RESUMO
The genus Claviceps (Clavicipitaceae) is famous for producing ergot alkaloids (EAs) in sclerotia. EAs can cause ergotism, resulting in convulsions and necrosis when ingested, making these compounds a serious concern for food safety. Agroclavine (2), a typical Clavine-type EA, is a causative agent of ergotism and is listed as a compound to be monitored by the European Food Safety Authority. Clavine-type EAs are known to cause cytotoxicity, but the mechanism has not been elucidated. We performed annexin V and PI double-staining followed by flow cytometric analysis to detect apoptosis in HepG2 and PANC-1 cells after exposure to Clavine-type EAs. Clavine-type EAs reduced cell viability and induced apoptosis in both cell lines. We then performed LC-MS analysis of EAs from 41 sclerotia samples of Claviceps collected in Japan. 24 out of 41 sclerotia extracts include peptide-type EAs (ergosine/inine: 4/4', ergotamine: 5, ergocornine/inine: 6/6', α-ergocryptine/inine: 8/8', and ergocristine/inine: 9/9') and 19 sclerotia extracts among 24 sclerotia detected peptide type EAs include Clavine-type EAs (pyroclavine: 1, agroclavine: 2, festuclavine: 3) by LC-MS. We then performed a metabolomic analysis of the EAs in the sclerotia using principal component analysis (PCA). The PCA score plots calculated for EAs suggested the existence of four groups with different EA production patterns. One of the groups was formed by the contribution of Clavine-type EAs. These results suggest that Clavine-type EAs are a family of compounds requiring attention in food safety and livestock production in Japan.
Assuntos
Claviceps , Alcaloides de Claviceps , Ergotismo , Humanos , Alcaloides de Claviceps/análise , Alcaloides de Claviceps/química , Japão , Claviceps/química , Claviceps/metabolismo , Peptídeos , ApoptoseRESUMO
BACKGROUND: Chimpi, the dried peel of Citrus unshiu or Citrus reticulata, has various pharmacological effects. Chimpi extract was recently shown to affect the skin, including its inhibitory effect against atopic dermatitis. In this study, we analyzed the effects of Chimpi extract on the functional molecule aquaporin-3 (AQP3), which is involved in water transport and cell migration in the skin. METHODS AND RESULTS: Chimpi extract was added to HaCaT human skin keratinocytes, and the AQP3 expression level was analyzed. A wound healing assay was performed to evaluate the effect of Chimpi extract on cell migration. The components of Chimpi extract and fractions obtained by liquid-liquid distribution studies were added to HaCaT cells, and AQP3 expression was analyzed. Chimpi extract significantly increased AQP3 expression in HaCaT cells at both the mRNA and protein levels. Immunocytochemical staining revealed that Chimpi extract also promoted the transfer of AQP3 to the cell membrane. Furthermore, Chimpi extract enhanced cell migration. Hesperidin, narirutin, and nobiletin did not increase AQP3 levels. Although the components contained in the fractions obtained from the chloroform, butanol, and water layer increased AQP3, the active components could not be identified. CONCLUSIONS: These results reveal that Chimpi extract may increase AQP3 levels in keratinocytes and increase the dermal water content. Therefore, Chimpi extract may be effective for the management of dry skin.
Assuntos
Aquaporina 3 , Citrus , Humanos , Aquaporina 3/genética , Aquaporina 3/metabolismo , Células Cultivadas , Queratinócitos/metabolismo , Água/metabolismo , Extratos Vegetais/farmacologia , Extratos Vegetais/metabolismoRESUMO
The degradation behavior of eight tricyclic antidepressants (TCAs; amitriptyline, amoxapine (AMX), imipramine, clomipramine, desipramine, doxepin, dothiepin, and nortriptyline) in artificial gastric juice was investigated to estimate their pharmacokinetics in the stomach. As a result, among the eight TCAs, only AMX was degraded in artificial gastric juice. The degradation was a pseudo first-order reaction; activation energy (Ea) was 88.70 kJ/mol and activation entropy (ΔS) was -80.73 J/K·mol. On the other hand, the recovery experiment revealed that the degradation product did not revert to AMX and accordingly, this reaction was considered to be irreversible. In the AMX degradation experiment, peaks considered to be degradation products A (I) and B (II) were detected at retention times of around 3 min and 30 min in LC/UV measurements, respectively. Structural analysis revealed that compound (I) was [2-(2-aminophenoxy)-5-chlorophenyl]-piperazin-1-yl-methanone, a new compound, and compound (II) was 2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one. As for the degradation behavior, it was estimated that AMX was degraded into (II) via (I), i.e., (II) was the final product. The results are expected to be useful in clinical chemistry and forensic science, including the estimation of drugs to be used at the time of judicial dissection and suspected drug addiction.
Assuntos
Amoxapina/química , Antidepressivos Tricíclicos/química , Suco Gástrico/química , Amoxapina/farmacocinética , Antidepressivos Tricíclicos/farmacocinética , Cromatografia Líquida , Humanos , Espectrometria de Massas , Estrutura MolecularRESUMO
Previously, we established a 1H NMR metabolomics method using reversed-phase solid-phase extraction column (RP-SPEC), and succeeded in distinguishing wild from cultivated samples of Saposhnikoviae radix (SR), and between SR and its substitute, Peucedanum ledebourielloides root (PR). Herein, we performed LC-HR/MS metabolomics using fractions obtained via RP-SPEC to identify characteristic components of SR and PR. One and three characteristic components were respectively found for SR and PR; these components were isolated with their m/z values and retention times as a guide. The characteristic component of SR was identified as 4'-O-ß-D-glucosyl-5-O-methylvisamminol (1), an indicator component used to identify SR in the Japanese Pharmacopoeia. In contrast, the characteristic components of PR were identified as xanthalin (2), 4'-O-ß-D-apiosyl (1 â 6)-ß-D-glucosyl-5-O-methylvisamminol (3), and 3'-O-ß-D-apiosyl (1 â 6)-ß-D-glucosylhamaudol (4) based on spectroscopic data such as 1D- and 2D-NMR, MS, and specific optical rotation. Among them, 4 is a novel compound. For the correlation between the NMR metabolomics results in the present and our previous report, only 1 and 2 were found to correlate with the chemical shifts, and the other compounds had no correlation. As the chemical shifts for compounds 1, 3, and 4 were similar to each other, especially for the aglycone moiety, they could not be distinguished because of the sensitivity and resolution of 1H NMR. Accordingly, combining NMR and LC/MS metabolomics with their different advantages is considered useful for metabolomics of natural products. The series of methods used in our reports could aid in quality evaluations of natural products and surveying of marker components.
Assuntos
Apiaceae/química , Apiaceae/classificação , Medicamentos de Ervas Chinesas/química , Extratos Vegetais/química , Raízes de Plantas/química , Cromatografia Líquida de Alta Pressão , Cumarínicos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Metabolômica/métodos , Extração em Fase SólidaRESUMO
Shimalactonesâ A and B are neuritogenic polyketides possessing characteristic oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene ring systems that are produced by the marine fungus Emericella variecolor GF10. We identified a candidate biosynthetic gene cluster and conducted heterologous expression analysis. Expression of ShmA polyketide synthase in Aspergillus oryzae resulted in the production of preshimalactone. Aspergillus oryzae and Saccharomyces cerevisiae transformants expressing ShmA and ShmB produced shimalactonesâ A and B, thus suggesting that the double bicyclo-ring formation reactions proceed non-enzymatically from preshimalactone epoxide. DFT calculations strongly support the idea that oxabicyclo-ring formation and 8π-6π electrocyclization proceed spontaneously after opening of the preshimalactone epoxide ring through protonation. We confirmed the formation of preshimalactone epoxide inâ vitro, followed by its non-enzymatic conversion to shimalactones in the dark.
Assuntos
Compostos Bicíclicos Heterocíclicos com Pontes/química , Lactonas/química , Lactonas/metabolismo , Aspergillus/genética , Aspergillus/metabolismo , Biotransformação , Ciclização , Família Multigênica/genética , Saccharomyces cerevisiae/genética , Saccharomyces cerevisiae/metabolismoRESUMO
Berberine (BBR) is a protoberberine alkaloid extracted from plants such as Coptis japonica (Ranunculaceae). In a previous report, we demonstrated the existence of a 11-hydroxylation pathway employed by BBR-utilizing bacteria for metabolism of BBR. In the present study, we report the identification of the genes brhA, brhB, and brhC as encoding a multicomponent BBR 11-hydroxylase in Burkholderia sp. strain CJ1. BrhA is belonging to the Rieske non-heme iron oxygenase (RO) family, a class of enzymes known to catalyze the first step in bacterial aromatic-ring hydroxylation. We further demonstrate that BrhA activity requires BrhB (ferredoxin reductase) and BrhC (ferredoxin) as electron transport chain components. A BLAST search revealed that BrhA exhibits 38% and 33% sequence identity to dicamba O-demethylase (DdmC; AY786443) and chloroacetanilide herbicides N-dealkylase (CndA; KJ461679), respectively. To our knowledge, this work represents the first report of a bacterial oxygenase catalyzing the metabolism of a polycyclic aromatic-ring alkaloid.Abbreviations: BBR: berberine; D-BBR: demethyleneberberine; H-BBR: 11-hydroxyberberine; HD-BBR: 11-hydroxydemethyleneberberine; HDBA: 2-hydroxy-3,4-dimethoxybenzeneacetic acid; PAL: palmatine; H-PAL: 11-hydroxypalmatine; BRU: berberrubine; Fd: ferredoxin; FdR: ferredoxin reductase; ETC: electron transport chain.
Assuntos
Berberina/metabolismo , Burkholderia/enzimologia , Burkholderia/genética , Oxigenases de Função Mista/genética , Proteínas de Bactérias/genética , Proteínas de Bactérias/metabolismo , Berberina/análogos & derivados , Alcaloides de Berberina/metabolismo , Escherichia coli/genética , Escherichia coli/metabolismo , Ferredoxinas/genética , Ferredoxinas/metabolismo , Genoma Bacteriano , Hidroxilação , Microrganismos Geneticamente Modificados , Oxigenases de Função Mista/metabolismo , Oxirredutases/genética , Oxirredutases/metabolismo , Filogenia , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismoRESUMO
Burkholderia sp. strain CJ1 was newly isolated as berberine (BBR) degrading bacteria from rhizosphere of Coptis japonica. CJ1 had the ability to utilize BBR as the sole carbon source and revealed that BBR metabolism via 11-hydroxylation and demethylenation pathway. It was also revealed that the 11-hydroxylation ability of BBR and palmatine (PAL) has induced by BBR.
Assuntos
Berberina/metabolismo , Burkholderia/metabolismo , Coptis/metabolismo , Coptis/microbiologia , Rizosfera , Alcaloides de Berberina/metabolismo , Biodegradação Ambiental , Hidroxilação , Microbiologia do SoloRESUMO
1H NMR-based metabolomics has been applied in research on food, herbal medicine, and natural products. Although excellent results were reported, samples were directly extracted with a deuterated solvent (e.g., methanol-d4 or D2O) in most reports. As primary metabolites account for most of the results, data for secondary metabolites are partially reflected. Consequently, secondary metabolites tend to be excluded from factor loading analysis, serving as a significant unfavorable feature of 1H NMR-based metabolomics when investigating biologically active or functional components in natural products and health foods. Reversed-phase solid-phase extraction column (RP-SPEC) was applied for sample preparation in 1H NMR-based metabolomics to overcome this feature. The methanol extract from Saposhnikoviae radix (SR), an important crude drug, was fractionated with RP-SPEC into 5% methanol-eluting fractions, and the remaining fraction was collected. Each fraction was subjected to 1H NMR-based metabolomics and compared to results from conventional 1H NMR-based metabolomics. Based on principal component analysis (PCA) and partial least squares projections to latent structures discriminant analysis (PLS-DA), the 5% methanol fraction and conventional method reflected the amount of saccharides such as sucrose on the PC1/PLS1 axes, and wild and cultivated samples were discriminated along those axes. The remaining fraction clearly distinguished SR from Peucedanum ledebourielloides root. The compounds responsible for this discrimination were deemed falcarindiol derivatives and other unidentified secondary metabolites from the s-plot on PLS-DA. The secondary metabolites from original plants were, therefore, presumed to be concentrated in the remaining fraction by RP-SPEC treatment and strongly reflected the species differences. The developed series is considered effective to perform quality evaluation of crude drugs and natural products.
Assuntos
Apiaceae/química , Misturas Complexas/química , Espectroscopia de Ressonância Magnética/métodos , Metabolômica/métodos , Raízes de Plantas/química , Extração em Fase Sólida/métodos , Espectroscopia de Prótons por Ressonância MagnéticaRESUMO
Coptidis rhizome (CR) is a widely used herbal medicine that contains protoberberine-type alkaloids. CR extract exhibits various pharmacologic activities. A previous study reported the isolation of Rhodococcus sp. strain BD7100 as a berberine (BBR)-utilizing bacterium, and the BBR-degradation pathway has been investigated. When we incubated strain BD7100 cells with CR extract, the number of viable cells declined with the degradation of components in the CR extract, and the culture broth exhibited antibacterial activity against strain BD7100. These results suggest that CR extract cultured in the presence of strain BD7100 contains one or more antibacterial agents. In this study, we isolated coptirhoquinone A (1) from CR extract incubated with strain BD7100 in Luria-Bertani (LB) medium, and the structure was elucidated using NMR and MS analysis. We also report the total synthesis and antimicrobial activities of 1 against bacteria, fungi, and Pythium sp.
Assuntos
Antibacterianos/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Rhodococcus/crescimento & desenvolvimento , Rhodococcus/metabolismo , Antibacterianos/química , Antifúngicos/farmacologia , Antiprotozoários/farmacologia , Berberina/metabolismo , Coptis chinensis , Medicamentos de Ervas Chinesas/química , Fungos/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Pythium/efeitos dos fármacos , Quinonas/química , Quinonas/isolamento & purificação , Quinonas/farmacologia , Rhodococcus/efeitos dos fármacosRESUMO
This research examined the production of fungal metabolites as a biological response to Kampo medicines. Shimbu-to (SMB) is a Kampo medicine composed of five herbal components: peony root (Shakuyaku), ginger (Shokyo), processed aconite root (Bushi), Poria sclerotium (Bukuryo), and Atractylodes lancea rhizomes (Sojutsu). High-performance liquid chromatography (HPLC) analysis of the fungus Aspergillus nidulans CBS 112.46 incubated in potato dextrose broth supplemented with SMB extract revealed emericellin (2) as the major peak and new xanthone analogues 24-hydroxyshamixanthone (1), shamixanthone (3), epishamixanthone (4), pre-shamixanthone (5), and variecoxanthone A (6) as minor peaks. The structure of 1 was determined by detailed analysis of 1D-NMR, 2D-NMR, and MS data. The results suggest that SMB extract regulates the biosynthesis of emericellin and its analogues in A. nidulans. Further investigations revealed that glucose induces the biosynthesis of emericellin and its analogues in A. nidulans in a concentration-dependent manner.
Assuntos
Aspergillus nidulans/metabolismo , Medicamentos de Ervas Chinesas/farmacologia , Xantonas/metabolismo , Aspergillus nidulans/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Medicina Kampo , Conformação Molecular , Xantonas/química , Xantonas/isolamento & purificaçãoRESUMO
Plants produce many specific secondary metabolites as a response to environmental stress, especially biological stress. These compounds show strong biological activities and high stability against degradation by microbes and animals. Berberine, a benzylisoquinoline alkaloid, is found in many plant species and has strong antimicrobial activity, and is often included in traditional herbal medicines. We previously investigated how berberine is degraded in nature and we isolated two berberine-utilizing bacteria. In this study, we characterized the gene encoding the enzyme that degrades the 2,3-methylenedioxy ring of berberine; this ring is important for its activity and stability. Further characterization of several other berberine-utilizing bacteria and the genes encoding key demethylenation enzymes revealed that these enzymes are tetrahydrofolate dependent and similar to demethylation enzymes such as GcvT. Because the degradation of O-methyl groups or the methylenedioxy ring in phenolic compounds such as lignin, lignan and many other natural products, including berberine, is the key step for the catabolism of these compounds, our discovery reveals the common origin of the catabolism of these stable chemicals in bacteria.
Assuntos
Bactérias/metabolismo , Proteínas de Bactérias/metabolismo , Berberina/metabolismo , Desmetilação , Enzimas/metabolismo , Bactérias/genética , Proteínas de Bactérias/genética , Biotransformação , Enzimas/genéticaRESUMO
To construct a model formula to evaluate the thermogenetic effect of ginger (Zingiber officinale Roscoe) from the ingredient information, we established transient receptor potential vanilloid subtype 1 (TRPV1)-stimulating activity prediction models by using a partial least-squares projections to latent structures (PLS) regression analysis in which the ingredient data from liquid chromatography-high-resolution mass spectrometry (LC-HRMS) and the stimulating activity values for TRPV1 receptor were used as explanatory and objective variables, respectively. By optimizing the peak extraction condition of the LC-HRMS data and the data preprocessing parameters of the PLS regression analysis, we succeeded in the construction of a TRPV1-stimulating activity prediction model with high precision ability. We then searched for the components responsible for the TRPV1-stimulating activity by analyzing the loading plot and s-plot of the model, and we identified [6]-gingerol (1) and hexahydrocurcumin (3) as TRPV1-stimulating activity components.
Assuntos
Extratos Vegetais/farmacologia , Canais de Cátion TRPV/análise , Zingiber officinale/química , Cromatografia Líquida de Alta Pressão , Manipulação de Alimentos , Células HEK293 , Humanos , Análise dos Mínimos Quadrados , Espectrometria de Massas , Canais de Cátion TRPV/metabolismoRESUMO
Seven novel spiromeroterpenoids, asnovolins A-G (1-7), one of which was shown to suppress fibronectin expression, were isolated from Aspergillus novofumigatus CBS117520 along with a known compound, novofumigatonin (8). The structures of asnovolins A-G were elucidated using MS and 2D-NMR data. Asnovolin E (5) suppressed fibronectin expression by normal human neonatal dermal fibroblast cells.
Assuntos
Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia , Terpenos/isolamento & purificação , Terpenos/farmacologia , Aspergillus/química , Ensaios de Seleção de Medicamentos Antitumorais , Fibronectinas , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Compostos de Espiro/química , Terpenos/químicaRESUMO
Based on the finding of a novel berberine (BBR)-utilizing bacterium, Rhodococcus sp. strain BD7100, we investigated the degradation of BBR and its analog berberrubine (BRU). Resting cells of BD7100 demethylenated BBR and BRU, yielding benzeneacetic acid analogs. Isolation of benzeneacetic acid analogs suggested that BD7100 degraded the isoquinoline ring of the protoberberine skeleton. This work represents the first report of cleavage of protoberberine skeleton by a microorganism.
Assuntos
Berberina/metabolismo , Rhodococcus/metabolismo , Berberina/análogos & derivados , Alcaloides de Berberina/metabolismo , Biotransformação , Meios de Cultura/química , Fenilacetatos/metabolismo , Rhodococcus/crescimento & desenvolvimentoRESUMO
Growth inhibitors were isolated from an arctic strain of Trichoderma polysporum, and the structures were elucidated and the in vitro inhibitory effects of these compounds against Pythium iwayamai were investigated. Eleven compounds were isolated; four showed a concentration-dependent growth-inhibitory effect against P. iwayamai. None of these compounds have been reported previously as substances with antimicrobial activity against P. iwayamai. One of these four compounds inhibited the growth of the pathogen at 33 µg ml(-1) concentration during a 15-day incubation at 20 °C. This effect was comparable to that of chloroneb (1: 1,4-dichloro-2,5-dimethoxybenzene), a fungicide with activity against P. iwayamai. Thus, the results of the present study show that the arctic strain of T. polysporum can be an effective source of antibiotics with activity against the snow rot pathogen, P. iwayamai.
Assuntos
Antifúngicos/farmacologia , Inibidores do Crescimento/farmacologia , Pythium/efeitos dos fármacos , Trichoderma/metabolismo , Antifúngicos/isolamento & purificação , Clorobenzenos/farmacologia , Relação Dose-Resposta a Droga , Inibidores do Crescimento/química , Inibidores do Crescimento/isolamento & purificação , Pythium/crescimento & desenvolvimento , Fatores de TempoRESUMO
Three new phthalide derivatives, emefuranones A1, A2 and B (1-3); six new phthalane derivatives, emefuran A, B1, B2, C1, C2 and D (4-9); three new farnesylated phthalide derivatives, farnesylemefuranones A-C (10-12); xylarinol C (13); and emericelloxide (14), along with four known compounds (dustanin, sorbicillin, aspergillodiol and xylarinol A), were isolated from the culture extracts of Emericella sp. IFM57991. Structures of 1-14 were elucidated on the basis of spectroscopic analysis and chemical evidence. Compounds 4-7 and 13 showed moderate antibacterial activities against Bacillus subtilis.
Assuntos
Anti-Infecciosos/farmacologia , Bacillus subtilis/efeitos dos fármacos , Benzofuranos/farmacologia , Meios de Cultura/química , Emericella/metabolismo , Ftalimidas/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Benzofuranos/química , Benzofuranos/isolamento & purificação , Testes de Sensibilidade a Antimicrobianos por Disco-Difusão , Emericella/crescimento & desenvolvimento , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , Ftalimidas/química , Ftalimidas/isolamento & purificaçãoRESUMO
Protoberberine alkaloids, including berberine, palmatine, and berberrubine, are produced by medicinal plants and are known to have various pharmacological effects. We isolated two berberine-utilizing bacteria, Sphingobium sp. strain BD3100 and Rhodococcus sp. strain BD7100, from soil collected at a natural medicine factory. BD3100 had the unique ability to utilize berberine or palmatine as the sole carbon and energy source. BD3100 produced demethyleneberberine in berberine-supplemented medium. In a resting-cell incubation with berberine, BD3100 produced 11-hydroxyberberine; the structure of 11-hydroxyberberine was determined by detailed analysis of NMR and MS spectroscopic data. α-Naphthoflavone, miconazole, and ketoconazole, which are known inhibitors of cytochrome P450, interfered with BD3100 metabolism of berberine in resting cells. Inhibition by miconazole led to the production of a new compound, 11-hydroxydemethyleneberberine. In a resting-cell incubation with palmatine, BD3100 generated 11-hydroxypalmatine. This work represents the first report of the isolation and characterization of novel berberine-utilizing aerobic bacteria for the production of 11-hydroxylation derivatives of berberine and palmatine.
Assuntos
Alcaloides de Berberina/química , Alcaloides de Berberina/metabolismo , Inibidores das Enzimas do Citocromo P-450/farmacologia , Sphingomonadaceae/metabolismo , Benzoflavonas/química , Berberina/análogos & derivados , Berberina/química , Berberina/metabolismo , Alcaloides de Berberina/farmacologia , Inibidores das Enzimas do Citocromo P-450/química , Hidroxilação , Japão , Testes de Sensibilidade Microbiana , Dados de Sequência Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Plantas Medicinais/química , Sphingomonadaceae/genéticaRESUMO
Talaromyces stipitatus ATCC 10500 possesses 17 non-reducing polyketide synthase (NR-PKS) genes. During the course of our functional analysis of PKS genes with a C-terminus methyltransferase domain from T. stipitatus, we expressed tspks2, tspks3 and tspks4 genes in the heterologous host Aspergillus oryzae, respectively. Although the tspks4 transformant gave no apparent product in HPLC analysis, a novel azaphilone pentaketide (3) was identified along with two known related products from the tspks2 transformant. Of four hexaketide products from the tspks3 transformant, two new compounds were identified to be 2-acetyl-7-methyl-3,6,8-trihydroxynaphthalene (4) and its derivative fused with α-methyl-α,ß-unsaturated γ-lactone (7).
Assuntos
Aspergillus oryzae/genética , Regulação Enzimológica da Expressão Gênica/genética , Metiltransferases/metabolismo , Policetídeo Sintases/metabolismo , Talaromyces/enzimologia , Benzopiranos/análise , Estrutura Molecular , Pigmentos Biológicos/análise , Policetídeo Sintases/genéticaAssuntos
Antineoplásicos/farmacologia , Ascomicetos/metabolismo , Glicosídeos/farmacologia , Peptídeos/farmacologia , Esteroides/farmacologia , Antineoplásicos/química , Antineoplásicos/metabolismo , Ascomicetos/química , Glicosídeos/química , Glicosídeos/metabolismo , Estrutura Molecular , Peptídeos/química , Peptídeos/metabolismo , Esteroides/química , Esteroides/metabolismoRESUMO
A new amino acid-sesquiterpene adduct, isoheleproline (1), was isolated from the roots of Inula helenium (elecampane), together with four known sesquiterpene lactones (2-5). The planar configuration of 1 was elucidated on the basis of spectroscopic data analysis, and the relative configuration of 1 was determined by performing a detailed analysis of NOESY correlations and comparing its physicochemical data with the D- and L-proline adducts of 2 obtained by Michael addition. This is the first report of a new amino acid-sesquiterpene adduct from Inula plants.