A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

八角超临界CO_2流体萃取产物化学成分的研究

本文采用GC和GC－MS技术对八角的超临界CO_2流体萃取物的化学成分进行了研究，并鉴定出34种化合物，它们的含量占出峰物质总面积的96．2％。同时与八角水蒸汽蒸馏产物的组成进行了比较。     

八角的超临界CO2流体萃取产物化学成分的研究

采用ＧＣ和ＧＣ－ＭＳ技术对八角的超临界ＣＯ２流体萃取物的化学成分进行了研究，共鉴定出３４种化合物，它们的含量占出峰物质总量的９６２％。同时与八角的水蒸汽蒸馏产物的组成进行了比较。     

上犹八角茴香挥发油化学成份的研究

八角茴香(Illicium verum Hook,f.)系木兰科(Magnoliaceae)八角属常绿乔木,是我国特产的芳香植物。主要分布于广西、广东、贵州、云南等省区。江西北纬26°以南地区从五十年代初开始引种。八角茴香的果实是广泛使用的调味香料,入药则有温中理气、健胃止呕的功效,并有很强的抑菌作用。     

Sesquiterpenes and Monoterpenes from the Leaves and Stems of Illicium simonsii and Their Antibacterial Activity

Two undescribed ether derivatives of sesquiterpenes, 1-ethoxycaryolane-1, 9β-diol (1) and 2-ethoxyclovane-2β, 9α-diol (3), and one new monoterpene glycoside, p-menthane-1α,2α,8-triol-4-O-β-D-glucoside (5), were obtained, together with eight known compounds from the stems and leaves of I. simonsii. Their structures were elucidated by spectroscopic methods. Compounds 1–11 were evaluated for their potency against Staphylococcus aureus and clinical methicillin-resistant S. aureus (MRSA). Among them, compound 3 was weakly active against S. aureus (MIC = 128 μg/mL), and compounds 6 and 7 exhibited good antibacterial activity against S. aureus and MRSA (MICs = 2–8 µg/mL). A primary mechanism study revealed that compounds 6 and 7 could kill bacteria by destroying bacterial cell membranes. Moreover, compounds 6 and 7 were not susceptible to drug resistance development.     

Comparison of Phytochemical Contents,Antioxidant and Antibacterial Activities of Various Solvent Extracts Obtained from ‘Maluma’ Avocado Pulp Powder

Although avocado is a superfood rich in phytochemicals with high antioxidant activities, studies on the antibacterial properties of its pulp are limited, except for seed and peel portions. In this study, three types of solvent (acetone, methanol, and diethyl ether) were used to obtain the extracts from “Maluma” avocado pulp powder prepared by infrared drying. The extracts were analyzed for total polyphenols, phytopigments (total chlorophylls and carotenoids), antioxidant activities (ferric-reducing antioxidant power (FRAP), 2,2-Diphenyl-1-picrylhydrazyl (DPPH), and 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays), and antibacterial activities against seven pathogens (Shigella sonnei ATCC 9290, Escherichia coli ATCC 8739, Salmonella typhi ATCC 6539, Vibrio parahaemolyticus ATCC 17802, Proteus mirabilis ATCC 25933, Staphylococcus aureus ATCC 6538, and Bacillus cereus ATCC 11778). The results showed that the acetone solvent could extract the highest polyphenols and chlorophylls with the highest antioxidant activity in terms of ABTS and DPPH assays. In contrast, diethyl ether exhibited the most significant content of carotenoids and FRAP values. However, the methanol extract was the best solvent, exerting the strongest antibacterial and meaningful antioxidant activities. For the bacterial activities, Gram-positive pathogens (Bacillus cereus and Staphylococcus aureus) were inhibited more efficiently by avocado extracts than Gram-negative bacteria. Therefore, the extracts from avocado powder showed great potential for applications in food processing and preservation, pharmaceuticals, and cosmetics.     

Rapid analysis of the essential oils from dried Illicium verum Hook. f. and Zingiber officinale Rosc. by improved solvent-free microwave extraction with three types of microwave-absorption medium

A new method of extracting essential oils from dried plant materials has been studied. By adding a microwave-absorption medium (MAM) to a reactor, solvent-free microwave extraction (SFME) was improved and can be used to extract essential oils from dried plant material without pretreatment. With a microwave irradiation power of 85 W it took only approximately 30 min to extract the essential oils completely. The whole extraction process is simple, rapid, and economical. Three types of MAM, iron carbonyl powder (ICP), graphite powder (GP), and activated carbon powder (ACP), and two types of dried plant material, Illicium verum Hook. f. and Zingiber officinale Rosc., were studied. The results were compared with those obtained by use of conventional SFME, microwave-assisted hydrodistillation (MAHD), and conventional hydrodistillation (HD), and the conclusion drawn was that improved SFME was a feasible means of extracting essential oils from dried plant materials, because there were few differences between the composition of the essential oils extracted by improved SFME and by the other methods.     

Microwave extraction of essential oils from dried fruits of Illicium verum Hook. f. and Cuminum cyminum L. using ionic liquid as the microwave absorption medium

Ionic liquid was used as microwave absorption medium and applied to the extraction of essential oils from dried fruits of the Illicium verum Hook. f. and Cuminum cyminum L. by microwave‐assisted extraction. The extraction time is less than 15 min at the microwave power of 440 W. The constituents of essential oils obtained by the proposed method were compared with those obtained by hydrodistillation. There is no obvious difference in the constituents of essential oils obtained by the two methods.     

顶空固相微萃取-气相色谱-质谱联用快速分析八角茴香中风味物质

采用顶空固相微萃取与气相色谱-质谱联用技术,对八角茴香中风味物质进行了分析。选用自制聚丙烯酸树脂涂层,对样品量、萃取时间、萃取温度、解吸时间等参数进行了优化,结果表明0．10g样品在60℃水浴中顶空萃取40min,250℃下解吸2min达到最佳条件。比较了顶空固相微萃取与传统水蒸气蒸馏两种前处理方法,分析结果非常相似。该方法可用于快速分析八角茴香中的风味物质。     

Phytochemical constituents of the pericarps of Illicium difengpi and their anti-inflammatory activity

Abstract

Phytochemical investigation on the pericarps of Illicium difengpi lead to the isolation and structure elucidation of a new sesquiterpene, sesquicaranoic acid C (1), a new neolignan, difengpiol C (2), and 10 known compounds. The structures and absolute configurations of two new compounds were determined by a combination of NMR and CD spectroscopic analyses. All isolates were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.     

Composition and Antimicrobial Activity of Ilex Leaves Water Extracts

Plants from the Ilex genus are known for properties such as antimicrobial and anti-inflammatory activity, can act as antiobesity agents and thus can be helpful in medicine. Some holly species, such as Ilex paraguariensis (widely known in the form of popular beverage: yerba mate), have been investigated, while others have been partially researched or remain unknown. Therefore, we performed qualitative and quantitative phytochemical analyses and screened antimicrobial properties of lesser-studied species (I. aquifolium L., I. aquifolium ‘Argentea Marginata’ and I. × meserveae ‘Blue Angel’). I. paraguariensis was used as a standard species for comparison purposes. Investigations were performed on water extracts due to their expected activity and composition. Antimicrobial research included evaluating minimal inhibitory, bactericidal (Staphylococcus aureus and Escherichia coli) and fungicidal concentration (Candida albicans, Alternaria alternata, Fusarium oxysporum, and Aspergillus niger) of extracts. The influence of the extracts on the production, eradication, and viability of bacterial biofilms was also analysed. It was established that Ilex paraguariensis possesses the richest profile of hydroxycinnamic acids derivatives in terms of component concentration and diversity. Ilex spp., especially I. × meserveae, contain a slightly higher amount of flavonoids and more different flavonoid derivatives than I. paraguariensis. However, the strongest antibacterial activity was shown by I. aquifolium L. and its cultivar ‘Argentea Marginata’ in terms of minimal inhibitory, bactericidal and fungicidal concentration, and biofilm assays. Extracts from both species significantly reduced the biofilm viability of S. aureus as well, which may be of use in the production of multicomponent lavaseptics, antiseptics, diuretics (supporting urinary tract infection therapy) and, due to their action on fungi, additives to growth media for specific fungi. The significant content of saponins enables Ilex extracts to be used as natural emulsifiers, for example, in cosmetics. Moreover, relatively high chlorogenic acid and rutin content may suggest use of Ilex spp. to treat obesity, digestive problems, in chemoprevention, and as preservatives in the food industry.     

Two new sesquiterpene lactones from the fruits of Illicium jiadifengpi

Two new seco-prezizaane-type sesquiterpenes, 3,4-dehydroneomajucin (1) and 1,2,3,4-tetradehydroneomajucin (2), were isolated from the fruits of Illicium jiadifengpi. The structure of these compounds was determined using 1D and 2D NMR and ESI-MS. The isolates were evaluated for their anti-hepatitis B virus activities on the Hep G2.2.15 cell line. The inhibitory rates of compounds 1 and 2 on the HBeAg and HBsAg expression were 30.08 ± 3.09% and 11.43 ± 1.92% at a concentrations of 68.00 μM and 7.88 ± 1.21% and 16.96 ± 4.24% at a concentration of 68.50 μM, respectively.     

Antioxidant,Antibacterial, and Antifungal Activities of the Ethanolic Extract Obtained from Berberis vulgaris Roots and Leaves

This work assessed the phenolic and flavonoid components and their antioxidant, antifungal, and antibacterial effects in the ethanolic extract of barberry leaf and roots. The antibactericidal activity of root and leaf extracts against pathogenic bacteria was tested using agar diffusion and microdilution broth production for the lowest inhibitory concentration (MIC). Berberis vulgaris root and leaf extracts inhibited Staphylococcus aureus ATCC9973, Escherichia coli HB101, Staphylococcus enteritis, and Escherichia coli Cip812. The disc assay technique was used to assess the bactericidal activity of the extracts versus both pathogenic Gram-positive and Gram-negative strains. Hydro alcoholic extract was more effective against bacterial than fungal strains. The results showed that Berberis vulgaris leaf and roots extract had similar antifungal activities. Berberis vulgaris root extract inhibited the mycelial growth of Penicillium verrucosum, Fusarium proliferatum, Aspergillus ochraceous, Aspergillus niger, and Aspergillus flavus. Berberis vulgaris root extract has excellent antioxidant, antibacterial, and antifungal effects. Berberis vulgaris exhibited antimicrobial activity in vitro, and MIC showed that Berberis vulgaris parts efficiently affected pathogens in vitro. In conclusion, both Berberis vulgaris roots and leaves have considerable antibacterial activity and can be used as a source of antibacterial, antioxidant, and bioactive compounds to benefit human health.     

Antioxidant and Antimicrobial Activities of Thai Edible Plant Extracts Prepared Using Different Extraction Techniques

This study investigated the antioxidant and antimicrobial activities of six Thai edible plant leaf extracts, including Cashew (CN), Chamuang (CM), Monpu (MP), Thurianthet (TT), Kradon (KD) and Pakliang (PL), extracted using ethanol extraction (EE), microwave-assisted extraction (MAE), and ultrasonic-assisted extraction (UAE). The leaf extracts were characterized for percentage yield, total phenolic content (TPC), total flavonoid content (TFC), 2,2-diphenyl-1-picrylhydrazyl (DPPH) and-ferric reducing antioxidant power (FRAP) activity, and antimicrobial activity against spoilage. MAE produced the highest percentage yields, among which MAE-extracted MP exhibited the highest yield. Furthermore, the highest TPC and TFC were obtained for MAE, with MAE-extracted KD and CN showing the highest TPC and TFC, respectively, among the samples. The highest DPPH and FRAP values were seen in MAE-processed CN, KD, and MP extracts. The inhibition zone of pathogenic bacteria, minimum inhibitory concentration, and minimum bacterial concentration were determined in all samples except TT. These findings indicate that, compared to EE and UAE, MAE improved the antioxidant and antimicrobial efficacy of the leaf extracts. The aforementioned extracts could be employed as natural food additives to prevent chemical and microbial spoilage of foods.     

Chemical Composition,Antioxidant, and Antimicrobial Activities of Leaves of Ajuga Iva

The main objective of this research was to study the biological characteristics in terms of antioxidant and antimicrobial activities of Ajuga iva and determine the best analytical and extraction methods applicable to this specie and studied compounds. A short screening of its nutritional value in terms of chemical composition is also included. A. iva leaves were analyzed for crude protein (CP), cell wall [neutral detergent fiber (NDF), acid detergent fiber (ADF), and acid detergent lignin (ADL)], minerals, fatty acids, essential oils, and phenolic compounds. Mature aerial parts of A. iva were randomly collected during the Spring season from Mograne-Zaghouan, Tunisia. Leaves of A. iva contained 13.4 ± 0.4% CP, 26.3 ± 0.35% NDF, 20.2 ± 0.42% ADF, and 5.13 ± 0.21% ADL. Mineral content (13.0 ± 0.45%) was mainly composed of potassium (4.5% g DM) and magnesium (4.25% DM). Leaves of A. iva had linolenic (26.29 ± 0.760%) and linoleic (37.66 ± 2.35%) acids as the main components of the acid profile. Thymol was found to be the most dominant (23.43%) essential oil, followed by 4-vinylguaiacol (14.27%) and linalool (13.66%). HPLC-PDA-ESI-MS/MS analysis pointed out the presence of phytoecdysteroids. Phenolic acids and flavonoids, such as glycosylated derivatives of naringenin, eriodyctiol, and apigenin, were detected in the methanol extract of A. iva leaves. Our results underline the importance of choosing proper extraction methods and solvents to extract and characterize the described compounds profile of A. iva leaves. Results also show A. iva leaves as a potential source of functional ingredients with beneficial health-promoting properties. Overall, leaves of A. iva have low biological activities (antioxidant and antimicrobial activities) with a chemical composition suitable as a feed for ruminants in rangeland pasture. It also has low-grade antibacterial or medicinal characteristics when fed to ruminants.     

3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus

Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 1–3 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 1–3 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9–66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential.     

Biological Activity and Chemical Composition of Propolis from Various Regions of Poland

Propolis is one of the bee products, with multiple biological properties used in numerous applications. The research objective was to determine the chemical composition and biological properties (antibacterial, antifungal, antiviral, antioxidant, and cytoprotective activity) of propolis extracts collected from various regions of Poland. The results indicated that the total content of phenols (116.16–219.41 mg GAE/g EEP) and flavonoids (29.63–106.07 mg QE/g EEP) in propolis extracts depended on their geographic origin. The high content of epicatechin, catechin, pinobanksin, myricetin, and acids: vanillic and syringic in propolis samples was confirmed by chromatographic analysis. Moreover, the presence of caffeic acid phenethyl ester was confirmed in all samples. The origin of propolis also influenced the biological properties of its extracts. The propolis extracts were characterized by moderate DPPH free radical scavenging activity (29.22–35.14%), and relatively low ferrous iron chelating activity (9.33–32.32%). The results indicated also that the propolis extracts showed high activity in the protection of human red blood cells against free radicals generated from 2,2’-azobis(2-methylpropionamidine) dihydrochloride (AAPH). The extracts exhibited diversified activity against the tested pathogenic bacteria and limited activity against fungal strains. The research of selected propolis extracts showed that only 2 of 5 examined samples showed moderate activity against HPV (human papillomaviruses) and the activity depended on its geographical distribution.     

Phytochemical Composition,Antibacterial, Antioxidant and Antidiabetic Potentials of Cydonia oblonga Bark

Cydonia oblonga is a medicinal plant that is used to treat a number of health complications in traditional medication systems. The objective of this study was to evaluate the phytochemical composition, and antibacterial, antioxidant, and ant-diabetic potentials of methanolic extracts of Cydonia oblonga bark. The Cydonia oblonga bark extraction was fractionated through HPLC and seven purified fractions labeled as F1, F2, F3, F4, F5, F6, and F7 were obtained. The HPLC-UV analysis of methanolic extract showed the presence of a number of possible compounds. The GC-MS and HPLC analysis confirmed the presence of the following bioactive compounds in the crude extract and purified fractions: malic acid, mandelic acid, quercetin, caffeic acid, catechin hydrate, as morin (HPLC analysis), BIS-(2-ethylhexyl)phthalate and diisooctyl phthalate (F1), carbamide (F2, used as fertilizer), octasiloxane and dimethylsiloxanecyclictrimer (F3), silicic acid and cyclotrisiloxane (F4), 6-AH-cAMP, 4H-cyclopropa[5′,6′]benz[1′,2′,7,8]azule, and 4-(4-chlorophenyl)-3-morpholinepyrol-2-yl)-butenedioic acid (F5), isopropyamine (F6), and 1-propylhydrazine (F7). The extract and purified fractions were then tested for biological activities. All the purified fractions and methanolic extract showed effective antibacterial activity; however, the highest activity was recorded for methanolic extract against Staphylococcus aureus and Streptococcus pneumonia. Antioxidant evaluation of methanolic extract and purified fractions against DPPH showed strong % inhibition of the synthetic free radical. The methanolic extract exhibited 87.41 ± 0.54% inhibition whereas fractions showed: F1, 85.45 ± 0.85; F2, 65.78 ± 0.68; F3, 58.61 ± 0.58; F4, 80.76 ± 0.59; F5, 571.29 ± 0.49; F6, 85.28 ± 0.94; and F7, 48.45 ± 0.62% inhibition. Ascorbic acid (standard) was used as a control with 94.88 ± 0.56% inhibition at a maximum concentration of 1000 µg/mL. The α-glucosidase inhibition assay of methanolic extract and purified fractions at a maximum concentration of 1000 µg/mL showed activities as: methanolic extract, 78.21 ± 0.67; F1, 55.01 ± 0.29; F2, 56.10 ± 0.24; F3, 62.44 ± 1.03; F4, 70.52 ± 0.15; F5, 62.18 ± 0.92; F6, 72.68 ± 0.2; and F7, 57.33 ± 0.05% inhibition. α-Amylase % inhibition of methanolic extract and purified fractions were noted as: methanolic extract, 77.98 ± 0.57; F1, 79.72 ± 0.02; F2, 79.72 ± 0.02; F3, 82.16 ± 0.48; F4, 77.37 ± 0.28; F5, 72.14 ± 0.30; F6, 74.24 ± 0.29; and F7, 56.58 ± 0.10 at the highest concentration of 1000 µg/mL. Acarbose (standard) showed 87.65 ± 0.71% inhibition of α-glucosidase and 85.99 ± 0.44% inhibition of α-amylase at the highest concentration of 1000 µg/mL. It was found that all biological activities of methanolic extract and purified fractions might be attributed to the fact that they are rich sources of phenolic and flavonoids along with other bioactive compounds. The total phenolic and flavonoid contents of methanolic extract were recorded higher as compared to purified fractions (TPC = 70% and TFC = 69%). Amongst the purified fractions, fraction 6 exhibited the highest TPC value (64%), and purified fraction 1 exhibited the highest value of TFC (58%). Recent research demonstrated that Cydonia oblonga may be considered an antibacterial medicinal plant. The result of the present study revealed that it might be utilized for the isolation of bioactive phytochemicals that can lead to new opportunities in the discovery of new antibiotics.     

Volatiles Composition and Antimicrobial Activities of Areca Nut Extracts Obtained by Simultaneous Distillation–Extraction and Headspace Solid-Phase Microextraction

The volatile components of areca nuts were isolated by headspace solid-phase microextraction (HS-SPME, DVB/CAR/PDMS fiber extraction) and simultaneous hydrodistillation–extraction (SHDE) and analyzed by gas chromatography/mass spectrometry. Furthermore, all SHDE fractions were tested for antimicrobial activity using the disk diffusion method on nine Gram-negative and Gram-positive bacteria (Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus agalactiae, Streptococcus canis, Streptococcus pyogenes, and Candida albicans). In total, 98 compounds (mainly alcohols, carbonyl compounds, fatty acids, esters, terpenes, terpenoids, and aliphatic hydrocarbons) were identified in SHDE fractions and by using SPME extraction Fatty acids were the main group of volatile constituents detected in all types of extracts. The microorganism most sensitive to the extract of the areca nut was Streptococcus canis. The results can provide essential information for the application of different treatments of areca nuts in the canning industry or as natural antibiotics.     

Comparison of extraction techniques for the isolation of explosives and their degradation products from soil

A comparison of four extraction techniques used for the isolation of 14 explosive compounds (Method 8330-Explosives) from spiked soil samples is described. Soxhlet warm extraction (SWE), pressurized solvent extraction (PSE), microwave assisted extraction (MAE) and supercritical fluid extraction (SFE) were included. The effects of basic extraction conditions – i.e. type of extraction solvent, temperature, pressure, and extraction time – were investigated. The best extraction recovery of the monitored compounds from spiked soil was obtained using pressurized solvent extraction. Recoveries of explosives using the PSE technique were in the range from 65 to 112%. Extraction recoveries by Soxhlet warm extraction and supercritical fluid extraction reached 65–99% and 52–75%, respectively. The lowest extraction recoveries (28–65%) were obtained using microwave assisted extraction. A very low extraction recovery for tetryl was observed in all cases but the best results were achieved by pressurized solvent extraction (58%).