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1.
Phytochemistry ; 190: 112888, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34358900

RESUMO

Six previously undescribed resin glycosides, calyhedins I-VI, were isolated from the rhizomes of Calystegia hederacea Wall., which are the first genuine resin glycosides isolated from C. hederacea. The structures of calyhedins I-VI were determined based on spectroscopic data and chemical evidence. All the compounds have macrolactone structures (jalapins), and their sugar moieties were partially acylated by five organic acids. Calyhedins I, II-V, and VI have 27-, 28-, and 23-membered rings, respectively, and calyhedins IV-VI are the first jalapins with a sugar chain consisting of seven monosaccharides. Additionally, the cytotoxic activity of calyhedins II and III toward HL-60 human promyelocytic leukemia cells was evaluated. Both compounds demonstrated almost the same activity as the positive control, cisplatin.


Assuntos
Calystegia , Glicosídeos , Estrutura Molecular , Resinas Vegetais , Rizoma
2.
Arch Virol ; 166(7): 2037-2040, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33900471

RESUMO

Sweet potato chlorotic stunt virus (SPCSV; genus Crinivirus, family Closteroviridae) is one of the most destructive viruses infecting sweet potatoes. In this study, we determined the complete genome sequence of an SPCSV-like isolate (CH) from Calystegia hederacea Wall. (Convolvulaceae), a weed species related to sweet potato, by combining next-generation sequencing and rapid amplification of cDNA ends. Comparisons of genome sequences and organization confirmed the classification of CH as SPCSV. However, the sequences and phylogenetic data revealed substantial genetic divergence between CH and all known SPCSV isolates. The amino acid sequence identity between the putative proteins in SPCSV-CH and the corresponding proteins in other known SPCSV isolates in each case was less than 85.0%. Phylogenetic analysis indicated that SPCSV-CH is separate from the groups of the known SPCSV isolates. Additionally, SPCSV-CH RNA1 lacks a p22 gene. A 10.1-kDa putative protein (p10) encoded by a sequence in the 5'-terminal region of RNA2 in SPCSV-CH is much larger than the corresponding protein in all known SPCSV isolates.


Assuntos
Calystegia/virologia , Crinivirus/genética , Genoma Viral/genética , Ipomoea batatas/virologia , Doenças das Plantas/virologia , Sequência de Aminoácidos , China , DNA Complementar/genética , Sequenciamento de Nucleotídeos em Larga Escala/métodos , Filogenia , RNA Viral/genética , Proteínas Virais/genética , Sequenciamento Completo do Genoma/métodos
3.
BMC Cancer ; 20(1): 192, 2020 Mar 06.
Artigo em Inglês | MEDLINE | ID: mdl-32143591

RESUMO

BACKGROUND: Altered glycosylation associated with hepatocellular carcinoma (HCC) is well documented. However, few reports have investigated the association between dedifferentiation and glycosylation. Therefore, the aim of this study was to analyze glycosylation associated with dedifferentiation of HCC within the same nodule and to investigate glycosyltransferase related to the glycosylation. METHODS: We analyzed resected HCC specimens (n = 50) using lectin microarray to comprehensively and sensitively analyze glycan profiles, and identify changes to glycosylation between well- and moderately-differentiated components within the same nodule. Moreover, we performed immunohistochemical staining of mannosyl(α-1,3-)-glycoprotein ß-1,2-N-acetylglucosaminyltransferase (MGAT1), which is an essential glycosyltransferase that converts high-mannose glycans to complex- or hybrid-type N-glycans. RESULTS: Four lectins from Narcissus pseudonarcissus agglutinin (NPA), Concanavalin A, Galanthus nivalis agglutinin, and Calystegia sepium agglutinin were significantly elevated in moderately-differentiated components of HCC compared with well-differentiated components, and all lectins showed binding specificity to high-mannose glycans. Therefore, these structures were represented to a greater extent in moderately-differentiated components than in well-differentiated ones. Immunohistochemical staining revealed significantly increased NPA expression and decreased MGAT1 expression in moderately-differentiated components. Low MGAT1 expression in moderately-differentiated components of tumors was associated with intrahepatic metastasis and had tendency for poor prognosis. CONCLUSION: Dedifferentiation of well-differentiated HCC is associated with an increase in high-mannose glycans. MGAT1 may play a role in the dedifferentiation of HCC.


Assuntos
Carcinoma Hepatocelular/metabolismo , Concanavalina A/metabolismo , Neoplasias Hepáticas/metabolismo , Lectinas de Ligação a Manose/metabolismo , Lectinas de Plantas/metabolismo , Idoso , Calystegia/química , Carcinoma Hepatocelular/patologia , Carcinoma Hepatocelular/cirurgia , Intervalo Livre de Doença , Feminino , Glicosilação , Humanos , Imuno-Histoquímica/métodos , Neoplasias Hepáticas/patologia , Neoplasias Hepáticas/cirurgia , Masculino , N-Acetilglucosaminiltransferases/metabolismo , Narcissus/química , Imagem Óptica/métodos , Polissacarídeos/química , Coloração e Rotulagem/métodos
4.
J Microbiol ; 58(5): 357-366, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32221820

RESUMO

Strain KSNA2T, a Gram-negative, moderately halophilic, facultatively anaerobic, motile, rod-shaped bacterium, was isolated from the surface-sterilized stem tissue of a beach morning glory (Cafystegia soldanella) plant in Chuja Island, Jeju-do, Republic of Korea. Phylogenetic analysis based on 16S rRNA gene and whole-genome sequences revealed that strain KSNA2T formed a distinct lineage within the family Enterobacteriaceae, with the highest 16S rRNA gene sequence similarity to Izhakiella australiensis KCTC 72143 (96.2%) and Izhakiella capsodis KCTC 72142T (96.0%), exhibited 95.5-95.9% similarity to other genera in the family Enterobacter-iaceae and Erwiniaceae. Conserved signature indels analysis elucidated that strain KSNA2T was delimited into family Enterobacteriaceae. KSNA2 genome comprises a circular chromosome of 5,182,800 bp with 56.1% G + C content Digital DNA-DNA relatedness levels between strain KSNA2T and 18 closely related species were 19.3 to 21.1%. Average nucleotide identity values were between 72.0 and 76.7%. Growth of strain KSNA2T was observed at 4 to 45°C (optimum, 25°C) and pH 5.0 to 12.0 (optimum, pH 7.0) in the presence of 0 to 11% (w/v) NaCl (optimum, 0-7%). The major cellular fatty acids (> 10%) were C16:o followed by summed feature 8 (C18ω7c and/or C18ω6c), summed feature 3 (C16:1 ω7c and/or C16:1 ω6c), C17:0cyclo, and C14:0. The major isoprenoid quinone was ubiquinone-8 (Q-8). With combined phylogenetic, genomic, phenotypic, and chemotaxo-nomic features, strain KSNA2T represents a novel species of a new genus in the family Enterobacteriaceae, for which the name Jejubacter calystegiae gen. nov., sp. nov. is proposed. The type strain is KSNA2T (= KCTC 72234T = CCTCC AB 2019098T).


Assuntos
Calystegia/microbiologia , Enterobacteriaceae/classificação , Filogenia , Técnicas de Tipagem Bacteriana , Composição de Bases , DNA Bacteriano/genética , Endófitos/classificação , Endófitos/isolamento & purificação , Enterobacteriaceae/isolamento & purificação , Ácidos Graxos/química , Hibridização de Ácido Nucleico , RNA Ribossômico 16S/genética , República da Coreia , Análise de Sequência de DNA , Ubiquinona/química
5.
J Nat Med ; 74(1): 200-211, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31691185

RESUMO

Resin glycosides are well known as the purgative ingredients, which are characteristic of convolvulaceous plants. Calystegia hederacea Wall. is a perennial herbaceous vine that is widespread throughout India and East Asia. All parts of this plant are used for the treatment of menoxenia, gonorrhea, etc. Alkaline hydrolysis of the crude resin glycoside fraction of the whole plants of C. hederacea yielded four new glycosidic acids, calyhedic acids A, B, C, and D, along with two known glycosidic acids, calysolic acids A and C, and three known organic acids, 2S-methylbutyric, tiglic, and 2R,3R-nilic acids. Their structures were characterized on the basis of spectroscopic data and chemical evidence. Calyhedic acids A, B, and D were penta-, hexa-, and hepta-glycosides of 12S-hydroxyhexadecanoic acid, respectively, and cayhedic acid C was an isomer of calyhedic acid D, in which the 12S-hydroxyhexadecanoyl residue of calyhedic acid D was replaced by a 11S-hydroxyhexadecanoyl residue. Additionally, cytotoxic activity toward HL-60 human promyelocytic leukemia cells of the crude resin glycoside fraction, the glycosidic acid fraction, calyhedic acid A, and calysolic acid A from C. hederacea was evaluated. Furthermore, to clarify the structure-activity relationship of resin glycosides, the activities of six genuine resin glycosides with calysolic acid A or calysolic acid C as the glycosidic acid, which were isolated from C. soldanella, were examined. Among them, the crude resin glycoside fraction and five genuine resin glycosides with macrolactone structures demonstrated clear cytotoxic activities, while the glycosidic acid fraction, calyhedric acid A, calysolic acid A, and a genuine non-macrolactone-type resin glycoside were either inactive or exhibited weaker activity than the tested macrolactone-type resin glycosides.


Assuntos
Calystegia/química , Glicosídeos/química , Resinas Vegetais/química , Humanos , Hidrólise , Estrutura Molecular , Oligossacarídeos , Plantas Medicinais/química , Relação Estrutura-Atividade
6.
Sci Rep ; 9(1): 8133, 2019 05 31.
Artigo em Inglês | MEDLINE | ID: mdl-31148556

RESUMO

Convolvulus arvensis is a troublesome weed that is naturally tolerant to glyphosate. This weed tolerates glyphosate at a rate 5.1 times higher than that of glyphosate-susceptible Calystegia hederacea. Glyphosate-treated C. arvensis plants accumulated less shikimic acid than C. hederacea plants. The overexpression of EPSPS genes from the two species in transgenic Arabidopsis thaliana resulted in similar glyphosate tolerance levels. qPCR of genomic DNA revealed that the EPSPS copy number in C. arvensis was approximately 2 times higher than that in C. hederacea. Moreover, glyphosate treatment caused a marked increase in EPSPS mRNA in C. arvensis compared to C. hederacea. GUS activity analysis showed that the promoter of CaEPSPS (CaEPSPS-P) highly improved GUS expression after glyphosate treatment, while no obvious differential GUS expression was observed in ChEPSPS-P transgenic A. thaliana in the presence or absence of glyphosate. Based on the obtained results, two coexisting mechanisms may explain the natural glyphosate tolerance in C. arvensis: (i) high EPSPS copy number and (ii) specific promoter-mediated overexpression of EPSPS after glyphosate treatment.


Assuntos
3-Fosfoshikimato 1-Carboxiviniltransferase/genética , Arabidopsis/efeitos dos fármacos , Calystegia/efeitos dos fármacos , Convolvulus/efeitos dos fármacos , Regulação da Expressão Gênica de Plantas , Glicina/análogos & derivados , 3-Fosfoshikimato 1-Carboxiviniltransferase/biossíntese , Arabidopsis/enzimologia , Bioensaio , Calystegia/enzimologia , Convolvulus/enzimologia , Bases de Dados Genéticas , Relação Dose-Resposta a Droga , Tolerância a Medicamentos , Glicina/química , Resistência a Herbicidas/genética , Herbicidas/química , Plantas Geneticamente Modificadas , Reação em Cadeia da Polimerase , Pós , Regiões Promotoras Genéticas , Ácido Chiquímico/metabolismo
7.
Glycobiology ; 27(12): 1120-1133, 2017 12 01.
Artigo em Inglês | MEDLINE | ID: mdl-28973127

RESUMO

Mannose-binding type Jacalin-related lectins (mJRLs) bind to branched N-glycans via conserved sugar-binding sites. Despite, significant 3D structural similarities, each mJRL is known to have a unique binding preference toward various N-glycans. However, the molecular basis of varying binding preference is substantially unknown. Here, we report a detailed comparison of N-glycan-binding preference for two mJRLs, Orysata and Calsepa using frontal affinity chromatography (FAC), X-ray and molecular modeling. The FAC analysis using a panel of N-glycans shows difference in N-glycan-binding preference between the lectins. Orysata shows broader specificity toward most high-mannose-type glycans as well as biantennary complex-type glycans bearing an extension on the Manα1-6 branch. Whereas, Calsepa shows narrow specificity to complex-type glycans with bisecting GlcNAc. The X-ray crystallographic structure reveals that two Orysata lectins bind to one biantennary N-glycan (2:1 binding) where one lectin binds to mannose of the α1-3 branch, while the other interacts with an N-acetylglucosamine of the α1-6 branch. In contrast, Calsepa shows 1:1 binding where α1-3 branch and core chitobiose region N-glycan interacts with lectin, while α1-6 branch is flipped-back to the chitobiose core. Molecular dynamics study of Orysata bound to N-glycans substantiate possibility of two-binding modes for each N-glycan. Binding free energies calculated separately for α1-3 and α1-6 branches of each N-glycan suggest both branches can bind to Orysata. Overall these results suggest that each branch of N-glycan has a distinct role in binding to mJRLs and the nonbinding branch can contribute significantly to the binding affinity and hence to the specificity.


Assuntos
Calystegia/química , Lectinas de Ligação a Manose/química , Oryza/química , Lectinas de Plantas/química , Polissacarídeos/química , Cristalografia por Raios X , Domínios Proteicos , Estrutura Secundária de Proteína
8.
Int J Oncol ; 50(2): 414-420, 2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-28101580

RESUMO

The representative halophyte Calystegia soldanella (L) Roem. et Schult is a perennial vine herb that grows in coastal dunes throughout South Korea as well as in other regions around the world. This plant has long been used as an edible and medicinal herb to cure rheumatic arthritis, sore throat, dropsy, and scurvy. Some studies have also shown that this plant species exhibits various biological activities. However, there are few studies on cytotoxicity induced by C. soldanella treatment in HepG2 human hepatocellular carcinoma cells. In this study, we investigated the viability of HepG2 cells following treatment with crude extracts and four solvent-partitioned fractions of C. soldanella. Of the crude extract and four solvent fractions tested, treatment with the 85% aqueous methanol (aq. MeOH) fraction resulted in the greatest inhibition of HepG2 cell proliferation. Flow cytometry showed that the 85% aq. MeOH fraction induced a G0/G1 and S phase arrest of the cell cycle progression. The 85% aq. MeOH fraction arrested HepG2 cells at the G0/G1 phase in a concentration-dependent manner, and resulted in decreased expression of cyclin D1, cyclin E, cyclin-dependent kinase (CDK)2, CDK4, CDK6, p21, and p27. Additionally, the 85% aq. MeOH fraction treatment also arrested HepG2 cells in the S phase, with decreased expression of cyclin A, CDK2, and CDC25A. Also, treatment with this fraction reduced the expression of retinoblastoma (RB) protein and the transcription factor E2F. These results suggest that the 85% aq. MeOH fraction exhibits potential anticancer activity in HepG2 cells by inducing G0/G1 and S phase arrest of the cell cycle.


Assuntos
Antineoplásicos/farmacologia , Calystegia , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Fitoterapia/métodos , Extratos Vegetais/farmacologia , Western Blotting , Carcinoma Hepatocelular/patologia , Sobrevivência Celular/efeitos dos fármacos , Células Hep G2 , Humanos , Neoplasias Hepáticas/patologia
9.
Nat Prod Res ; 31(22): 2660-2664, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28105860

RESUMO

A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-ß-d-glucopyranosyl-(1 → 3)-O-(2-O-2S-methylbutyryl,4-O-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 → 2)-[O-ß-d-glucopyranosyl-(1 → 6)-O-(34-di-O-2S-methylbutyryl)-ß-d-glucopyranosyl-(1 → 3)]-O-ß-d-glucopyranosyl-(1 → 2)-ß-d-quinovopyranoside, intramolecular 1,2″'″'-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC50 value 2.3 µM.


Assuntos
Antivirais/química , Antivirais/farmacologia , Calystegia/química , Herpesvirus Humano 1/efeitos dos fármacos , Resinas Vegetais/química , Animais , Chlorocebus aethiops , Avaliação Pré-Clínica de Medicamentos/métodos , Glicosídeos/química , Glicosídeos/farmacologia , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta/química , Raízes de Plantas/química , Células Vero
10.
Ecology ; 96(1): 222-30, 2015 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26236907

RESUMO

Ants often visit flowers, but have only seldom been documented to provide effective pollination services. Floral visitation by ants can also compromise plant reproduction in situations where ants interfere with more effective pollinators. Introduced ants may be especially likely to reduce plant reproductive success through floral visitation, but existing experimental studies have found little support for this hypothesis. Here, we combine experimental and observational approaches to examine the importance of floral visitation by the nonnative Argentine ant (Linepithema humile) on plant species native to Santa Cruz Island, California, USA. First, we determine how L. humile affects floral visitor diversity, bee visitation rates, and levels of pollen limitation for the common, focal plant species island morning glory (Calystegia macrostegia ssp. macrostegia). Second, we assess the broader ecological consequences of floral visitation by L. humile by comparing floral visitation networks between invaded and uninvaded sites. The Argentine ant and native ants both visited island morning glory flowers, but L. humile was much more likely to behave aggressively towards other floral visitors and to be the sole floral occupant. The presence of L. humile in morning glory flowers reduced floral visitor diversity, decreased rates of bee visitation, and increased levels of pollen limitation. Network comparisons between invaded and uninvaded. sites revealed differences in both network structure and species-level attributes. In. invaded sites, floral visitors were observed on fewer plant species, ants had a higher per-plant interaction strength relative to that of other visitors, and interaction strengths between bees and plants were weaker. These results illustrate that introduced ants can negatively affect plant reproduction and potentially disrupt pollination services at an ecosystem scale.


Assuntos
Formigas , Abelhas , Calystegia/fisiologia , Espécies Introduzidas , Polinização , Animais , Biodiversidade , Sementes/crescimento & desenvolvimento
11.
Chem Pharm Bull (Tokyo) ; 63(8): 641-8, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26235171

RESUMO

Four new resin glycosides, named calysolins XIV (1), XV (2), XVI (3), and XVII (4) were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM.. et SCHULT. (Convolvulaceae). Their structures were determined based on spectroscopic and chemical evidence, and consisted of two different types: those (1) with a macrolactone structure and those (2-4) with a non-macrolactone structure. Their sugar moieties were partially acylated by specific organic acids, including tiglic, 2S-methylbutyric, and 2S,3S-nilic acids. Additionally, evaluation of the antiviral activity of 1-4 revealed effects against the herpes simplex virus type 1.


Assuntos
Antivirais/química , Antivirais/farmacologia , Calystegia/química , Glicosídeos/química , Glicosídeos/farmacologia , Herpesvirus Humano 1/efeitos dos fármacos , Antivirais/isolamento & purificação , Glicosídeos/isolamento & purificação , Herpes Simples/tratamento farmacológico , Humanos
12.
Nat Prod Commun ; 10(3): 429-32, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-25924521

RESUMO

Coastal species are exposed to severe environmental stresses, e.g. salt and UV-B. The plants adapt themselves to such harsh environment by controlling morphological features and chemical defense systems. Flavonoids are known as efficient anti-stress polyphenols produced by plants. Most flavonoids show antioxidant activity, and their properties are important for plants to survive under high-stress conditions such as those in a coastal area. Among the compounds, ortho-dihydroxylated flavonoids act as strong antioxidants. In this survey, we elucidated the flavonoid composition of a seashore species Calystegia soldanella, which is distributed not only on the seashore, but also by the inland freshwater lake, Lake Biwa. Seven flavonol glycosides, i.e. quercetin 3-0- rutinoside, 3-O-glucoside, 3-O-rhamnoside and 3-O-apiosyl-(1-->2)-[rhamnosyl-(1-->6)-glucoside], and kaempferol 3-O-rutinoside, 3-O-glucoside and 3-0- rhamnoside were isolated from the leaves of C. soldanella. In addition, it was shown that the quercetin (Qu) to kaempferol (Km) ratio of coastal populations was higher than that of lakeshore populations. In general, these differences of Qu/Km ratio depend on flavonoid 3'-hydroxylase (F3'H) transcription. RT-PCR analysis suggested that F3'H of C. soldanella is regulated translationally or post-translationally, but not transcriptionally. Furthermore, quantitative and qualitative differences in flavonoid composition occurred among three Calystegia species, C. soldanella, C. japonica and C. hederacea.


Assuntos
Calystegia/química , Convolvulaceae/química , Flavonoides/química , Calystegia/metabolismo , Convolvulaceae/metabolismo , Flavonoides/metabolismo , Estrutura Molecular , Especificidade da Espécie
13.
Nat Prod Commun ; 9(11): 1585-8, 2014 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-25532287

RESUMO

In this report, the PTP1B inhibitory effect of Calystegia soldanella was investigated. Bioassay-guided fractionation of the crude extracts revealed that the n-hexane fraction had the strongest PTP1B inhibitory effect. Nine known alkyl p-coumarates were isolated from the n-hexane fraction, and each compound was evaluated for its effect on PTP1B. All compounds effectively inhibited PTP1B activity. The IC50 values of the compounds were 3 (10.8 µg/mL) > 2 (15.5 µg/mL) > 7 (26.6 µg/mL) > 1 (37.0 µg/mL) > 8 (41.2 µg/mL) > 9 (43.4 µg/mL) > 5 (44.7 µg/mL) > 4 (> 50 µg/mL) > 6 (> 50 µg/mL).


Assuntos
Calystegia/química , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Animais , Hexanos/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores
14.
Chem Pharm Bull (Tokyo) ; 62(8): 839-44, 2014.
Artigo em Inglês | MEDLINE | ID: mdl-25087638

RESUMO

Four new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)-XIII (4), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The sugar moieties of 1-4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1-4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.


Assuntos
Antivirais/química , Calystegia/química , Glicosídeos/química , Herpesvirus Humano 1/efeitos dos fármacos , Lactonas/química , Resinas Vegetais/química , Antivirais/isolamento & purificação , Antivirais/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Herpes Simples/tratamento farmacológico , Humanos , Lactonas/isolamento & purificação , Lactonas/farmacologia
15.
Chem Pharm Bull (Tokyo) ; 62(1): 97-105, 2014.
Artigo em Inglês | MEDLINE | ID: mdl-24390499

RESUMO

Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.


Assuntos
Antivirais/química , Antivirais/farmacologia , Calystegia/química , Glicosídeos/química , Glicosídeos/farmacologia , Herpesvirus Humano 1/efeitos dos fármacos , Lactonas/química , Lactonas/farmacologia , Resinas Vegetais/química , Resinas Vegetais/farmacologia
16.
Oecologia ; 174(3): 651-63, 2014 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-24213627

RESUMO

Stress factors may severely constrain the range of plant physiological responses in harsh environments. Convergence of traits is expected in coastal dunes because of environmental filtering imposed by severe abiotic factors. However, the wide range of morphological and phenological traits exhibited by coexisting dune species suggests considerable variation in functional traits. We hypothesized that the constraints imposed by structural traits ought to translate into physiological differences. Five dominant species with different morphological traits, but coexisting in a homogeneous dune area in Northwest Spain, were selected for study. Soil characteristics and leaf functional traits were measured in April, June and November 2008. Integrated water-use efficiency (assessed by C isotope discrimination) and N acquisition and use strategies (estimated by N isotope composition) varied significantly among species and the differences changed over time. Species differences in specific leaf area, relative water content, leaf N and C:N ratio, also varied over time. The species differed in stomatal density but not in soil characteristics, with the exception of pH. Species differences in functional traits related to the use of resources suggest species niche segregation. Species-specific temporal effects on the use of these resources support temporal niche differentiation. Somewhat in contrast to the findings of previous studies on harsh environments, this study revealed a considerable level of functional diversity and complexity, suggesting that dune plant species have evolved species-specific strategies to survive by partitioning growth-limiting resources.


Assuntos
Ecossistema , Magnoliopsida/metabolismo , Nitrogênio/metabolismo , Folhas de Planta/metabolismo , Água/metabolismo , Calystegia/anatomia & histologia , Calystegia/metabolismo , Isótopos de Carbono/metabolismo , Eryngium/anatomia & histologia , Eryngium/metabolismo , Euphorbia/anatomia & histologia , Euphorbia/metabolismo , Magnoliopsida/anatomia & histologia , Isótopos de Nitrogênio/metabolismo , Fotossíntese , Folhas de Planta/anatomia & histologia , Estômatos de Plantas/fisiologia , Análise de Componente Principal , Solo/química , Espanha , Luz Solar
17.
J Basic Microbiol ; 53(7): 630-4, 2013 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-22961506

RESUMO

Fourteen endophytic fungi with different colony morphologies were isolated from the roots of Calystegia soldanella. Endophytic fungi isolated from C. soldanella were identified by internal transcribed spacer (ITS) region. To verify plant growth promotion (PGP), culture filtrates of isolated endophytic fungi were treated in Waito-c rice (WR) and C. soldanella seedlings. Culture filtrates of Cs-8-1 fungal strain had advanced PGP activity. The presence of physiologically bioactive gibberellins (GA) GA(1) (1.213 ng ml(-1)), GA(3) (1.292 ng ml(-1)), GA(4) (3.6 ng ml(-1)), GA(7) (1.328 ng ml(-1)), other inactive GA(9) (0.796 ng ml(-1)) and GA(12) (0.417 ng ml(-1)), GA(20) (0.302 ng ml(-1)), GA(24) (1.351 ng ml(-1)), GA(34) (0.076 ng ml(-1)), and GA(53) (0.051 ng ml(-1)) in culture filtrates of Cs-8-1 fungal strain was detected. The Cs-8-1 fungal strain was confirmed as a producer of GAs. Molecular analysis of sequences showed high similarity of 99% to Cadophora malorum. Consequentially, the Cs-8-1 fungal strain was identified as a new C. malorum producing GAs.


Assuntos
Ascomicetos/isolamento & purificação , Calystegia/microbiologia , Giberelinas/isolamento & purificação , Reguladores de Crescimento de Plantas/isolamento & purificação , Ascomicetos/metabolismo , DNA Fúngico/química , DNA Fúngico/metabolismo , Oryza/crescimento & desenvolvimento , Oryza/microbiologia , Filogenia , Raízes de Plantas/microbiologia
18.
J Chem Ecol ; 38(8): 1017-30, 2012 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-22730108

RESUMO

The Palearctic planthopper Hyalesthes obsoletus is the natural vector of the grapevine yellow disease Bois noir. Grapevine is an occasional host plant of this polyphagous planthopper. To deepen our knowledge of the role of plant volatile organic compounds for H. obsoletus host plant searching, we carried out behavioral, morphological, and electrophysiological studies. We tested the attraction of H. obsoletus to nettle, field bindweed, hedge bindweed, chaste tree, and grapevine by using a Y-shaped olfactometer. The results showed a significant attraction of male H. obsoletus to chaste tree, and of the females to nettle. Male H. obsoletus were repelled by odor from hedge bindweed. Ultrastructural studies of the antennae showed at least two types of olfactory sensilla at the antennal pedicel: plaque organs and trichoid sensilla. Volatile organic compounds from nettle and chaste tree were collected, and the extracts were analyzed by coupling gas-chromatography to both mass-spectrometry and electroantennography. The volatile organic compounds that elicited electrophysiological responses in male and female antennae were identified. These findings are discussed with respect to behavior of H. obsoletus males and females in the field.


Assuntos
Hemípteros/fisiologia , Compostos Orgânicos Voláteis/farmacologia , Animais , Comportamento Animal/efeitos dos fármacos , Calystegia/química , Convolvulus/química , Fenômenos Eletrofisiológicos , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Hemípteros/efeitos dos fármacos , Masculino , Odorantes , Percepção , Urtica dioica/química , Vitex/química , Vitis/química , Compostos Orgânicos Voláteis/química
19.
J Biosci ; 36(5): 793-808, 2011 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-22116277

RESUMO

Dimeric banana lectin and calsepa, tetrameric artocarpin and octameric heltuba are mannose-specific beta-prism I fold lectins of nearly the same tertiary structure. MD simulations on individual subunits and the oligomers provide insights into the changes in the structure brought about in the protomers on oligomerization, including swapping of the N-terminal stretch in one instance. The regions that undergo changes also tend to exhibit dynamic flexibility during MD simulations. The internal symmetries of individual oligomers are substantially retained during the calculations. Energy minimization and simulations were also carried out on models using all possible oligomers by employing the four different protomers. The unique dimerization pattern observed in calsepa could be traced to unique substitutions in a peptide stretch involved in dimerization. The impossibility of a specific mode of oligomerization involving a particular protomer is often expressed in terms of unacceptable steric contacts or dissociation of the oligomer during simulations. The calculations also led to a rationale for the observation of a heltuba tetramer in solution although the lectin exists as an octamer in the crystal, in addition to providing insights into relations among evolution, oligomerization and ligand binding.


Assuntos
Simulação de Dinâmica Molecular , Lectinas de Plantas/química , Sequência de Aminoácidos , Artocarpus , Calystegia , Cristalografia por Raios X , Helianthus , Ligação de Hidrogênio , Modelos Moleculares , Dados de Sequência Molecular , Complexos Multiproteicos , Musa , Ligação Proteica , Multimerização Proteica , Estrutura Quaternária de Proteína , Estrutura Secundária de Proteína , Homologia Estrutural de Proteína , Termodinâmica
20.
J Nat Prod ; 74(11): 2414-9, 2011 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-21992192

RESUMO

Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella , along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.


Assuntos
Calystegia/química , Glicosídeos/isolamento & purificação , Resinas Vegetais/isolamento & purificação , Sequência de Carboidratos , Glicosídeos/análise , Glicosídeos/química , Estrutura Molecular , Folhas de Planta/química , Raízes de Plantas/química , Caules de Planta/química , Resinas Vegetais/análise , Resinas Vegetais/química
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