| Clausena lansium(Lour.)Skeels is a plant of the genus Clausena of the Rutaceae family,native to the tropical and subtropical areas of South China,and widely distributed in China,Taiwan,Fujian,Guangdong and Guangxi etc.Up to now,a large number of studies have been carried out on the plants and found that the main chemical constituents are alkaloids(carbazole is the major type of the alkaloids)and coumarins,and their biological activities mainly include anti-tumor,promoting intelligence,antibacterial,neuroprotective and hypoglycemic.In order to look for the new compounds which present potent biological activity,as well as to enrich the amide alkaloids and other chemical components from wampee,the phytochemical study on the wampee seeds were carried out.In this paper,41 compounds were isolated from the ethyl acetate fraction of ethanol extract from the seeds of wampee using various column chromatography,and identified with physical and chemical properties of the compounds as well as their spectral analysis.The isolated compounds included 21 amide alkaloids,identified as:N-methyl-cinnamamide(1),3-phenylacrylamide(2),clausenalansamide A(3),3-dehydroxy-3-methoxyl-clausenalansamide A(4),clausenalansamide B(5),(2’R)-N-(2’-phenylethyl)-N-methylcinnamamide 2’-O-β-D-glucopyranoside(6),lansiumamide B(7),N-2-phenylethyl-cinnamamide(8),lansiumamide C(9),2’-dehydroxy-2’-oxo-clausenalansamide B(10),lansamide-I(11),2’-dehydroxy-2’-acetoxyl-clausenalansamide B(12),1 ’-methoxyl-clausenalansamide B(13),3-dehydroxy-3-methoxyl-secoclausenamide(14),neoclausenamide-B(15),neoclausenamide-A(16),anhydroelausenamide(17),1,5-dihydro-5-methoxy-1-methyl-3,5-diphenyl-2H-pyrrol-2-one(18),1,5-dihydro-5-hydroxy-l-methyl-3,5-diphenyl-2H-pyrrol-2-one(19),lansamide-7(20),homoclausenamide(21);and 20 other types of compounds identified as:N-(2’-phenylethy1)-N-cinnamamide 2’-O-β-glucopyranoside(22),3-hydroxy-N-methyl-(2’-phenylethyl)-N-cinnamamide 2’-O-β-glucopyranoside(23),isorhamnetin-3-O-neohesperidoside(24),7-hydroxy-1-benzopiran-2-one(25),wampetin(26),lansiumarin-C(27),claucoumarin A(28),clausenalansimin A(29),(E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen(30),dihydroindicolactone(31),2-phenylacetaldehyde(32),/p-coumaric acid(33),(4R,6R)-6-hydroxypiperitone(34),(4S,6R)-6-hydroxypiperitone(35),(1S,2S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol(36),subamone(37),methyl(1R,2R,2’Z)-2-(5’-hydroxy-pent-2’-enyl)-3-oxo-cyclopentaneacetate(38),5-hydroxy-4-phenyl-2(5H)-furanone(39),(-)-loliolide(40),xylogranatinin(41).Among them,compounds 12-16 were new amide alkaloid,compounds 22-24 were new glycoside,compounds 18-21 were new natural product,and compounds 34-41 were isolated from the genus for the first time.Some of the compounds were tested for the a-glucosidase inhibitory activity by a PNPG method.Results showed that compounds 12,13,25,27 and 29 displayed moderate inhibitory activity(inhibition rate range from 21.83±2.01%to 37.12±6.01%),while compound 41 presented strong inhibitory activity,with the inhibition rate up to 93.56±1.97%,significantly higher than that of the positive control of acarbose(inhibition rate of 54.25±4.74%).The lethal activity of Panagrellus redivivusl was screened as well,and results showed that compounds 1,4,7,9,21 and 38 presented strong lethal activity(revised lethality rate range from 71.49%to 100%),among which the lethality rate of compounds 1,9,21 and 38 were even higher than that of the positive control avermectin(revised lethality rate of 80.63%).Through the phytochemical study on the amide alkaloids and other chemical constituents as well as their biological activities from wampee seeds,some compounds with potent lethal activity of Panagrellus redivivusl and a-glucosidase inhibitory activity were screened,providing chemical structures for the study of the related pharmacological effects,also a theoretical basis and reference for the further utilization of wampee. |
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