries.In China, phytochemical works on Zephyranthes candida have not been attached importance to and there are no reports on chemical composition and pharmacological activity to date, and even the genus Zephyranthes Herb or family Amaryllidaceae.In order to furtherly understand the pharmacological value of Zephyranthes candida, studies were carried systematically on the chemical constituents and pharmacological activities of this plant collected in the nursery of Nanjing Agricultural University.On account of this, we undertook a thorough chemical investigation of the methanol extract of the plant, using macroreticular resin, sephadex LH-20,ODS, and silica gel chromatography. Forty compounds were isolated and identified and the structures of them were elucidated by chemical and spectural technology (infrared spectroscopy IR, mass spectroscopy MS,nuclear magnetic resonance NMR, ultraviolet spectroscopy UV).These novel ceramides and known compounds are listed as follows: Zec-1:lycorine;Zec-2:β-daucosterin;Zec-3:β-sitosterol;Zec-4:benzo[1,3]dioxol-5-y]-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol;Zec-7:pseudolycorine;Zec-8:(2S,3S,4R,8E,2’R)-2-[N-(2’-hydroxyoctadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol;Zec-9:1,3,5,6-tetrahydroxy-2-(2’-hydroxytetracosanoylamino)-8-(E)-octadecadiene;Zec-10:(Z)-9’-octadecenoie acid;Zee-11a:(2S)-3’,7-dihydroxy-4’-methoxyflavan;Zec-11b:(2S)-4’-hydroxy-7-methoxyflavan;Zec-11c:(2S)-4’,7-dihydroxy-8-methoxyflavan;Zec-11d:(2S)-4’,7-dihydroxy-8-methoxyflavan;Zec-11e:(2S)-4’,7-dihydroxyflavan;Zec-12:haemanthidine;Zec-14:O-methyllycorenine;Zec-15:(1S,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-l-ol;Zec-16:(+)-5-Methoxy-9-O-demethylhomolycorine;Zec-17:(2S,3S,4R)-1,3,4-trihydroxy-2-octacosanoylamino-hexadecene;Zec-18:1,3,4,5,6-pentahydroxy-2-(2’-hydroxytetracosanoylamino)-7-(E)-tetracosene;Zec-19:stigmasta-5,22-dien-3β-ol; Zec-20:9-demethylhomolycorine;Zec-21:stigmasterol; Zec-23:stearic acid; Zec-24:butylisobutyl phthalat;Zec-25:ambrettolide; Zec-26:heptacosane; Zec-28:linoleic Acid;Zec-29:3β-acetoxyurs-11-en-28,13-olide;Zec-31:(2S,6E,1"E,13R,16R,2’R)-39-methyl-3,4,5-hydroxymethyl-2-[N-(2’-hydroxyhexadecanoyl)-N-(3",4"-dihydroxyethyl)-amino]-6,13,16,1"-tetraconta-1,8,10,21-triol;Zec-32:(2S,3S,4R,513E)-1,3,4-trihydroxy-2-[(2’R)-2’-hydroxytetracosanoylamino]-13-octadecene;Zec-33:(2S,3S,4R,21E,2’R)-2-[N-(2’-hydroxynonadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-21-hexacosene-1,3,4-triol;Zec-36:vanillic acid;Zec-37:1,3,4,5,6-pentahydroxy-2-(2’-hydroxyhexacosanoylamino)-18-(E)-tetracosene;Zec-38:lycoramine; Zec-39:galanthamine; Zec-40:α-Tocopherol;Zec-41:2-hydroxy-4-methoxyphenyl)ethanol; Zec-50:rutin; Zec-51:pancratistatin; Zec-53:3,11-O-(3’,3"-dihydroxybutanoyl)hamayne oAmong them, compounds8、9、17、18、31、32、33、37are8novel ceramides,and they are isolated from the genus Zephyranthes and family Amaryllideceae for the first time. compounds4、15are2new natural compounds.compounds lla、11b、11c、111d、11e are5flavans. And there are10Amaryllideceae alkaloids numbered as1、12、14、16、2038、39、51、53. Apart from compound1, all these compounds were isolated from this herb for the first time.Ceramides are a unique class of secondary metabolites, and various ceramides have been isolated from a number of marine organisms, fungi, and some plants, some of which exhibit cytotoxic, antifungal, antimicrobial, antileishmanial and immunomodulatory, and cytostatic activities. Due to their promising biological and pharmacological activities, they have aroused much increasing research interest. It is a challenging task for pharmaceutical researchers to isolate and identify the ceramides from the plants.A significant review on the isolation, purification, structure analysis and pharmacological activities of the phyto-ceramides and cerebrosides were given on the basis of the references of recent ten years and our own study work. In addition, the presumed biosynthesis pathway of phyto-ceramides and cerebrosides in this plant was discussed according to the references reported previously.Also, MTT method were used to screen effective activities of some novel ceramides, mainly for their cytotoxic activity. The pharmacological experiments showed weak activity in inhibiting Hela carcinoma cell line. This study will be the basis of a better medicinal research and development of the plant Zephyr anthes candida (Lindl.) Herb.