Studies On The Chemical Constituents Of The Fruits Of Illicium Lanceolatum And Their Bioactivities

Illicium lanceolatum A.C.Smith,also known as "Mangcao",is classified in the lllicium genus.Illiciaceae family is mainly distributed in China’s middle and lower reaches of the Yangtze River provinces and regions."Flora of China" records its root and bark,which can be used to treat blood congestion,rheumatoid arthritis and so on.At present,few researches were reported about investigate the phytochemistry of I.lanceolatum.The unique,highly oxidized seco-prezizaane sesquiterpenes were obtained from the fruits of Illicium genus.The diverse and various structures of those compounds are formed by means of cyclization,cleavage and rearrangement.Anisatin is a GABA non-competitive inhibitor with strong neurotoxicity,while other seco-prezizaane sesquiterpenes compounds displayed effective neuroprotective effects.Therefore,a comprehensive research on the phytochemistry of the water-soluble fraction and their biological activities were carried out.Forty-two compounds were isolated from 95%EtOH extract of I.lanceolatum,including twenty-four seco-prezizaane sesquiterpenes,four monoterpene glycosides,three hexalactone derivatives,a pair of new oxaspiro-carbon epimeric glycosides and seven other compounds.New compounds 1-10 and 27-31 are reported in this thesis firstly.Based on the spectral and chemical methods,they are identified and elucidated as lanceolatin A(1),lanceolatin B(2),lanceolatin C(3),lanceolatin D(4),lanceolatin E(5),lanceolatin F(6),lanceolatin G(7),lanceolatin H(8),lanceolatin I(9),lanceolatin J(10),lanceolactone A(27),lanceolactonoside A(28),lanceolactone B(29),spirolancinoside A(30),spirolancinoside B(31).The absolute configurations of compounds 1 and 5 were determined according to the X-ray Crystal Diffraction method.And the absolute configurations of compounds 27-29 were established based on their CD spectra using the interpretation of Beecham’s rules of lactone.The results of bioassays showed that compounds 4,14,17,30 and 31 displayed potent neuroprotective effects in the monosodium glutamate induced neuroblastoma SH-SY5Y cell damage model with protection rates of 22.74%,24.27%,21.40%,19.08%,22.96%respectively,at 10-5 mol·L-1.In addition,these compounds were evaluated for cytotoxic activity,anti-inflammatory activity and antiviral activity.