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Studies On The Antibacterial Chemical Constituents Of Senecio Cannabifolius Less.

Posted on:2005-07-28Degree:DoctorType:Dissertation
Country:ChinaCandidate:B WuFull Text:PDF
GTID:1104360122490677Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
Doctor Candidate: Bin Wu Supervisor: Prof. Lijun WuProf. Chulsa KimSenecio cannabifolius Less., whose another name is "Kuan Ye Fan Hun Cao", as one species of Senecio genus of Compositae family, distributes mainly in the North east and Hebei Province of China, Korea, Japan and far east of pre-Soviet Union.The taste of this plant is bitter, and natured character is cool. While its function shows the effects on dispelling ecchymoma, anastalsis and analgesic. As one kind of folk medicine, it's usually used to treat the diseases, such as virus influenza and many kinds of inflammatories.The character on its chemical constituents lies in the pyrrolizidine alkaloids, which exhibited the chronical hepatotoxicity (liver toxicity) and cancerigenic possibility to the human beings and domestic animals.In 2004, the importing of many kinds of preparations made from the species of Senecio genus from China had been prohibited by American and Europe drug administrative departments.In order to deal with the contradiction between the toxicity and efficiency on the treatment, to find the antibacterial compounds and made cooperation on the exploitation of this plant with Chang Chun Hua kang Pharm. Co. Ltd., the further research on the chemical constituents and their anti-virus activity were studied.Pharmacodynamics tests showed that the aqueous extract of Senecio cannabifolius Less, had the effect on antibiosis, antivirus, analgesic- antipyretic, anti-inflammatory antihechic, antianaphylaxis and immunoregulatory, etc., and also showed the same effect when it was used for clinical treatment.By many kinds of isolation method, such as silica gel chromatographies, Lobar column, semi-PHPLC and so on, 52 compounds were obtained and the structures of thirty of them were identified by their physico-chemical character and spectra, and comparison the data with the reference for them.Among the 30 compounds, ten of them were novel compounds. They were identified as Cannabiloid A (E-10), Cannabiloid B (B-6), Cannabiloid C (B-9), Cannabiloid D (B-10), Cannabiside A (E-15), Cannabiside B (B-2), Cannabiside C (B-5), Cannabiside D (B-13), Cannabiside E (B-20), Cannabilactone A(C-4). One new natural compound: 4-(pyrrolidin-2-one)-phenyl acetic acid (C-1). At same time, fourteen of them were isolated from the Senecio genus for the first time. They were elucidated as methyl p-hydroxy benzeneacetate (E-3), 3,4-dihydroxy benzoic acid (E-4), 2,5-dihydroxyl benzeneacetic acid (E-5), methyl 2,5-dihydroxy benzeneacetate (E-8), 3-hydroxy-4-methoxy benzoic acid (E-11), methyl-5-hydroxy-2-pyridinecarboxy-late (E-13), (6R,7aS)6-Hydroxy-7,7a-dihydro-2(6H)-benzofuranone (E-14), 2-(1,4-di-hydroxycyclohexanyl)-acetic acid (E-16), 3-hydroxycyclohexanecarboxylic acid (E-17), 4-hydroxy benzaldehyde (B-14), benzyl 6-O-a-L-arabinopyranosyl-B-D-glucopyrano-side (B-16), (6S,9S)9-O-B-D-glucopyranosyloxy-6-hydroxy-3-oxo-a-ionol (B-18), (6S, 9R)9-O-B-D-glucopyranosyloxy-6-hydroxy-3-oxo-a-ionol (B-19), (+)liriodendrin (C-2).By the anti-bacteria (screening) assay in vitro, the CHCI3, EtOAc and n-BuOH soluble fractions, except for the water layer also showed the potent anti-bacteria activities. Among them, the EtOAc layer exhibited the best result, which gave the potent activity against gram-positive bacilli, such as Staphylococcus aureus, Bacillus subtilis. By the chemical isolation, the main compounds of this part were phenolic constituents, and structure-activity relationship of compounds E-1~E-12 were discussed simply.The general pharmacological studies indicated that the high, medium and low dose of the extract had no influence on the central nervous system, cardiovascular and respiratory system. At same time, the tests of the extract on acute toxicity and secular toxicity showed no toxicity.Contents, such as chlorogenic acid, caffeic acid and oligosaccharides from the extrat of Senecio cannabofolius Less, were examined by HPLC and spectrophoto-metry with uniform design, and six factors, such as the extent of crush, amount of water,...
Keywords/Search Tags:Senecio cannabofolius Less., Senecio genus, antibacterial activity, chemical constituents, phenolic acids, turbidimotric assay method, MIC, uniform design, no-aqueous potentiometric titration
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