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Studies On The Chemical And Bioactivities On Chimonanthus Praecox,Clerodendrum Trichotomum, And Paecilomyces Hepiali

Posted on:2013-02-26Degree:MasterType:Thesis
Country:ChinaCandidate:W X WangFull Text:PDF
GTID:2214330374467400Subject:Chemical Biology
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Two ornamental plants, Chimonanthus praecox and Clerodendrum trichotomum, as well as a fungus Paecilomces hepiali were investigated for their chemical constituents and bio-activities. Nine new and forty-two known compounds were isolated by column chromatography (CC) over silica gel, RP-silica gel, MCI gel, macroporous resin, Sephadex LH-20, and semipreparative HPLC. Their structures were determined based on1D/2D NMR, HR-ESIMS, IR, UV, CD spectra, X-ray diffraction analysis and computational chemistry methods.From the fruits and leaves of C. praecox, one (1) new and seven (2-8) know sesquiterpenoids, four dimeric tryptamine-related alkaloids (9-12), and six glycosides (13-18) were isolated. Based on its spectroscopic data, the new structure of compound1, an oppositane-type sesquiterpenoid, was elucidated to be the C-4epimer of bullatantriol (2). All isolated compounds were evaluated for their cytotoxicities against an small panel of human cancer cell lines (NUGC3, SHSY-5Y, SNU739, MCF-7), and only the chimonanthine-type alkaloids (10-12) were found to have cytotoxic effects against gastric carcinoma NUGC3and hepatocarcinoma SNU739cancer cells, with IC50values ranging from10.3to19.7μM.Seven (19-25, named trichotomones A-G) new and eight (27-34) known abietane-type diterpenoids were isolated from the roots of Clerodendrum trichotomum. Additionally, one new steroid (26) were also obtained. The new structures were elucidated by means of spectroscopic methods, single crystal X-ray diffraction analysis, and ECD computational chemistry methods. All isolated compounds were tested for their cytotoxicities against five human cancer cell lines (BGC-823, Huh-7, KB, KE-97, Jurkat) using the CellTiter GloTM Luminescent cell viability assay. Among them, compounds22,24,32, and34showed significant cytotoxic effects with IC50values from0.83to29.41μM, and the possible structure activity relationship (SAR) was discussed. The chemical taxonomy of C. trichotomum was briefly discussed herein as well.From P. hepiali, ten compounds were isolated and determined, which did not show any activities in cytotoxicity assay.
Keywords/Search Tags:Calycanthaceae, Lamiaceae, Chimonanthus praecox, Clerodendrum trichotomum, Paecilomces hepiali, Sesquiterpenoids, Abietane-typediterpenoids, Alkaloids, Cytotoxicities
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