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At least 523 records · Page 29Linked to original sources
PubMed2000

Potent inhibition of macrophomate synthase by reaction intermediate analogs.

Potent inhibitors for macrophomate synthase, which has recently been found to catalyze a highly unusual five-step chemical transformation, were explored. Among 11 oxalacetate analogs tested, only three analogs had moderate to relatively strong inhibitory activities (I50 1.3-8.1 mM). On the other hand, among 35 bicyclic intermediate analogs synthesized, two diacids were found to be the most potent inhibitors (I50 0.80, 0.84 mM) which had a much higher affinity than that of the natural substrate 2-pyrone. (-)-Enantiomers of the diacids showed 30 times stronger activity (I50 0.34, 0.41 mM) than (+)-ones. The I50/Km values (0.20, 0.24) showed their potent inhibitions. Competitive inhibitions were observed in two representative inhibitors.

Binding, Competitive↗
PubMed2004

Browning and decomposed products of model orange juice.

A model solution of orange juice containing sugars, ascorbic acid, and citric acid was prepared and its browning during storage was examined. The solution gradually turned brown. Ascorbic acid (AsA) most contributed to the browning. Citric acid and such amino acids as Arg and Pro promoted the browning. DTPA, a strong chelator, inhibited the browning. 3-Hydroxy-2-pyrone (3OH2P), 5-hydroxymethylfurfural (HMF), furfural, 5-hydroxymaltol, and 2-furoic acid were identified as decomposed products in the stored solution. When 3OH2P was stored, the solution turned slightly brown. Furfural solution added with amino acids turned yellow. 3OH2P showed a positive relation with the browning of retail orange juice during storage.

Amino Acids↗
PubMed2005

Tipranavir.

Tipranavir is a newly approved protease inhibitor that belongs to the class of 4-hydroxy-5,6-dyhydro-2-pyrones. It exhibits potent in vitro activity against both human immunodeficiency virus (HIV)-1 and HIV-2, including clinical isolates with multiple protease inhibitor-resistant mutations. Tipranavir requires coadministration with ritonavir to achieve clinically meaningful serum concentration. In randomized, phase III, open-label trials, it was found to be superior to the currently available boosted protease inhibitors in highly treatment-experienced patients with multiple protease inhibitor mutations. Thus, it provides a welcome new option for salvage antiretroviral therapy. The most common adverse effects associated with tipranavir are diarrhea, nausea and vomiting. Common laboratory abnormalities include elevations of total cholesterol, triglycerides and liver enzymes.

Clinical Trials as Topic↗
PubMed2002

Production of coconut aroma by fungi cultivation in solid-state fermentation.

The production of 6-pentyl-alpha-pyrone (6-PP), an unsaturated D-lactone with a strong coconut-like aroma was studied and compared with liquid and solid substrates. A fungi strain that produces coconut aroma compound was selected. The liquid medium of the submerged culture was used to impregnate a solid support of sugarcane bagasse in SSF (Solid State Fermentation). This substrate was adequate for growth and aroma production; the concentration obtained using SSF was higher than using liquid fermentation process. In the present work, it is demonstrated that, by solid-state-fermentation process, it is possible to produce 6-PP. The amount of 6-PP produced using a solid state substrate, following a 5 d culture, was 3 mg/g dry matter. Therefore, the amount of 6-PP produced during solid-state-fermentation process is higher than that reported in literature for submerged process.

Cocos↗
PubMedDate not supplied

Mariannaepyrone--a new inhibitor of thromboxane A2 induced platelet aggregation.

Mariannaeapyrone ((E)-2-(1,3,5,7-tetramethyl-5-nonenyl)-3,5-dimethyl-6-hydroxy-4H-pyran-4-one) is a new fungal metabolite isolated from fermentations of the common mycophilic deuteromycete Mariannaea elegans. The chemical structure of the 4-pyrone was determined by spectroscopic techniques. Mariannaeapyrone is a selective inhibitor of the thromboxane A2 induced aggregation of human platelets, whereas only weak cytotoxic and antimicrobial effects could be observed.

Blood Platelets↗
PubMed2003

Tipranavir: a novel non-peptidic protease inhibitor for the treatment of HIV infection.

Tipranavir (TPV) is a non-peptidic protease inhibitor belonging to the class of 4-hydroxy-5,6-dihydro-2-pyrones, which exhibits potent and specific activity against HIV type I (HIV-1) and 2 (HIV-2). Clinically effective plasma levels of TPV are achieved by concomitant administration of ritonavir (RTV). Therefore, TPV has been coadministered with RTV in clinical trials. TPV has demonstrated antiviral activity against HIV-1 isolates that are resistant to reverse-transcriptase and selected peptidic protease inhibitors. Therefore, TPV is emerging as one of the newer drugs in the armamentarium against HIV-1 in patients demonstrating multi-drug resistance. TPV administered orally to humans exhibits linear pharmacokinetics at doses of 100 - 2000 mg. Steady-state plasma levels are attained within 7 days of initiating multiple dosing. The half-life of the drug is approximately 6 h at steady-state. The plasma concentration is lower with repeated dosing than predicted from single-dose studies due to induction of the cytochrome p450 3A4 isoform of the liver microsomal enzyme system. Phase II clinical trials have shown that the administration of TPV and RTV in combination is safe and generally well-tolerated in HIV-1-infected adults. Phase III trials are underway to compare the efficacy of this drug versus other antiretroviral regimens. Gastrointestinal toxicity has been described with TPV, the most frequently reported side effects being diarrhoea, nausea, vomiting and abdominal pain. There is no known evidence of teratogenicity or effect on fertility. TPV dosed twice-daily, in the range of 500 - 1250 mg and combined with 100 - 200 mg of RTV has been shown to substantially and durably reduce viral load in HIV-1-infected drug-naive and experienced patients.

Clinical Trials as Topic↗
PubMed2005

Tipranavir: a novel second-generation nonpeptidic protease inhibitor.

Tipranavir is a new nonpeptidic protease inhibitor and belongs to the class of 4-hydroxy-5, 6-dihydro-2-pyrones. Chemically, tipranavir is based on coumarin and sulfonamide compounds, amongst others. It exhibits potent and specific activity against both HIV-1 and -2. Tipranavir 500 mg in combination with ritonavir 200 mg twice daily results in optimum viral load reduction and suppresses both wild-type and protease inhibitor-resistant virus. It is metabolized by the cytochrome P4503A4 enzyme and its pharmacokinetic parameters are enhanced when combined with ritonavir. Tipranavir is excreted primarily in the feces, with minimal excretion in urine. In early trials, tipranavir/ritonavir was demonstrated to be safe and well tolerated, with mild gastrointestinal side effects. Preliminary data indicate pharmacokinetic interaction with nucleotide reverse transcriptase inhibitors; however, no dose adjustments are recommended at this time. Virologic response is not adequate when combined with other ritonavir-boosted protease inhibitors, and is currently not recommended. As with other protease inhibitors, tipranavir interacts with fluconazole, atorvastatin, clarithromycin and rifabutin and absorption is reduced when taken with antacids and didanosine (enteric coated formulation). Phase III trials are underway to compare the efficacy of tipranavir/ritonavir with other antiretroviral agents.

Animals↗
PubMed1993

Germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551.

During germination spores of Streptomyces viridochromogenes NRRL B-1551 excrete a compound, germicidin, which has an inhibitory effect on the germination of its own arthrospores at a concentration as low as 200 pM (40 pg/ml). At higher concentrations germicidin inhibits porcine Na+/K(+)-activated ATPase and retards the germination of the cress Lepidium sativum. Germicidin is the first known autoregulative inhibitor of spore germination in the genus Streptomyces and was isolated from the supernatant of germinated spores, but also from the supernatant of the submerged culture. Spectroscopic analysis and derivatization reactions revealed germicidin to be 6-(2-butyl)-3-ethyl-4-hydroxy-2-pyrone (C11H16O3). Crude isolates of germicidin from the supernatant of submerged culture, but not from the spores, contained a second, structurally very similar compound (C10H14O3), in which in contrast to germicidin a 2-propyl instead of the 2-butyl chain was bound to C-6 and which did not show any activity in the germination and ATPase assay. The germination assay was evaluated as a new screening model for specifically active compounds.

Fermentation↗
PubMed1993

Isolation, structure determination and biological activities of a novel antifungal antibiotic, S-632-C, closely related to glutarimide antibiotics.

A new antifungal antibiotic, S-632-C, was extracted with ethyl acetate from the culture filtrate of Streptomyces hygroscopicus S-632 and isolated through a combination of column and preparative thin-layer chromatographies on silica gel. The structure of S-632-C was determined by analysis of 1H and 13C-NMR, MS, UV and IR spectra in comparison with those of S-632-A2 (9-methylstreptimidone). The signals were assigned on the basis of 2D NMR experiments, which involved 1H-1H DQF COSY, HMQC and HMBC spectral analysis. From these results, the chemical structure of S-632-C was elucidated as 6-(3,5-dimethyl-2-oxo-4,6-octadienyl)-4-carbamoylmethyl-3,4, 5,6-tetrahydro-2- pyrone. The antibiotic exhibited exclusively weak in vitro antifungal activity against Saccharomyces spp. and similar cytotoxic activity against KB carcinoma cells, as compared with the glutarimide antibiotic S-632-A2. In addition, this antibiotic had the ability to change the morphology of ras(ts)-transformed NRK cells to that of normal cells, also a characteristic S-632-A2 and B1.

Antifungal Agents↗
PubMed1997

NF00659A1, A2, A3, B1 and B2, novel antitumor antibiotics produced by Aspergillus sp. NF 00659. I. Taxonomy, fermentation, isolation and biological activities.

Five novel cytotoxic antibiotics, NF00659A1 (1), A2 (2), A3 (3), B1 (4) and B2 (5) were discovered. They were isolated from a culture mycelium of Aspergillus sp. These compounds were proved to have 4,5-seco-tricyclic diterpene alpha-pyrone structure by spectroscopic analyses. They showed potent antitumor activities against human ovarian carcinoma A2780 and human colorectal adenocarcinoma SW480 cells, but did not show any antimicrobial activities at 1,000 micrograms/ml against Gram-positive and Gram-negative bacteria, yeasts and fungi.

Adenocarcinoma↗
PubMed1997

NF00659A1, A2, A3, B1 and B2, novel antitumor antibiotics produced by Aspergillus sp. NF 00659. II. Structural elucidation.

NF00659A1, A2, A3, B1 and B2, having insecticidal and antitumor activities, were isolated from a culture mycelium of Aspergillus sp. NF 00659. The novel structure of NF00659s were determined mainly by spectroscopic studies including various NMR measurements. NF00659s have a common structure which consists of acyl, alpha-pyrone and 4,5-seco-tricyclic diterpene moieties.

Antibiotics, Antineoplastic↗
PubMed2000

Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. II. Structure elucidation.

The structures of novel topoisomerase I inhibitors, topopyrones A, B, C and D were elucidated by spectral analysis of the chemical derivatives. These compounds are an anthraquinone type containing a fused 1,4-pyrone moiety. Topopyrones A and B contain a chlorine atom, however C and D do not. It was suggested that topopyrones B and D are converted from topopyrones A and C, respectively by Wessely-Moser type rearrangement.

Anthraquinones↗
PubMed2001

SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. I. Taxonomy, fermentation, isolation and biological activities.

SNF4435C and D, novel nitrophenyl pyrones, have been isolated from the culture broth of an actinomycete strain SNF4435. The strain was identified as Streptomyces spectabilis from its morphological and cultural characteristics. SNF4435C and D showed a potent immunosuppressive activity in vitro and selectively suppressed B-cell proliferation induced by LPS versus T-cell proliferation induced by Con A.

Animals↗
PubMed2001

SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. II. Structure elucidation.

SNF4435C and D are new immunosuppressants isolated from the culture broth of a strain of Streptomyces spectabilis. Their molecular formulas were determined as C28H31NO6 based on the HRFAB-MS analyses. The structures of SNF4435C and D were elucidated to be novel nitrophenyl pyrones having an intriguing tricyclic ring system and diastereoisomers of each other by spectroscopic analyses including various NMR measurements.

Fermentation↗
PubMed2003

New diketopiperazines from the entomopathogenic fungus Verticillium hemipterigenum BCC 1449.

Two new diketopiperazines, bisdethiodi(methylthio)-1-demethylhyalodendrin and 1-demethylhyalodendrin tetrasulfide, together with two known cyclodepsipeptides, enniatins B and B4, and two known pyrones, pyrenocines A and B, were isolated from a culture broth of the entomopathogenic fungus Verticillium hemipterigenum BCC 1449. These structures were elucidated using spectroscopic methods and X-ray crystallography. Antimalarial and cytotoxic activities of these compounds were evaluated.

Animals↗
PubMed2002

Novel fluorescent compound (DDP) in calf, rabbit, and human articular cartilage and synovial fluid.

OBJECTIVE: To investigate the presence of and quantify 2,6-dimethyldifuro-8-pyrone (DDP), a novel fluorescent compound identified as in various calf, rabbit, and human tissue/fluid samples, to determine the DDP level in articular cartilage (AC) laminae, and to investigate the changes in cartilage DDP content with cartilage maturation. METHODS: Samples were obtained from calf (< 2 years), rabbit (< 2 weeks to 2 years) or human AC and synovial fluid (SF) as well as other non-cartilaginous tissues. SF and tissue samples were hydrolyzed with 6 M HCl (24 hours at 110 degrees C), lyophilized, and dissolved in HPLC mobile phase. DDP and collagen crosslink peaks were measured using a fluorescence detector at excitation and emission wavelengths of 295 and 395 nm, respectively. RESULTS: DDP was detected from calf metacarpophalangeal joint AC (362 +/- 48 pmol/mg dry weight), SF (4.5 +/- 0.3 pmol/microl SF), and intervertebral disc (24 +/- 4 pmol/mg). DDP was not detected in calf ligament, tendon, bone, ocular lens, cornea, or elastic cartilage. The DDP amount was greater in mid-deep cartilage lamina (448 +/- 63 pmol/mg) than superficial-mid lamina (129 +/- 52 pmol/mg) (p = 0.008). DDP level decreased with maturation in rabbit knee joint AC from 185 +/- 40 (< 2 weeks) to 27 +/- 3 (2 years) pmol/mg dry weight. DDP was not detected in adult rabbit ligament, tendon, meniscus, or bone. DDP was detected in human knee joint AC and SF. The DDP level in osteoarthritic lesions was present in lower concentrations (range: 0 to 96 pmol/mg dried AC) compared to intact AC (range: 63 to 236 pmol/mg) of the same knee. CONCLUSION: DDP is a hyaline cartilage specific compound present in all articular cartilage samples from various articulating joints/animal species. DDP level increases with AC depth and decreases with cartilage maturation. DDP is a potential indicator of cartilage metabolism during normal growth, ageing, and cartilage disease.

Aged↗
PubMed1998

[Isolation and structure of 6'-O-caffeylerigeroside from Erigeron multiradiatus].

The plant, Erigeron multiradiatus (Wall.) Benth(Family: Compositae), is a perennial herb distributed abundantly in the mountainous area of the southwestern part in China. It is used in folk medicine for the treatment of common cold, panting cough, rheumatic, enteritis and toothache. In this paper, we report a new glycoside named as 6'-O-caffeylerigeroside isolated from Erigeron Multiradiatus (Family: Compositae) together with four known compounds. The known compounds were identified as pyromeconic acid(I), scopoletin(II), 4-hydroxybenzoic acid(III) and vanillic acid(IV). The structure of 6'-O-caffeylerigeroside was elucidated as gamma-pyrone-3-O-[6"-(3',4'-dihydroxy-cinnamoyl)]-beta-D-glucoside(V) on the basis of chemical evidence and spectral data.

Asteraceae↗