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Molecules (Basel, Switzerland) Jan 2020Lignans are widely produced by various plant species; they are a class of natural products that share structural similarity. They usually contain a core scaffold that is... (Review)
Review
Lignans are widely produced by various plant species; they are a class of natural products that share structural similarity. They usually contain a core scaffold that is formed by two or more phenylpropanoid units. Lignans possess diverse pharmacological properties, including their antiviral activities that have been reported in recent years. This review discusses the distribution of lignans in nature according to their structural classification, and it provides a comprehensive summary of their antiviral activities. Among them, two types of antiviral lignans-podophyllotoxin and bicyclol, which are used to treat venereal warts and chronic hepatitis B (CHB) in clinical, serve as examples of using lignans for antivirals-are discussed in some detail. Prospects of lignans in antiviral drug discovery are also discussed.
Topics: Antiviral Agents; Benzodioxoles; Biological Products; Biphenyl Compounds; Drug Development; Furans; Lignans; Masoprocol; Plants; Podophyllotoxin
PubMed: 31906391
DOI: 10.3390/molecules25010183 -
The Journal of Organic Chemistry Feb 2014A series of single-walled carbon nanotube precursors, C3h-symmetric cyclotri(ethynylene)(biphenyl-2,4'-diyl) and cyclotri(ethynylene)(p-terphenyl-2,4″-diyl), have been...
A series of single-walled carbon nanotube precursors, C3h-symmetric cyclotri(ethynylene)(biphenyl-2,4'-diyl) and cyclotri(ethynylene)(p-terphenyl-2,4″-diyl), have been prepared by a linear stepwise oligomerization-cyclization route and by statistical intermolecular cyclooligomerization. In addition to producing these members of a novel class of arylene ethynylene macrocycles, 1 and 2, the latter statistical process produces the smaller cyclic dimer, cyclodi(ethynylene)(p-terphenyl-2,4″-diyl) and the larger cyclic tetramer cyclotetra(ethynylene)(biphenyl-2,4'-diyl). These macrocycles display large Stokes shifts in their fluorescence spectra. Their biphenyl or terphenyl connectivity prevents these macrocycles from achieving full planarity in the ground state, and the ethynylene moieties could provide synthetic access to cyclic arylene oligomers and discrete carbon nanotube segments.
Topics: Alkynes; Biphenyl Compounds; Fluorescence; Macrocyclic Compounds; Molecular Structure; Nanotubes, Carbon; Photochemical Processes; Terphenyl Compounds
PubMed: 24506215
DOI: 10.1021/jo4023809 -
Molecules (Basel, Switzerland) Jan 2018Bioactivity-guided fractionation for the stems of leaves of Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three...
Bioactivity-guided fractionation for the stems of leaves of Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three new compounds with an unprecedented skeleton in nature (-) and three known compounds (-). Their structures were elucidated through extensive spectroscopic analysis. The three new compounds were elucidated as two new spiroketones, nitidaones A (), and B () and one new biphenyl analog, nitidaol (). The known compounds were identified as nordihydroguaiaretic acid (), 7,3',4'-tri--methylquercetin () and ayanin (). All the isolates were tested for their inhibitory activity against IL-6 production in HMC-1 cells. Of them, compounds , - showed potent anti-inflammatory activity, with IC values of 12.8, 17.5, 14.9, 22.9, and 17.8 µM, respectively.
Topics: Anti-Inflammatory Agents; Biphenyl Compounds; Cell Line; Humans; Interleukin-6; Larrea; Mast Cells; Plant Leaves; Plant Stems; Spironolactone
PubMed: 29385086
DOI: 10.3390/molecules23020302 -
Organic & Biomolecular Chemistry Oct 2018Partial agonists of the transcription factor PPARγ (peroxisome proliferator-activated receptor γ) have shown potential for the treatment of metabolic and inflammatory...
Partial agonists of the transcription factor PPARγ (peroxisome proliferator-activated receptor γ) have shown potential for the treatment of metabolic and inflammatory conditions and novel activators serve as valuable tool and lead compounds. Based on the natural product magnolol (I) and recent structural information of the ligand-target interaction we have previously developed magnolol dimer (II) which has been shown to have enhanced affinity towards PPARγ and improved selectivity over RXRα (retinoid X receptor α), PPARγ's heterodimerization partner. In this contribution we report the synthesis and evaluation of three fragments of the dimeric lead compound by structural simplifications. Sesqui magnolol A and B (III and IV) were found to exhibit comparable activities to magnolol dimer (II) and selectivity over RXRα persisted. Computational studies suggest a common pharmacophore of the distinctive biphenyl motifs. Truncated magnolol dimer (V) on the other hand does not share this feature and was found to act as an antagonist.
Topics: Biphenyl Compounds; Crystallography, X-Ray; Dimerization; Drug Discovery; HEK293 Cells; Humans; Ligands; Lignans; Molecular Docking Simulation; PPAR gamma; Protein Binding; Retinoid X Receptor alpha
PubMed: 30232493
DOI: 10.1039/c8ob01745j -
Fitoterapia Dec 2011Phytochemical investigation on Clusia burlemarxii (Clusiaceae) led to isolation and identification of nine compounds. Were isolated from leaves 3-O-α-L-...
Phytochemical investigation on Clusia burlemarxii (Clusiaceae) led to isolation and identification of nine compounds. Were isolated from leaves 3-O-α-L- rhamnopyranosylquercetin, 3-O-α-L-rhamnopyranosylkaempferol, 4-hydroxy-5,5-dimethyldihydrofuran-2-one, 2Z-δ-tocotrienoloic acid and friedelin and were isolated from trunk betulinic acid, protocatechuic acid, lyoniresinol, and a new biphenyl 2,2-dimethyl-3,5-dihydroxy-7-(4-hydroxyphenyl)chromane. The structures were determined by ¹H, ¹³C-NMR, DEPT, HMBC, HMQC, HRESIMS. The Minimal Inhibitory Concentration against Streptococcus mutans, Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Escherichia coli, Salmonella choleraesuis, Pseudomonas aeruginosa, Aspergillus niger and Cladosporium cladosporioides was also determined. Extracts and compounds showed significant activity against tested Gram-positive bacteria, none activity against tested Gram-negative bacteria and fungi.
Topics: Anti-Bacterial Agents; Antifungal Agents; Biphenyl Compounds; Clusia; Fungi; Gram-Positive Bacteria; Microbial Sensitivity Tests; Molecular Structure; Plant Extracts; Plant Leaves; Plant Stems
PubMed: 21893172
DOI: 10.1016/j.fitote.2011.08.012 -
International Journal of Molecular... Aug 2018The past few decades have witnessed widespread research to challenge carcinogenesis; however, it remains one of the most important health concerns with the worst... (Review)
Review
The past few decades have witnessed widespread research to challenge carcinogenesis; however, it remains one of the most important health concerns with the worst prognosis and diagnosis. Increasing lines of evidence clearly show that the rate of cancer incidence will increase in future and will create global havoc, designating it as an epidemic. Conventional chemotherapeutics and treatment with synthetic disciplines are often associated with adverse side effects and development of chemoresistance. Thus, discovering novel economic and patient friendly drugs that are safe and efficacious is warranted. Several natural compounds have proved their potential against this dreadful disease so far. Magnolol is a hydroxylated biphenyl isolated from the root and stem bark of Magnolia tree. Magnolol can efficiently prevent or inhibit the growth of various cancers originating from different organs such as brain, breast, cervical, colon, liver, lung, prostate, skin, etc. Considering these perspectives, the current review primarily focuses on the fascinating role of magnolol against various types of cancers, and the source and chemistry of magnolol and the molecular mechanism underlying the targets of magnolol are discussed. This review proposes magnolol as a suitable candidate that can be appropriately designed and established into a potent anti-cancer drug.
Topics: Animals; Antineoplastic Agents, Phytogenic; Biphenyl Compounds; Humans; Lignans; Magnolia; Neoplasms
PubMed: 30103472
DOI: 10.3390/ijms19082362 -
Cell Death & Disease Jan 2018Honokiol is a natural product and an emerging drug for a wide variety of malignancies, including hematopoietic malignancies, sarcomas, and common epithelial tumors. The...
Honokiol is a natural product and an emerging drug for a wide variety of malignancies, including hematopoietic malignancies, sarcomas, and common epithelial tumors. The broad range of activity of honokiol against numerous malignancies with diverse genetic backgrounds suggests that honokiol is inhibiting an activity that is common to multiple malignancies. Oncogenic transcription factor FOXM1 is one of the most overexpressed oncoproteins in human cancer. Here we found that honokiol inhibits FOXM1-mediated transcription and FOXM1 protein expression. More importantly, we found that honokiol's inhibitory effect on FOXM1 is a result of binding of honokiol to FOXM1. This binding is specific to honokiol, a dimerized allylphenol, and was not observed in compounds that either were monomeric allylphenols or un-substituted dihydroxy phenols. This indicates that both substitution and dimerization of allylphenols are required for physical interaction with FOXM1. We thus demonstrate a novel and specific mechanism for FOXM1 inhibition by honokiol, which partially may explain its anticancer activity in cancer cells.
Topics: Animals; Biphenyl Compounds; Cell Line, Tumor; Down-Regulation; Forkhead Box Protein M1; Humans; Lignans; Mice; Proteasome Inhibitors; Transcriptional Activation
PubMed: 29367668
DOI: 10.1038/s41419-017-0156-7 -
Current Opinion in Immunology Oct 2007Apoptosis is essential for tissue homeostasis, particularly in the hematopoietic compartment, where its impairment can elicit neoplastic or autoimmune diseases. Whether... (Review)
Review
Apoptosis is essential for tissue homeostasis, particularly in the hematopoietic compartment, where its impairment can elicit neoplastic or autoimmune diseases. Whether stressed cells live or die is largely determined by interplay between opposing members of the Bcl-2 protein family. Bcl-2 and its closest homologs promote cell survival, but two other factions promote apoptosis. The BH3-only proteins sense and relay stress signals, but commitment to apoptosis requires Bax or Bak. The BH3-only proteins appear to activate Bax and Bak indirectly, by engaging and neutralizing their pro-survival relatives, which otherwise constrain Bax and Bak from permeabilizing mitochondria. The Bcl-2 family may also regulate autophagy and mitochondrial fission/fusion. Its pro-survival members are attractive therapeutic targets in cancer and perhaps autoimmunity and viral infections.
Topics: Animals; Antineoplastic Agents; Apoptosis; Apoptosis Regulatory Proteins; Autophagy; BH3 Interacting Domain Death Agonist Protein; Biphenyl Compounds; Humans; Metabolic Networks and Pathways; Mitochondria; Molecular Mimicry; Neoplasms; Nitrophenols; Piperazines; Proto-Oncogene Proteins c-bcl-2; Sulfonamides
PubMed: 17629468
DOI: 10.1016/j.coi.2007.05.004 -
Journal of the Formosan Medical... Feb 2021Honokiol and magnolol are natural components isolated from Magnolia bark that is used in traditional Chinese and Japanese herbal medicine. These two isomers are used as...
BACKGROUND/PURPOSE
Honokiol and magnolol are natural components isolated from Magnolia bark that is used in traditional Chinese and Japanese herbal medicine. These two isomers are used as a component of dietary supplements and cosmetic products. In this study, we investigated the antimicrobial effect of honokiol and magnolol on pathogens causing oral diseases, their mechanism of action in biofilm formation and drug resistance of oral pathogens, and inflammatory regulation in mammalian cells.
METHODS
We determined the minimum inhibitory concentration and minimum bactericidal concentration of honokiol and magnolol, and their stability at different temperatures and pH. We also evaluated their effect on biofilm formation, antibiotic-resistance gene expression in MRSA, and pro-inflammatory gene expression in mammalian cells.
RESULTS
Honokiol showed better antimicrobial activity than magnolol. Both honokiol and magnolol showed stable bacterial inhibitory activity over a wide range of temperature and pH, reduced biofilm formation, and antibiotic resistance in oral pathogens. The biofilm formation- and antibiotic resistance-related gene expression was consistent with the respective phenotypes. Furthermore, these two isomers repressed the expression of pro-inflammatory genes in RAW264.7 cells.
CONCLUSION
Our study provides evidence of the potential application of honokiol and magnolol in dental medicine to cure or prevent oral diseases.
Topics: Animals; Anti-Bacterial Agents; Biphenyl Compounds; Humans; Inflammation; Lignans; Macrophages
PubMed: 32978046
DOI: 10.1016/j.jfma.2020.09.002 -
Journal of Neuroinflammation Jun 2012The cannabinoid type-2 G protein-coupled (CB₂) receptor is an emerging therapeutic target for pain management and immune system modulation. In a mouse model of...
The cannabinoid type-2 G protein-coupled (CB₂) receptor is an emerging therapeutic target for pain management and immune system modulation. In a mouse model of Alzheimer's disease (AD) the orally administered natural product 4'-O-methylhonokiol (MH) has been shown to prevent amyloidogenesis and progression of AD by inhibiting neuroinflammation. In this commentary we discuss an intriguing link between the recently found CB₂ receptor-mediated molecular mechanisms of MH and its anti-inflammatory and protective effects in AD animal models. We argue that the novel cannabimimetic MH may exert its beneficial effects via modulation of CB₂ receptors expressed in microglial cells and astrocytes. The recent findings provide further evidence for a potential role of CB₂ receptors in the pathophysiology of AD, spurring target validation and drug discovery.
Topics: Alzheimer Disease; Animals; Biphenyl Compounds; Humans; Inflammation; Lignans; Plants, Medicinal; Receptor, Cannabinoid, CB2; Receptors, Cannabinoid
PubMed: 22716035
DOI: 10.1186/1742-2094-9-135