气相色谱-质谱法测定姜黄挥发油化学成分

采用水蒸气蒸馏法提取姜黄挥发油,用气相色谱－质谱联用技术分离和鉴定姜黄挥发油的化学成分。经计算机ＮＢＳ谱库检索,发现姜黄挥发油中至少有１５个峰,鉴定出α－姜黄烯、α－姜烯、桉叶油素和球姜酮等１５种组分;另外还有１－（３－环戊基醛）－２,４－二甲基苯、β－倍半水芹烯、大根香叶酮、大根香叶烷、顺双环［３,３,１］酮－２－烯－９－醇等成分。姜黄挥发油中主要成分为α－姜黄烯。     

Chemical composition,antioxidant and antiproliferative activities of essential oil from rhizome and leaves of Curcuma mutabilis Škorničk., M. Sabu & Prasanthk., endemic to Western Ghats of India

Abstract

Hydro-distilled essential oils, from fresh rhizomes and leaves of Curcuma mutabilis ?korni?k., M.Sabu & Prasanthk., characterized by GC–MS revealed the presence of thirty three and twenty three compounds therein respectively. Whilst estrone methyl ether (3-Methoxyestra-1,3,5(10)-trien-17-one) was the major component in rhizome oil (47.35%), sesquiterpene hydrocarbons predominated as the major group (63.92%) in leaf oil with a higher preponderance of β-caryophyllene (25.48%), β-farnesene (19.47%) and α-humulene (11.01%). Weak antioxidant activities observed in these oils determined by DPPH and ABTS methods were apparently influenced both by the oil composition and the assay conditions. Rhizome oil showed higher antiproliferative activity than leaf oil against leukemic K562 (IC₅₀-6.8µg/mL) and colorectal HCT116 (IC₅₀-8.5µg/mL) cancer cell lines. This first report reveals composition and biological activities of essential oils from C. mutabilis.     

Characterization of polysaccharides having activity on the reticuloendothelial system from the rhizome of Curcuma longa

Three polysaccharides, named ukonan A, ukonan B and ukonan C, were isolated from the rhizomes of Curcuma longa L. They were homogeneous on electrophoresis and gel chromatography, and showed remarkable reticuloendothelial system-potentiating activity in a carbon clearance test. They are composed of L-arabinose: D-xylose: D-galactose: D-glucose: L-rhamnose: D-galacturonic acid in the molar ratios of 12:4:12:1:4:10 (ukonan A), 12:4:12:1:2:4 (ukonan B) and 8:3:6:14:2:3 (ukonan C), in addition to small amounts of peptide moiety. Methylation analysis, carbon-13 nuclear magnetic resonance and periodate oxidation studies indicated the structural features of ukonan B, the major one in terms of the activity. It has acidic arabino-galactan type structural units.     

Composition of essential oil and antioxidant capacity of Centaurea drabifolia Sm. subsp. detonsa (Bornm.) Wagenitz, endemic to Turkey

In this study, composition of essential oil and antioxidant capacity of Centaurea drabifolia subsp. detonsa were investigated. The antioxidant capacity of the methanolic extract was evaluated by various methods including measuring the total phenolic content, total antioxidant capacity, free radical scavenging activity (DPPH assay), β-carotene/linoleic acid bleaching assay and ferric and cupric ion reducing power assay. The composition of essential oil was identified by using gas chromatography-mass spectrometry. Totally, 41 compounds were described in the essential oil. Germacrene D (44.829%) was determined as the major compound of the essential oil. The total phenolic content, total antioxidant capacity, inhibition rate of oxidation of linoleic acid, IC(50) (in DPPH assay) and EC(50) (in reducing power) value were found to be 40.454?mg?GAE/g, 100.840?mg?AAE/g, 65.639%, 39.584?μg?mL(-1) and 0.603?mg?mL(-1), respectively. The results indicated that the extract of C. drabifolia subsp. detonsa has strong antioxidant properties and this species can be used as a natural antioxidant in food processing and pharmaceutical industries.     

Standardization of the ayurvedic formulation Haridra Khanda using high-performance thin-layer chromatography-densitometry

The present study aimed to standardize the Ayurvedic preparation Haridra Khanda containing Curcuma longa as a major ingredient. Various physicochemical parameters such as alcohol-soluble extractive, water-soluble extractive, total ash, and acid-insoluble ash were determined according to the Ayurvedic Pharmacopoeia of India. Microscopic evaluation of the formulation revealed the presence of various diagnostic cell structures of C. longa. Trace metal analysis indicated the absence of toxic metals such as As, Cd, Hg, and Pb. High-performance thin-layer chromatographic (HPTLC) fingerprint patterns at multiple wavelengths (254, 366, and 430 nm) identified the number of components present at each wavelength. The bioactive markers curcumin (C1), demethoxycurcumin (C2), and bisdemethoxycurcumin (C3) were quantified by using a simple, rapid, and efficient HPTLC method using plates precoated with silica gel 60F254 stationary phase. The instrumental precision [coefficient of variation (CV)] was 0.51, 0.64, and 0.79% and the repeatability of the method (CV) was 0.89, 1.11, and 0.95%, respectively, for C1 to C3. Limits of detection and quantitation for compounds C1 to C3 were 20, 20, and 15 ng and 50, 40, and 50 ng, respectively. Response was a linear function in the ranges of 50-350, 40-240, and 50-300 ng with correlation coefficient (r) = 0.9998, 0.9995, and 0.9992, respectively, for C1 to C3. The mean recovery values of 99.63 (C1), 98.65 (C2), and 98.97% (C3) indicated the excellent accuracy of the method. It is shown that HPTLC can be applied successfully for the marker evaluation of the formulation containing C. longa.     

反相高效液相色谱法同时测定姜黄药材中3个组分的含量

建立了一种反相高效液相色谱方法,同时测定中药材姜黄块根中3组分的含量。采用KromasilTMC18柱(5μm,200mm×4.6mm),以磷酸水溶液(pH=2.5)和乙腈溶剂为流动相,梯度洗脱,流速0.9mL/min,柱温40℃,检测波长为425nm,10min内即可将3种组分分离测定。该方法快速、简便、准确,可为评价不同产地的姜黄质量提供依据。     

Antimicrobial and antioxidant activities of Artemisia herba-alba essential oil cultivated in Tunisian arid zone

This study was conceived to examine the antimicrobial and antioxidant activities of four essential oil types extracted by hydrodistillation from the aerial parts of Artemisia herba-alba cultivated in southern Tunisia. The chemical composition was investigated using both capillary GC and GC/MS techniques. β-thujone, α-thujone, α-thujone/β-thujone and 1,8-cineole/camphor/α-thujone/β-thujone were respectively, the major components of these oil types. The antimicrobial activity of different oils was tested using the diffusion method and by determining the inhibition zone. The results showed that all examined oil types had great potential of antimicrobial activity against strains. In addition, antioxidant capacity was assessed by different in vitro tests and weak activity was found for these A. herba-alba oils.     

Simultaneous determination of 11 characteristic components in three species of Curcuma rhizomes using pressurized liquid extraction and high-performance liquid chromatography

A high-performance liquid chromatography coupled with diode array detection (HPLC-DAD) and pressurized liquid extraction was developed for simultaneous quantitative determination of 11 characteristic compounds, including curcumenone, curcumenol, neocurdione, curdione, isocurcumenol, furanodienone, curcumol, germacrone, curzerene, furanodiene and beta-elemene, in rhizomes of three species of Curcuma. The analysis was performed on an ODS C18 column. The mobile phase consisted of (A) water and (B) acetonitrile using a gradient elution. The peaks were monitored at both 214 nm and 256 nm. All calibration curves showed good linearity (r2 > 0.9996) within test ranges. This method showed good repeatability for the quantification of these eleven components in three species Curcuma rhizomes with intra- and inter-day variations of less than 1.57% and 1.98%, respectively. The validated method was successfully applied to quantify 11 investigated components in eighteen samples of three species of Curcuma, which is helpful to control their quality.     

Antioxidant, total phenolic content and cytotoxicity evaluation of selected Malaysian plants

Aqueous and ethanol extracts of different traditional Malaysian plants (Polygonum minus, Andrographis paniculata, Curcuma xanthorrhiza, Momordica charantia and Strobilanthes crispus) were evaluated for their antioxidant properties, total phenolic content and cytotoxic activity. Antioxidant activity was evaluated by using 1,1-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays. The results showed that ethanol extracts contain high antioxidant activities compared to aqueous extracts. The findings exhibited a strong correlation between antioxidant activity and the total phenol contents. In addition, all the plant extracts showed non-toxic effects against a normal human lung fibroblast cell line (Hs888Lu). Although traditionally aqueous extracts are used, we determined that ethanol extracts usually achieved better activity in the assays.     

In vitro enzyme inhibition activities of crude ethanolic extracts derived from medicinal plants of Pakistan

Twenty two crude ethanolic extracts from 14 indigenous medicinal plants were subjected to enzyme inhibition screening against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase enzymes (LO). Three extracts showed activity against AChE, nine extracts were found to be active against BChE and four extracts inhibited the enzyme LO. The most significant inhibition activities (> or =50%) were found in extracts derived from Aloe vera (leaves), Alpinia galanga (rhizome), Curcuma longa (rhizome), Cymbopogon citratus (leaves), Ocimum americanum (leaves), Ocimum americanum (stem) and Withania somnifera (roots).     

Antiradical efficiency of 20 selected medicinal plants

The antioxidant system of a plant comprises a group of chemicals that are highly diverse in their sources, effects and uses. These antioxidants are capable of contracting and damaging free radicals. This investigation deals with a screening and comparison of the antioxidant activities of 20 selected medicinal plants and their parts, individually and in combination with vitamins A, C or E, using the DPPH radical scavenging method. Phyllanthus emblica L., Santalum album L., Syzygium cumini L. and Trigonella foenum-graecum L. presented highly significant antiradical efficiency (AE) singly and in combination with either vitamin A, C or E. Further, Curcuma longa L., Momordica charantia L., S. cumini, T. foenum-graecum, Moringa oleifera Lam and S. album have also shown fairly significant AE in a vitamin combination dose of 0.001 mM concentration.     

Curcuma ecalcarata – new natural source of pinocembrin and piperitenone

Phytochemical analysis of the rhizome extract of Curcuma ecalcarata, a hitherto uninvestigated south Western Ghats endemic species, resulted in the isolation and identification of the diaryl heptanoid trans, trans-1,7-diphenyl-5-hydroxy-4,6-heptadiene-3-one (1), steroid β-sitosterol (2), flavanone pinocembrin (4) and monoterpenoids piperitenone (3) and 8-hydroxy piperitone (5). HPTLC estimation of pinocembrin in the rhizome revealed the plant as a rich source of pinocembrin (0.37% dry wt.). The rhizome essential oil was isolated by hydrodistillation and analysed by GC–FID, GC–MS and ¹³C NMR. Among the 30 constituents identified in the oil, monoterpenoids predominated (94.2%) followed by sesquiterpenoids (5.8%). The major compound consisting of 65.2% of the oil was isolated and identified as piperitenone (3). The study highlights the plant as a rich source of the flavanone pinocembrin and the volatile aroma compound piperitenone.     

Sesquiterpenoids from Curcuma wenyujin dreg and their biological activities

Four new sesquiterpenoids,4,8-dioxo-6β-hydroxyl-7β,1 1-epoxycarabrane(1),4,8-dioxo-6β-hydroxyl-7,1 1-epoxycarabrane(2),wenyujinins Q and R(3-4),and nine known sesquiterpenoids(5-13) were isolated from the Curcuma wenyujin(C wenyujin) dreg.Their structures and relative configurations were elucidated using 1D,2D NMR,and HR-ESI-MS data.All the compounds were isolated for the first time from the C.wenyujin dreg and evaluated for their antibacterial and antifungal activities.Compounds 3,5-8 exhibited strong broad-spectrum antifungal activities against tested nine pathogenic fungi.     

Phenolic acid contents, essential oil compositions and antioxidant activities of two varieties of Salvia euphratica from Turkey

This study was designed to evaluate the in vitro antioxidant activities of n-hexane (Hex), dichloromethane (DCM), methanol (MeOH) and essential oils (EO) extracts obtained from Salvia euphratica var. euphratica and Salvia euphratica var. leiocalycina and to determine their essential oil and phenolic acid compositions. The samples were screened for their antioxidant activity by using DPPH and β-carotene/linoleic acid assays. Methanol extracts of both varieties exhibited strong antioxidant activities. Our results showed that rosmarinic acid was dominant phenolic acid of MeOH extracts (39.4 and 55.8?μg?mg?1, respectively). The chemical compositions of essential oils of two varieties were analysed and their main components were determined as eucalyptol (18.4%) and trans-pinocarvyl acetate (24.9%), respectively. It can be said that these varieties could be used as natural antioxidant.     

Chemical characteristics and antioxidant properties of crude water soluble polysaccharides from four common edible mushrooms

Four crude water soluble polysaccharides, CABP, CAAP, CFVP and CLDP, were isolated from common edible mushrooms, including Agaricus bisporus, Auricularia auricula, Flammulina velutipes and Lentinus edodes, and their chemical characteristics and antioxidant properties were determined. Fourier Transform-infrared analysis showed that the four crude polysaccharides were all composed of β-glycoside linkages. The major monosaccharide compositions were D-galactose, D-glucose and D-mannose for CABP, CAAP and CLDP, while CFVP was found to consist of L-arabinose, D-galactose, D-glucose and D-mannose. The main molecular weight distributions of CABP and the other three polysaccharides were <5.1 × 10(4) Da and >66.0 × 10(4) Da, respectively. Antioxidant properties of the four polysaccharides were evaluated in in vitro systems and CABP showed the best antioxidant properties. The studied mushroom species could potentially be used in part of well-balanced diets and as a source of antioxidant compounds.     

Radical scavenging and antimicrobial activities of Croton zehntneri,Pterodon emarginatus and Schinopsis brasiliensis essential oils and their major constituents: estragole,trans-anethole, β-caryophyllene and myrcene

The essential oils (EOs) from the Brazilian species Croton zehntneri, Pterodon emarginatus and Schinopsis brasiliensis were examined for their chemical constituents, and antioxidant and antimicrobial activities. The composition of EOs was determined by using gas chromatography coupled with mass spectrometry analysis, while the antioxidant activity was evaluated through the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) assays. Furthermore, the antimicrobial activity was investigated against Escherichia coli and Pseudomonas aeruginosa (both Gram-negative), Staphylococcus aureus (Gram-positive) and Candida parapsilosis (fungus). The main components of C. zehntneri, P. emarginatus and S. brasiliensis were identified as estragole, trans-anethole, β-caryophyllene and myrcene. Among the EOs, P. emarginatus showed the highest antioxidant activity, with an IC₅₀ of 7.36 mg/mL and a Trolox equivalent antioxidant capacity of 3748 μmol/g determined by DPPH and ORAC assays, respectively. All EOs showed low activities against the bacterial strains tested, whereas the C. zehntneri oil and its main constituent estragole exhibited an appreciable antifungal activity against C. parapsilosis.     

Antioxidant activity of crude extracts and essential oils from flower buds and leaves of Cistus creticus and Cistus salviifolius

Volatile oils from flowers and leaves of C. creticus L. and C. salviifolius L. were extracted by two extraction methods; namely, hydrodistillation and solid-phase micro-extraction (SPME). The chemical composition of essential oils was analyzed by GC and GC–MS. The volatile extracted from leaves and flowers of C. criticus using SPME was dominated by monoterpenes and sesquiterpenes hydrocarbon with α-pinene, camphene and α-cubebene as major components. In hydrodistillation, the oil extracted from leaves was dominated by oxygenated diterpenes and diterpenes hydrocarbon with manoyl oxide and sclarene as major components, whereas, the oil extracted from flowers was dominated by oxygenated diterpenes and diterpenes hydrocarbon with manoyl oxide and abietatriene as major components. The volatile from flowers and leaves of C. salviifolius obtained by SPME were dominated by monoterpenes and sesquiterpenes with δ-3-carene, α-pinene, β-pinene, and E-caryophyllene as major constituents. On the other hand, the oils from flowers and leaves of C. salviifolius obtained by hydrodistillation were dominated by oxygenated diterpenes, diterpenes hydrocarbon and esters with dehydro abietol, abietol, manoyl oxide and methyl octadecenoate as major components. In the leaves, the major components of the oil were manoyl oxide, E-ethyl cinnamate, and Z-ethyl cinnamate. These oils showed weak antioxidant activity when compared to the positive controls α-tocopherol, ascorbic acid, and EDTA, while the crude extracts aq. MeOH, butanol, and water showed good antioxidant activity. Discriminating between the studied plants based on the extraction method was also possible upon applying Principle component analysis (PCA) to the obtained GC–MS data.     

Chemical composition and antioxidant activity of the essential oil of endemic Viola tianshanica

The composition and in vitro antioxidant activities of the essential oil and methanol extract of the aerial parts of Viola tianshanica were evaluated in this research. GC-MS analysis of the essential oil resulted in the identification of 15 constituents, representing 89.67% of the oil. The major compounds detected in the essential oil were dibutyl phthalate (15.19%), hexadecanoate methyl (8.65%), n-hexadecanoic acid (3.07%) and 2,3-pentanedione (2.62%). Essential oil and methanol extract were tested for their antioxidant activities using 1,1-diphenyl-2-picryl-hydrazyl free radical scavenging and β-carotene linoleic acid assay. In addition, the total phenol of essential oil, polar subfraction and non-polar subfraction were determined.     

Chemical composition and antioxidant activity of the essential oil of Schisandra chinensis fruits

This study was designed to examine the composition and in vitro antioxidant activity of the essential oil of Schisandra chinensis fruits. Gas chromatography/mass spectrometry was used to determine the composition of the essential oil. Forty components were identified, representing 90.80% of the oil; ylangene (37.72%), β-himachalene (10.46%) and α-bergamotene (8.57%) were the main components. Antioxidant and radical-scavenging properties were evaluated by means of 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and β-carotene bleaching assay. In the DPPH assay, IC(50) value of the S. chinensis essential oil was determined as 4.17 mg mL(-1). In the β-carotene bleaching assay, the essential oil (1.0 mg mL(-1)) exhibited 25.89% inhibition against linoleic acid oxidation. In both systems, antioxidant capacity of butylated hydroxytoluene was also determined in parallel experiments.