RESUMO
There is substantial interest regarding the understanding and designing of nanoengineered bacteria to combat various fatal diseases. Here, we report the nanoengineering of Bifidobacterium bifidum using Cremophor EL to encapsulate organic dye molecules by simple incubation and washing processes while maintaining the bacterial morphology and viability. The prepared functional bacteria exhibit characteristics such as optical absorbance, unique fluorescence, powerful photothermal conversion, low toxicity, excellent tumor targeting, and anticancer efficacy. They also displayed significant in vivo fluorescent expression in implanted colorectal cancerous tumors. Moreover, the powerful photothermal conversion of the functional bacteria could be spatiotemporally evoked by biologically penetrable near-infrared laser for effective tumor regression in mice, with the help of immunological responses. Our study demonstrates that a nanoengineering approach can provide the strong physicochemical traits and attenuation of living bacterial cells for cancer immunotheranostics.
Assuntos
Bifidobacterium bifidum , Nanopartículas , Neoplasias , Animais , Linhagem Celular Tumoral , Fluorescência , Camundongos , Nanopartículas/química , Rotação Ocular , FototerapiaRESUMO
A phytochemical investigation was conducted on Euphorbia helioscopia, resulting in the isolation of thirteen compounds, including nine undescribed diterpenoids, Euphzycopias A - I (1-9), of which the skeletons of compounds 1-4 were found in E. helioscopia L. Compounds 1-3 had 5/7/6 cyclic systems, while compound 4 had a 4/11 polycyclic system with a 4,7-cyclic ether between C-4 and C-7. The anti-inflammasome test using the isolated compounds (1-6, 8-13) showed that the diterpenes from E. helioscopia L. had a strong inhibitory effect on NLRP3 inflammasomes with IC50 values of 3.34-14.92 µM.
Assuntos
Diterpenos/farmacologia , Euphorbia/química , Inflamassomos/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Humanos , Inflamassomos/química , Inflamassomos/isolamento & purificação , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Proteína 3 que Contém Domínio de Pirina da Família NLR/antagonistas & inibidores , Rotação Ocular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Espectrofotometria InfravermelhoRESUMO
Three new limonoids, walsurauias A-C (1-3), along with four known ones, were isolated from the leaves and twigs of Walsura yunnanensis C. Y. Wu. Their structures were determined on the basis of comprehensive spectroscopic data analysis. The new limonoids were screened for their cytotoxic activity (IC50 0.81-5.73 µM) against four human cancer cell lines, including A549, HepG2, HCT116 p21KO and CNE-2. And α,ß-unsaturated ketone moieties in rings A and B are essential for their cytotoxic activity. Selected compounds were further investigated. Compounds 1-3 effectively induced G2/M cell cycle arrest and apoptosis in a dose-dependent manner in cancer cells. In addition, compounds 1-3 inhibited the colony formation and compounds 2 and 3 suppressed the migration of cancer cells.
Assuntos
Limoninas/toxicidade , Meliaceae/química , Apoptose , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Fina , Citometria de Fluxo , Humanos , Concentração Inibidora 50 , Limoninas/química , Limoninas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Rotação Ocular , Folhas de Planta/química , Caules de Planta/química , Espectrofotometria Infravermelho , Cicatrização/efeitos dos fármacosRESUMO
Melodicochinines A - D (1-4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7).
Assuntos
Apocynaceae/química , Extratos Vegetais/química , Alcaloides de Triptamina e Secologanina/isolamento & purificação , China , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Rotação Ocular , Extratos Vegetais/isolamento & purificação , Caules de Planta/química , Alcaloides de Triptamina e Secologanina/química , Espectrofotometria InfravermelhoRESUMO
Two unprecedented ent-18,19-dinoricetexane diterpenoid glycosides, named abieshanesides A (1) and B (2), together with seven known compounds, have been isolated from the dead trunks and branches of Abies beshanzuensis M.H. Wu. To our knowledge, abieshanesides A and B represent the first ent-18,19-dinoricetexane diterpenoid glycosides found in natural sources. Their structures and absolute configurations were elucidated by using a combination of spectroscopic techniques and comparison of experimental and calculated electronic circular dichroism (ECD) data. The MTT experiments showed that (E)-resveratrol (7) could inhibit viability of MH7A cells with the IC50 value of 12.5 µM. Compound 7 was able to block MH7A cell proliferation and was associated with G0/G1-phase cell cycle arrest. Flow cytometric analysis showed that the treatment by 7 significantly induced the proliferation of MH7A cells in a dose-dependent manner.
Assuntos
Abies/química , Diterpenos/química , Glicosídeos/química , Linhagem Celular , Sobrevivência Celular , China , Diterpenos/isolamento & purificação , Glicosídeos/isolamento & purificação , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Rotação Ocular , Caules de Planta/químicaRESUMO
Marine-derived fungi can usually produce structurally novel and biologically potent metabolites. In this study, a new diketopiperazine alkaloid (1) and two new polyketides (10 and 11), along with 8 known diketopiperazine alkaloids (2-9) were isolated from marine-derived fungus Penicillium sp. TW58-16. Their structures were fully elucidated by analyzing UV, IR, HR-ESI-MS, 1D, and 2D NMR spectroscopic data. The absolute configurations of the new compounds 1, 10 and 11 were ascertained by X-ray diffraction (Cu Kα radiation) and comparing their CD data with those reported. In addition, the antibacterial activities of these compounds against Helicobacter pylori in vitro were assessed. Results showed that compounds 3, 6, 8 and 9 displayed moderate antibacterial activity against standard strains and drug-resistant clinical isolates of H. pylori in vitro. This result demonstrates that diketopiperazine alkaloids could be lead compounds to be explored for the treatment of H. pylori infection.
Assuntos
Alcaloides/farmacologia , Antibacterianos/farmacologia , Dicetopiperazinas/farmacologia , Helicobacter pylori/efeitos dos fármacos , Penicillium/química , Policetídeos/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Antibacterianos/química , Antibacterianos/isolamento & purificação , Cromatografia em Gel , Cromatografia Líquida , Cristalografia por Raios X , Dicetopiperazinas/química , Dicetopiperazinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Rotação Ocular , Policetídeos/química , Policetídeos/isolamento & purificação , Água do Mar , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , TaiwanRESUMO
Ten undescribed cadinane-type sesquiterpenes (1-10) were isolated from the whole plant of Eupatorium chinense. Their planar structures were mainly elucidated by extensive analysis of spectroscopic data and DFT NMR calculations. The absolute configurations of 1, 2, and 3 were determined by TDDFT ECD calculations while those of compounds 4-7 and 9 were confirmed by single crystal X-ray diffraction experiments. Compounds 2 and 3 are a pair of C-10 epimers, compounds 4 and 5 a pair of C-1 epimers, and compounds 9 and 10 a pair of compounds isomerized at both C-1 and C-10. A possible biosynthetic pathway for these new sesquiterpenes was proposed.
Assuntos
Asteraceae/química , Extratos Vegetais/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Rotação Ocular , Extratos Vegetais/química , Extratos Vegetais/metabolismo , Sesquiterpenos/química , Sesquiterpenos/metabolismo , Espectroscopia de Infravermelho com Transformada de Fourier , Difração de Raios XRESUMO
Two new isoquinoline alkaloids, cryptowrayines A (1) and B (2), along with one known pavine alkaloid (-)-12-hydroxyeschscholtzidine (3), were isolated from the twigs of Cryptocarya wrayi. The structures of new compounds were elucidated by extensive spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Both compounds 1 and 2 exhibited moderate quinone reductase inducing activity in Hepa 1c1c7 cells.
Assuntos
Alcaloides/isolamento & purificação , Cryptocarya/química , Isoquinolinas/isolamento & purificação , Alcaloides/química , Alcaloides/metabolismo , Glucosidases/antagonistas & inibidores , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/metabolismo , Concentração Inibidora 50 , Isoquinolinas/química , Isoquinolinas/metabolismo , Espectroscopia de Ressonância Magnética , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/análise , Rotação OcularRESUMO
Five new iridal-type triterpenoid derivatives with 6/5/6 tricyclic ring skeleton (1-5) were obtained from the rhizomes of Belamcanda chinensis. Their structures were determined on the basis of detailed spectroscopic data and ECD calculation. Compounds 1-5 possessed the same 6/5/6-fused carbon skeleton as Belamchinenin A, which further enriched this kind of iridals. In vitro bioassay, compounds 2 and 3 exhibited 51.95 and 54.52% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 µM. A putative biogenetic pathway for compounds 1-5 was proposed.
Assuntos
Antioxidantes/metabolismo , Iridaceae/química , Rizoma/química , Triterpenos/química , Triterpenos/isolamento & purificação , Bioensaio , Dicroísmo Circular , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Rotação Ocular , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , Triterpenos/metabolismo , Triterpenos/toxicidadeRESUMO
Juniperus formosana Hayata (J. formosana) is a commom needlebush cultivar growing in China. Six new compounds (1-6), including four cadinene sesquiterpenoids (1-4), one abietane diterpenoid (5), and one ß-naphthol derivative (6), along with 18 known compounds (7-24) were isolated and identified through phytochemical investigation on the heartwood of J. formosana. The structures of these compounds were fully elucidated by their 1D and 2D NMR, HR-ESI-MS, UV, and IR spectral data analyses. The absolute configurations of compounds 1, 3, and 5 were confirmed by experimental and calculated electronic circular dichroism (ECD) data. Moreover, X-ray crystallographic analysis was carried out to characterize the structure of compound 4. The inhibitory effects on the nitric oxide (NO) production of all the isolated compounds were initially examined in RAW264.7 macrophages induced by lipopolysaccharide (LPS). The results showed that compounds 3 and 12 possessed significant inhibitory potency on NO generation with IC50 values of 3.41 µM and 6.15 µM among the new and known compounds, respectively. The expressions of IL-1ß, IL-6, and TNF-α were measured in LPS-stimulated RAW264.7 cells to evaluate the anti-inflammatory effects of compounds 1-24. Compounds 1-6 and 9-12 exhibited potent anti-inflammatory effects. Additionally, the expressions of p38, Erk, and IκBα proteins were further determined to explore the anti-inflammatory mechanism of the most potent compounds 3 and 12. Overall, our findings indicate the potential of J. formosana for developing medicine candidates as the treatments of inflammation.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Juniperus/química , Sesquiterpenos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Western Blotting , Cromatografia em Camada Fina , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Rotação Ocular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho , Madeira/químicaRESUMO
Chemical fractionation of the EtOH extract of a medicinal macro fungus, Inonotus obliquus, afforded an array of lanostane-type triterpenoids (1-11) including two new ones (1 and 8). The structures of these compounds were determined on the basis of spectroscopic analyses, single crystal X-ray crystallography of 3-6 and biosynthetic considerations. With the confirmatory structural information provided by X-ray diffraction analysis in hand, several previously reported 21,24-cyclolanostanes, such as inonotsutriols A-C and (20R,21S,24S)-21,24-cyclopenta-3ß,21,25-trihydroxylanosta-8-ene, were structurally corrected. In addition, the NMR data of other types of 21,24-cyclo triterpenoids were also re-examined and structural revisions were thus suggested. Compounds 2, 6 and 8 showed significant cytostatic effects against a panel of tumor cell lines with IC50 values ranging from 7.80 to 18.5 µM. Further assays established that compound 2 exerted promising in vitro anti-breast cancer potential by inhibiting the proliferation and migration of 4T1 cells.
Assuntos
Inonotus/química , Triterpenos/isolamento & purificação , Bioensaio , Linhagem Celular , Sobrevivência Celular , Cristalografia por Raios X , Carpóforos/química , Concentração Inibidora 50 , Estrutura Molecular , Rotação Ocular , Triterpenos/química , Triterpenos/metabolismo , Triterpenos/toxicidade , Difração de Raios XRESUMO
Eight new compounds (1-8), along with three known related compounds (9-11) were isolated from the leaves of Sauropus spatulifolius Beille. Their structures and configurations were elucidated by means of spectrometric and the modified Mosher's method. Among the new compounds, compounds 1 and 2 were identified as ethyl 3, 6-anhydro-2-deoxy-ß-D-arabino-hexofuranoside (1) and ethyl 3, 6-anhydro-2-deoxy- hexofuranoside (2). Compounds 3-5 were the 2-acetylpyrrole derivatives and identified as 2-(2-acetyl-1H-pyrrol-1-yl)-4-hydroxybutyric acid (3), methyl 4-(2-acetyl-lH-pyrrol- 1-yl) butanoate (4) and 1, 4-bis (2-acetyl-1H-pyrrol-1-yl) butane (5), respectively. Compound 6 was elucidated as 7-megastigmane-3, 8, 9-triol. Compounds 7, 8 were identified as kaempferol-3-O-2-deoxy-ß-D-glucoside (7) and kaempferol-3-O-ß-D- glucopyranosyl-(1-6)-2-deoxy-ß-D-glucoside (8). In addition, the cytotoxic activities of all the compounds were also evaluated, where compounds 3, 5, 7, 9\10 and 11 exhibited the magnificent inhibition activity on lung fibroblast differentiation induced by TGF-ß1with low toxicity against the RLE-6TN cell.
Assuntos
Flavonoides/isolamento & purificação , Glicosídeos/isolamento & purificação , Malpighiales/metabolismo , Extratos Vegetais/isolamento & purificação , Animais , Bioensaio , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular , Fibroblastos/citologia , Fibroblastos/efeitos dos fármacos , Flavonoides/química , Flavonoides/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Pulmão/citologia , Pulmão/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Malpighiales/química , Camundongos , Estrutura Molecular , Rotação Ocular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Folhas de Planta/metabolismo , CoelhosRESUMO
A phytochemistry of the whole plant of Agrimonia pilosa led to the discovery of two new nortriterpenoids, agrimonorterpenes A and B (1 and 2), together with one known triterpenoid fupenzic acid (3) and seven known sesquiterpenoids (4-10). The new structures were determined as 19α-hydroxy-2-oxo-nor-A (3)-urs-11,12-dien-28-oic acid (1) and 2, 19ß-dihydroxy-3-oxo-23-noroleana-1, 4, 12-trien-28-oic acid (2) by the spectroscopic data of UV, IR, HR-ESI-MS, and NMR. Notably, the structure of 1 possessed a rare five-membered A- ring. And this is the first time to discover the sesquiterpenoids (4-10) from A. pilosa. Compound 3 displayed the selective cytotoxicity against HCT116, BGC823, and HepG2 cell lines with the IC50 values of 16.31 µM, 21.94 µM, and 23.40 µM, respectively.
Assuntos
Agrimonia/química , Sesquiterpenos/isolamento & purificação , Triterpenos/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/toxicidade , Espectroscopia de Ressonância Magnética , Rotação Ocular , Sesquiterpenos/química , Sesquiterpenos/toxicidade , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Triterpenos/química , Triterpenos/toxicidadeRESUMO
Seven new merosesquiterpenoids, trichothecrotocins D-J (1-7), two new trichothecene sesquiterpenoids, trichothecrotocins K (12) and L (13), and six known compounds (8-11, 14, and 15), were isolated from a potato-associated fungus, Trichothecium crotocinigenum. Compounds 5 and 6 were racemates which were further separated as pure enantiomers. Structures together with absolute configurations were established by extensive spectroscopic analysis, as well as quantum chemistry calculations on ECD and optical rotations. Compounds 1-4 are rare meroterpenoids featuring a seco-phenyl group, while 1 and 2 possessed a novel 6-6/5 fused ring system. Compounds 1-4, 8, 11, and 12 showed antifungal activity against four plant pathogens with MIC values of 8-128 µg/mL. It is suggested that the meroterpenoids produced by T. crotocinigenum may play an important role in the antifungal property of the fungus, thereby protecting the host plant, i.e., potato.
Assuntos
Antifúngicos/química , Antifúngicos/farmacologia , Hypocreales/química , Solanum tuberosum/microbiologia , Fermentação , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Rotação Ocular , Doenças das Plantas/microbiologia , EstereoisomerismoRESUMO
Eight pairs of enantiomeric neolignans, norlignans, and sesquineolignans (1a/1b-8a/8b), together with five known neolignans (9a/9b and 10-12), have been isolated from 70% acetone extract of the whole plants of Phyllanthus glaucus Wall. (Euphorbiaceae). The racemic or partial racemic mixtures were successfully separated by chiral HPLC using different types of chiral columns with various mobile phases. Their structures were elucidated on the basis of extensive spectroscopic data. The absolute configurations of 2a/2b were determined by computational analysis of their electronic circular dichroism (ECD) spectrum, and the absolute configurations of other isolates were ascertained by comparing their experimental ECD spectra and optical rotation values with those of structure-relevant compounds reported in literatures. Compounds 4a/4b featured unique sesquineolignan skeletons with a novel 7-4'-epoxy-8'-8''/7'-2'' scaffold, consisting of an aryltetrahydronaphthalene and a dihydrobenzofuran moiety. The planar structures of compounds 2, 3, 7, and 8 were documented previously; however, their absolute configurations were established for the first time in this study. The antioxidant activities of 1a/1b-8a/8b were evaluated using DPPH free radical scavenging assay, and the results demonstrated that compounds 1b and 3b showed potent DPPH radical scavenging activities with IC50 values of 5.987 ± 1.212 and 9.641 ± 0.865 µg/mL, respectively.
Assuntos
Lignanas/química , Phyllanthus/química , Extratos Vegetais/química , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Conformação Molecular , Rotação Ocular , Phyllanthus/metabolismo , Extratos Vegetais/isolamento & purificação , Espectrofotometria Ultravioleta , EstereoisomerismoRESUMO
A unique method to produce highly optically-active l-lactic acid and soil amendments that promote plant growth from food waste was proposed. Three Bacillus strains Bacillus subtilis KBKU21, B. subtilis N3-9 and Bacillus coagulans T27, were used. Strain KBKU21 accumulated 36.9 g/L l-lactic acid with 95.7% optical activity and 98.2% l-lactic acid selectivity when fermented at 43°C for 84 h in a model kitchen refuse (MKR) medium. Residual precipitate fraction (anaerobically-fermented MKR (AFM) compost) analysis revealed 4.60%, 0.70% and 0.75% of nitrogen (as N), phosphorous (as P2O5), and potassium (as K2O), respectively. Additionally, the carbon to nitrogen ratio decreased from 13.3 to 10.6. AFM compost with KBKU21 promoted plant growth parameters, including leaf length, plant height and fresh weight of Brassica rapa (Komatsuna), than that by chemical fertilizers or commercial compost. The concept provides an incentive for the complete recycling of food waste, contributing towards a sustainable production system.
Assuntos
Bacillus/metabolismo , Brassica rapa/crescimento & desenvolvimento , Brassica rapa/metabolismo , Resíduos de Alimentos , Ácido Láctico/química , Ácido Láctico/metabolismo , Solo/química , Bacillus/classificação , Reatores Biológicos , Carbono/análise , Carbono/metabolismo , Fermentação , Fertilizantes , Alimentos , Ácido Láctico/biossíntese , Nitrogênio/análise , Nitrogênio/metabolismo , Rotação Ocular , Fósforo/análise , Potássio/análise , Reciclagem , Microbiologia do SoloRESUMO
A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 µM) in the range of 81.5-7.2â%. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14 mM.
Assuntos
Ácidos Cafeicos/química , Cinamatos/química , Dipeptidil Peptidase 4/química , Serina Endopeptidases/química , Inibidores de Serina Proteinase/química , Ácidos Cafeicos/isolamento & purificação , Cinamatos/isolamento & purificação , Dipeptidil Peptidase 4/isolamento & purificação , Espectrometria de Massas , Ressonância Magnética Nuclear Biomolecular , Rotação Ocular , Prolil OligopeptidasesRESUMO
Structural elucidation of natural products is always one of the most important tasks for natural product researchers in related fields. Particularly, the absolute configuration (AC), being a great challenge for natural product chemists, has attracted much attention. During the past few decades, many techniques and approaches have been developed to determine the AC of natural products, including direct (or absolute) methods, e.g. X-ray diffraction (XRD), electronic and vibrational circular dichroism (ECD and VCD), and Raman optical activity (ROA), as well as indirect (or relative) methods using a reference or a derivatizing agent with known AC, e.g. CD with empirical rules and nuclear magnetic resonance (NMR) utilizing anisotropic effects of chiral derivatizing agents. However, none of the currently applied techniques is capable of dominating AC determination, since they each have their respective limitations corresponding to the different structural features. This mini review summarizes most of the techniques and methods which are commonly used in AC assignment of natural products, or have potential application prospects, and briefly describes their principles, advantages and limitations.
Assuntos
Produtos Biológicos/química , Dicroísmo Circular , Estrutura Molecular , Rotação Ocular , Difração de Raios XRESUMO
Chemical investigation of the insect-derived actinomycete Amycolatopsis sp. HCa1 with NMR-guided fractionation led to the isolation of eight new tetrasaccharide derivatives containing an unusual nonreducing glucotetraose skeleton, named actinotetraoses A-H (1-8), and one known compound, tigloside (9). The structures of these compounds were determined on the basis of analyses of their spectroscopic data. The in vitro immunosuppressive activity and cytotoxicity of these compounds were evaluated by T cell viability and MTT assays, respectively. Only actinotetraose E (5) displayed weak immunosuppressive activity.
Assuntos
Actinobacteria/química , Gafanhotos/microbiologia , Imunossupressores/isolamento & purificação , Oligossacarídeos/isolamento & purificação , Linfócitos T/efeitos dos fármacos , Actinobacteria/isolamento & purificação , Animais , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Células HeLa , Células Hep G2 , Humanos , Imunossupressores/química , Imunossupressores/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Micélio/química , Oligossacarídeos/química , Oligossacarídeos/farmacologia , Rotação OcularRESUMO
The dichloromethane extract from taproots of Hortia oreadica afforded six limonoids, these are 9,11-dehydro-12α-acetoxyhortiolide A, hortiolide C, 11α-acetoxy-15-deoxy-6-hydroxyhortiolide C, hortiolide D, hortiolide E, 12ß-hydroxyhortiolide E, in addition to the known limonoid, guyanin. The dichloromethane extract from stems of H. oreadica also afforded two limonoids 9,11-dehydro-12α-hydroxyhortiolide A and 6-hydroxyhortiolide C. As a result of this study and literature data, Hortia has been shown to produce highly specialized limonoids that are similar to those from the Flindersia (Flindersioideae). The taxonomy of Hortia has been debatable, with most authors placing it in the Toddalioideae. Considering the complexity of the isolated limonoids, Hortia does not show any close affinity to the genera of Toddalioideae. That is, the limonoids appear to be of little value in resolving the taxonomic situation of Hortia.