Study On The Chemical Constituents Of The Fruit Of Xanthium Mellifera

The genus Xanthium in the family Compositae contains approximately 25 species distributed throughout northern and central America,Europe,Asia,and northern Africa.Chemical investigations of the genus have resulted in the isolation of sesquiterpenoids,diterpenoid glycosides,flavonoids,lignans,thiazinediones,and fatty oils.The fruits of the genus X.are commonly used in clinical medicine for the treatment of rheumatism,headache,stuffy nose,runny nose,nasosinusitis,etc.Xanthium has a certain toxicity,and excessive use or improper processing can lead to poisoning and even death.Studies have shown that the main toxic components in the genus Xanthium are two water-soluble glycosides,carboxyatractyloside and atractyloside,which were controlled by limiting in the Chinese Pharmacopoeia.X.chinense Mill,is a widely distributed species in China.To extend the resources of X.in clinical medicine and make use of X.more safely,a study on the n-BuOH extraction of the fruits of X.chinense was carried out.29 compounds were isolated from the fruits of X.chinense,including 5 diterpenoid glycosides,5 monoterpenoid glycosides and 16 other compounds.Their structures were established on the basis of extensive spectroscopic analysis and comparison with literature data.The isolates are fructusnoid D(1),fructusnoid E(2),(E)-2-methyl-6-methyleneocta-2,7-dien-1-ol O-?-D-apiofuranosyl-(1?6)-?-D-glucopyranoside(3),(Z)-2-methyl-6-methyleneocta-2,7-dien-1-ol ?-D-apiofuranosyl-(1?6)-?-D-glucopyranoside(4),3',4'-desulphated-atractyloside(5),atractyloside(6),4'-desulphated-atractyloside(7),neryl 6-O-?-D-apiofuranosyl-?-D-glucopyranoside(8),geranyl 6-O-?-D-apiofuranosyl-?-D-glucopyranoside(9),myrtenol 6-O-?-D-apiofuranosyl-?-D-glucopyranoside(10),7-[(?-D-apiofuranosyl-1?6)-?-D-glucopyranosyl)oxymethy]-8,8-dimethyl-4,8-dihydrobenzo[1,4]thiazine-3,5-dione(11),icariside F2(12),(7R,8S)-dihydrodehydroconiferyl(13),(6R,9S)-3-oxo-a-ionol-?-D-glucopyranoside(14),crypto-chlorogenic acid methyl ester(15),chlorogenic acid methyl ester(16),(4S,5R)-4-hydroxy-3,3,5-trimethyl-4-[(E)-3-oxobut-1-en-1-yl]-cyclohexan-1-one(17),umbelliferone(18),dehydrovomifoliol(19),grasshopper ketone(20),epiloliolide(21),3-isopropyl-5-ace-toxycyclohexene-2-one-1(22),(E)-2,5-dihydroxycinnamic acid(23),caffeic acid(24),caffeic acid ethyl ester(25),axillarin(26),including 4 new compounds(1-4).