TY - JOUR. T1 - Parthenolide induces superoxide anion production by stimulating EGF receptor in MDA-MB-231 breast cancer cells.. AU - Emanuele, Sonia. AU - Lauricella, Marianna. AU - Di Fiore, Riccardo. AU - DAnneo, Antonella. AU - Vento, Renza. AU - Carlisi, Daniela. AU - Buttitta, Giuseppina. AU - Vento, Renza. AU - Tesoriere, null. AU - Tesoriere, Giovanni. PY - 2013. Y1 - 2013. N2 - The sesquiterpene lactone parthenolide (PN) has recently attracted considerable attention because of its anti-microbial, anti-inflammatory and anticancer effects. However, the mechanism of its cytotoxic action on tumor cells remains scarcely defined. We recently provided evidence that the effect exerted by PN in MDA-MB-231 breast cancer cells was mediated by the production of reactive oxygen species (ROS). The present study shows that PN promoted the phosphorylation of EGF receptor (phospho-EGFR) at Tyr1173, an event which was observed already at 1 h of incubation with 25 µM PN and reached a peak at 8-16 h. ...
TY - THES. T1 - Total synthesis of cis-Hydroazulene sesquiterpenes : base-induced and -directed elimination and rearrangement reactions of perhydronaphthalene-1,4-diol monosulfonate esters. AU - Jenniskens, L.H.D.. N1 - WU thesis 1539 Proefschrift Wageningen. PY - 1992. Y1 - 1992. N2 - The total synthesis of a number of cis-fused hydroazulene sesquiterpenes is described in this thesis. In this synthetic study, ample attention is paid to the mechanistic aspects of the base- induced and -directed rearrangement and elimination reactions of perhydronaphthalene-1,4-diol monosulfonate esters. These reactions form the key steps in the synthetic routes that were followed.A general introduction into the chemistry of terpenes, with emphasis laid on the sesquiterpenes with a hydroazulene skeleton, is given in Chapter 1.In Chapter 2, an overview of the literature on the synthesis of these hydroazulene sesquiterpenes is presented. The different synthetic strategies towards the hydroazulene skeleton and their ...
TY - JOUR. T1 - Zerumbone enhances the Th1 response and ameliorates ovalbumin-induced Th2 responses and airway inflammation in mice. AU - Shieh, Ying Hua. AU - Huang, Huei Mei. AU - Wang, Ching Chiung. AU - Lee, Chen Chen. AU - Fan, Chia Kwung. AU - Lee, Yueh Lun. PY - 2015. Y1 - 2015. N2 - Zerumbone is a sesquiterpene compound isolated from the rhizome of wild ginger, Zingiber zerumbet Smith. The rhizomes of the plant are used as a spice and traditional medicine. Zerumbone was shown to possess anticarcinogenic, anti-inflammatory, and antioxidant properties. However, the antiallergic activity and the underlying mechanism of zerumbone have not been reported. Herein, we investigated the immunomodulatory effects of zerumbone on antigen-presenting dendritic cells (DCs) in vitro and its potential therapeutic effects against ovalbumin (OVA)-induced T helper 2 (Th2)-mediated asthma in mice. In the presence of zerumbone, lipopolysaccharide-activated bone marrow-derived DCs enhanced T cell proliferation ...
Abstract: Sesquiterpene lactones have long been used in traditional Chinese medicines to treat inflammatory diseases. Recently, sesquiterpene lactone family compounds have been recognized as potential anticancer agents. Thus, it is necessary to explore new sesquiterpene lactones and their antitumor mechanism for cancer treatments. In the present study, we have explored the potential anti-cancer activity of a novel sesquiterpene lactone compound "santamarine" (STM) in HepG2 cells. It inhibited proliferation and induced apoptosis dose-dependently with IC50 ~ 70 μM. Induction of apoptosis was found to be linked with increased reactive oxygen species (ROS) generation, decreased activity of thioredoxin reductase (TrxR), glutathione (GSH) depletion, mitochondrial membrane potential (ΔΨm) dissipation, Bcl-2 family proteins modulation, cytochrome c release, caspases-9, -8 and -3 activation and PARP cleavage. Further mechanistic study demonstrated that STM inhibited the constitutive and TNF-α-induced ...
Beta-caryophyllene is an odoriferous bicyclic sesquiterpene found in various herbs and spices. Recently, it was found that beta-caryophyllene is a ligand of the cannabinoid receptor 2 (CB2). Activation of CB2 will decrease pain, a major signal for inflammatory responses. We hypothesized that beta-caryophyllene can affect wound healing by decreasing inflammation. Here we show that cutaneous wounds of mice treated with beta-caryophyllene had enhanced re-epithelialization. The treated tissue showed increased cell proliferation and cells treated with beta-caryophyllene showed enhanced cell migration, suggesting that the higher re-epithelialization is due to enhanced cell proliferation and cell migration. The treated tissues also had up-regulated gene expression for hair follicle bulge stem cells. Olfactory receptors were not involved in the enhanced wound healing. Transient Receptor Potential channel genes were up-regulated in the injured skin exposed to beta-caryophyllene. Interestingly, there were sex
Contribution to the elucidation of the anti-inflammatory activity of sesquiterpene lactones [Elektronische Ressource] / vorgelegt von Alfonso J. García Piñeres : Contribution to the Elucidation of the Anti-inflammatory Activity of Sesquiterpene Lactones Inaugural-Dissertation zur Erlangung der Doktorwürde der Fakultät für Chemie, Pharmazie und Geowissenschaften der Albert-Ludwigs-Universität Freiburg im Breisgau vorgelegt von Alfonso J. García Piñeres aus San José, Costa Rica April 2003 Gedruckt mit Unterstützung
Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. Sesquiterpenes are found naturally in plants and insects, as semiochemicals, e.g. defensive agents or pheromones. The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation of farnesene then provides sesquiterpenoids such as farnesol. There are more cyclic sesquiterpenes than cyclic monoterpenes because of the increased chain length and additional double bond. In addition to common six-membered ring systems such as is found in zingiberene (a constituent of the oil from ginger), cyclization of one end of the chain to the other end can ...
Parthenin and parthenolide are natural products that are closely related in structure to artemisinin, which is also a sesquiterpene lactone (SQL) and one of the most important antimalarial drugs available. Parthenin, like artemisinin, has an effect onPlasmodiumblood stage development. We extended the evaluation of parthenin as a potential therapeutic for the transmissible stages ofPlasmodium falciparumas it transitions between human and mosquito, with the aim of gaining potential mechanistic insight into the inhibitory activity of this compound. We posited that if parthenin targets different biological pathways in the parasite, this in turn could pave the way for the development of druggable compounds that could prevent the spread of artemisinin-resistant parasites. We examined parthenins effect on male gamete activation and the ookinete-to-oocyst transition in the mosquito as well as on stage V gametocytes that are present in peripheral blood. Parthenin arrested parasite development for each ...
Five new tremulane-type sesquiterpenes, 11,12-dihydroxy-1-tremulen-5-one (1), 11,12-epoxy-12 beta-hydroxy-1-tremulen-5-one (2), 5 alpha, 12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (3), 2 alpha, 11-dihydroxy-1(10)-tremulen-5,12-olide (4), and 10 beta,11-dihydroxy-5,6-seco-1,6(13)-tremuladien-5,12-olide (5), as well as three new aliphatic diketones, 2,3-dihydroxydodecane-4,7-dione (9 and 10) and 1-hydroxydecane-2,5-dione (11), together with three known sesquiterpene analogues, tremulenediol A (6), conocenol B (7), and conocenolide A (8), were isolated from cultures of the basidiomycete Conocybe siliginea ...
TY - JOUR. T1 - Melampodium leucanthum, a source of cytotoxic sesquiterpenes with antimitotic activities. AU - Robles, Andrew J.. AU - Peng, Jiangnan. AU - Hartley, Rachel M.. AU - Lee, Brigette. AU - Mooberry, Susan L.. PY - 2015/3/27. Y1 - 2015/3/27. N2 - A new tricyclic sesquiterpene, named meleucanthin (1), was isolated from an extract of the leaves and branches of Melampodium leucanthum, along with four known germacranolide sesquiterpene lactones, leucanthin-A (2), leucanthin-B (3), melampodin-A acetate (4), and 3α-hydroxyenhydrin (5). The chemical structure of 1 was elucidated by analysis of 1D and 2D NMR and mass spectrometric data. All compounds exhibited antiproliferative and cytotoxic efficacy against PC-3 and DU 145 prostate cancer cells, as well as HeLa cervical cancer cells, with IC50 values ranging from 0.18 to 9 μM. These compounds were effective in clonogenic assays and displayed high cellular persistence. They were also found to be capable of circumventing ...
Five new triquinane-type sesquiterpenes, antrodins A-E (1-5) and a new gymnomitrane sesquiterpene, antrodin F (6), together with three known compounds 7-9 were isolated from fermentation of Antrodiella albocinnamomea. Their structures were elucidated through extensive spectroscopic methods including 2D NMR and HRMS analyses. The absolute configurations of 1 and 6 were determined using single-crystal X-ray diffraction analyses. The isolated compounds were investigated for their cytotoxicities against five human cancer cell lines. (C) 2015 Elsevier B.V. All rights reserved ...
Sesquiterpenoids (C15 terpenoids) are a group of terpenoids consisting of three isoprene units. They are derive from farnesyl diphosphate (FPP) and can be cyclized to produce various skeletal structures. Sesquiterpenoid biosynthesis begins with the loss of diphosphate from FPP under the action of sesquiterpene synthesis enzymes, generating an allylic cation that is highly susceptible to intramolecular attacks. Cyclization of the farnesyl cation may take place onto either of the remaining double bonds with the result that 6-, 10-, or 11-membered rings may be formed. Many sesquiterpenoids have been isolated from plants, fungi, marine organisms, and Streptomyces species. This map shows a few examples of acyclic and cyclic sesquiterpenoids ...
Sesquiterpenoids (C15 terpenoids) are a group of terpenoids consisting of three isoprene units. They are derive from farnesyl diphosphate (FPP) and can be cyclized to produce various skeletal structures. Sesquiterpenoid biosynthesis begins with the loss of diphosphate from FPP under the action of sesquiterpene synthesis enzymes, generating an allylic cation that is highly susceptible to intramolecular attacks. Cyclization of the farnesyl cation may take place onto either of the remaining double bonds with the result that 6-, 10-, or 11-membered rings may be formed. Many sesquiterpenoids have been isolated from plants, fungi, marine organisms, and Streptomyces species. This map shows a few examples of acyclic and cyclic sesquiterpenoids ...
Definition of parthenolide in US English - A sesquiterpene lactone, C₁₅H₂₀O₃, with antibacterial and cytotoxic properties which is the active ingredient in prepara
A series of pyripyropene A-based compounds were designed and synthesized by opening the upper section of the A-ring, which… Expand ...
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5185 The potent induction of apoptosis in various types of tumor cells, contrasted to largely reversible non-apoptotic effects in normal cells is one of the hallmarks of a novel dual-action DNA- and protein-alkylating drug, irofulven (hydroxymethylacylfulvene). Previous studies suggested the contribution of both nuclear and cytoplasmic signaling to apoptosis by irofulven. To better understand the nature of the differential responses of tumor and normal cells, we used a cell-free apoptosis mimicking system consisting of isolated nuclei and cytosolic extracts. We examined homologous and heterologous mixes of nuclei and cytosols from cancer cells (CEM and LNCaP-Pro5), which initiate apoptosis in response to irofulven, and from normal cells (NCM 460), which display a non-apoptotic cytostatic response. Cytosols were obtained either from untreated or drug-treated cells. In the latter case, irofulven concentrations were adjusted to provide equal levels of intracellular drug-macromolecule adducts in ...
Beta-caryophyllene, a common cannabis terpene, can help you manage pain. Learn more about these high-caryophyllene strains & where you can find them.
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Welcome to 4hbtalk.com - The largest 4 Hour Body forum. This forum is a place where you can ask questions about exercises, the slow carb diet, the PAGG stack or anything related to creating your four hour body. The forum was built around The 4-Hour body book by Tim Ferris. This community is in no way affiliated with the 4 Hour Body or Tim Ferris.
Welcome to 4hbtalk.com - The largest 4 Hour Body forum. This forum is a place where you can ask questions about exercises, the slow carb diet, the PAGG stack or anything related to creating your four hour body. The forum was built around The 4-Hour body book by Tim Ferris. This community is in no way affiliated with the 4 Hour Body or Tim Ferris.
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Learn more about Huperzine A at Doctors Hospital of Augusta Uses Principal Proposed Uses Alzheimers Disease and Other Forms of Dementia ...
Display omitted] New sesquiterpene quinones, metachromins X (1) and Y (2), together with the known metachromins C (3), J (4), and T (5), were isolated as ...
Cancers energy source can be thwarted by a naturally-occurring molecule which stops affected cells from consuming sugar, according to a new study. Koningic acid (KA) was found to disrupt the metabolism of cancerous cells. Published in Cell...
article{76337ac6-36e6-4fff-b6e8-dfb8093c0fd5, abstract = {A clone encoding farnesyl diphosphate synthase (FPPS) was obtained by PCR from a cDNA library made from young leaves of Artemisia annua. A cDNA clone encoding the tobacco epi-aristolochene synthase (eAS) was kindly supplied by J. Chappell (University of Kentucky, Lexington, KY, USA). Two fusions were constructed, i.e. FPPS/eAS and eAS/FPPS. The stop codon of the N-terminal enzyme was removed and replaced by a short peptide (Gly-Ser-Gly) to introduce a linker between the two ORFs. These two fusions and the two single cDNA clones were separately introduced into a bacterial expression vector (pET32). Escherichia coli was transformed with the expression vectors and enzymatically active soluble proteins were obtained after induction with isopropyl thio-beta-d-thiogalactoside. The recombinant enzymes were purified using immobilized metal affinity chromatography on Co2+ columns. The fusion enzymes produced epi-aristolochene from isopentenyl ...
Sesquiterpene cyclase, a branch point enzyme in the general isoprenoid pathway for the synthesis of phytoalexin capsidiol, was induced in detached leaves of Capsicum annuum (pepper) by UV treatment. The inducibility of cyclase enzyme activities paralleled the absolute amount of cyclase protein(s) of pepper immunodetected by monoclonal antibodies raised against tobacco sesquiterpene cyclase. A cDNA library was constructed with poly(A)+ RNA isolated from 24 h UV-challenged leaves of pepper. A cDNA clone for sesquiterpene cyclase in pepper was isolated by using a tobacco 5-epi aristolochene synthase gene as a hetero-logous probe. The predicted protein encoded by this cDNA was comprised of 559 amino acids and had a relative molecular mass of 65,095. The primary structural information from the cDNA clone revealed that it shared 77%, 72% and 49% identity with 5-epi aristolochene, vetispiradiene, and cadinene synthase, respectively. The enzymatic product catalyzed by the cDNA clone in bacteria was ...
Read "WRKY45-dependent priming of diterpenoid phytoalexin biosynthesis in rice and the role of cytokinin in triggering the reaction, Plant Molecular Biology" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips.
Principal Investigator:KODAMA Shoji, Project Period (FY):1994 - 1995, Research Category:Grant-in-Aid for General Scientific Research (C), Research Field:Obstetrics and gynecology
The diseased wood, agarwood, from the tropical tree taxa Aquilaria, is famed for its unique fragrance and medicinal values, mainly due to its richness in secondary metabolites such as the sesquiterpenes. The presence of sesquiterpenes in high numbers and amounts correlates with agarwood of high quality. To understand the synthesis of this important compound, we cloned two candidate genes in the terpenoid synthesis pathway from Aquilaria malaccensis Lam., a major agarwood tree species. The genes encoding sesquiterpene synthase (AmSesTPS1) and δ-guaiene synthase (AmGuaiS1) were successfully cloned from callus RNA, using specific primers derived from transcriptomic data, in a reverse transcription PCR reaction. The full-length complementary DNA (cDNA) sequence of AmSesTPS1 was 1632 bp encoding for 544 amino acids, and AmGuaiS1 was 1644 bp encoding for 547 amino acids. Sequence alignment analysis showed that AmSesTPS1 shared between 99 to 100 % identity with sesquiterpene synthase from Aquilaria sinensis
The current evolutionary hypothesis and the previous phylogenetic tree (Bohlmannet al. 1998b) both affirm that plant terpene synthases involved in secondary metabolism have a common ancestral origin from a terpene synthase involved in primary metabolism. However, these models differ in the placement of the class III terpene synthases (Figures 6, A and B, and 7). The inferred phylogenetic tree in Figure 6A suggests that the class III types (angiosperm terpene synthases) involved in secondary metabolism are descendants (evolving by divergent evolution) of the class II types (gymnosperm monoterpene and/or sesquiterpene synthases) involved in secondary metabolism, whereas Figure 6B indicates that class III types are not direct descendants of class II types, yet share a common ancestor. The latter (including the gene architecture information as valid) infers that gymnosperm and angiosperm terpene synthases involved in secondary metabolism diverged prior to the three loss events illustrated in Figure ...
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The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic
Two new marine-derived caryophyllene-type sesquiterpenoids, rumphellols A and B (1 and 2), were obtained from the gorgonian coral, Rumphella antipathies, collected off the waters of Taiwan. Although caryophyllene-type sesquiterpenes are rarely found in marine organisms, compounds of this type could be principal components of R. antipathies. The structures of new Compounds 1 and 2 were determined by analysis of their spectroscopic data, including 1D and 2D NMR experiments. Caryophyllene 1 and 2 were evaluated in terms of their anti-inflammatory activity by examining their inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.
Citation: N/A Interpretive Summary: Technical Abstract: Phytoalexins are inducible biochemicals that locally protect plant tissues against biotic attack. Due to their agronomic significance, maize and rice have been extensively investigated for their terpenoid-based defenses which include insect-inducible monoterpene and sesquiterpene volatiles. Rice also produces a complex array of non-volatile pathogen-inducible terpenoid phytoalexins; however, until recently analogous pathways in maize were unknown. We recently discovered the existence of a complex series of sesquiterpene and diterpene phytoalexins in maize stalks following attack by the European corn borer (Ostrinia nubilalis) and pathogenic fungi. The predominant acidic sesquiterpene and diterpene phytoalexins, termed zealexins and kauralexins, are likely derived from ß-macrocarpene and ent-kaur-15-ene, respectively. Following induction, the predicted volatile terpenoid precursors exist at relatively low levels compared to the oxygenated ...
The liver is the only organ that can be continually regenerated and that is because humans have evolved to eat plants, and phytoalexins take their toll on the liver. As plants are digested and absorbed in the small intestines and transported to the liver, phytoalexins accompany the nutrients. Most of the phytochemicals are chemically detoxified by liver enzymes, but the phytoalexins kill some liver cells with each meal and some of the phytoalexins circulate in the blood and reach other tissues. The phytoalexins are evolutionarily adapted to bind to proteins to disrupt essential enzymes of microorganisms and herbivores, and like pharmaceuticals to which they are chemically and functionally related, they have numerous side effects. The chemical reactivity is what is detected as the "antioxidant" property of phytoalexins. Antioxidant is nutritionally meaningless and basically reflects the chemical toxicity of phytochemicals. After all, you cant easily sell chemicals that are inherently toxic. Meat ...
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delta-selinene synthase: a sesquiterpene synthase from Grand fir, Abies grandis; forms a total of 34 different sesquiterpenes, chiefly delta-selinene; MW 68 kDa; amino acid sequence in first source; GenBank U92267
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the trivial name for any of four possible stereoisomers of 3,7,11‐trimethyl‐2,6,10‐dodecatrien‐1‐ol; a sesquiterpene alcohol. The 2E,6E‐isomer is found in many essential oils. The 2Z,6E‐isomer is a minor constituent of some essential oils.. [...] ...
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Dihydroartemisinin (DHA), the main active metabolite of artemisinin derivatives strongly inhibits human papillomavirus-induced tumor formation.
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Last week, Lab Land noticed similarities between two independent lines of research from the Escayg and Traynelis/Yuan labs at Emory. Both were published recently and deal with rare forms of genetic epilepsy, in which molecular understanding of the cause leads to individualized treatment, albeit with limited benefit.. Both conditions are linked to an excess of neuronal excitation, and both can be addressed using medications that have also been tested for Alzheimers. A critical difference is that memantine is FDA-approved for Alzheimers, but huperzine A is not.. ...
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In the world of cannabis science, few things are more exciting than our developing knowledge of the world of terpenes.. Terpenes can be found in the essential oils of all plants. In cannabis, they play a major role in how our bodies interact with particular strains. Terpenes give us a better understanding of how strains may interact with us individually and can allow us to better curate the experience were looking for. Most famously, terpenes are responsible for the way cannabis hits your nose. Those lemon, grape and fuel smells that denote world-class cannabis for many connoisseurs are actually variations in the concentration of particular terpenes from strain to strain!. Researchers have identified more than 140 terpenoids in cannabis that include terpenes and their variations, called diterpenes and sesquiterpenes. Of those 140 terpenoids, 17 have been found to be the most common in most cannabis strains.. Currently, were expanding our knowledge around the synergistic effects of cannabinoids ...