RESUMO
The Heracleum sosnowskyi is a highly invasive plant species known for its rapid spread and the significant threat it poses to the ecosystem and human health, primarily due to its furanocoumarin content. In the present study, for the first time the pyrolysis process (200-600 °C) of Heracleum was conducted, demonstrating its efficacy in utilizing the material as feedstock and generating valuable solid by-products. It was found that biochar produced at temperatures of 200-300 °C is suitable for solid fuel production (HHV 20.2-24.1 MJ·kg-1) and has strong hydrophobic properties, while pyrolysis over 400 °C promotes the improvement of fertilizing properties by increasing the content of micro and macronutrients (K=112.4 g·kg-1 at 600 °C). The mass and energy analysis proved that in specific conditions (for dry > 300 °C; for wet > 400 °C), pyrolysis can be an effective way for Heracleum biomass conversion into valuable biochar without the need for external energy.
Assuntos
Carvão Vegetal , Heracleum , Pirólise , Carvão Vegetal/química , Heracleum/química , Biomassa , Meio AmbienteRESUMO
Sosnowski hogweed is an invasive weed in eastern-middle Europe that is dangerous to human health and the environment. The efficacy of its control using chemical and mechanical methods is limited. Electromagnetic radiation (microwaves) could be an environmentally friendly alternative for controlling this species. This study aims to: (1) Determine the effect of varying microwave treatment (MWT) durations on the control of S. hogweed using a device emitting microwaves at 2.45 GHz, 32.8 kW/m2; (2) Evaluate the impact of MWT on soil by an ecotoxicological bioassays; (3) Analyze biochemical changes occurring in the roots during the process. A field study was performed to assess the efficacy of S. hogweed control using MWT in times from 2.5 to 15 min. The MWT-treated soil was collected immediately after treatment (AT) and tested using bioassays (Phytotoxkit, Ostracodtoxkit, and Microtox). Fourteen days AT, the MWT hogweed roots were dug out, air-dried, and analyzed for the content and composition of essential oil, sugars, and fatty acids. According to the ecotoxicological biotests, the MWT soils were classified as non-toxic or low-toxic. The regeneration of hogweed was observed only in non-treated plants (control). Hogweed MWT for 2.5-15 min did not regenerate up to 14 days AT. The average weight of roots in hogweed MWT for 15.0 min was ca. two times smaller than the control plants. Those roots contained significantly higher amounts of sugars and saturated fatty acids than the control. We did not find a correlation between S. hogweed root essential oil content and composition and MWT time. The main compounds of essential oil were pcymene and myristicin. No highly photosensitizing compounds were identified in the tested root oil. We conclude that MWT of S. hogweed could be an environmentally safe and prospective control method, but more studies are needed.
Assuntos
Ecotoxicologia , Heracleum , Micro-Ondas , Raízes de Plantas , Raízes de Plantas/efeitos da radiação , Raízes de Plantas/efeitos dos fármacos , Heracleum/química , Ecotoxicologia/métodos , Solo/química , Plantas Daninhas/efeitos da radiação , Plantas Daninhas/efeitos dos fármacos , Óleos Voláteis/farmacologia , Ácidos Graxos/análiseRESUMO
There are various types of bioactivities that have been reported for Heracleum persicum species, such as antioxidant, anti-inflammatory, and cytotoxicity properties. In the current study, the bio-accessibility of H. persicum bioactive compounds was improved by purifying its phenolic-enriched fractions (PEF) and encapsulating them into nanoliposomes to analyze its cytotoxic impacts on mice testicular tissue and their fertility status. Nano liposomal H. persicum PEF (NL-HPEF) was prepared by ultrasound-based encapsulation of HPEF and L-agranular lecithin mixture. The size, morphology, and stability of NL-HPEF were characterized by dynamic light scattering, field emission scanning electron microscopy, and zeta potential analysis. The 18 white male Balb/c mice (20-25 g) at 3 treatment groups were provided to study the NL-HPPF cytotoxicity by measuring the mice liver enzyme including aspartate aminotransferase (AST), ALP and alanine aminotransferase (ALT), testis lipid peroxidation, and testicular tissue destruction levels. Moreover, the mice's fertility was evaluated by studying the Adam3, Prm1, Spata19, and Tnp2 gene expression in the testicular tissues. The obtained results manifested that the synthesized NL-HPEF was stable (193.7 nm) and exhibited a notable cytotoxic impact on the mice's liver (ALT and AST enhancement levels) and testicular tissues. Moreover, their increasing treatment doses impaired the male mice's fertility by decreasing the sperm count, viability, and motility. In addition, fertility suppression was verified by decreasing serum testosterone and downregulating the Adam3, Prm1, Spata19, and Tnp2 gene expression in their testicular tissues. The male mice's fertility was significantly (p < 0.05) suppressed by increasing treatment doses of NL-HPEF. Hence, the NL-HPEF could be considered a promising alternative to replace the male chemical contraceptives drugs.
Assuntos
Heracleum , Masculino , Camundongos , Animais , Heracleum/química , Camundongos Endogâmicos BALB C , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Sementes , EspermatogêneseRESUMO
BACKGROUND: One of the most important aromatic species of the Apiaceae family is Heracleum persicum Desf. ex Fisch., C.A.Mey. & Avé-Lall, which used as a spice and condiment in food. It is widely used in traditional Iranian medicine due to its anti-toxic properties. The aim of this study was to evaluate the essential oil of this plant in terms of content and ingredients, cytotoxicity and antimicrobial activity. METHODS: The fruit of H. persicum was collected in June 2019 from Maragheh region of Kashan, Iran. The essential oil was extracted by water distillation using Clevenger for 3 h. Identification analysis of H. persicum fruit essential oil (HPFEO) components was performed using gas chromatography-mass spectrometry (GC-MS). Evaluation of the effect of the HPFEO on the growth and proliferation of ovarian cancer cell line (OVCAR-3) was performed using MTT colorimetric method. Its antimicrobial activity was evaluated by agar diffusion method, minimum inhibitory concentration (MIC) and minimum bactericidal/fungal lethality concentration (MBC/MFC). RESULTS: The results of analysis of the HPFEO by GC-MS showed that there were 35 compounds with 99.54% relative content. Hexyl butyrate (35.24%), octyl 2-methylbutyrate (11.65%), octyl isobutyrate (9.23%), and octyl acetate (8.42%) were the predominant compounds. Examination of cell survival showed that the viability of cells decreased depending on the concentration of the HPFEO in 24 h and had value of IC50 ~ 12.08 µg/ml against OVCAR-3 cell line. The strongest inhibitory activity of the HPFEO was against Gram-negative bacteria Pseudomonas aeruginosa and Salmonella paratyphi-A serotype (MIC < 62.50 µg/mL). Also, the strong inhibitory and lethal activity of this essential oil against Candida albicans (MIC and MBC 250 µg/mL was one degree weaker compared to nystatin (MIC = 125 µg/mL). CONCLUSIONS: Thus, HPFEO, in addition to its traditional use, may have a strong and potential potential for the production of anti-proliferative and antimicrobial drugs.
Assuntos
Anti-Infecciosos , Heracleum , Óleos Voláteis , Neoplasias Ovarianas , Feminino , Humanos , Heracleum/química , Óleos Voláteis/química , Frutas/química , Irã (Geográfico) , Apoptose , Linhagem Celular Tumoral , Neoplasias Ovarianas/tratamento farmacológico , Anti-Infecciosos/químicaRESUMO
Heracleum persicum Desf. ex Fischer seeds are a rich source of essential oils (EOs) with high antimicrobial and antioxidant effects. In order to determine the phytochemical variability in various Iranian H. persicum populations, seed samples were collected from 10 different climatic locations. The current study indicated that hexyl butyrate (20.9-44.7%), octyl acetate (11.2-20.3%), hexyl-2-methylbutyrate (4.81-8.64%), and octyl 2-methyl butyrate (3.41-8.91%) were the major components of the EOs. The maximum (44.7%) and the minimum (20.9%) content of hexyl butyrate were obtained from Kaleibar and Sari populations, respectively. Moreover, the octyl acetate content ranged from 2% (in Mahdasht) to 20.3% in Torghabeh population. The CA and PCA analysis divided the 10 Iranian H. persicum populations into three major groups. Populations from Khanghah, Kaleibar, Shebeilo, Showt, Mahdasht, and Amin Abbad showed a distinct separation in comparison with the other populations, having high contents of hexyl butyrate (39.8%) and low contents of octyl acetate (13.5%) (Chemotype II). According to correlation analysis, the highest correlation coefficient was among habitat elevation and hexyl butyrate content. In addition, the mean annual precipitation was negatively correlated with the content of hexyl butyrate. Although octyl acetate content showed high correlation with soil EC and mean annual temperature, it was not statistically significant. In general, in order to have plants with a high content of hexyl butyrate, it is recommended to harvest these plants from regions with high altitude and low rainfall such as Kaleibar.
Assuntos
Anti-Infecciosos , Heracleum , Óleos Voláteis , Acetatos , Antioxidantes , Butiratos , Heracleum/química , Irã (Geográfico) , Óleos Voláteis/química , SoloRESUMO
Sosnovsky's hogweed, Heracleum sosnowskyi has a high photosensitizing ability. Although Sosnovsky's hogweed is known as a poisonous plant, its chemical composition and phototoxicity are poorly studied. We analyzed the chemical composition of the Sosnovsky's hogweed juice that grew in natural conditions. It was found that the content of 8-methoxypsoralen in the juice is 1332.7 mg/L, and that of 5-methoxypsoralen is 34.2 mg/L. We have developed and analyzed liposomes containing furanocoumarins of Sosnovsky's hogweed juice and studied their photocytotoxicity in L929 mouse fibroblast cell culture. It was found that liposomes containing furanocoumarins of Sosnovsky's hogweed juice are more toxic for L929 cells in comparison with liposomal forms of pure substances 8-methoxypsoralen and 5-methoxypsoralen. It was found that when exposed to UV radiation at 365 nm at a dose of 22.2 J/cm2, the liposomal form of furanocoumarins Sosnovsky's hogweed is 3 times more toxic to L929 cells than in the dark. It was found that the photocytotoxic effect of liposomal furanocoumarins Sosnovsky's hogweed is a strongly stimulation of apoptosis.The data obtained suggest that the raw material of Sosnovsky's hogweed claims to be a source of furanocoumarins, and the liposomal form, given the hydrophobic properties of furanocoumarins, is very suitable for creating a phototherapeutic drug.
Assuntos
Furocumarinas , Heracleum , Animais , Furocumarinas/toxicidade , Heracleum/química , Lipossomos , Metoxaleno , Camundongos , Raios UltravioletaRESUMO
The study aims to develop gel beads with improved functional properties and biocompatibility from hogweed (HS) pectin. HS4 and AP4 gel beads were prepared from the HS pectin and apple pectin (AP) using gelling with calcium ions. HS4 and AP4 gel beads swelled in PBS in dependence on pH. The swelling degree of HS4 and AP4 gel beads was 191 and 136%, respectively, in PBS at pH 7.4. The hardness of HS4 and AP4 gel beads reduced 8.2 and 60 times, respectively, compared with the initial value after 24 h incubation. Both pectin gel beads swelled less in Hanks' solution than in PBS and swelled less in Hanks' solution containing peritoneal macrophages than in cell-free Hanks' solution. Serum protein adsorption by HS4 and AP4 gel beads was 118 ± 44 and 196 ± 68 µg/cm2 after 24 h of incubation. Both pectin gel beads demonstrated low rates of hemolysis and complement activation. However, HS4 gel beads inhibited the LPS-stimulated secretion of TNF-α and the expression of TLR4 and NF-κB by macrophages, whereas AP4 gel beads stimulated the inflammatory response of macrophages. HS4 gel beads adsorbed 1.3 times more LPS and adhered to 1.6 times more macrophages than AP4 gel beads. Thus, HS pectin gel has advantages over AP gel concerning swelling behavior, protein adsorption, and biocompatibility.
Assuntos
Heracleum , Malus , Adsorção , Géis/química , Heracleum/química , Lipopolissacarídeos , Pectinas/química , Pectinas/farmacologiaRESUMO
A new coumarin named (9 R, 10 R)-9, 10-dihydro-10-hydroxy-9-methoxy-bergapten (1) and 13 known compounds (2-14) were isolated from the roots of Heracleum dissectum Ledeb., in which compounds (2-13) were obtained from H. dissectum for the first time. Their structures were illuminated by HR-ESI MS, 1 D and 2 D NMR, optical rotation and comparison with literatures. All compounds were evaluated against hepatocellular carcinoma HepG2 cell lines and the results showed that candinol C (8) had moderate cytotoxic activity against HepG2 cells with IC50 value at 57.6 ± 1.1 µM.
Assuntos
Heracleum , Cumarínicos/química , Heracleum/química , Extratos Vegetais/química , Raízes de Plantas/químicaRESUMO
The parsnip webworm, Depressaria pastinacella, is restricted to two hostplant genera containing six structurally diverse furanocoumarins. Of these, imperatorin is detoxified by a specialized cytochrome P450, CYP6AB3. A previous whole-larva transcriptome analysis confirmed the presence of nine transcripts that belong to the CYP6AE subfamily. Here, by examining midgut-specific gene expression patterns we determined that CYP6AE89 transcripts were highly expressed and furanocoumarin-inducible. Computer docking and energy-minimization of a CYP6AE89 model with all six furanocoumarins showed that 5-methoxylated bergapten and 8-methoxylated xanthotoxin had the smallest distances from the heme to the proton-donor residue in the catalytic I-helix, and that the 5,8-dimethoxylated isopimpinellin and bergapten had the smallest energy-minimized distance from the heme oxygen to the furan ring double bond. To evaluate this prediction, we expressed the CYP6AE89 protein in an Escherichia coli system, and used it to detect high catalytic activity against the two mono-methoxylated linear furanocoumarins - bergapten and xanthotoxin - and weak activity against isopimpinellin. Thus, CYP6AE89, like CYP6AB3, is probably specialized for detoxifying only a subset of hostplant furanocoumarins. A maximum-likelihood tree built with six representative lepidopterans with manually annotated cytochrome P450s shows that CYP6AE89 may have evolved much faster than the other CYP6AE proteins, possibly indicative of host selection pressure.
Assuntos
Sistema Enzimático do Citocromo P-450 , Furocumarinas/metabolismo , Mariposas/enzimologia , Animais , Furocumarinas/química , Trato Gastrointestinal/metabolismo , Perfilação da Expressão Gênica , Heracleum/química , Inativação Metabólica , Larva/enzimologia , Larva/genética , Larva/metabolismo , Mariposas/genética , Mariposas/metabolismo , Pastinaca/químicaRESUMO
BACKGROUND: Heracleum moellendorffii roots (HM-R) have been long treated for inflammatory diseases such as arthritis, backache and fever. However, an anti-inflammatory effect and the specific mechanism of HM-R were not yet clear. In this study, we for the first time explored the anti-inflammatory of HM-R. METHODS: The cytotoxicity of HM-R against RAW264.7 cells was evaluated using MTT assay. The inhibition of NO and PGE2 production by HM-R was evaluated using Griess reagent and Prostaglandin E2 ELISA Kit, respectively. The changes in mRNA or protein level following HM-R treatment were assessed by RT-PCR and Western blot analysis, respectively. RESULTS: HM-R dose-dependently blocked LPS-induced NO and PGE2 production. In addition, HM-R inhibited LPS-induced overexpression of iNOS, COX-2, IL-1ß and IL-6 in RAW264.7 cells. HM-R inhibited LPS-induced NF-κB signaling activation through blocking IκB-α degradation and p65 nuclear accumulation. Furthermore, HM-R inhibited MAPK signaling activation by attenuating the phosphorylation of ERK1/2, p38 and JNK. HM-R increased nuclear accumulation of Nrf2 and HO-1 expression. However, NAC reduced the increased nuclear accumulation of Nrf2 and HO-1 expression by HM-R. In HPLC analysis, falcarinol was detected from HM-R as an anti-inflammatory compound. CONCLUSIONS: These results indicate that HM-R may exert anti-inflammatory activity by inhibiting NF-κB and MAPK signaling, and activating ROS/Nrf2/HO-1 signaling. These findings suggest that HM-R has a potential as a natural material for the development of anti-inflammatory drugs.
Assuntos
Anti-Inflamatórios/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Heme Oxigenase-1/imunologia , Heracleum/química , Fator 2 Relacionado a NF-E2/imunologia , NF-kappa B/imunologia , Espécies Reativas de Oxigênio/imunologia , Animais , Ciclo-Oxigenase 2/genética , Ciclo-Oxigenase 2/imunologia , Heme Oxigenase-1/genética , Lipopolissacarídeos/farmacologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Fator 2 Relacionado a NF-E2/genética , NF-kappa B/genética , Raízes de Plantas/química , Células RAW 264.7RESUMO
Heracleum moellendorffii Hance is a medicinal vegetable species, and the seed dormancy of this species has caused many agricultural problems. One stratification technique involves alternating layers of seeds and substrate to allow post-ripening of dormant seeds under appropriate environmental conditions and to release dormancy. Non-stratified seeds (NS), cotyledon-stage-embryo seeds (CS) and germinated seeds (GS) represent key stages of H. moellendorffii seeds during stratification. To better understand the breaking of dormancy caused by stratification, tandem mass tag (TMT) mass spectrometry (MS)/MS was used to detect proteins among NS, CS and GS. A total of 876 proteins were identified, which were subjected to Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) analyses. The results showed that carbohydrate metabolic processes, responses to stress and ribosome biogenesis were the main biological processes. The changes in protein accumulation were validated by qRT-PCR. The results showed that starch, sucrose, pyruvate and fatty acid metabolism played significant roles and that the contents of stored substances were gradually degraded during stratification. This study provides a theoretical basis in terms of proteomics for exploring the post-ripening and germination of H. moellendorffii seeds.
Assuntos
Germinação , Heracleum , Proteínas de Plantas , Proteômica , Sementes , Heracleum/química , Heracleum/metabolismo , Dormência de Plantas , Proteínas de Plantas/química , Proteínas de Plantas/genética , Proteoma , Sementes/química , Sementes/genética , Sementes/metabolismo , Espectrometria de Massas em Tandem , TemperaturaRESUMO
Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied for their furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities. Quantification of the furanocoumarins was performed by 1 H-NMR. Pimpinellin was found to be the main component in the roots of all studied species. Bergapten and imperatorin were the major compounds in the fruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H. ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavenging activity and TEAC (IC50 0.58â mg/mL and 1.83â mm, respectively). The root extracts of H. verticillatum and H. angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34â mg/mL, respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7) towards α-amylase.
Assuntos
Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Furocumarinas/farmacologia , Heracleum/química , Hipoglicemiantes/farmacologia , Picratos/antagonistas & inibidores , Acetilcolinesterase/metabolismo , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/metabolismo , Animais , Antioxidantes/síntese química , Antioxidantes/química , Diabetes Mellitus Tipo 2/tratamento farmacológico , Electrophorus , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Furocumarinas/síntese química , Furocumarinas/química , Humanos , Hipoglicemiantes/síntese química , Hipoglicemiantes/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Suínos , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismoRESUMO
Spreading of the plant species in new areas is supported by the hypothesis in which chemicals produced by alien species are allopathic to native plants. A novel weapon hypothesis was tested by using essential oil of dangerous alien species Heracleum mantegazzianum in laboratory conditions. Aboveground plant material was collected in south-east part of Slovakia, dried and hydrodistilled for essential oil isolation. Dominant compounds as octyl acetate (62.6%), hexyl 2-metylbutyrate (10.7%), hexyl isobutyrate (7.5%) and hexyl butyrate (6.5%) were identified by GC-MS. Potential phytotoxic activity was tested on three dicot plant species garden cress (Lepidium sativum L.), radish (Raphanus sativus L.) and lettuce (Lactuca sativa L.) and on one monocot plant species wheat Triticum aestivum L. Germination of the seeds of model plant species after influencing by different doses of essential oil of H. mantegazzianum as well as the roots length was evaluated. Lepidium sativum L. and Raphanus sativus L. were generally not sensitive to applied doses of essential oil although a little stimulation effect at some concentrations prevailed over inhibition effect. Similarly, in monocot species Triticum aestivum L., stimulation was visible in both root length and root number at two or one highest doses, respectively.
Assuntos
Heracleum/química , Óleos Voláteis/química , Extratos Vegetais/química , Sementes/química , Acetatos/química , Alelopatia , Ácido Butírico/química , Germinação , Lepidium sativum/efeitos dos fármacos , Lactuca/efeitos dos fármacos , Óleos Voláteis/toxicidade , Raphanus/efeitos dos fármacos , Triticum/efeitos dos fármacosRESUMO
Heracleum sphondylium L. subsp. ternatum (Velen.) Brummitt. commonly known as "hogweed" is traditionally used to manage several human ailments. This investigation assessed, for the first time, the enzyme inhibitory properties, antioxidant activity, phytochemical profile, antimutagenic, and antimicrobial potential of the ethyl acetate, methanol, and water extracts of H. sphondylium. We also established the possible interactions of identified phenolic compounds with cholinesterases, amylase, glucosidase, and tyrosinase using in silico docking studies. Chlorogenic acid was found in high amounts in the methanol extract of H. sphondylium. The methanol extract was an effective inhibitor of acetylcholinesterase (1.70 mg galantamine equivalent (GALAE)/g extract) while the ethyl acetate extract showed pronounced inhibitory action against butyrylcholinesterase (1.77 mg GALAE/g extract). The extracts exhibited low inhibition against amylase (0.12-0.84 mmol acarbose equivalent (ACAE)/g extract) and a more pronounced inhibition against glucosidase (2.29-3.65 mmol ACAE/g extract). In silico results showed that rutin and quercetin (-70.4 and -72.2 Kcal/mol, for rutin and quercetin respectively) docked to the enzymatic cavity of acetylcholinesterase but these phenolic compounds showed less affinity with butyrylcholinesterase (-15.0 and -5.2 Kcal/mol, for rutin and quercetin respectively). The extracts did not induce any mutations on the bacterial strains, while they have excellent antimutagenic capacity against well-known mutagens (inhibition values 98%, 97% and 96%). The methanol extract (0.78 mg/ml) showed moderate antifungal activity while the ethyl acetate extract (0.78-3.12 mg/ml) showed weak to moderate antimicrobial activity. This study provides valuable baseline data which might serve for the development of future pharmacophores for the management of human ailments.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Inibidores Enzimáticos/farmacologia , Heracleum/química , Extratos Vegetais/farmacologia , Acetilcolinesterase/metabolismo , Amilases/antagonistas & inibidores , Amilases/metabolismo , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Bactérias/efeitos dos fármacos , Butirilcolinesterase/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Fungos/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificaçãoRESUMO
Continually phytochemical study of the roots of Heracleum dissectum had led to the isolation of three previously undescribed polyacetylene glycosides (1-3), together with seven known compounds, including one polyacetylene (8) and six coumarins (4-7 and 9-10) using diverse chromatographic methods. The structures of these three new compounds were characterized and identified as deca-4,6-diyn-1-yl ß-d-glucopyranosyl-(1â6)-ß-d-glucopyranosyl-(1â2)-ß-d-glucopyranoside (1), (8Z)-dec-8-ene-4,6-diyn-1-yl ß-d-glucopyranosyl-(1â6)-ß-d-glucopyranosyl-(1â2)-ß-d-glucopyranoside (2), and (8E)-dec-8-ene-4,6-diyn-1-yl ß-d-glucopyranosyl-(1â6)-ß-d-glucopyranosyl-(1â2)-ß-d-glucopyranoside (3) based on their physicochemical properties and extensive analyses of various spectroscopic data. Their triglycerides accumulating activities were assayed and the results showed that the three new polyacetylene glycosides (1-3) exhibited triglyceride accumulating activities in 3T3-L1 adipocytes.
Assuntos
Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Heracleum/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Polímero Poliacetilênico/química , Triglicerídeos/metabolismo , Células 3T3-L1 , Animais , Configuração de Carboidratos , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Glicosídeos/química , Metanol/química , Camundongos , Extratos Vegetais/química , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
The composition of the essential oils and the furanocoumarin profiles of CH2 Cl2 extracts from underground parts and fruits of nine Heracleum taxa (Apiaceae) from Southeastern Europe were statistically analyzed to evaluate their chemosystematic significance. Eight investigated taxa (H. orphanidis and members of H. sphondylium group: H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii and H. verticillatum) belong to the type section of the genus. Additionally analyzed taxon, H. austriacum subsp. siifolium, belongs to H. sect. Wendia. Qualitative and quantitative analysis of the essential oils was performed by GC-FID and GC/MS, and of the furanocoumarins by LC/MS. Furanocoumarins were identified using standards and/or based on UV, MS, 1 H- and ROESY NMR spectra. Multivariate statistics (PCA, nMDS, UPGMA) of analyzed metabolites showed that the investigated taxa were grouped according to their taxonomic classification. PCA revealed the significance of some monoterpenes and (Z)-falcarinol of the underground parts oils, octyl esters of the fruit oils, and most of the total of 12 identified furanocoumarins.
Assuntos
Furocumarinas/química , Heracleum/química , Óleos Voláteis/química , Cromatografia Gasosa , Cromatografia Líquida de Alta Pressão , Frutas/química , Frutas/metabolismo , Furocumarinas/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Heracleum/metabolismo , Espectrometria de Massas , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Análise de Componente PrincipalRESUMO
Heracleum persicum Desf. ex Fisch is used in Iranian traditional medicines, for the treatment of various diseases including neurological, gastrointestinal, respiratory, rheumatological and urinary tract diseases. In phytochemical analysis of H. persicum, several classes of natural chemicals including volatile (aliphatic esters, carbonyls, phenyl propenes and terpenes) and nonvolatile (flavonoids, furanocoumarins, tannins and alkaloids) constituents as well as different minerals have been identified. Scientific studies on H. persicum proved that it has a wide range of biological and pharmacological activities. This article has provided comprehensive information on Iranian traditional uses, phytochemistry and pharmacological activities of H. persicum.
Assuntos
Heracleum/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Humanos , Irã (Geográfico) , Medicina TradicionalRESUMO
Conspecific populations of plants in their native range are expected to show considerable variation due to long-term ecological and evolutionary factors. We investigated the levels of secondary metabolites in Heracleum including H. persicum a valuable medicinal plant to depict the magnitude of cryptic variation and the potential significance of novel chemical traits. The essential oil volatiles from fruits of 34 populations from different species of Heracleum in Iranian distribution range and a native of H. sphondylium and an invasive population of H. persicum from Norway were analyzed with GC/MS. Out of 48 compounds identified, a contrasting pattern in the level of two major compounds, octyl acetate and hexyl butyrate was found among all studied species. Interestingly, a significant geographic pattern was observed; the hexyl butyrate/octyl acetate ratio was high (range 1.8 - 3.2) in the northwestern Iranian populations of H. persicum compared to that in northern and central populations (range 0.3 - 0.9). Four populations from Zagros mountains also exhibited a unique composition. Anethole was found in two populations of H. persicum from central Zagros, which has not been previously reported for essential oil of fruits of Heracleum so far. The results suggest high efficiency of large scale sampling from distribution range of species in identifying novel compounds. The unique pattern of geographic structuring also provides novel information to unravel cryptic variation in Heracleum.
Assuntos
Geografia , Heracleum/química , Óleos Voláteis/química , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Heracleum/classificação , Espécies Introduzidas , Irã (Geográfico) , Noruega , Plantas Medicinais/química , Especificidade da EspécieRESUMO
From the roots of Heracleum dissectum Lebb., one new cinnamic acid glycoside derivative named dissectumoside (1), together with eight known compounds including three phenolics, three phenolic glycosides and two phenylpropanoic glycoside were isolated using various chromatographic methods. Among them compound 2-9 was isolated from the plant for the first time. Their structures were elucidated and identified on the basis of their physicochemical properties and by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. The results of triglyceride accumulation screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited significantly accelerating activities of adipogenesis in adipocytes.
Assuntos
Cinamatos/isolamento & purificação , Glicosídeos/isolamento & purificação , Heracleum/química , Extratos Vegetais/química , Células 3T3-L1 , Adipócitos/efeitos dos fármacos , Adipogenia/efeitos dos fármacos , Animais , Glicosídeos Cardíacos , Cinamatos/química , Glicosídeos/química , Camundongos , Fenóis/química , Raízes de Plantas/químicaRESUMO
Application of essential oils of medicinal plants is considered a safe and acceptable method for plant disease management to protect plants from pathogenic microorganisms. Thus, in recent study, essential oils (EOs) from Zhumeria majdae, Heracleum persicum (two Iranian endemic plants) and Eucalyptus sp. were assayed for their antifungal potential against ten phytopathogenic fungi, including Fusarium graminearum, Fusarium asiaticum, Fusarium redolens f.sp. dianthus, Fusarium verticillioides, Fusarium oxysporum f.sp. lentis, Sclerotinia sclerotiorum, Aspergillus flavus, Aspergillus tubingensis, Botrytis cinerea and Cladosporium cladosporioides. Chemical composition of these oils was identified by GC-MS analysis. Based on our results, Z. majdae essential oil exhibited the best antifungal activity among tested essential oils, completely inhibiting growth of five fungal species. EOs of Eucalyptus sp. and H. persicum showed moderate and poor antifungal capacity, respectively. GC-MS analysis demonstrated that linalool and camphor were the main components of the essential oils of Z. majdae; furthermore, 1,8-cineole and hexyl ester formed the major portions of Eucalyptus sp. and H. persicum EOs. Due to the significant inhibition of some EOs, additional research about their use for control of plant diseases caused by these fungi is recommended.