Cytotoxic lignans from Larrea tridentata (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.
Lignans: a versatile source of anticancer drugs
Beni-Suef University Journal of Basic and Applied Sciences
Background Cancer is considered as the second deadliest disease globally. Plants have continuously offered unique secondary metabolites with remarkable biological applications. Lignans have gained great importance due to their biological activity. Previous studies revealed that the most remarkable bioactivity of lignan class of molecules is anticancer. They are derived from the oxidative dimerization of two phenylpropanoid units. This review covers the isolated anticancer lignans and their mechanistic aspects. Main body A bibliographic investigation was performed by analyzing the information available on anticancer lignans in the internationally accepted scientific databases including Web of Science, SciFinder, PubMed, Scopus, and Google Scholar. In this review we have tried to sum up the isolated anticancerous lignan, its source, active plant part, extract and various cell lines used to establish different studies. Here we have included a total number of 113 natural lignans. Many s...
Structural determinants of plant lignans for growth of mammary tumors and hormonal responses in vivo
The Journal of Steroid Biochemistry and Molecular Biology, 2005
Low risk of breast cancer (BC) has been proposed to be associated with high intake of lignans. Some plant lignans are converted to mammalian lignans, e.g., enterolactone (ENL), suggested to be the biologically active lignan forms. Until now, little attention has been paid to the possible biological activities of plant lignans, even though some plant lignans are absorbed and present in serum and urine. In this study, we have investigated the antitumorigenic and endocrine-modulatory activities of different plant lignans in order to clarify the structure-activity relationships. 7-Hydroxymatairesinol (HMR) is not converted to ENL, and both HMR and ENL inhibit the growth of 7,12-dimethylbenz[a]anthracene (DMBA)-induced mammary cancer. Nortrachelogenin (NTG) resembles HMR, but has a hydroxyl group at C-8 instead of C-7 and is not converted to ENL. In DMBA-model, NTG showed no inhibition of tumor growth, but increased the uterine weight. Furthermore, lifelong exposure to NTG increased uterine weight in immature females and ventral prostate weight in adult males. In contrast, lifelong exposure to HMR had no effects on uterine or prostate weights at any age. Our results indicate that a difference in the position of one hydroxyl group results in distinct biological responses in vivo, as well as different lignan metabolite profiles.
Lignans from the fruits of cornus kousa burg. and their cytotoxic effects on human cancer cell lines
Archives of Pharmacal Research, 2007
The fruits of Cornus kousa Burg. were extracted with 80% aqueous MeOH, and the concentrated extract partitioned with EtOAc, n-BuOH and H2O. Six lignans were isolated from the EtOAc fraction through repeated silica gel, ODS and Sephadex LH-20 column chromatographies. From the physico-chemical data, including NMR, MS and IR, the chemical structures of the compounds were determined to be (+)-pinoresinol (1), (-)-balanophonin (2), (+)-laricresinol (3), erythro-guaiacylglycerol-β-coniferyl aldehyde ether (4), threo-guaiacylglycerol-β-coniferyl aldehyde ether (5) and dihydrodehydrodiconiferyl alcohol (6), which were isolated for the first time from this plant. Most of these compounds showed cytotoxicity against human colon carcinoma (HCT-116) and human hepatocellular carcinoma (HepG2) cell lines in vitro, with IC50 values ranging from 19.1 to 71.3 μg/mL.
9Experimental studies on lignans and cancer
Baillière's Clinical Endocrinology and Metabolism, 1998
Mammalian lignans are produced from plant precursors such as secoisolariciresinol diglycoside (SDG) and matairesinol via the action of bacteria in the human or animal colon. While precursors are found in many plant foods, flaxseed is the richest source of SDG and was therefore used as a model to determine the anti-cancer effects of lignans. This paper reviews the experimental studies in animals and humans demonstrating the anti-cancer effects of flaxseed and its SDG as well as other studies relevant to the clinical use of lignans, such as those on their food sources, bio-availability and safety.
Lignans and lignins are among the main metabolic products of phenylpropanoid metabolism in vascular plants. They are compounds representing the building blocks of plant cell walls. Moreover they have a broad range of biological activities such as antitumoral, antimitotic, antiviral and cytotoxic and are thought to be involved in the plant defense against pathogens and pests. In this paper we report a survey of the past and current literature about lignans and neolignans and their germination inhibitory activity on cultivated and wild species from plants of the Mediterranean area. Some examples of synthetic methodologies of these molecules have also been reported.
Natural Product Communications, 2009
The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 μM, 5.41 μM and 2.06 μM, respectively).
Journal of Medicinal Food, 2010
An optimization of an extraction procedure of lignans from flaxseed has been developed. The influence of some parameters was investigated : preliminary extraction step with alcoholic solvent, solvent polarity and pH of the extract. All these conditions affected total lignan content but the most critical variables were preliminary extraction and solvent polarity. The optimized procedure was applied to 500 g of flaxseed and resulted in the isolation of secoisolariciresinol and anhydrosecoisolariciresinol with a high purity level. The ability of these two compounds and of secoisolariciresinol diglucoside to modulate the growth of human breast cancer MCF-7 and MDA-MB-231 cell lines was evaluated. Our results show that lignans modulate breast cancer cells development. The most intense effect was observed for anhydrosecoisolariciresinol which significantly decreased cells growth at 50 and 100 M.
Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells
Journal of Cancer Research and Clinical Oncology, 2003
Plant-derived lignans caused cell loss by apoptosis in colorectal adenoma and carcinoma cells. Nordihydroguaiaretic acid (NDGA), commonly used for the inhibition of lipoxygenase isoenzymes, showed the strongest growth inhibition with an IC 50 of 1.9±0.5 lg followed by epiashantin (IC 50 =9.8± 4.5 lM) and arctigenin (IC 50 =16.5±8.5 lM). The lignans caused a time-and dose-dependent loss of mitochondrial membrane potential (MMP), down regulation of the anti-apoptotic protein bcl xl and an increase of the apoptotic index. The time interval until loss of MMP and down modulation of bcl xl became evident correlated with the efficiency of growth inhibition by NDGA, epiashantin and yangambin. Bcl 2 and caspase 3 were not involved. NDGA also induced a shift of the culture population to the G 2 /M phase of the cell cycle. With respect to these results, naturally occurring lignans could be useful in the therapy and chemoprevention of colorectal tumors.