Schisandrene, a Dibenzocyclooctadiene Lignan from Schisandra c hinensis : Structure−Antioxidant Activity Relationships of Dibenzocyclooctadiene Lignans ⊥ (original) (raw)
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An update on bioactive plant lignans
Natural Product Reports, 2005
Lignans are a class of secondary plant metabolites produced by oxidative dimerization of two phenylpropanoid units. Although their molecular backbone consists only of two phenylpropane (C 6 -C 3 ) units, lignans show an enormous structural diversity. There is a growing interest in lignans and their synthetic derivatives due to applications in cancer chemotherapy and various other pharmacological effects. This review deals with lignans possessing anticancer, antioxidant, antimicrobial, anti-inflammatory and immunosuppressive activities, and comprises the data reported in more than 100 peer-reviewed articles, so as to highlight the recently reported bioactive lignans that could be a first step towards the development of potential new therapeutic agents.
Scientific reports, 2018
Antioxidants are a diverse group of chemicals with proven health benefits and thus potential preventive medicine and therapeutic applications. While most of these compounds are natural products, determining their mechanism of radical scavenging and common motifs that contribute to antioxidant activity would allow the rational design of novel antioxidants. Here the origins of the antioxidant properties of ten natural products of the lignan family were studied in silico by calculating their thermochemical properties by using ROB3LYP/6-311++G(2df,2p)//B3LYP/6-311G(d,p) model chemistry. Three conditions were modelled: gas phase, ethanol and water solvents. The results allowed assigning the antioxidant activity to specific moieties and structural features of these compounds. It was found that the benzylic hydrogen atoms are the most likely to be abstracted to form radicals and hence define antioxidant properties in most of the studied compounds. The results also suggested that the most l...
Zeitschrift für Naturforschung B, 2010
Investigation of the fruits of Schisandra sphenanthera led to the isolation of two new dibenzocyclooctadiene lignans, methylgomisin O (1) and chloromethyl schisantherin B (2), together with twelve known lignans (3 - 14). Their structures were elucidated by using extensive spectroscopic techniques including 1D and 2D NMR spectra. Compound 2 was identified as a cyclooctadiene moiety substituted with a chloromethyl group, which is rarely found in natural products, especially in terrestrial higher plants. Among these isolates, compounds 1 and 7 exhibited considerable inhibitory activity against tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) production, and did not display any cellular toxicity against RAW264.7 cells.
Food Research International, 2002
Sesame seed contains lignans and lignan glycosides. The antioxidative activity of the crude extract of lignan glycosides obtained from unroasted defatted black sesame seeds was investigated in this study. The components responsible for the antioxidative activity were also studied. The unroasted black sesame seeds, after defatted with n-hexane, were extracted with 80% methanolic solution to prepare for the crude extract of lignan glycosides. After chromatographic separation of this crude extract with octadecylsilane (ODS) column (2.5 cm i.d.Â100 cm), four fractions (Fr1, Fr2, Fr3, Fr4) of the crude extract were obtained from the eluents of 25, 50, 75% aqueous methanolic solution and 100% methanol, respectively. Among them, Fr2 and Fr3 showed better antioxidative activity by 2,2-Diphenyl-1-picrylhydrazyl hydrate (DPPH) antioxidative assay. These two fractions were further purified by preparative HPLC (Hyperprep 100 C18 column; 20 mm i.d.Â250 mm) and the main constituents were found to be lignan glycosides and some unknown brown materials. It was interesting to find that the brown materials (in Fr2) exhibited exceptional DPPH free radical scavenging effect, whereas the identified sesaminol triglucoside in Fr2 and sesaminol diglucoside in Fr3 possess no such activity. Using Cu +2 -induced oxidation of human low-density lipoprotein (LDL) for the antioxidative assay, similar results were observed. Seaminol triglucoside and sesaminol diglucoside showed no effect on the extension of lag phase, while the brown materials had excellent inhibitory effect on the oxidation of LDL. Furthermore, natural antioxidants such as g-tocopherol, sesamol and sesaminol were not detected in the crude extract of lignan glycosides. Our findings suggest that the brown materials present in Fr2 had a significant contribution to the antioxidative activity of the crude extract of lignan glycosides. Identification of the responsible components is underway. #
Lignans: Insight to Chemistry and Pharmacological Applications-An Overview
Lignans are widely distributed in the plant kingdom and have been found in species belonging to more than seventy families. These are found in several foods, mostly in seeds, beans and berries. Sesame seed lignans are perhaps best known for their positive health effects as antioxidants. In recent times, lignans attracted much interest in the researchers due to their wide range of biological applications and their utility as useful synthons. This review describes up to date developments in the lignan chemistry, with a more emphasis on their natural sources, methods developed for synthetic analogues and critical discussion on biological activities.
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010
Previous studies of Schisandra species have reported lignans with various beneficial pharmacological effects such as antihepatitis, antitumor, and anti-human immunodeficiency virus (HIV) activities as typical of this genus. 1-4) Recent researches also showed that some triterpenoids isolated from this genus exhibited anti-HIV activities and inhibitory activities toward cholesterol biosynthesis. 5-9) Schisandra lancifolia, one of species of this genus, is a climbing plant mainly distributed in Mainland of China. 10) In our previous work, some new highly oxygenated nortriterpenoids were isolated from this plant. To search for more new bioactive compounds from this plant, we examined the leaves and stems of S. lancifolia, which led to the isolation of three new dibenzocyclooctadiene lignans, schilancifolignans A-C (1-3), along with thirteen known compounds. In addition, the anti-HIV-1 activities of new compounds 1-3 were evaluated. Described in this paper are their structure elucidation and biological activities.
Molecules, 2022
The effect-directed detection (EDD) of Schisandra rubriflora fruit and leaves extracts was performed to assess their pharmacological properties. The EDD comprised TLC—direct bioautography against Bacillus subtilis, a DPPH assay, as well as α-glucosidase, lipase, tyrosinase, and acetylcholinesterase (AChE) inhibition assays. The leaf extracts showed stronger antioxidant activity than the fruit extract as well as inhibition of tyrosinase and lipase. The fruit extract was found to be extremely active against B. subtilis and to inhibit α-glucosidase and AChE slightly more than the leaf extracts. UHPLC–MS/MS analysis was carried out for the bioactive fractions and pointed to the possible anti-dementia properties of the dibenzocyclooctadiene lignans found in the upper TLC fractions. Gomisin N (518 mg/100 g DW), schisanhenol (454 mg/100 g DW), gomisin G (197 mg/100 g DW), schisandrin A (167 mg/100 g DW), and gomisin O (150 mg/100 g DW) were the quantitatively dominant compounds in the frui...
Antiradical and antioxidant activities of new bio-antioxidants
Biochimie, 2012
Antioxidants could be promising agents for management of oxidative stress-related diseases. New biologically active compounds, belonging to a rare class of natural lignans with antiangiogenic, antitumoral and DNA intercalating properties, have been recently synthesized. These compounds are benzo[kl]xanthene lignans (1,2) and dihydrobenzofuran neolignans (3,4). The radical scavenging and chain-breaking antioxidant activities of compounds 1-4 were studied by applying different methods: radical scavenging activity by DPPH rapid test, chain-breaking antioxidant activity and quantum chemical calculations. All studied compounds were found to be active as DPPH scavengers but reaction time with DPPH and compounds' concentrations influenced deeply the evaluation. The highest values of radical scavenging activity (%RSAmax) and largest rate constants for reaction with DPPH were obtained for compounds 2 and 3. Comparison of %RSAmax with that of standard antioxidants DL-α-tocopherol (TOH), caffeic acid (CA) and butylated hydroxyl toluene (BHT) give the following new order of %RSA max: TOH (61.1%) > CA (58.6%) > 3 (36.3%) > 2 (28.1%) > 4 (6.7%) > 1 (3.6%) = BHT (3.6%). Chain-breaking antioxidant activities of individual compounds (0.1-1.0 mM) and of their equimolar binary mixtures (0.1 mM) with TOH were determined from the kinetic curves of lipid autoxidation at 80 °C. On the basis of a comparable kinetic analysis with standard antioxidants a new order of the antioxidant efficiency (i.e., protection factor, PF) of compounds 1-4 were obtained: 2 (7.2) ≥ TOH (7.0) ≥ CA (6.7) > 1 (3.1) > 3 (2.2) > ferulic acid FA (1.5) > 4 (0.6); and of the antioxidant reactivity (i.e. inhibition degree, ID): 2 (44.0) > TOH (18.7) > CA (9.3) > 1 (8.4) > 3 (2.8) > FA (1.0) > 4 (0.9). The important role of the catecholic structure in these compounds, which is responsible for the high chain-breaking antioxidant activity, is discussed and a reaction mechanism is proposed. Higher oxidation stability of the lipid substrate was found in the presence of equimolar binary mixtures 2 + TOH, 3 + TOH and 4 + TOH. However, an actual synergism was only obtained for the binary mixtures with compounds 3 and 4. The geometries of compounds and all possible phenoxyl radicals were optimized using density functional theory. For description of the scavenging activity bond dissociation enthalpies (BDE), HOMO energies and spin densities were employed. The best correlation between theoretical and experimental data was obtained for compound 2, with the highest activity, and for compound 4 with the lowest activity. The BDE is the most important theoretical descriptor, which correlates with the experimentally obtained antioxidant activity of the studied benzo[kl]xanthene lignans and dihydrobenzofuran neolignans.