lignans and naphthalene

This review article presents 342 aromatic glycosides, isolated from and identified in plants and microorganisms, that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antioxidant, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been classified into several groups, including simple aromatic compounds, stilbenes, phenylethanoids, phenylpropanoids, naphthalene derivatives, and anthracene derivatives.

Topics: Anthracenes; Glycosides; Humans; Hydrocarbons, Aromatic; Lignans; Naphthalenes; Stilbenes; Surface-Active Agents

Arylnaphthalene lignan lactones are a class of natural products containing the phenyl-naphthyl skeleton. Some arylnaphthalene lignan lactones have been used in clinical practice as antitumor agents, due to their cytotoxicity and inhibitory activities against DNA topoisomerase I (Topo I) and topoisomerase II (Topo II).. This study presents the design and synthesis of arylnaphthalene lignan lactones derivatives. The inhibitory activities against Topo I and Topo IIα and antitumor activities of these compounds were assayed.. A series of arylnaphthalene lignan lactones derivatives have been designed and synthesized, using the Diels-Alder reaction and Suzuki reaction as the key steps. Their antiproliferation activities were evaluated by sulforhodamine B assay on human breast cancer MDAMB-231, MDA-MB-435 and human cervical cancer HeLa cells. DNA relaxation assays were employed to examine the inhibitory activity of compounds 1-22 on Topo I and Topo IIα in vitro. Flow cytometry analysis was performed to study the drug effects on cell cycle progressions.. This work indicates that arylnaphthalene lignan lactones derivatives represent a novel type of Topo IIα inhibitory scaffold for developing new antitumor chemotherapeutic agents.

Topics: Apoptosis; Cell Line, Tumor; Chemistry Techniques, Synthetic; DNA Topoisomerases, Type I; DNA Topoisomerases, Type II; Drug Design; HeLa Cells; Humans; Lactones; Lignans; Naphthalenes; Topoisomerase I Inhibitors; Topoisomerase II Inhibitors

Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2-carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticated cascade process occurred to give 9-aminonaphtho[2,3-c]furan-1(3H)-ones in good yields. By using this tandem reaction as a key step, a concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lactone lignans has been developed.

Topics: Chemistry Techniques, Synthetic; Esters; Lactones; Lignans; Naphthalenes; Nitriles

Mature seeds of 20 Linum species were analyzed for their content of lignans. The seeds of common flax (Linum usitatissimum L.) are known to contain as characteristic lignan sesoisolariciresinol diglucoside (SDG), whose presence in seeds of some other Linum species has also been reported. In order to investigate the material for the presence of such very polar lignans as well as for less polar non-glycosidic lignans as frequently found in aerial parts of Linum species, polar and non-polar extracts of each sample were analyzed by HPLC/ESI-MSMS. SDG was detected in 15 of 16 investigated seed samples of taxa representing sections Linum and Dasylinum. None of eight samples of taxa from sections Syllinum and Linopsis contained detectable amounts of SDG. Quite interestingly, most of the SDG-positive samples contained the 8R,8'R-isomer exclusively while only three (including L. usitatissimum) contained the 8S,8'S-stereoisomer as the predominant form. As a most noteworthy finding, the dichloromethane extracts obtained from seeds of several Linum species were found to contain significant concentrations of non-polar cyclolignans of the arylnaphthalene/-dihydronaphthalene lactone type or, alternatively of the aryltetralin lactone type. Thus, seeds of Linum perenne L. as well as those of several other representatives of sections Linum and Dasylinum were found to contain significant concentrations of the arylnaphthalene justicidin B along with further compounds of this type and some aryldihydronaphthalene-type lignans. On the other hand, seeds of Linum flavum and further representatives of section Syllinum were found to contain aryltetralin-type lignans, mainly in the form of esters with aliphatic carboxylic acids, such as 6-methoxypodophyllotoxin-7-O-n-hexanoate, whose occurrence in L. flavum seeds has very recently been reported by us for the first time. Various chemosystematic and biogenetic aspects are discussed in the light of these results.

Topics: Butylene Glycols; Flax; Glucosides; Hydrolysis; Lignans; Methylene Chloride; Naphthalenes; Seeds

Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied.

Topics: Acetylene; Alkynes; Biological Products; Carbon Dioxide; Catalysis; Cinnamates; Cyclization; Hydrocarbons, Brominated; Lactones; Lignans; Models, Chemical; Naphthalenes; Silver

The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring.

Topics: Carbazoles; Catalysis; Chemistry, Organic; Cyclization; Esterification; Indicators and Reagents; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Naphthalenes; Podophyllotoxin; Stereoisomerism

Topics: Humans; Lignans; Naphthalenes; Tetrahydronaphthalenes