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Topic: Sesquiterpene

In the News (Fri 25 Dec 09)

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	Use of sesquiterpene lactones for treatment of severe inflammatory disorders (US5905089)
		Sesquiterpene lactones are useful in suppressing the early proinflammatory cytokines, and in ameliorating septic shock and other severe inflammatory disorders.
		Sesquiterpene lactones with an α-methylene-γ-lactone functional group suppress the expression of the inducible cyclooxygenase-2 and proinflammatory cytokines (Interleukin-1α and β, IL-1, and tumor necrosis factor-α (TNFα)) in mammalian macrophages stimulated with lipopolysaccharide.
		Hwang et al., "Inhibition of the Expression of Inducible Cyclooxygenase and Proinflammatory Cytokines by Sesquiterpene Lactones in Macrophages Correlates with the Inhibition of MAP Kinases," Biochem.
	www.delphion.com /details?&pn=US05905089__ (442 words)

	Nutrition Toxicology Sesquiterpene Lactones
		Because sesquiterpene lactones are responsible for the toxicity of several livestock poisons it is useful to focus on their effects on mammals such as cattle, sheep and horses that are most commonly exposed to sesquiterpene lactone poisoning.
		Sesquiterpene lactones constitute a large and diverse group of biologically active plant chemicals that have been identified in several plant families.
		Sesquiterpene lactones (SQL) are a class of naturally occurring plant terpenoids that are formed from "head-total condensation of three isoprene units and subsequent cyclization and oxidative transformation to produce a cis or trans-fused lactone.
	www.ansci.cornell.edu /plants/toxicagents/sesqlactone/sesqlactone.html (613 words)

	Patent 7,125,911
		However, for administration to a large, unspecified number of individuals, an extremely low concentration of sesquiterpene alcohol is preferably dispersed in the space and its vicinity where the administration takes place, so as to allow it to be administered through the nasal mucosa or respiratory tract through the natural respiration of the individuals.
		In these cases, the sesquiterpene alcohol should be vaporized at a concentration of between 0.01 to 100 ppb in the air, as too low a concentration will not afford the desired results, while too high a concentration will result in the condensation of fine particles in the air.
		The sesquiterpene alcohols of the present invention also have an effect on the expression of emotions (moods) and the state thereof, which is influenced by the higher central nervous system governing preferences.
	www.pharmcast.com /Patents100/Yr2006/Oct2006/102406/7125911_Nerve102406.htm (1377 words)

	Reference.com/Encyclopedia/Sesquiterpene
		Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C
		In addition to common six-membered ring systems such as is found in zingiberene, a consitituent of the oil from ginger, cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene.
		In addition to common six-membered rings such as in the cadinenes, one classic bicyclic sesquiterpene is caryophyllene, from the oil of cloves, which has a nine-membered ring and cyclobutane ring.
	www.reference.com /browse/wiki/Sesquiterpenes (263 words)

	At Berkeley: Intelligently designed molecular evolution
		For their model enzyme, they selected a sesquiterpene synthase produced by the Grand fir tree, which has the capacity to develop into any of 52 different sesquiterpenes from a sole substrate.
		The Berkeley researchers identified the plasticity residues for the Grand fir sesquiterpene synthase, then systematically recombined mutations of these residues through site-directed mutagenesis, based on a mathematical model developed by Yoshikuni.
		Construction of the seven sesquiterpene synthases was accomplished with the screening of fewer than 2,500 mutants.
	www.eurekalert.org /pub_releases/2006-02/dbnl-abi022306.php (995 words)

	ARS \| Publication request: Environmental Impacts on Sesquiterpene Lactone Composition of Forage Chicory
		These differences suggest that sesquiterpene lactone concentrations in chicory are determined, in part, by conditions at the site where the plants are grown.
		Soil-P deficiency and warm soil temperature correlate with elevated sesquiterpene lactone concentrations in the herbage.
		Sesquiterpene lactone concentrations tended to be higher in herbage from N-fertilized plants and adequately watered plants than in corresponding deprived plants.
	www.ars.usda.gov /research/publications/publications.htm?seq_no_115=146117 (374 words)

	In vitro and in vivo anti-inflammatory effects of a sesquiterpene lactone extract from chicory (Cichorium intybus L.) - ...
		The method of claim 15 wherein the inflammation or autoimmune disease is caused by a disease selected from rheumatoid arthritis, asthma, inflammatory bowel disease, Crohn's disease, multiple sclerosis, psoriasis and skin rushes, chronic obstructive pulmonary disease, allergic rhinitis, cardiovascular disease, lupus, and metabolic syndrome.
		Sesquiterpene lactones are C.sub.15 terpenoid compounds that have a range of biological and pharmaceutical activities.
		Various modes of administration, including all modes known in the art, are contemplated for use in delivering the chicory extract to a mammal such as a human patient.
	www.freepatentsonline.com /7226623.html (4668 words)

	Complete Arnica information from Drugs.com
		The sesquiterpene lactones helenalin and 11-alpha, 13-dihydrohelenalin have been shown to inhibit platelet aggregation by interacting with platelet sulfhydryl groups.
		Sesquiterpene lactones helenalin, helenalin acetate, and helenalin methacrylate are the primary sources of this type of allergy.
		The plant's sesquiterpene lactones are responsible for its oxytocic activity.
	www.drugs.com /npp/arnica.html (1696 words)

	BG - Abstract - Seasonal variation of mono- and sesquiterpene emission rates of Scots pine
		The seasonal variation of mono-and sesquiterpene emission rates of Scots pine was measured from April to October in 2004.
		Branch A had a higher sesquiterpene emission potential than branch B and the emission maximum occurred concomitant with the high concentration of airborne pathogen spores suggesting a potential defensive role of the sesquiterpene emissions.
		Sesquiterpene and 1,8-cineol emissions were equally well described by the temperature dependent and the temperature and light dependent algorithms.
	www.biogeosciences.net /3/93/2006/bg-3-93-2006.html (387 words)

	Antiplaque oral compositions - Patent 5116602
		An antiplaque oral composition containing a low concentration of a sesquiterpene alcohol flavor compound to inhibit the formation of dental plaque in the presence of an additive selected from the group consisting of benzoic acid, a preservative, and a polycarboxylate and mixtures thereof, in an oral vehicle having a low pH of about 3-5.
		Another object of the present invention is to provide an oral product containing a sesquiterpene alcohol flavor component selected from the group consisting of farnesol, nerolidol, bisabolol and santalol (sandalwood oil) to inhibit the formation of dental plaque in the presence of benzoic acid and at a low pH.
		The antiplaque sesquiterpene alcohol flavor compound may be incorporated into oral compositions generally, such as mouthrinses, mouthrinse concentrates, dentifrices, lozenges, chewing gum or dental floss containing a dental vehicle.
	www.freepatentsonline.com /5116602.html (4295 words)

	Combinations of sesquiterpene lactones and ditepene triepoxide lactones for synergistic inhibition of cyclooxygenase-2 ...
		Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sesquiterpene lactones in macrophages correlates with the inhibition of.
		It is discovered in the present invention that the combination of diterpene triepoxide lactones and an active sesquiterpene lactone provides for a synergistic effect on the activity of diterpene triepoxide lactones or an active sesquiterpene lactone.
		In addition to the combination of diterpene triepoxide lactones and sesquiterpene lactones, the present composition for dietary application may include various additives such as other natural components of intermediary metabolism, vitamins and minerals, as well as inert ingredients such as talc and magnesium stearate that are standard excipients in the manufacture of tablets and capsules.
	www.freepatentsonline.com /6908630.html (8665 words)

	Arnica montana
		Sesquiterpene lactones appear to be responsible Hausen 1979
		Sesquiterpene lactones, the main active compounds of Arnica flowers are effective in the treatment of rheumatic diseases by inhibiting the transcription factors NF-kappa B and NF-AT.
		Sesquiterpenes of supercritical carbon dioxide commercial extract of arnica were characterized by two-dimensional homonuclear (1)H-(1)H correlated spectroscopy and two-dimensional reverse heteronuclear shift correlation spectroscopy.
	www.herbmed.org /Herbs/Herb92.htm (2219 words)

	Arnica - David L. Hoffmann B.Sc. (Hons), M.N.I.M.H. - HealthWorld Online
		Sesquiterpene lactones, including the pseudoguanolidesarnifolin, the arnicolides, helenalin, and the recently isolated 6-0isobutyryl-tetrahydrohelenalin and 2 [[beta]]-ethoxy-6-0-isobutyryl-2, 3-dihydrohelenalin.
		Arnica has been shown to be an immuno-stimulant, as both the sesquiterpene lactone helenalin and the polysaccharide fraction stimulate phagocytosis.
		Sesquiterpene lactones are known to have anti-inflammatory activity and their biological effects appear to be mediated through immunological processes.
	www.healthy.net /asp/templates/article.asp?PageType=article&ID=2055 (536 words)

	Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications -- Trapp and Croteau 158 (2): ...
		Monoterpenes, sesquiterpenes, and diterpenes are derived from the prenyl diphosphate substrates geranyldiphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP), respectively, and are produced in both angiosperms and gymnosperms.
		The cytosolic pool of IPP, which serves as a precursor of farnesyl diphosphate (FPP) and, ultimately, the sesquiterpenes and triterpenes, is derived from mevalonic acid (left).
		The enzymatic classification as a monoterpene, sesquiterpene, or diterpene synthase is represented by C
	www.genetics.org /cgi/content/full/158/2/811 (7939 words)

	Application of Direct Search Optimization for Pharmacokinetic Parameter Estimation
		Some sesquiterpene lactones isolated from Arnica species were tested on human carcinoma cell line as well as on COLO 320, a human colorectal cancer cell lines, where they showed cytotoxic activity (3).
		The IC50 measurements of the cytotoxic activity for the modified sesquiterpene lactones were 16.4 mM in HeLa cells and 40.0 mM in SW620 cells for compound III and 30.3 mM in HeLa cells and 42.0 mM in SW620 cells for compound IV (Figure 3 and Table 1).
		It is known also that sesquiterpene lactones inhibit a large number of enzymes involved in key biological processes such as DNA and RNA synthesis, purine synthesis, glycolisis, and citric cycle and mitochondrial electron transport chain (11,12).
	www.ualberta.ca /~csps/JPPS2(3)/A.Quintero/antitumoral.htm (1771 words)

	[No title]
		The number of alkylating sites present in a sesquiterpene lactone appears to be related to the inhibitory activity on mitochondrial oxidative phosphorylation, however, the structure-activity relationship of these lactones is not clear at present.
		The isolation and structural elucidation of isohelenol, a new antileukemic sesquiterpene lactone, and isohelenalin from Helenium microcephalum.
		In: J Nat Prod (1987 Jul-Aug) 50(4):690-5 ISSN: 0163-3864 Tenulin [1], a sesquiterpene lactone from Helenuim amarum, is a potent antifeedant to the European corn borer Ostrinia nubilalis.
	www.swsbm.com /Abstracts/Helenium-AB.txt (2090 words)

	News \| Gainesville.com \| The Gainesville Sun \| Gainesville, Fla. (Site not responding. Last check: 2007-10-31)
		Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C
		Biosynthetically, when geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene.
		thumbright100pxδ-Cadinene, a sesquiterpene In addition to common six-membered rings such as in the cadinenes, one classic bicyclic sesquiterpene is caryophyllene, from the oil of cloves, which has a nine-membered ring and cyclobutane ring.
	www.gainesville.com /apps/pbcs.dll/section?category=NEWS&template=wiki&text=sesquiterpene (232 words)

	BoDD (Botanical Dermatology Database): COMPOSITAE: Ambrosia
		The biochemical basis of the cross-sensitivity is the presence of structurally related sesquiterpene lactones in the plants (Mitchell and Dupuis 1971).
		Patients were found to be sensitive to a number of sesquiterpene lactones (desacetylconfertiflorin, psilostachyin, psilostachyin B, psilostachyin C, ambrosiol, damsin, tamaulipin A, tamaulipin B, isabelin, and reynosin) as well as to burweed marshelder and feverfew (unidentified species if Iva L. and Chrysanthemum L. respectively) and liverworts belonging to the genus Frullania Raddi (fam.
		The sesquiterpene lactones ambrosin and damsin have been reported from this species which is found in the Florida Keys and Caribbean region (Yoshioka et al.
	bodd.cf.ac.uk /BotDermFolder/BotDermC/COMP-2.html (2432 words)

	Celastraceae Sesquiterpenes as a New Class of Modulators That Bind Specifically to Human P-Glycoprotein and Reverse ...
		absence of sesquiterpenes with 2 µmol/L of daunomycin.
		S is the concentration of sesquiterpene, and n is the Hill coefficient.
		Photolabeling was done in the presence of 10 µmol/L sesquiterpenes (100-fold molar excess with respect to the probe) or the same concentration of verapamil and vinblastine for comparison.
	cancerres.aacrjournals.org /cgi/content/full/64/19/7130 (5931 words)

	Phytomedics licenses plant-derived drug compound
		The US patent (5,905,089) refers to the anti-inflammatory properties of sesquiterpene lactones, which were originally discovered and developed jointly by researchers at the Pennington Biomedical Research Centre in LA and Louisiana State University.
		Sesquiterpene lactones (SLs) are the active constituents of a variety of medicinal plants used in traditional medicine for the treatment of inflammatory diseases.
		Studies stretching as far back as 1979 have shown that sesquiterpene lactones, especially those containing an alpha-methylene-gamma.-lactone group, have been shown to possess activity against tumour growth and general inflammatory reactions.
	www.drugresearcher.com /news/news-ng.asp?n=61106-phytomedics-licenses-plant (664 words)

	Natural antibiotics, antifeedant sesquiterpenes from antibiotic Lactarius fungi
		This is due to lactarane or marasmane sesquiterpenes, natural antibiotics with lactone or furan ring, antifeedant, and repellent activity.
		Sesquiterpene lactones were also isolated from many other Lactarius and Russula antibiotic fungi.
		Sesquiterpenes from Russula or Lactarius antibiotic fungi should be used in medical area by a pharmaceutical company.
	www.geocities.com /jerzor/absart01.html (520 words)

	[No title]
		The hypothesis that this toxic effect is due specifically to the presence in the sesquiterpene lactone of the potentially reactive alpha-methylene function was tested on rabbit isolated aortic ring preparations.
		This was done (a) by comparing the effects of two plant-derived sesquiterpene lactones purified from yellow star thistle (Centaurea solstitialis): cynaropicrin (an alpha- methylenebutyrolactone) and solstitialin 13-acetate (lacking the alpha-methylene function), and (b) by chemically inactivating the alpha-methylene functions in cynaropicrin and parthenolide by reaction with cysteine.
		Further studies on sesquiterpene lactones and methylated flavones resulted in the isolation of lactones with alpha- methylene gamma-lactone and methylene side chain on the cyclopentyl ring as well as of four methylated flavones (hispidulin, nepetin, cirsiliol, jaceosidin) structurally closely related to the cytotoxic flavonoids of other Compositae plants.
	www.swsbm.com /Abstracts/Centaurea-AB.txt (1876 words)

	Parthenolide : by Ray Sahelian, M.D., parthenolide benefits
		The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells.
		Parthenolide is a sesquiterpene lactone purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium.
		The antitumor activity of the sesquiterpene lactone parthenolide, an active ingredient of medicinal plants, is believed to be due to the inhibition of DNA binding of transcription factors NF-kappaB and STAT-3, reduction in MAP kinase activity and the generation of reactive oxygen.
	www.raysahelian.com /parthenolide.html (2098 words)

	Sesquiterpene Lactone (Site not responding. Last check: 2007-10-31)
		Sesquiterpene lactones may have anti-inflammatory and anticancer effects.
		Plants containing sesquiterpene lactones have been used in some cultures to treat certain medical problems.
		TheHealthEncyclopedia.com is a purely informational website, and should not be used as a substitute for professional legal, medical or technical advice.
	www.thehealthencyclopedia.com /term/sesquiterpene_lactone (74 words)

	Feverfew
		The sesquiterpene lactones contain an a-methylbutyrolactone unit as part of their structure, which is capable of blocking cellular sulfhydryl (SH) groups.
		It was postulated that the sesquiterpene lactones may have decomposed during prolonged storage or due to reactions with thiols or other nucleophilic centers in intrinsic proteins.
		Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sesquiterpene lactones in macrophages correlates with the inhibition of MAP kinases.
	www.uspharmacist.com /oldformat.asp?url=newlook/files/alte/acf2f84.htm (2317 words)

	Allemann (Site not responding. Last check: 2007-10-31)
		While sesquiterpene cyclases are relatively slow enzymes, their specificity is stupefying and has fascinated chemist and biochemists for more than a century.
		Sesquiterpene cyclases convert their substrate farnesylpyrophosphate (FPP) to more than 200 different sesquiterpene scaffolds with exquisite regio- and stereoselectivity.
		Sesquiterpene cyclases therefore serve as high-fidelity templates for FPP that channel conformation and stereochemistry during the reactions and provide an ideal target to study the mechanisms that control specificity and selectivity during enzymatic transformations.
	www.cardiff.ac.uk /chemy/staff/allemann/ProjectSummary.html (991 words)

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