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The Separation And Structural Modification Of Chinensiolide Compounds

Posted on:2013-02-27Degree:MasterType:Thesis
Country:ChinaCandidate:X Y LiangFull Text:PDF
GTID:2234330374496554Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Chinensiolide compounds is Guanianolide-type sesquiterpene compounds extracted form Ixeris chinensis(Thunb) Nakai, it is the main active constituents. To obtain more this kind compounds, the article studided the chemical constituents of the Ixeris chinensis (Thunb.) Nakai. By the modern chromatography and the nuclear magnetic resonance (NMR) ect spect-roscopy spectrum, we have isolated and identified23monomer compounds at last. They are: Ixerin D (1), Apigenin-7-O-β-D-glucopyranoside (2),3β,10a-dihidroxy-guaia-11(13)-ene-12,6-lactone (3),3β,10α-dihidroxy-guaia-4(15),11(13)-diene-12,6-lactone (4), Chinensiolide B (5),E-3-hexenyl-β-D-pyranglucopyranoside (6),10α-hidroxy-guaia-4(15),11(13)-diene-12,6-1-actone-3β-(O-β-Z-D-(6’-p-hidroxyphenylacetyl)glucopyranoside (7), Butyl-O-β-D-glucopyranos-ide(8),Benzyl-O-β-D-glucopyranoside(9),(6S,9R)-6-hidroxy-3-oxo-α-ionol-9-O-β-D-glucop-yranoside (10), Chlorogenic acid butyl este (11), Chinensiolide J (12), Chinensiolide K (13),4-glucosyl methyl phenylacetate (14), Chinensiolide H (15), Chinensiolide I (16), Macroclini-side A (17), Ixerochinoside (18), n-hexacosanol (19), butyl-4-hydroxylphenylacetate (20), methy1-4-hydroxylphenylacetate (21), octacosyl alcohol (22), Chinensiolide G (23). In these compounds, there are twelve Chinensiolide compounds (1,3,4,5,7,12,13,15,16,17,18,23), and Compounds8and14are new, compounds6,9,10,11,21and22are isolated from this plant.for the first time.In addition, this article also did a series of structural modification about Ixerin D (1), which is the maximum constituent in Ixeris chinensis (Thunb) Nakai, and we got three monomer compounds:4,24,26. We tested ten monomer compounds’effect to A549(Lung Cancer) cell activity by MTT. The results show that the stutures and activities of sesquiterpene compounds in Ixeris chinensis have the following relationships:most of Guanianolide-type sesquiterpene glycosides compounds not show activity or show little activity in vitro test; the substituent of3-have important effect to activity, and the hydrophobization of the substituent benefits strengthening activity; the double bond of4,15-has a stronger activity than4,5-, and the exist of4,5-will make activity lower.
Keywords/Search Tags:Ixeris chinensis(Thunb.)Nakai, Chinensiolide compounds, Sesquiterpenecompounds, Structural modification, Structural and activity
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