ABSTRACT
The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide (2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity.
Subject(s)
Antineoplastic Agents/pharmacology , Lactones/chemistry , Plant Extracts/pharmacology , Plant Roots/metabolism , Saussurea/metabolism , Sesquiterpenes/chemistry , Cell Line, Tumor , Chemistry, Pharmaceutical/methods , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Mass Spectrometry , Stereoisomerism , Structure-Activity RelationshipABSTRACT
A series of 8-aminomethylated derivatives (1a-1j) were prepared by Mannich reaction of oroxylin A (1) with appropriate primary or secondary amines and para-formaldehyde. All the compounds were tested for their alpha-glucosidase inhibition activity against both yeast and rat intestinal alpha-glucosidase. Some of the compounds demonstrated significantly better alpha-glucosidase inhibitory activity than the parent compound (oroxylin A).
Subject(s)
Flavonoids/chemistry , Flavonoids/pharmacology , Glycoside Hydrolase Inhibitors , Animals , Intestines/enzymology , Rats , Saccharomyces cerevisiae/enzymology , Structure-Activity RelationshipABSTRACT
Nimbolide (1), a limonoid isolated from Azadirachta indica, is the chief cytotoxic principle in Neem leaves extract. Using nimbolide as a lead compound for anti-cancer analogue design, a series of nimbolide derivatives have been synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 10 compounds screened 2g, 2h and 2i showed potent activity.
Subject(s)
Amides/chemistry , Antineoplastic Agents/pharmacology , Limonins/chemistry , Azadirachta/metabolism , Cell Line, Tumor , Chemistry, Pharmaceutical/methods , Drug Design , Humans , Inhibitory Concentration 50 , Models, Chemical , Plant Extracts/metabolism , Plant Leaves , Plants, Medicinal/metabolismABSTRACT
The natural product, chrysin (5,7-dihydroxy flavone), obtained from Oroxylum indicum, exhibits numerous biological activities including anticancer, anti-inflammatory, and antiallergic activities. Three series of chrysin analogues were prepared, in which chrysin and heterocyclic moieties are separated by 3-carbon, 4-carbon, and 6-carbon spacers. All the derivatives were screened for antibacterial activity against a panel of susceptible and resistant Gram-positive and Gram-negative organisms. It was observed that most of the derivatives displayed significant activity as compared to their parent compound (chrysin).
Subject(s)
Anti-Infective Agents/pharmacology , Chemistry, Pharmaceutical/methods , Flavonoids/chemistry , Flavonoids/chemical synthesis , Plant Extracts/metabolism , Anti-Allergic Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents/pharmacology , Carbon/chemistry , Drug Design , Drug Evaluation, Preclinical , Flavonoids/metabolism , Microbial Sensitivity Tests , Models, Chemical , Morpholines/chemistry , Structure-Activity RelationshipABSTRACT
A series of Oroxylin A derivatives, prepared by alkylation and condensation, were fully characterized by spectroscopic methods. All the derivatives were screened for antibacterial activity against a panel of susceptible and resistant Gram-positive and Gram-negative organisms. It was observed that acylation of 7-OH group in Oroxylin A significantly enhanced the activity as compared to their parent compound (Oroxylin A).
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Flavonoids/chemical synthesis , Alkylation , Anti-Bacterial Agents/pharmacology , Flavonoids/pharmacology , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Microbial Sensitivity Tests , Structure-Activity RelationshipABSTRACT
The hexane extract of dried fruits of Piper longum on fractionation afforded a new alkamide, isodihydropiperlonguminine and two phenyl propanoic acid derivatives. The structures of these compounds are established based on spectroscopic evidence and synthesis.
Subject(s)
Phenylpropionates/chemistry , Phenylpropionates/isolation & purification , Piper/chemistry , Fruit/chemistry , Polyunsaturated Alkamides , Propionates/chemistry , Propionates/isolation & purification , Spectrum AnalysisABSTRACT
Several natural piper amides and their mimics were synthesized by developing a new strategy of amide formation. The piper amides were tested against both gram +ve and gram -ve bacterial strains and found that they are particularly more active against Staphylococcus aureus and Chromobacterium violaceum strains.
Subject(s)
Amides/chemical synthesis , Amides/pharmacology , Piper/chemistry , Chromobacterium/drug effects , Microbial Sensitivity Tests/methods , Plant Extracts/pharmacology , Staphylococcus aureus/drug effectsABSTRACT
The bioassay-guided chemical examination of the rhizomes of R. emodi resulted in the isolation of two new oxanthrone esters, revandchinone-1, revandchinone-2, a new anthraquinone ether revandchinone-3 and a new oxanthrone ether, revandchinone-4. Their structures were established based on spectroscopic and degradative evidence. Occurrence of oxanthrone ether is reported for the first time. The anti bacterial and anti fungal activity of the isolates is studied.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Esters/isolation & purification , Ethers/isolation & purification , Rheum/chemistry , Rhizome/chemistry , Anthraquinones/chemistry , Anthraquinones/isolation & purification , Anthraquinones/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Esters/chemistry , Esters/pharmacology , Ethers/chemistry , Ethers/pharmacology , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Molecular StructureABSTRACT
An activity-directed fractionation and purification process was used to identify the antioxidant components of Cedrus deodara. Dried heartwood powder of C. deodara was first defatted with petroleum ether and then extracted with chloroform. The chloroform extract showed strong antioxidant activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical. This fraction was then subjected to separation and purification using silica gel column chromatography. Three compounds with potent antioxidant activity were isolated in significant yields and identified by spectroscopic methods ((1)H NMR, (13)C NMR, IR, and MS). They were identified as (-)-matairesinol, (-)-nortrachelogenin, and a dibenzylbutyrolactollignan (4,4',9-trihydroxy-3,3'-dimethoxy-9,9'-epoxylignan). This is the first report of the occurrence of these compounds in C. deodara.
