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Study On The Chemical Constituents And Bioactivities From Dragon’s Blood Of Dracaena Cambodiana

Posted on:2012-02-13Degree:MasterType:Thesis
Country:ChinaCandidate:Y LuoFull Text:PDF
GTID:2283330335484932Subject:Biochemistry and Molecular Biology
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Dragon’s blood, known as a famous traditional medicine, is red resin excreted by a part of plants of the genus of Dracaena when encounter external injury or microbial invasion. Modern pharmacological research have proved that it possessed anti-inflammatory, analgesic, anti-dysentery, anti-diarrhea, anti-bleeding, anti-ulcer, anti-bacterial and anti-tumor activities. Dracaena cambodiana Pierre ex Gagnep. (Agavaceae), an endemic and rare medicinal plant in China, is also one of the origin plants of dragon’s blood. However, few studies on chemical constituents from dragon’s blood of D. cambodiana or their pharmacological properties were reported. In this paper, secondary metabolites from dragon’s blood of D. cambodiana were isolated and identified, and their antitumor and antibacterial activities were evaluted. It is very important to the development and sustainable utilization of this resource.Twenty-four compounds were isolated from the EtOAc fraction of ethanol extract of dragon’s blood of D. cambodiana by column chromatography, and their structures were indentified by physicochemical and spectral data (UV, IR, MS, 1D NMR,2D NMR) as cambodianin A (1), cambodianin B (2),4,4’-dihydroxy-2,3’-dimethoxydihydrochalcone (3),5, 7-dihydroxy-4’-methoxy-8-methylflavane (4), (2S)-7,3’-dihydroxy-4’-methoxyflavane (5), (2R)-7,4’-dihydroxy-8-methylflavane (6),7,4’-dihydroxy-8-methoxyhomoisoflavane (7), 4,2’,4’-trihydroxychalcone (8), 4,4’-dihydroxy-2’-methoxychalcone (9),3,2’,3’,4’-tetrahydroxy-4-methoxychalcone (10), 3,2’,4’-trihydroxy-4-methoxychalcone (11); 4,4’-dihydroxy-2-methoxydihydrochalcon (12), 4,4’-dihydroxy-2,6-dimethoxydihydro-chalcone (13), 7,4’-dihydroxyflavanone (14), 7,4’-dihydroxydihydro- homoisoflavone (15), syringaresinol (16), pinoresinol (17), 2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (18), epipinoresinol (19), balanophonin (20), 1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione (21), sinapaldehyde (22), (25R)-spirost-5-ene-3β-o1 (23) and (25R)-spirost-5-ene-3β,17a-diol (24). Among them, compounds 1,2 and 3 were new flavonoids, and the others were isolated from dragon’s blood of D. cambodiana for the first time. The antimicrobial activities of all the compounds were examined by the filter paper disc agar diffusion method. Flavonoids 1,2,3,5,6,8,9,12 and 14 showed inhibitory activity against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Compounds 4,13 and 24 showed inhibitory activity against S. aureus. Compound 21 showed inhibitory activity against MRSA. Compounds 5 and 6 showed modern inhibitory activity against Candidaalbicans. The antitumor activities of all the compounds in vitro were tested by MTT assay. Compounds 9,2 and 13 showed inhibitory activity against chronic myelogenous leukemia (K562), human gastric carcinoma (SGC-7901), as well as human hepatoma (SMMC-7721) cell lines. Compound 6 showed inhibitory activity against chronic myelogenous leukemia (K562) and human gastric carcinoma (SGC-7901). Compounds 1,4 and 5 only showed inhibitory activity against chronic myelogenous leukemia (K562). Thus, flavonoids were defined as the active compounds of the dragon’s blood of D. cambodiana.The liposoluble components of the stem and dragon’s blood of D. cambodiana were extracted by solvent method and were identified by GC-MS. For the first time, twenty-one and thirty-three ingredients were identified from the liposoluble components of the stem and dragon’s blood of D. cambodiana, respectively. The main constituents of liposoluble components of the stem of D. cambodiana are diisooctyl phthalate (10.33%) and cycloartanol (8.51%), while those of the dragon’s blood of D. cambodiana are diosgenin (10.62%) and 7-hydroxy-4’-methoxyflavan (9.88%). Eight ingredients exist in both liposoluble components of stem and dragon’s blood of D. cambodiana. The study showed that the constituents of. liposoluble components of the stem and dragon’s blood of D. cambodiana are different, so they should be dealt with differently in clinical application and research.A HPLC fingerprint analysis method was established and used in the analysis of chemical constituents of D. cambodiana and its dragon’s blood. The chemical constituents and their antibacterial activities, antitumor activities of stem and dragon’s blood of D.cambodiana, and dragon’s blood of D. cochinchinensis were compared. The result showed that most of the chemical constitutents from dragon’s blood of D. cambodiana are the same as those compounds discovered in the stem of D. cambodiana and dragon’s blood of D. cochinchinensis in the medium polarity part So they should have the same pharmacological activity.The antioxidant activities of the petroleum ether, ethyl acetate, n-BuOH and water extract fractions from the stem of D. cambodiana were evaluated in this study. The ethyl acetate fraction contained the highest amount of total phenolics and total flavonoids, and showed the greatest DPPH’, ABTS+ and superoxide anion radical-scavenging capacities. The DPPH’, ABTS+ and superoxide anion radical-scavenging capacities of 9 compounds isolated from the ethyl acetate fraction were also evaluated. The results indicated that these compounds contributed to the antioxidant activity of D. cambodiana. Therefore, D. cambodiana and these compounds have potential as natural antioxidants.
Keywords/Search Tags:Dracaena cambodiana, Dragon’s blood, Chemical constituents, Antimicrobial activity, Antitumor activity, Flavonoids, GC-MS, Antioxidant activity
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