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At least 19 recordsLinked to original sources
PubMed1975

Sesquiterpene lactones. XVI. In vitro studies on cytotoxic properties of sesquiterpene lactones in tissue cultures of human and animal malignant cells.

Cytoxicity of 18 new sesquiterpene lactones and related compounds was studied by tissue culture method using human malignant KB and HeLa cells, normal RK 13 animal cells, and by the modified plate test of Miyamura. On the basis of criteria of CCNSC HIH, USA, seven compounds with ED50 activities between 0-41 and 3-5 mug/ml were qualified for further investigation in vivo. Cytotoxic activity of sesquiterpene lactones was dependent on presence of an unsaturated lactone ring, (see article). As a rule activity of germacranolids was higher than that of guaianolides.

Animals↗
PubMed1992

Inhibition of 5-lipoxygenase and cyclo-oxygenase in leukocytes by feverfew. Involvement of sesquiterpene lactones and other components.

Leaves or infusions of feverfew, Tanacetum parthenium, have long been used as a folk remedy for fever, arthritis and migraine, and derived products are widely available in U.K. health food shops. Previous reports have suggested interactions with arachidonate metabolism. Crude chloroform extracts of fresh feverfew leaves (rich in sesquiterpene lactones) and of commercially available powdered leaves (lactone-free) produced dose-dependent inhibition of the generation of thromboxane B2 (TXB2) and leukotriene B4 (LTB4) by ionophore- and chemoattractant-stimulated rat peritoneal leukocytes and human polymorphonuclear leukocytes. Approximate IC50 values were in the range 5-50 micrograms/mL, and inhibition of TXB2 and LTB4 occurred in parallel. Isolated lactones (parthenolide, epoxyartemorin) treated with cysteine (to neutralize reactive alpha-methylene butyrolactone functions of the sesquiterpenes). Inhibition of eicosanoid generation appeared to be irreversible but not time-dependent. We conclude that feverfew contains a complex mixture of sesquiterpene lactone and non-sesquiterpene lactone inhibitors of eicosanoid synthesis of high potency, and that these biochemical actions may be relevant to the claimed therapeutic actions of the herb.

Animals↗
PubMed1979

Anti-inflammatory activity of sesquiterpene lactones and related compounds.

Some sesquiterpene lactones and related compounds were tested for anti-inflammatory activity in rodents. In the edema-induced carrageenan inflammation screen, the alpha-methylene-gamma-lactone moiety of the sesquiterpene lactones was required for inhibitory activity. The 6-hydroxy group of helenalin also was required for potency. In the tenulin series, the 2,3-epoxy derivatives were marginally active. The same structure was required for inhibition of the writhing reflex. In the chronic adjuvant arthritic screen, compounds containing the alpha-methylene-gamma-lactone moiety, the beta-unsubstituted cyclopentenone ring, and the alpha-epoxy cyclopentenone system afforded significant inhibition at 2.5 mg/kg/day. The sesquiterpene lactones were marginally effective against induced pleurisy. The delayed hypersensitivity was suppressed by these agents whereas immunoglobulin synthesis was slightly stimulated. No delerious side effects were observed with these agents from the limited tests performed.

Anaphylaxis↗
PubMed1979

Formation of adducts of parthenin and related sesquiterpene lactones with cysteine and glutathione.

Parthenin, the major sesquiterpene lactone of Parthenium hysterophorus, a weed responsible for dermatitis in man is primarily restricted to leaf and stem trichomes. Parthenin forms a monoadduct with L-cysteine through the alpha-methylene group of the gamma-lactone and a biadduct with the endocyclic double bond on the cyclopentenone ring. Studies with other sesquiterpene lactones support the view that the types of adducts formed are correlated with the biological activity of the sesquiterpene lactones.

Allergens↗
PubMed1992

The cytotoxicity of helenalin, its mono and difunctional esters, and related sesquiterpene lactones in murine and human tumor cells.

Naturally occurring sesquiterpene lactones and their semisynthetic derivatives, such as the O = C-C = CH-bearing helenalin and its esters, have been shown to demonstrate potent cytotoxicity against the growth of murine L1210 lymphoid leukemia and human Tmolt3 leukemia, colon adenocarcinoma, HeLaS3, lung bronchogenic, KB, osteosarcoma, and glioma cells. The modes of action of helenalin in L1210 cells are the inhibition of DNA, RNA, and protein syntheses. This study confirms that thiol bearing enzymes of nucleic acid metabolism were significantly inhibited, e.g. DNA polymerase alpha, IMP hydrogenase, and ribonucleoside reductase. The addition of GSH to the reaction medium demonstrated total recovery of L1210 ribonucleoside reductase activity. Helenalin reduced cellular GSH levels in L1210 cells. Helenalin also reduced all four pool levels of d(NTP)s which would account for part of the observed inhibition of DNA synthesis. Reductions in the ribonucleotide pool levels were also generally evident after drug treatment. Thus, the sesquiterpene lactones appear to have more than one mode of action in L1210 cells. All of the modes of actions of helenalin are feasible mechanisms to lower nucleic acid synthesis and cause cell death of the L1210 leukemia cells.

Animals↗
PubMed1975

Effect of zexbrevins A and B. Two new sesquiterpene lactones, on the immune response of mice.

Two newly described sesquiterpene lactones, Zexbrevin A and Zexbrevin B, were administered to mice at microgram doses before a single immunizing dose of sheep red blood cells (SRBC), bovine serum albumine (BSA), or Egg albumin (Ea). It was found out that drug treated and immunized animals displayed high numbers of specific spleen rosette forming cells (RFC), as well as elevated titers of circulating antibodies, as compared with mice stimulated solely with antigens. 500 mug of Zexbrevin A and Zexbrevin B was about the best dose for rosette increase; 700 mug or lesser amounts of both drugs induced a decline in the rosette numbers. It was evident that Zexbrevins had to be administered 48 hours before antigen stimulation; no potentiation was obtained if the drugs were given 3 to 11 days before the antigen. No effect was obtained, as well, when mice were treated with drug and antigen on the same day. In the presence of Zexbrevins the radioactive thymidine uptake of cultured normal mouse spleen cells will not increase above controls, indicating that mitogenic effects appear not to be involved in the potentiation. It is concluded that the sesquiterpene lactones exert in mice a potent stimulation of the in vivo response.

Animals↗
PubMed1992

Inhibitory effects of dihydroagarofuran sesquiterpenes on Epstein-Barr virus activation.

To search for possible antitumor promoters, we carried out a primary screening of thirty-seven dihydroagarofuran sesquiterpenes from Tripterygium wilfordii Hook fil. var. regelii Makino and Euonymus sieboldianus Blume, using their possible inhibitory effects on the Epstein-Barr virus early antigen (EBV-EA) activation which is induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Some of these sesquiterpenes, triptofordin F-2 (Takaishi et al., 1988), 1,2,6,8,15-pentaacetoxy-9-benzoyloxy-4-hydroxy-beta-dihydroagarofuran and triptogelin A-1 (Takaishi et al., 1990) were observed to significantly inhibit the EBV-EA activation at low doses. Based on the results, the structural requirements for the activity of these compounds were discussed [corrected].

Anticarcinogenic Agents↗
PubMed2026

Maize terpene synthase 8 (ZmTPS8) produces a blend of sesquiterpenes and contributes to defense against pests and pathogens.

Maize (Zea mays) produces terpenoid-based chemical defenses through a large family of terpene synthases, but the contributions of individual enzymes to specific compounds and stress resistance remain difficult to predict. Maize terpene synthase 8 (ZmTPS8) produces multiple sesquiterpenes in heterologous systems, but its in planta function remains unknown. We integrated a metabolite genome-wide association study (mGWAS), CRISPR/Cas9 generated tps8 loss-of-function mutants, metabolite profiling, and biotic stress assays to define ZmTPS8's role in terpene synthesis and biotic stress responses. The mGWAS identified ZmTPS8 as the primary locus associated with herbivore-induced emission of the sesquiterpene volatile germacrene D. Consistently, ZmTPS8 expression was induced by foliar and root herbivory, and tps8 mutants exhibited reduced emission of germacrene D, α-copaene, and δ-cadinene during Spodoptera frugiperda feeding. Loss of ZmTPS8 increased S. frugiperda larval growth but did not affect the belowground herbivore Diabrotica virgifera virgifera. ZmTPS8 also contributed to resistance against sugarcane mosaic virus, and the fungal pathogen Fusarium verticillioides, affecting terpenoid profiles, global metabolism, and fungal toxin production, but had no impact on Cochliobolus heterostrophus or Pythium spp. susceptibility. Together, these results demonstrate that ZmTPS8 contributes to maize defense in a threat-dependent manner, shaping volatile emissions and defense outcomes.

Zea mays↗
PubMed1978

Allergic contact dermatitis due to sesquiterpene lactones. A comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives.

Several compounds containing the alpha-methylene-gamma-butyrolactone moiety have been tested on human volunteers and on guinea-pigs; the animals were experimentally sensitized by alantolactone, isoalantolactone and laurel oil. Of the two new lactones, spirolactone was the more reactive: this was confirmed by both animal and human testing. The synthetic lactones are less reactive than natural ones. alpha-Methylene-gamma-butyrolactone itself does not elicit cross-reactions in guinea pigs sensitive either to alantolactone or to isoalantolactone, or in patients sensitive to sesquiterpene lactones. The alpha-methylene-gamma-butyrolactone group is necessary for cross-reaction, but to be active, it has first to be substituted. It was also found that isoalantolactone, allegedly not allergenic, is in fact a sensitizer and cross-reacts with alantolactone. The cross-reaction between laurel and Frullania, found in man, also occurs in guinea-pigs. It is more evident when sesquiterpene lactone is the sensitizer and laurel used to elicit reaction.

4-Butyrolactone↗
PubMed1992

A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones.

The use of a lymphocyte transformation test (LTT) to provide evidence of allergic contact dermatitis was investigated. The haptens studied were alantolactone and isoalantolactone, two moderate allergens from Inula helenium L., a decorative and medicinal plant. Only alantolactone showed a significant response in vivo and in vitro in mice sensitized epicutaneously, without using Freund's complete adjuvant. Isoalantolactone did not show any sensitizing capacity in the murine model studied. The comparison of in vitro lymphocyte proliferation and in vivo allergenic capacity showed a good correlation and clearly demonstrates that, of the two sesquiterpene lactones, alantolactone is the better sensitizer.

Animals↗
PubMed1977

Sesquiterpene antitumor agents: inhibitors of cellular metabolism.

Helenalin and tenulin injected into CF1 male mice bearing Ehrlich ascites tumors inhibit DNA synthesis and DNA polymerase enzymatic activity in the tumor cells. Helenalin inhibited protein synthesis. Both drugs increased the concentration of adenosine 3',5'-monophosphate, and interfered with glycolytic and mitochondrial energy processes. Cholesterol synthesis was also inhibited, resulting in lower serum cholesterol levels in tumor-bearing animals. Data obtained in vitro indicate that the cyclopentenone-bearing sesquiterpene lactone and related compounds do not alkylate puring bases of nucleic acids but rather undergo a Michael-type addition reaction with the sulfhydryl groups of reduced glutathione and l-cysteine. Thus, the inhibition of cellular enzyme activities and metabolism that has been observed with these drugs might be explained by the occurrence of a Michael-type teaction.

Alkylation↗
PubMed1978

Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L.

The germacranolide sesquiterpene lactones costunolide, parthenolide, and costunolide diepoxide were isolated from the leaves of Magnolia grandiflora L. Costunolide diepoxide might be, at least in part, an artifact derived from air oxidation of parthenolide. The root bark yielded only costunolide together with the two eudesmanolides, santamarine and reynosin. In an attempt to synthesize costunolide diepoxide, the action of m-chloroperbenzoic acid on parthenolide and on costunolide was studied. The products were costunolide diepoxide from parthenolide and the two cyclized derivatives, santamarine and reynosin, from costunolide. The elusive 1,10-epoxide was obtained by epoxidizing costunolide using a biphasic system containing sodium bicarbonate. Under these conditions, epoxidation of costunolide took place without cyclization.

Cyclization↗
PubMed1976

[Sesquiterpene hydrocarbons from grapes (author's transl)].

After separation by column chromatography on silicagel and preparative gas chromatography 14 sesquiterpene hydrocarbons have been identified in aroma extracts from grapes by gas chromatography--mass spectrometry: alpha-copaene, beta-ylangene, beta-bourbonene, beta-caryophyllene, alpha-guaiene, alpha-humulene, alpha- and gamma-muurolene, germacren D, beta-selinene, alpha-farnesene, gamma- and delta-cadinene and calamenene.

Chemical Phenomena↗
PubMed1992

Potentiation of antifungal activity of sesquiterpene dialdehydes against Candida albicans and two other fungi.

The antifungal activity of two drimane sesquiterpene dialdehydes, polygodial (1) and warburganal (2), alone and in combination with several other substances, was examined against three fungi, Candida albicans, Saccharomyces cerevisiae and Pityrosporum ovale employing a broth dilution method. Anethole significantly synergized the activity of the two sesquiterpenoids against C. albicans and S. cerevisiae; however, it had only an additive effect against P. ovale. By contrast, two antioxidants, ascorbic acid (vitamin C) and BHA (butylated hydroxyanisole), noticeably enhanced the activity of the sesquiterpenoids against P. ovale, but had no effect against C. albicans and S. cerevisiae.

Allylbenzene Derivatives↗