Chemical Composition and Biological Activities of Prangos ferulacea Essential Oils

Prangos ferulacea (L.) Lindl, which belongs to the Apiaceae family, is a species that mainly grows in the eastern Mediterranean region and in western Asia. It has been largely used in traditional medicine in several countries and it has been shown to possess several interesting biological properties. With the aim to provide new insights into the phytochemistry and pharmacology of this species, the essential oils of flowers and leaves from a local accession that grows in Sicily (Italy) and has not yet been previously studied were investigated. The chemical composition of both oils, obtained by hydrodistillation from the leaves and flowers, was evaluated by GC-MS. This analysis allowed us to identify a new chemotype, characterized by a large amount of (Z)-β-ocimene. Furthermore, these essential oils have been tested for their possible antimicrobial and antioxidant activity. P. ferulacea essential oils exhibit moderate antimicrobial activity; in particular, the flower essential oil is harmful at low and wide spectrum concentrations. They also exhibit good antioxidant activity in vitro and in particular, it has been shown that the essential oils of the flowers and leaves of P. ferulacea caused a decrease in ROS and an increase in the activity of superoxide dismutase (SOD), catalase (CAT) and glutathione S-transferase (GST) in OZ-stimulated PMNs. Therefore, these essential oils could be considered as promising candidates for pharmaceutical and nutraceutical preparations.     

Essential Oil of the Plants Growing in the Brazilian Amazon: Chemical Composition,Antioxidants, and Biological Applications

Essential oils are biosynthesized in the secondary metabolism of plants, and in their chemical composition, they can be identified different classes of compounds with potential antioxidant and biological applications. Over the years in the Amazon, several species of aromatic plants were discovered and used in traditional medicine. The literature has shown that essential oils extracted from amazon species have several biological activities, such as antioxidant, antibacterial, antifungal, cytotoxic, and antiprotozoal activities. These activities are related to the diversified chemical composition found in essential oils that, by synergism, favors its pharmacological action. In light of this vital importance, this study aimed at performing a review of the literature with particular emphasis on the chemical composition and biological activities in studies conducted with species collected in the Amazon, taking into consideration in particular the last 10 years of collection and research.     

Chemical Composition and Antioxidant Activity of Essential Oils from Leaves of Two Specimens of Eugenia florida DC.

Eugenia florida DC. belongs to the Myrtaceae family, which is present in almost all of Brazil. This species is popularly known as pitanga-preta or guamirim and is used in folk medicine to treat gastrointestinal problems. In this study, two specimens of Eugenia florida (Efl) were collected in different areas of the same region. Specimen A (EflA) was collected in an area of secondary forest (capoeira), while specimen B (EflB) was collected in a floodplain area. The essential oils (EOs) were extracted from both specimens of Eugenia florida by means of hydrodistillation. Gas chromatography coupled to mass spectrometry (GC/MS) was used to identify the volatile compounds present, and the antioxidant capacity of the EOs was determined by antioxidant capacity (AC-DPPH) and the Trolox equivalent antioxidant (TEAC) assay. For E. florida, limonene (11.98%), spathulenol (10.94%) and α-pinene (5.21%) were identified as the main compounds of the EO extracted from sample A, while sample B comprised selina-3,11-dien-6α-ol (12.03%), eremoligenol (11.0%) and γ-elemene (10.70%). This difference in chemical composition impacted the antioxidant activity of the EOs between the studied samples, especially in sample B of E. florida. This study is the first to report on the antioxidant activity of Eugenia florida DC. essential oils.     

Chemical Composition of Essential Oils of Seven Polygonum Species from Turkey: A Chemotaxonomic Approach

Medicinal plants and herbal preparations are gaining attention in the scientific community today, as they are often used intermittently in the treatment of various diseases. The genus of Polygonum (Polygonaceae), known locally as “madimak”, is an aromatic plant widely used in world flavors. The chemical composition of the essential oils of dried aerial parts of seven of Polygonum was analyzed by GC-MS. These species are Polygonum lapathifolium L., Polygonum persicaria L., Polygonum arenastrum Bor., Polygonum bellardii All., Polygonum arenarium Waldst. Et Kit., Polygonum aviculare L., and Polygonum cognatum Meissn. Qualitative and quantitative differences were found in the essential oil analysis of the seven Polygonum species. The major compounds were determined as (E)-β-farnesene (19. 46%), dodecanal (15.92%), β-caryophyllene (12.95%), in P. aviculare; (E)-β-farnesene (25.00%), dodecanal (20.45%), β-caryophyllene (9.38%), and caryophyllene oxide (8. 26%) in P. persicaria; dodecanal (25.65%), caryophyllene oxide (13.35%), β-caryophyllene (7.95%), and (E)-β-farnesene (6.20%) in P. lapathifolium, and dodecanal (19.65%), (E)-β-farnesene (13.86%), β-caryophyllene (8.06%), and α-terpineol (7.2%) in P. arenarium, dodecanal (16.23%), β-caryophyllene (16.09%), (E)-β-farnesene (12.26%), caryophyllene oxide (7.94%) in P. bellardii, (E)-β-farnesene (20.75%), dodecanal (17.96%), β-caryophyllene (13.01%), α-terpineol (4.97%) in P. arenastrum, (E)-β-farnesene (9.49%), dodecanal (14.01%), β-caryophyllene (11.92%), geranyl acetate (9.49%), and undecanal (7.35%) in P. cognatum. This study is the most comprehensive study conducted to determine the essential oil components of Polygonum species. In addition, a literature review on the composition of the essential oils of these Polygonum taxa was performed. The essential oil components of the species in our study were revealed for the first time with this study.     

3-(噁唑-5-基)吲哚类天然产物生物活性及其衍生物的合成研究进展

3-(噁唑-5-基)吲哚类天然产物如Pimprinine,Streptochlorin等,广泛存在于海洋微生物中,因其具有多样的生物活性,在医药和农药领域中很有研究潜力.3-(噁唑-5-基)吲哚类天然产物的合成方法有很多研究报道,在吲哚结构上构建噁唑环是合成此类天然产物的关键.总结了已报道的3-(噁唑-5-基)吲哚类天然产物的生物活性,并对构建3-(噁唑-5-基)吲哚骨架的合成方法及部分主要反应机理进行了综述,探讨了3-(噁唑-5-基)吲哚类骨架作为一种优势活性结构在未来的应用前景.     

Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties

Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the world and the chemical and biological properties of their essential oils. Chemically, 110 oil records are reported with significant variability of volatile constituents, according to their seasonality and collection sites. Monoterpenes and sesquiterpenes with acyclic (C₁₀ and C₁₅), p-menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeleton-types, were the primary constituents. The essential oils showed various biological activities, including antioxidant, antifungal, antibacterial, phytotoxic, larvicidal, anti-inflammatory, and cytotoxic properties. This review contributes to the Psidium species rational and economic exploration as natural sources to produce new drugs.     

Chemical Composition and Biological Activities of Essential Oils from the Leaves,Stems, and Roots of Kadsura coccinea

The chemical composition and biological activities of the essential oils from the leaves, stems, and roots of Kadsura coccinea (K. coccinea) were investigated. The essential oils were extracted by hydro distillation and analyzed by gas chromatography mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Antioxidant activities of the essential oils were examined with DPPH radical scavenging assay, ABTS cation radical scavenging assay, and ferric reducing antioxidant power assay. Antimicrobial activities were evaluated by determining minimum inhibitory concentrations (MIC) and minimum microbiocidal concentrations (MMC). Acetylcholinesterase and butyrylcholinesterase inhibitory activity of the essential oils were also tested. A total of 46, 44, and 47 components were identified in the leaf, stem, and root oils, representing 95.66%, 97.35%, and 92.72% of total composition, respectively. The major compounds of three essential oils were α-pinene (16.60–42.02%), β-pinene (10.03–18.82%), camphene (1.56–10.95%), borneol (0.50–7.71%), δ-cadinene (1.52–7.06%), and β-elemene (1.86–4.45%). The essential oils were found to have weak antioxidant activities and cholinesterase inhibition activities. The essential oils showed more inhibitory effects against Staphylococcus aureus (S. aureus) than those of other strains. The highest antimicrobial activity was observed in the root oil against S. aureus, with MIC of 0.78 mg/mL. Therefore, K. coccinea essential oils might be considered as a natural antibacterial agent against S. aureus with potential application in food and pharmaceutical industries.     

Study on the Chemical Composition and the Biological Activities of Vitis vinifera Stem Extracts

Vitis vinifera (V. vinifera) is a herbaceous plant, cultivated worldwide and known for its biological benefits. The aim of this study is the investigation of the chemical composition as well as the determination of the biological potential of different grape stem extracts obtained by maceration and accelerated solvent extraction (ASE). The HPLC analysis of the tested extracts led to the identification of 28 compounds of which 17 were identified for the first time in grape plants, in addition to seven revealed in the stem part for the first time. Twenty-nine volatile molecules have been detected by GC-MS in the grape stem part; among them seven were identified for the first time in the grape plant. For the biological analysis, the ethyl acetate extract (EtOAc) obtained by maceration showed a significant potential regarding antioxidant activity (IC₅₀ = 42.5 µg/mL), anti-Alzheimer (IC₅₀ = 14.1 µg/mL), antidiabetic (IC₅₀ = 13.4 µg/mL), cytotoxic with HCT-116 (IC₅₀ = 12.5 µg/mL), and anti-inflammatory (IC₅₀ = 26.6 µg/mL) activities, as well as showing the highest polyphenol content (207.9 mg GAE/g DW).     

Chemical Composition,Biological Activities and In Silico Analysis of Essential Oils of Three Endemic Prangos Species from Turkey

In this study, the essential oils (EOs) obtained from three endemic Prangos species from Turkey (P. heyniae, P. meliocarpoides var. meliocarpoides, and P. uechtritzii) were studied for their chemical composition and biological activities. β-Bisabolenal (12.2%) and caryophyllene oxide (7.9%) were the principal components of P. heyniae EO, while P. meliocarpoides EO contained sabinene (16.7%) and p-cymene (13.2%), and P. uechtritzii EO contained p-cymene (24.6%) and caryophyllene oxide (19.6%), as the most abundant components. With regard to their antioxidant activity, all the EOs were found to possess free radical scavenging potential demonstrated in both DPPH and ABTS assays (0.43–1.74 mg TE/g and 24.18–92.99 mg TE/g, respectively). Additionally, while no inhibitory activity was displayed by P. meliocarpoides and P. uechtritzii EOs against both cholinesterases (acetyl- and butyryl-cholinesterases). Moreover, all the EOs were found to act as inhibitors of tyrosinase (46.34–69.56 mg KAE/g). Molecular docking revealed elemol and α-bisabolol to have the most effective binding affinity with tyrosinase and amylase. Altogether, this study unveiled some interesting biological activities of these EOs, especially as natural antioxidants and tyrosinase inhibitors and hence offers stimulating prospects of them in the development of anti-hyperpigmentation topical formulations.     

The Chemical Composition and Biological Activities of Essential Oil from Korean Native Thyme Bak-Ri-Hyang (Thymus quinquecostatus Celak.)

Thymus quinquecostatus Celak. (Korean name: bak-ri-hyang) is an important medicinal and aromatic herb in Korea, which is named for the spread of its fragrance over a distance of approximately 40 km. In traditional Korean systems of medicine, T. quinquecostatus has been used to treat cancer, constipation, hepatic disease, arteriosclerosis, poor circulation in women, constipation, and menstrual irregularities. At present, T. quinquecostatus is used only for ornamental and ground cover purposes. A literature search was conducted to retrieve information regarding the essential oil composition and biological properties of T. quinquecostatus from PubMed, Science Direct, Wiley, Springer, Taylor and Francis, Wiley, and other literature databases. T. quinquecostatus can be divided into different chemotypes, such as γ-terpinene, thymol, phenol, carvacrol, and geraniol, according to the presence of major components in its essential oil. Further, the essential oil from T. quinquecostatus has been reported to possess various therapeutic properties such as antioxidant, antimicrobial, anticancer, anti-inflammatory, analgesic, sleep prolonging, soothing, skin protection and whitening, anti-aging, anti-obesity, and anti-acne properties. In conclusion, this review will be helpful for utilizing the T. quinquecostatus plant in different industries including food, pharmaceuticals, pesticides, perfumery, and cosmetics.     

Chemical Composition and Biological Activities of the Essential Oils from <em>Duguetia lanceolata</em> St. Hil. Barks

Essential oils of Duguetia lanceolata barks, obtained at 2 (T2) and 4 h (T4), were identified by gas chromatography and gas chromatography/mass spectrometry. β-Elemene (12.7 and 14.9%), caryophyllene oxide (12.4 and 10.7%) and β-selinene (8.4 and 10.4%) were the most abundant components in T2 and T4, respectively. The essential oils inhibited the growth of Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Candida albicans. The essential oils were cytotoxic against brine shrimp. The extraction time influenced the chemical composition and biological activities of essential oils obtained from the barks of D. lanceolata.     

Assessment of Chemical Composition and Anti-Penicillium Activity of Vapours of Essential Oils from Abies Alba and Two Melaleuca Species in Food Model Systems

The possibilities of the practical utilization of essential oils (EOs) from various plant species in the food industry have attracted the attention of the scientific community. Following our previous studies, the antifungal activities of three further commercial EOs, Melaleuca armillaris subsp. armillaris (rosalina; REO), Melaleuca quinquenervia (niaouli; NEO), and Abies alba (fir; FEO), were evaluated in the present research in respect to their chemical profiles, over four different concentrations, 62.5 μL/L, 125 μL/L, 250 μL/L, and 500 μL/L. The findings revealed that the major compounds of REO, NEO, and FEO were linalool (47.5%), 1,8-cineole (40.8%), and α-pinene (25.2%), respectively. In vitro antifungal determinations showed that the inhibition zones of a Penicillium spp. mycelial growth ranged from no inhibitory effectiveness (00.00 ± 00.00 mm) to 16.00 ± 1.00 mm, indicating a very strong antifungal activity which was detected against P. citrinum after the highest REO concentration exposure. Furthermore, the in situ antifungal efficacy of all EOs investigated was shown to be dose-dependent. In this sense, we have found that the highest concentration (500 µL/L) of REO, NEO, and FEO significantly reduced (p < 0.05) the growth of all Penicillium strains inoculated on the bread, carrot, and potato models. These results indicate that the investigated EOs may be promising innovative agents in order to extend the shelf life of different types of food products, such as bread, carrot and potato.     

Chemical Composition and Antioxidant Activity of Essential Oils from Eugenia patrisii Vahl,E. punicifolia (Kunth) DC., and Myrcia tomentosa (Aubl.) DC., Leaf of Family Myrtaceae

Essential oils (EOs) were extracted from Eugenia patrisii, E. punicifolia, and Myrcia tomentosa, specimens A and B, using hydrodistillation. Gas chromatography coupled with mass spectrometry (GC/MS) was used to identify the volatile constituents present, and the antioxidant capacity of EOs was determined using diphenylpicryl-hydrazyl (DPPH) and trolox equivalent antioxidant capacity (TEAC) assays. For E. patrisii, germacrene D (20.03%), bicyclogermacrene (11.82%), and (E)-caryophyllene (11.04%) were identified as the major constituents of the EOs extracted from specimen A, whereas specimen B primarily comprised γ-elemene (25.89%), germacrene B (8.11%), and (E)-caryophyllene (10.76%). The EOs of E. punicifolia specimen A contained β-Elemene (25.12%), (E)-caryophyllene (13.11%), and bicyclogermacrene (9.88%), while specimen B was composed of (E)-caryophyllene (11.47%), bicyclogermacrene (5.86%), β-pinene (5.86%), and γ-muurolene (5.55%). The specimen A of M. tomentosa was characterized by γ-elemene (12.52%), germacrene D (11.45%), and (E)-caryophyllene (10.22%), while specimen B contained spathulenol (40.70%), α-zingiberene (9.58%), and γ-elemene (6.89%). Additionally, the chemical composition of the EOs was qualitatively and quantitatively affected by the collection period. Furthermore, the EOs of the studied specimens, especially specimen A of E. punicifolia, showed a greater antioxidant activity in DPPH rather than TEAC, as represented by a significantly high inhibition percentage (408.0%).     

大叶黄杨叶、茎、果挥发油成分及抗病毒作用

研究了大叶黄杨叶、茎、果挥发油的化学成分及抗病毒活性。 采用超临界二氧化碳萃取,应用气相色谱-质谱联用(GC-MS) 法鉴定挥发油化学成分,考察体外抗病毒作用。 共鉴定133个化合物,大叶黄杨叶挥发油中主要有2-乙氧丙烷(41.92%)、(E)-2-己烯-1-醇(17.8%)、 (E)-香叶醇(7.86%)、甲基环己烷(6.60%)等;大叶黄杨茎挥发油中主要有甲氧基苯基肟(33.10%)、二十八烷(14.34%)、α-甲基-α-[4-甲基-3-戊烯基]环氧乙烷甲醇(12.48%)、甲苯(11.88%)、二十一烷(7.74%) 等;大叶黄杨果挥发油中主要有苯甲醛(15.52%)、甲苯(15.03%)、甲基环己烷(14.76%)、(Z)-3-己烯-1-醇(10.98%)等。 大叶黄杨叶、茎、果的环己烷、乙醚萃取挥发油对特定病毒有显著抑制效果。 大叶黄杨叶、茎、果中挥发油萃取部位成分差异明显,有特定抗病毒活性。     

Phytochemical Profile and Herbicidal (Phytotoxic), Antioxidants Potential of Essential Oils from Calycolpus goetheanus (Myrtaceae) Specimens,and in Silico Study

The essential oil (EO) of Calycolpus goetheanus (Myrtaceae) specimens (A, B, and C) were obtained through hydrodistillation. The analysis of the chemical composition of the EOs was by gas chromatography coupled with mass spectrometry CG-MS, and gas chromatography coupled with a flame ionization detector CG-FID. The phytotoxic activity of those EOs was evaluated against two weed species from common pasture areas in the Amazon region: Mimosa pudica L. and Senna obtusifolia (L.) The antioxidant capacity of the EOs was determined by (DPPH^•) and (ABTS^•+). Using molecular docking, we evaluated the interaction mode of the major EO compounds with the molecular binding protein 4-hydroxyphenylpyruvate dioxygenase (HPPD). The EO of specimen A was characterized by β-eudesmol (22.83%), (E)-caryophyllene (14.61%), and γ-eudesmol (13.87%), while compounds 1,8-cineole (8.64%), (E)-caryophyllene (5.86%), δ-cadinene (5.78%), and palustrol (4.97%) characterize the chemical profile of specimen B’s EOs, and specimen C had α-cadinol (9.03%), δ-cadinene (8.01%), and (E)-caryophyllene (6.74%) as the majority. The phytotoxic potential of the EOs was observed in the receptor species M. pudica with percentages of inhibition of 30%, and 33.33% for specimens B and C, respectively. The EOs’ antioxidant in DPPH^• was 0.79 ± 0.08 and 0.83 ± 0.02 mM for specimens A and B, respectively. In the TEAC, was 0.07 ± 0.02 mM for specimen A and 0.12 ± 0.06 mM for specimen B. In the results of the in silico study, we observed that the van der Waals and hydrophobic interactions of the alkyl and pi-alkyl types were the main interactions responsible for the formation of the receptor–ligand complex.     

Myrcia paivae O.Berg (Myrtaceae) Essential Oil,First Study of the Chemical Composition and Antioxidant Potential

The Myrtaceae family is one of the most representative in the Amazon. Several species have high added-value pharmacological potential. In order to contribute to the knowledge of the aromatic profile of Myrtaceae species from the Amazon, the present study presents the first report on the productivity, chemical composition, and antioxidant profile of the essential oil (EO) of Myrcia paivae. Dry leaves of the species were submitted to hydrodistillation to obtain their EO. The EO performance was calculated on a moisture-free basis and the analysis of the chemical profile was carried out by GC/MS. The determination of the antioxidant capacity was assessed by means of the antioxidant capacity equivalent to the inhibition Trolox of the ABTS^•+ and DPPH^• radicals. The results indicate that EO performance was equivalent to 1.69%. As for the chemical composition, hydrocarbon monoterpenes were predominant in the sample (>77%); terpinolene (14.70%), α-phellandrene (14.69%), γ-terpinene (9.64%), sylvestrene (7.62%), α-thujene (6.46%), and α-pinene (6.39%) were the constituents with higher content. Regarding the antioxidant capacity, the results show that the EO presented good results in the inhibition of ABTS^•+ (0.886 ± 0.226 mM L⁻¹) and DPPH^• (2.90 ± 0.083 mM L⁻¹), which can be attributed to the high monoterpene content in the sample.     

Antioxidant,Antimicrobial and In Silico NADPH Oxidase Inhibition of Chemically-Analyzed Essential Oils Derived from Ballota deserti (Noë) Jury

Ballota deserti (Noë) Jury (B. deserti) is a medicinal plant used in Ayurvedic medicine. The chemical composition, antioxidant, antibacterial, and antifungal properties of essential oils from B. deserti (EOBD) against drug-resistant microorganisms were examined in this work. Hydrodistillation was used to extract EOBD, and gas chromatography–mass spectrometry was used to identify its constituents. Ferric reducing antioxidant power (FRAP), 1,1-diphenyl-2-picrylhydrazyl (DPPH), and total antioxidant capacity (TAC) were used to assess the antioxidant effect of EOBD. The disc diffusion agar and the microdilution tests were used in the assessment of the antibacterial properties of EOBD against clinically resistant pathogenic microorganisms. An in silico approach was used to evaluate the inhibitory potential of EOBD against NADPH oxidase. The yield of EOBD was 0.41%, and was primarily composed of linalool (37.82%), cineole (12.04%), and borneol (11.07%). EOBD had good antioxidant potency, with calculated values of 19.82 ± 1.14 µg/mL (DPPH), 64.78 ± 5.21 µg/mL (FRAP), 996.84 ± 20.18 µg EAA/ mg (TAC). Both Gram-negative and Gram-positive bacteria were inhibited by EOBD with inhibition zones ranging from 17.481.75 mm to 28.471.44 mm. EOBD exhibited MICs ranging from 10.78 g/mL to 22.48 g/mL when tested against bacteria using the minimum inhibitory concentration (MIC) assay. Similarly, impressive antifungal activity was observed against fungal strains with inhibition zone widths ranging from 16.761.83 to 36.791.35 mm. Results of MICs assay against fungi showed that EOBD had MICs values ranging from 15.32 ± 1.47 to 23.74 ± 1.54 µg/mL. Docking results showed that thujone, o-cymene, and butanoic acid contained in EOBD possessed strong activity against NADPH oxidase, with glide scores of −5.403, −5.344, and −4.973 Kcal/mol, respectively. In light of these findings, the EOBD may be seen as a potential source of chemical compounds with significant biological capabilities that can be advantageous as natural antioxidants and develop an effective weapon against a wide range of pathogenic bacteria.     

二维大环网状结构的双(三环已基锡)二元酸酯的合成、结构及生物活性

三环己基氢氧化锡分别与辛二酸和壬二酸进行甲醇溶剂热反应,合成了2个双(三环已基锡)二元酸酯(CH₂)_n(CO₂SnCy₃)₂[(n:6(1),7(2)],并用IR、¹H和¹³C NMR、元素分析和X射线单晶衍射表征结构。化合物1、2均属单斜晶系,空间群分别为P2₁/n和P2₁/c,在化合物的晶体中,1通过Sn-O共价键,2通过Sn-O和Sn…O弱作用,分别形成了四锡核30元(1)和32元(2)二维大环网状结构。化合物1、2对人癌细胞Colo205、HepG2、MCF-7、Hela、NCI-H460均具有良好的体外抑制活性,对S. Aureus、B. Subtilis、E. Coli和S. Typhi具有选择性的抑菌作用。