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At least 325 records · Page 18Linked to original sources
PubMed2006

Major volatile constituents of Annona squamosa L. bark.

The volatile constituents of Annona squamosa L. bark were identified from the essential oil obtained by steam distillation and studied by GC/MS. Six major components were identified as 1H-Cycloprop(e)azulene (3.46%), germacrene D (11.44%), bisabolene (4.48%), caryophyllene oxide (29.38%), bisabolene epoxide (3.64%) and kaur-16-ene (19.13%). The oil was also screened for its antimicrobial activity, which exhibited a significant antimicrobial activity against Bacillus subtilis and Staphylococcus aureus.

Annona↗
PubMed2004

[(E)- and [(Z)-2-[alpha,beta-bis(methoxycarbonyl)vinyl]cyclopentadien-1-ylidene]triphenylphosphorane.

The Ramirez ylide undergoes electrophilic substitution with dialkyl acetylenedicarboxylates, yielding a mixture of the Z and E adducts. The crystal structure analyses of the two adducts formed using dimethylacetylene, viz. dimethyl (E)- and (Z)-1-[2-(triphenylphosphoranylidene)cyclopentadien-1-yl]ethylenedicarboxylate, both C(29)H(25)O(4)P, explain an unusual chemical shift observed for the vinyl H atom of the Z adduct, which had previously precluded a definitive assignment of the isomers. In addition, the structures explain why only one of the isomers reacts further with acetylene esters to produce azulenes with a rare substitution pattern.

Journal Article↗
PubMed2002

Effects of HNS-32, a novel antiarrhythmic agent, on guinea-pig myocardium.

The electrophysiological and mechanical effects of HNS-32, a novel azulene-1-carboxamidine derivative with antiarrhythmic activity, were studied in isolated guinea-pig myocardial preparations. HNS-32 (10(-6)-10(-4) mol/l) concentration-dependently decreased the maximum rate of rise (V(max)) of action potential in isolated papillary muscle; the potency was the same or slightly higher than that of disopyramide. At 10(-4) mol/l, HNS-32 also shortened the action potential duration (APD) and depolarized the resting membrane potential; these effects were similar to those of 10(-5) mol/l verapamil. HNS-32 (10(-7)-10(-4) mol/l), as well as verapamil (10(-8)-10(-5) mol/l) and disopyramide (10(-6)-10(-3) mol/l), had concentration-dependent negative chronotropic and negative inotropic effects on isolated right atrial and right ventricular papillary muscle preparations, respectively. The concentration-response relationship for the positive chronotropic effect of isoproterenol was not affected by HNS-32 (10(-5) mol/l). In isolated ventricular myocytes, HNS-32 (10(-6)-10(-4) mol/l) concentration-dependently inhibited the peak amplitude of the L-type Ca(2+) current. These results suggest that NHS-32 has V(max) reducing activity on myocardial tissue, which may be responsible for antiarrhythmic effect. The drug may also have additional effect on the Ca(2+) channel at higher concentrations.

Action Potentials↗
PubMed2006

Two new sesquiterpene lactones from the leaves of Laurus nobilis.

As a part of our ongoing interest in new bioactive compounds from natural sources, we studied Laurus nobilis (Lauraceae). This plant is widespread in the Mediterranean area and is used for medicinal and economic purposes. Chromatographic separations on active extracts led to the isolation of two new sesquiterpene lactones, 5a,9-dimethyl-3-methylene-3,3a,4,5,5a,6,7,8-octahydro-1-oxacyclopenta[c]azulen-2-one (1) and 3beta-chlorodehydrocostuslactone (2). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high resolution mass spectrometry. The cytotoxic activity was also evaluated against three different tumor cell lines of human origin.

Cell Line, Tumor↗
PubMed1994

[Preventive effects of troxipide on a newly developed model of acute gastric mucosal lesion (AGML) induced by ischemia/reperfusion plus ammonia in the rat].

We have developed a unique rat AGML model produced by ischemia/reperfusion plus 0.2% ammonia (I/R.NH3), either treatment which would not induce mucosal injury when used alone. The effects of troxipide and other gastric mucosal defensive drugs were investigated with this I/R.NH3-induced AGML model and other AGML models in rats. The following results were obtained: 1) Like allopurinol, troxipide at 50-200 mg/kg, p.o. dose-dependently prevented I/R.NH3-induced development of AGML and also the ischemia/reperfusion-induced increase of gastric mucosal thiobarbituric acid (TBA)-reactive substances; 2) Troxipide at 10(-6)-10(-4) M, like allopurinol, inhibited concentration-dependently in vitro xanthine oxidase activity in gastric mucosal homogenates; 3) Troxipide at 50-200 mg/kg, p.o. inhibited AGMLs induced by bleeding plus 0.2% ammonia and by 1.0% ammonia alone; and 4) Troxipide and sofalcone were similar in preventing all AGMLs tested and also the increase of mucosal TBA-reactive substances, but somewhat differed from teprenone, cetraxate hydrochloride, azulene plus L-glutamine and sucralfate. These findings suggest that troxipide may inhibit I/R.NH3-induced AGML development by preventing generation of oxygen free radicals and by protecting against mucosal fragility due to reduced energy metabolism from poor blood flow and also against ammonia-induced disruption of the gastric mucosal barrier. Therefore, troxipide may be highly effective for various AGMLs with multifactor involvement.

Acute Disease↗
PubMed1999

Probing for the threshold energy for visual transduction: red-shifted visual pigment analogs from 3-methoxy-3-dehydroretinal and related compounds.

While azulenic retinal analogs failed to yield a red-shifted visual pigment analog, the 9-cis isomers of the push-pull polyenals 3-methoxy-3-dehydroretinal and 14F-3-methoxy-3-dehydroretinal yielded iodopsin pigment analogs with absorption maxima at, respectively, 663 and 720 nm. The former gave a relatively stable batho product (700 nm) and was able to activate transducin. A lower activity was observed for the latter. One possible explanation for the combined results is that the excitation energies of these red-shifted pigments are approaching the threshold energy for visual transduction (although at this time we cannot rigorously exclude a role of the added F-atom in reducing the transducin activity).

Retinal Pigments↗
PubMed1998

[Study on the volatile oils of Murraya microphylla].

The essential oils from the leaves of Murraya microphylla (Merr. et Chun) Swing. growing in Sangya city, Hainan province have been studied by GC-MS and 22 compounds have been isolated and identified. Major compounds are identified as beta-terpinene (27.86%), decahdro-1, 1,7-trimethylene-1H-cyclopop[e] azulene (24.572%), 1,2,3,4,4 alpha, 5,6,8 alpha-octahydro-7-methyl-1-(1-methyl) naphthalene (11.426%), 3-carene (10.125%), 1, 1-dimethy1-2-(3-methyl-1, 3-butadienyl) cyclopropane (5.581%). According to Mr. Bipeixi's opinion, it exists two distinct sections within Murraya microphylla (Merr. et Chun) Swing. belongs to Murraya section Bergera. Monoterpene must be the dominated volatile fractions according Li Qian's opinion, but it is a exception. Maybe it has special taxonomic significance.

Chromatography, Gas↗
PubMed1999

[GC-MS analysis of essential oil from the leaves of Psidium guajava].

The constituents of essential oils from the leaves of Psidium guajava Linn were analyzed by GC-MS qualitatively and quantitatively. Sixty compounds of the essential oils were identified at rate 90.56%. The major components were caryophyllene (18.81%), copaene (11.80%), [1aR-(1a alpha, 4a alpha, 7 alpha, 7a beta, 7b alpha)]-decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e] azulene(10.27%), eucalyptol(7.36%).

Cyclohexanols↗
PubMed2002

Antifungal activity of essential oils from leaves and flowers of Inula viscosa (Asteraceae) by Apulian region.

Some essential oils from several plants (Artemisia verlotorum, Lavandula augustifolia, Ocimum gratissimum) have proved to have acaricidal, antifungal and antibacterial activity. Inula viscosa Ait. (Asteraceae), a plant growing spontaneously in the Mediterranean area, is currently used by popular medicine for its therapeutic effects. Flavonoids, azulenes, sesquiterpenes, and essential oils have been isolated and identified from its leaves. This paper reports the results of the composition and antifungal activity in vitro against dermatophytes and Candida spp. of the four essential oils obtained by steam distillation of the leaves, flowers, whole plant and whole plants without flower extracts of I. viscosa. All the extracts proved to have a significant antifungal activity against dermatophytes even at low concentrations (0.01 mg/ml). The leaf extracts exhibited the greatest antifungal efficacy. The high concentration of the sesquiterpene (carboxyeudesmadiene), occurring in the leaf extracts, may explain its greater antifungal activity.

Antifungal Agents↗
PubMed2004

[Investigation of chemical composition of propolis extract].

Propolis is a natural product, produced by bees and containing exudates from plants, mixed with bee wax. Propolis and its ethanolic extract are usually used for treatment and prevention of different diseases. Propolis has antibacterial, antiviral, antifungal, anti-inflammatory, anesthetic and immunomodulating properties. Till now there is no data about chemical composition of Lithuanian propolis. Thus, the aim of our work was to investigate the chemical composition of Lithuanian propolis and its ethanolic extract by using gas chromatography / mass spectrometry. We found, that the main structural types of compounds were terpenoids, aromatic and aliphatic acid esters. The most of terpenoids were mono- and sesquiterpens: azulene, alpha-bisabolol, citral, valerenol, etc. Thus, our data show, that the composition of propolis is various and depends on the origin of plants, from where propolis was collected.

Anti-Infective Agents↗
PubMed2004

[Influence of extraction methods on the composition of essential oils].

The aim of this work is to demonstrate our results on comparison of composition of essential oil fractions obtained by traditional steam distillation and supercritical fluid extraction. The plant materials for the various extraction methods were selected from the Lamiaceae, Apiaceae and Asteraceae families. For the supercritical fluid extraction (SFE) carbon dioxide was used as supercritical solvent. The extracts were collected by stage wise precipitation in two separators. The waxy product and extract rich in essential oil were collected in the 1st and in the 2nd separator respectively. The traditional water steam distillation (SD) was carried out in the special apparatus of the Hungarian Pharmacopoea (7th ed.). GC analysis was carried out on capillary silica fused columns coated with DB-1701 and the specific chiral columns coated with Rt-beta DEX m or Rt-beta DEX sm. Comparing the composition of steam distilled oils with that of volatile SFE fractions the following general characteristics were established. The SFE fractions were richer in monoterpene-esters and poorer in alcohols than the traditional essential oils (clary sage, lavander, moldavian dragonhead). Regarding the distribution of the monoterpene and sesquiterpene compounds, the SFE fractions contained sesquiterpenes in higher percentage than the distilled oils (Salvia fruticosa). Furthermore, the proportion of sesquiterpenes increased in SFE fractions collected successively with time (Salvia officinalis) similar to the ratio of oxygenated monoterpenes to monoterpene hydrocarbons (Rosmarinus officinalis). The phtalides of lovage (Satureja hortensis) did not show regular change during the supercritical extraction. In other cases it was verified that part of the mono- and sesquiterpenes were present originally in bound form (glycosides) in plants. Thus they appeared only in essential oil fractions after previous acidic treatment (Thymus, Origanum, Satureja species). During the super-critical extraction the azulenogene sesquiterpene lactones did not transform to azulenes (chamomile, yarrow), but SFE fractions of some Asteraceae plants contained sesquiterpene-gamma-lactones of unchanged structure.

Apiaceae↗
PubMed1987

Antitumor activity of a novel antitumor antibiotic, quinocarmycin citrate (KW2152).

A novel antitumor antibiotic, 2a,3,4,5,6,6a,7,11b-octahydro-11-methoxy-12-methyl-3,6-imino-1H-2-oxa-11 c- azanaphth(1,2,3-cd)azulene-5-carboxylic acid monocitrate (quinocarmycin citrate; KW2152) was selected for investigation in a number of experimental tumor systems because of its efficacy against P388 leukemia. In the initial studies with P388 leukemia (i.p.-i.p.), KW2152 gave an increase in life span of greater than 80%. The activity was schedule dependent and daily administration was the most effective. KW2152 caused marginal activity against L1210 leukemia, B16 melanoma, and M5076 sarcoma. The effect on cultured cells suggested that KW2152 was not cross-resistant to Adriamycin (ADM) but was cross-resistant to mitomycin C (MMC); however, KW2152 caused prolongation of life span against mice bearing P388/ADM or P388/MMC. In tests against human tumors xenografted s.c. in nude mice, KW2152 significantly inhibited the growth of MX-1 mammary carcinoma with all tumors cured at i.v. doses of 4.4 mg/kg/day and p.o. doses of 26.2 mg/kg/day given daily for 7 days. KW2152 also inhibited distinct human gastric carcinomas, St-4 and St-15 tumors, and colon carcinoma Co-3 by daily administration for 7 days. Against St-4, KW2152 gave a treated versus control percentage of 27, compared to 52 for cis-diamminedichloroplatinum. Against Co-3, KW2152 was at least as effective as MMC, ADM, cis-diamminedichloroplatinum, and bleomycin, giving a treated versus control percentage of 18 at a dose of 8.6 mg/kg/day given daily for 7 days. KW2152 showed growth inhibitory activity against cultured murine tumors and human cells. The order of in vitro efficacy of KW2152 against murine tumors, P388 leukemia greater than L1210 leukemia, B16 melanoma, correlated with the order of the sensitivity on the i.p.-i.p. systems of these tumors. The 50% inhibitory concentrations against P388 leukemia cells were 5.3 X 10(-6) and 1.1 X 10(-7) M after 1 and 72 h exposure, respectively. KW2152 caused significant inhibition of RNA synthesis after a short time exposure. In P388 leukemia cells exposed for 1 h with KW2152, the 50% inhibitory concentration for RNA synthesis was 10(-5) M, 30-fold less than that for DNA synthesis. White blood cell depression or platelet depression was not significant after administration of the i.v. 10% lethal dose given daily for 7 days. Because of its good activity against human mammary tumor MX-1 and some effectiveness against other gastric and colon carcinomas and its water solubility, a novel antitumor antibiotic, KW2152, is being developed as a Phase I anticancer agent.

Animals↗
PubMed1983

Synthesis and pharmacological study of the thiophene analogue of taclamine, QM-7184, a new neuroleptic drug with potent alpha-adrenoceptor blocking activity.

The method of synthesis and the pharmacological evaluation of (+/-)-6-trans-8b,9,10,11,12,13-trans-13a-Octahydro-5H-7-thia-12a-azabenzo[f]naphth[1,2,3-c,d] azulene (QM-7184), a thiophene analogue of taclamine, are reported. This new drug shows, at variance with the prototype, a neuroleptic profile in rodents. QM-7184 decreases the spontaneous motor activity, blocks the stereotyped behaviour induced by dopaminergic stimulants and reduces conditioned avoidance responses. In all of these tests, the new drug is less potent than the typical neuroleptics haloperidol or butaclamol. Taclamine does not show, as expected, any neuroleptic activity. Like other neuroleptics, QM-7184 blocks striatal dopaminergic receptors and consequently increases the concentration of homovanillic acid and displaces [3H]spiperone binding, although it is a less potent displacer than haloperidol or butaclamol. QM-7184 shows, however, a high affinity for alpha-noradrenergic receptors, both in the cortex and in the striatum, which is about 20 and 90 times higher than those of haloperidol and butaclamol, respectively. In view of the recently suggested role for norepinephrine in the etiology of schizophrenia, it is speculated that drugs of this type may be of interest in the treatment of psychotic illness.

Adrenergic alpha-Antagonists↗
PubMedDate not supplied

[Clinical statistical evaluation of the antiplaque efficacy of therapeutic aids].

The results of a blind comparison of different types of toothpaste carried out for two months are reported. It was noted that the paste based on azulene, sodium chloride and benzalkonium chloride produces a more marked regression in the gingival index, whereas that based on chlorhexidine produces a more marked reduction in the plaque index. The differences were not statistically significant, however. With an equal quantity of tooth-paste, it was shown that two initial sessions of ultrasonic detartrasis produce a statistically significant benefit as regards gingival index regression, but an only apparent one for the plaque index. Detartrasis alone, not followed by regular oral hygiene practice, leads to momentary benefits but, as the weeks go by, the difference between the indices of those submitted to detartrasis alone and those who also adopt recommended toothpastes regularly becomes increasingly significant.

Adolescent↗
PubMed1950

[Azulenol].

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Azulenes↗
PubMed1998

Enhanced oxygen radical production in a transgenic mouse model of familial amyotrophic lateral sclerosis.

Mutations of the SOD1 gene encoding copper/zinc superoxide dismutase (CuZnSOD) cause an inherited form of amyotrophic lateral sclerosis. When expressed in transgenic mice, the same SOD1 mutations cause progressive loss of spinal motor neurons with consequent paralysis and death. In vitro biochemical studies indicate that SOD1 mutations enhance free radical generation by the mutant enzyme. We investigated those findings in vivo by using a novel, brain-permeable spin trap, azulenyl nitrone. Reaction of azulenyl nitrone with a free radical forms a nitroxide adduct that then fragments to yield the corresponding azulenyl aldehyde. Transgenic mice expressing mutant SOD1-G93A show enhanced free radical content in spinal cord but not brain. This correlates with tissue-specific differences in the level of transgene expression. In spinal cord, the increase in free radical content is in direct proportion to the age-dependent increase in mutant human CuZnSOD expression. This increase precedes motor neuron degeneration. The higher level of human CuZnSOD expression seen in spinal cord compared with brain, and consequent difference in free radical generation, provides a basis for understanding the selective vulnerability of the spinal cord in this disease model.

Aging↗