Base de dados : MEDLINE
Pesquisa : D20.080 [Categoria DeCS]
Referências encontradas : 13 [refinar]
Mostrando: 1 .. 10   no formato [Longo]

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  1 / 13 MEDLINE  
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PMID:25329789
Autor:Panten J; Surburg H; Hölscher B
Endereço:Symrise AG, Scent & Care Innovations, Mühlenfeldstrasse 1, D-37603 Holzminden. johannes.panten@symrise.com.
Título:Recent results in the search for new molecules with ambergris odor.
Fonte:Chem Biodivers; 11(10):1639-50, 2014 Oct.
ISSN:1612-1880
País de publicação:Switzerland
Idioma:eng
Resumo:The synthesis of new odorant molecules is still a challenging task for the fragrance chemist, because now as ever it is difficult to predict the odor properties of small organic molecules. Therefore, certain tools, such as, e.g., lead-structure optimization of existing odorants, are helpful techniques. In this article, we describe the synthesis and the odor properties of a new molecule derived by the so-called 'seco' lead-structure optimization of the ambergris compound Ambroxide(®) . Based on these results, more representatives with similar structures have been synthesized and evaluated for their olfactory properties.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Ambergris); 0 (Heterocyclic Compounds, 3-Ring); 0 (Perfume)


  2 / 13 MEDLINE  
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PMID:23113661
Autor:Schalk M; Pastore L; Mirata MA; Khim S; Schouwey M; Deguerry F; Pineda V; Rocci L; Daviet L
Endereço:Biotechnology Department, Corporate R&D Division, FIRMENICH SA, Geneva CH-1211, Switzerland. Michel.Schalk@firmenich.com
Título:Toward a biosynthetic route to sclareol and amber odorants.
Fonte:J Am Chem Soc; 134(46):18900-3, 2012 Nov 21.
ISSN:1520-5126
País de publicação:United States
Idioma:eng
Resumo:Ambergris, a waxy substance excreted by the intestinal tract of the sperm whale, has been a highly prized fragrance ingredient for millenia. Because of supply shortage and price inflation, a number of ambergris substitutes have been developed by the fragrance industry. One of the key olfactory components and most appreciated substitutes of ambergris, Ambrox is produced industrially by semisynthesis from sclareol, a diterpene-diol isolated from Clary sage. In the present study, we report the cloning and functional characterization of the enzymes responsible for the biosynthesis of sclareol. Furthermore, we reconstructed the sclareol biosynthetic pathway in genetically engineered Escherichia coli and reached sclareol titers of ~1.5 g/L in high-cell-density fermentation. Our work provides a basis for the development of an alternative, sustainable, and cost-efficient route to sclareol and other diterpene analogues.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Ambergris); 0 (Diterpenes); 0 (Perfume); B607NP0Q8Y (sclareol)


  3 / 13 MEDLINE  
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PMID:21459294
Autor:Wheeler CE
Título:Ambergris, crocus and tiger lily. 1922.
Fonte:Homeopathy; 100(1-2):18-20, 2011 Jan-Apr.
ISSN:1476-4245
País de publicação:Scotland
Idioma:eng
Tipo de publicação: BIOGRAPHY; CLASSICAL ARTICLE; HISTORICAL ARTICLE; JOURNAL ARTICLE
Nome de pessoa como assunto: Wheeler C
Nome de substância:0 (Ambergris)


  4 / 13 MEDLINE  
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PMID:20058254
Autor:Nätscher JB; Laskowski N; Kraft P; Tacke R
Endereço:Universität Würzburg, Institut für Anorganische Chemie, Am Hubland, 97074 Würzburg, Germany.
Título:Lower homologues of okoumal and disila-okoumal: synthesis and olfactory characterization of novel ambergris odorants.
Fonte:Chembiochem; 11(3):315-9, 2010 Feb 15.
ISSN:1439-7633
País de publicação:Germany
Idioma:eng
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Ambergris); 0 (SR13904); 0 (Thiazoles); 7631-86-9 (Silicon Dioxide)


  5 / 13 MEDLINE  
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PMID:18936989
Autor:Cheng LP; Xu L; Mao HF; Wang GL
Endereço:School of Chemical Engineering, Shanghai Institute of Technology, 120 Caobao Road, Shanghai, People's Republic of China. chengliping@sit.edu.cn
Título:Study of structural and electronic origin of ambergris odor of some compounds.
Fonte:J Mol Model; 15(1):1-8, 2009 Jan.
ISSN:0948-5023
País de publicação:Germany
Idioma:eng
Resumo:The correlation between structural, stereochemical as well as electronic features and ambergris odor of some tricyclic ethers is established based on quantum chemical calculation method. A definite structural fragment (a "new ambergris triangle") with certain electronic properties determining the origin of the odor is revealed. The influence of HOMO-LUMO energy gaps and total energies of some ambergris compounds on their odor intensity is investigated.
Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Nome de substância:0 (Ambergris); 0 (Polycyclic Compounds)


  6 / 13 MEDLINE  
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PMID:17616951
Autor:Büttner MW; Burschka C; Junold K; Kraft P; Tacke R
Endereço:Universität Würzburg, Institut für Anorganische Chemie, Am Hubland, 97074 Würzburg, Germany.
Título:Disila-okoumal: a silicon analogue of the ambergris odorant okoumal.
Fonte:Chembiochem; 8(12):1447-54, 2007 Aug 13.
ISSN:1439-4227
País de publicação:Germany
Idioma:eng
Resumo:Two-fold sila-substitution (C/Si exchange) in the saturated ring of the tetrahydronaphthalene skeleton of the ambery odorant okoumal (5) provides disila-okoumal (6). The okoumal isomers 5 a-d were synthesized from 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)ethanone (7), and the silicon analogues 6 a-d were synthesized from 1-(5,5,8,8-tetramethyl-5,8-disila-5,6,7,8-tetrahydro-2-naphthyl)ethanone (8). Detailed olfactory properties of 5 a-d and 6 a-d are reported, together with the respective threshold values. All enantiomers of okoumal and disila-okoumal exhibit typical ambery odor notes with woody facets, as is characteristic of okoumal and karanal, but a stereocenter at the 2-position was found to be of utmost importance for the odor thresholds; the lowest value of 0.31 ng per L air was measured for the 2R-configured silicon compounds 6 a and 6 c.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Ambergris); Z4152N8IUI (Silicon)


  7 / 13 MEDLINE  
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PMID:17408835
Autor:Raza M; Alorainy MS; Alghasham AA
Endereço:Department of Pharmacology and Therapeutics, College of Medicine, Qassim University, PO Box 6655, Buraydah 51452, Qassim, Saudi Arabia. mrsheikh@ksu.edu.sa
Título:Evaluation of ambrein and epicoprostanol for their antioxidant properties: protection against adriamycin-induced free radical toxicity.
Fonte:Food Chem Toxicol; 45(9):1614-9, 2007 Sep.
ISSN:0278-6915
País de publicação:England
Idioma:eng
Resumo:Ambrein and epicoprostanol were evaluated for their antioxidant potential in vitro by chemiluminescence (CL), as well as in vivo using lipid peroxides and glutathione levels as indicators in liver tissue of rats treated with adriamycin (doxorubicin) a well known free radicals producing drug. In the in vitro test, the inhibition in CL by ambrein was dose dependent. Both the high concentrations of ambrein (20-40 microg/ml) inhibited CL response significantly (P<0.05 and P<0.01, respectively) when compared to control. Similarly two low concentrations (5-20 microg/ml) of epicoprostanol inhibited CL significantly (P<0.001 and P<0.01, respectively) in comparison of DMSO control. The high concentration (40 microg/ml) of epicoprostanol behaved exceptionally and caused an increase in CL response that was more than control and significantly (P<0.001) higher than both the low concentrations. In the in vivo studies adriamycin treatment significantly (P<0.05) increased malondialdehyde (MDA) and decreased non-protein sulfhydryl (NP-SH) contents in the liver tissue of mice after 5 days treatment. Ambrein (25 and 50 mg/kg) treatment as a solo therapy at both the dose levels significantly (P<0.001) decreased MDA contents in the liver tissue. On the other hand, in the combined treatment the high dose effectively prevented any rise in MDA contents and it remained around the levels of ambrein alone. In the same experiment, adriamycin declined NP-SH contents significantly (P<0.001). Ambrein alone at both the dose levels caused a decline (P<0.01) in NP-SH contents when compared to adriamycin group. But in the combined treatment this decline in NP-SH was significantly (P<0.05) different from adriamycin alone. In the experiments dealing with epicoprostanol, adriamycin treatment increased MDA contents significantly (P<0.05) that declined significantly (P<0.001) with epicoprostanol (10- or 20mg/kg) treatment. In the same experiment co-treatment with adriamycin prevented any rise in MDA contents significantly (P<0.001) as it was observed in adriamycin alone group. Although, this treatment failed to prevent any decline in NP-SH contents either alone or in combination with adriamycin. Epicoprostanol itself had the comparative declining effect on the contents of NP-SH as seen in adriamycin group. From the results of our experiments it seems that ambrein at all concentrations behaves like antioxidant in in vitro studies but the same time it decreased NP-SH contents in vivo accompanied by a decline in MDA contents. Whereas, epicoprostanol at two low concentrations had a decline in CL indicating a possible antioxidant potential but the high concentration increased CL showing a tendency towards oxidant prospective. However, in animal studies it has shown a clear protection against adriamycin induced free radical damage.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Ambergris); 0 (Antibiotics, Antineoplastic); 0 (Antioxidants); 0 (Cholestanols); 0 (Free Radicals); 0 (Naphthols); 0 (Triterpenes); 0 (epicoprostanol); 1N9JB373FJ (ambrein); 4Y8F71G49Q (Malondialdehyde); 80168379AG (Doxorubicin); GAN16C9B8O (Glutathione)


  8 / 13 MEDLINE  
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PMID:17315955
Autor:Shen YC; Cheng SY; Kuo YH; Hwang TL; Chiang MY; Khalil AT
Endereço:School of Pharmacy, College of Medicine, National Taiwan University, Taipei, Taiwan 100, Republic of China. ycshen@ntu.edu.tw
Título:Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (sperm whale).
Fonte:J Nat Prod; 70(2):147-53, 2007 Feb.
ISSN:0163-3864
País de publicação:United States
Idioma:eng
Resumo:Ten new derivatives (2-11) of ambrein (1), isolated from ambergris, were prepared by chemical transformation. Oxidation and/or cyclization were effected by reactions with selenium oxide or p-toluenesulfonyl chloride or with the use of shortwave UV light. The structures of 2-12 were elucidated by spectroscopic analysis, with the structure and relative configuration of 9 confirmed by single-crystal X-ray crystallography. The cytotoxic activities of 1-12 were investigated against human liver carcinoma (Hepa59T/VGH), colon adenocarcinoma (WiDr), lung carcinoma (A-549), and human breast adenocarcinoma (MCF-7) cell lines. The anti-inflammatory activities of 1-11, in terms of the inhibition of human neutrophil function, were also evaluated.
Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Nome de substância:0 (Ambergris); 0 (Anti-Inflammatory Agents, Non-Steroidal); 0 (Antineoplastic Agents); 0 (Naphthols); 0 (Triterpenes); 1N9JB373FJ (ambrein); EC 3.4.21.36 (Pancreatic Elastase)


  9 / 13 MEDLINE  
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PMID:15844445
Autor:Kovatcheva A; Golbraikh A; Oloff S; Feng J; Zheng W; Tropsha A
Endereço:Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria.
Título:QSAR modeling of datasets with enantioselective compounds using chirality sensitive molecular descriptors.
Fonte:SAR QSAR Environ Res; 16(1-2):93-102, 2005 Feb-Apr.
ISSN:1062-936X
País de publicação:England
Idioma:eng
Resumo:Shape descriptors used in 3D QSAR studies naturally take into account chirality; however, for flexible and structurally diverse molecules such studies require extensive conformational searching and alignment. QSAR modeling studies of two datasets of fragrance compounds with complex stereochemistry using simple alignment-free chirality sensitive descriptors developed in our laboratories are presented. In the first investigation, 44 alpha-campholenic derivatives with sandalwood odor were represented as derivatives of several common structural templates with substituents numbered according to their relative spatial positions in the molecules. Both molecular and substituent descriptors were used as independent variables in MLR calculations, and the best model was characterized by the training set q2 of 0.79 and external test set r2 of 0.95. In the second study, several types of chirality descriptors were employed in combinatorial QSAR modeling of 98 ambergris fragrance compounds. Among 28 possible combinations of seven types of descriptors and four statistical modeling techniques, k nearest neighbor classification with CoMFA descriptors was initially found to generate the best models with the internal and external accuracies of 76 and 89%, respectively. The same dataset was then studied using novel atom pair chirality descriptors (cAP). The cAP are based on a modified definition of the atomic chirality, in which the seniority of the substituents is defined by their relative partial charge values: higher values correspond to higher seniorities. The resulting models were found to have higher predictive power than those developed with CoMFA descriptors; the best model was characterized by the internal and external accuracies of 82 and 94%, respectively. The success of modeling studies using simple alignment free chirality descriptors discussed in this paper suggests that they should be applied broadly to QSAR studies of many datasets when compound stereochemistry plays an important role in defining their activity.
Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
Nome de substância:0 (Ambergris); 0 (Cyclopentanes); 0 (Ecdysteroids)


  10 / 13 MEDLINE  
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PMID:15534702
Autor:Takane SY; Mitchell JB
Endereço:Unilever Centre for Molecular Science Informatics, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
Título:A structure-odour relationship study using EVA descriptors and hierarchical clustering.
Fonte:Org Biomol Chem; 2(22):3250-5, 2004 Nov 21.
ISSN:1477-0520
País de publicação:England
Idioma:eng
Resumo:Structure-odour relationship analyses using hierarchical clustering were carried out on a diverse dataset of 47 molecules. These molecules were divided into seven odour categories: ambergris, bitter almond, camphoraceous, rose, jasmine, muguet, and musk. The alignment-independent descriptor EVA (EigenVAlue) was used as the molecular descriptor. The results were compared with those of another kind of descriptor, the UNITY 2D fingerprint. The dendrograms obtained with these descriptors were compared with the seven odour categories using the adjusted Rand index. The dendrograms produced by EVA consistently outperformed those from UNITY 2D in reproducing the experimental odour classifications of these 47 molecules.
Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Nome de substância:0 (Ambergris); 0 (Fatty Acids, Monounsaturated); 095I377U8F (musk)



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