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16 pages, 1146 KiB

Open AccessArticle

A Comprehensive and Rapid Quality Evaluation Method of Traditional Chinese Medicine Decoction by Integrating UPLC-QTOF-MS and UFLC-QQQ-MS and Its Application

by Yinfang Chen, Riyue Yu, Li Jiang, Qiyun Zhang, Bingtao Li, Hongning Liu and Guoliang Xu

Molecules 2019, 24(2), 374; https://doi.org/10.3390/molecules24020374 - 21 Jan 2019

Cited by 11 | Viewed by 4420

Abstract

Decoction is one of the oldest forms of traditional Chinese medicine and it is widely used in clinical practice. However, the quality evaluation and control of traditional decoction is a challenge due to the characteristics of complicated constituents, water as solvent, and temporary [...] Read more.

Decoction is one of the oldest forms of traditional Chinese medicine and it is widely used in clinical practice. However, the quality evaluation and control of traditional decoction is a challenge due to the characteristics of complicated constituents, water as solvent, and temporary preparation. ShenFu Prescription Decoction (SFPD) is a classical prescription for preventing and treating many types of cardiovascular disease. In this article, a comprehensive and rapid method for quality evaluation and control of SFPD was developed, via qualitative and quantitative analysis of the major components by integrating ultra-high-performance liquid chromatography equipped with quadrupole time-of-flight mass spectrometry and ultra-fast-performance liquid chromatography equipped with triple quadrupole mass spectrometry. Consequently, a total of 39 constituents were tentatively identified in qualitative analysis, of which 21 compounds were unambiguously confirmed by comparing with reference substances. We determined 13 important constituents within 7 min by multiple reaction monitoring. The validated method was applied for determining five different proportion SFPDs. It was found that different proportions generated great influence on the dissolution of constituents. This may be one of the mechanisms for which different proportions play different synergistic effects. Therefore, the developed method is a fast and useful approach for quality evaluation of SFPD. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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13 pages, 829 KiB

Open AccessArticle

Qualitative and Quantitative Analysis of C-glycosyl-flavones of Iris lactea Leaves by Liquid Chromatography/Tandem Mass Spectrometry

by Dan Chen, Yu Meng, Yan Zhu, Gang Wu, Jun Yuan, Minjian Qin and Guoyong Xie

Molecules 2018, 23(12), 3359; https://doi.org/10.3390/molecules23123359 - 18 Dec 2018

Cited by 11 | Viewed by 3760

Abstract

Iris lactea Pall. var. chinensis (Fisch.) Koidz. is a traditional medicinal plant resource. To make full use of the I. lactea plant resources, constituents of I. lactea leaves were determined by high performance liquid chromatography (HPLC)-quadrupole time-of-flight tandem mass spectrometry and 22 C [...] Read more.

Iris lactea Pall. var. chinensis (Fisch.) Koidz. is a traditional medicinal plant resource. To make full use of the I. lactea plant resources, constituents of I. lactea leaves were determined by high performance liquid chromatography (HPLC)-quadrupole time-of-flight tandem mass spectrometry and 22 C-glycosylflavones were identified or tentatively identified. Optimal extraction of I. lactea leaves was established via single factor investigations combined with response surface methodology. Then, HPLC coupled with a diode array detector was used to quantitatively analyze the six main components of 14 batches of I. lactea leaves grown in different areas. The results showed the C-glycosylflavones were the main components of I. lactea leaves, and the total contents of detected components were relatively stable for the majority of samples. These results provide a foundation for the development and utilization of I. lactea leaves. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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14 pages, 1423 KiB

Open AccessArticle

Evaluation of Antioxidant Capacity, Protective Effect on Human Erythrocytes and Phenolic Compound Identification in Two Varieties of Plum Fruit (Spondias spp.) by UPLC-MS

by Karen L. Hernández-Ruiz, Saul Ruiz-Cruz, Luis A. Cira-Chávez, Laura E. Gassos-Ortega, José de Jesús Ornelas-Paz, Carmen L. Del-Toro-Sánchez, Enrique Márquez-Ríos, Marco A. López-Mata and Francisco Rodríguez-Félix

Molecules 2018, 23(12), 3200; https://doi.org/10.3390/molecules23123200 - 04 Dec 2018

Cited by 29 | Viewed by 3877

Abstract

Plum edible part was used to obtained extracts by during a 4 h maceration process using three different solvents (ethanol, methanol and water) for the determination of total phenols and flavonoids, antioxidant capacity by (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hemolysis [...] Read more.

Plum edible part was used to obtained extracts by during a 4 h maceration process using three different solvents (ethanol, methanol and water) for the determination of total phenols and flavonoids, antioxidant capacity by (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hemolysis inhibition in human blood assays. Subsequently, phenolic compounds were identified using ultra-performance liquid chromatography (UPLC-MS). The results indicated that the ethanolic extract of plum fruit being a good source of phenolic (12–18 mg GAE/g FW) and flavonoids (2.3–2.5 mg QE/g FW) content in both varieties of plum. Also, the fruits proved a good source of antioxidants as measured by DPPH and ABTS; likewise, plum aqueous extracts showed the highest protective effect on human erythrocytes with 74.34 and 64.62% for yellow and red plum, respectively. A total of 23 bioactive compounds were identified by UPLC-MS, including gallic acid, rutin, resorcinol, chlorogenic acid, catechin, and ellagic acid, and the antioxidant capacity can be attributed to these species. The edible part of plum contains compounds of biological interest, suggesting that this fruit has antioxidant potential that can be exploited for various technologies. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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11 pages, 2462 KiB

Open AccessFeature PaperArticle

A Design of Experiment Approach for Ionic Liquid-Based Extraction of Toxic Components-Minimized Essential Oil from Myristica fragrans Houtt. Fruits ^†

by Daniela Lanari, Maria Carla Marcotullio and Andrea Neri

Molecules 2018, 23(11), 2817; https://doi.org/10.3390/molecules23112817 - 30 Oct 2018

Cited by 12 | Viewed by 4602

Abstract

The effect of the addition of ionic liquids (ILs) during the hydrodistillation of Myristica fragrans Houtt. (nutmeg) essential oil was studied. The essential oil of M. fragrans is characterized by the presence of terpenes, terpenoids, and of phenylpropanoids, such as methyl eugenol and [...] Read more.

The effect of the addition of ionic liquids (ILs) during the hydrodistillation of Myristica fragrans Houtt. (nutmeg) essential oil was studied. The essential oil of M. fragrans is characterized by the presence of terpenes, terpenoids, and of phenylpropanoids, such as methyl eugenol and safrole, that are regarded as genotoxic and carcinogenic. The aim of the work was to determine the best ionic liquid to improve the yield of the extraction of M. fragrans essential oil and decrease the extraction of toxic phenylpropanoids. Six ILs, namely 1,3-dimethylimidazolium chloride (1), 1,3-dimethylimidazolium dimethylphosphate (2), 1-(2-hydroxyethyl)-3-methylimidazolium chloride (3), 1-(2-hydroxyethyl)-3-methylimidazolium dimethylphosphate (4), 1-butyl-3-methylimidazolium chloride (5), and 1-butyl-3-methylimidazolium dimethylphosphate (6), were prepared by previously reported, innovative methods and then tested. An experimental design was used to optimize the extraction yield and to decrease the phenylpropanoids percentage using the synthesized ILs. The influence of the molarity of ILs was also studied. MODDE 12 software established 0.5 M 1-butyl-3-methylimidazolium chloride as the best co-solvent for the hydrodistillation of M. fragrans essential oil. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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8 pages, 897 KiB

Open AccessArticle

Development and Validation of an HPLC-ELSD Method for the Quantification of 1-Triacontanol in Solid and Liquid Samples

by Stefania Sut, Clizia Franceschi, Gregorio Peron, Gabriele Poloniato and Stefano Dall’Acqua

Molecules 2018, 23(11), 2775; https://doi.org/10.3390/molecules23112775 - 26 Oct 2018

Cited by 3 | Viewed by 5544

Abstract

1-Triacontanol (TRIA) is gaining a lot of interest in agricultural practice due to its use as bio-stimulant and different types of TRIA-containing products have been presented on the market. Up to date, TRIA determination is performed by GC analysis after chemical derivatization, but [...] Read more.

1-Triacontanol (TRIA) is gaining a lot of interest in agricultural practice due to its use as bio-stimulant and different types of TRIA-containing products have been presented on the market. Up to date, TRIA determination is performed by GC analysis after chemical derivatization, but in aqueous samples containing low amounts of TRIA determination can be problematic and the derivatization step can be troublesome. Hence, there is the need for an analysis method without derivatization. TRIA-based products are in general plant extracts that can be obtained with different extraction procedures. These products can contain different ranges of concentration of TRIA from units to thousands of mg/kg. Thus, there is the need for a method that can be applied to different sample matrices like plant materials and different plant extracts. In this paper we present a HPLC-ELSD method for the analysis of TRIA without derivatization. The method has been fully validated and it has been tested analyzing the content of TRIA in different dried vegetal matrices, plant extracts, and products. The method is characterized by high sensitivity (LOD = 0.2 mg/L, LOQ = 0.6 mg/L) and good precision (intra-day: <11.2%, inter-day: 10.2%) being suitable for routine analysis of this fatty alcohol both for quality control or research purposes. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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16 pages, 300 KiB

Open AccessArticle

Free Radical-Scavenging Capacities, Phenolics and Capsaicinoids in Wild Piquin Chili (Capsicum annuum var. Glabriusculum)

by Yolanda Del Rocio Moreno-Ramírez, Guillermo C. G. Martínez-Ávila, Víctor Arturo González-Hernández, Cecilia Castro-López and Jorge Ariel Torres-Castillo

Molecules 2018, 23(10), 2655; https://doi.org/10.3390/molecules23102655 - 16 Oct 2018

Cited by 24 | Viewed by 4410

Abstract

The total phenolic compounds content, free radical-scavenging capacity and capsaicinoid content in populations of wild Piquin chili (C. annuum) were studied. Aqueous and hydroalcoholic extracts from nine ecotypes were evaluated. High contents of phenolic compounds and free radical-scavenging capacities were observed [...] Read more.

The total phenolic compounds content, free radical-scavenging capacity and capsaicinoid content in populations of wild Piquin chili (C. annuum) were studied. Aqueous and hydroalcoholic extracts from nine ecotypes were evaluated. High contents of phenolic compounds and free radical-scavenging capacities were observed for both extracts; however, the values that were found for the hydroalcoholic phase were substantially higher. LC-MS analysis allowed for the detection of 32 compounds, where apigenin-8-C-glucoside followed by vanillic acid 1-O-β-o-glucopyranosylester (Isomer I or II) and 7-ethoxy-4-methylcoumarin were the most widely distributed; they were found in more than 89% of the ecotypes. The diversity of identified phenolic compounds was different among ecotypes, allowing them to be distinguished by chemical diversity, free radical-scavenging capacities and heat Scoville units. The total capsaicinoid content was higher in Population I (23.5 mg/g DW) than in Populations II and III, which had contents of 15.3 and 10.7 mg/g DW, respectively. This variability could lead to phytochemical exploitation and the conservation of the natural populations of wild chili. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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17 pages, 1774 KiB

Open AccessArticle

Phytochemical Profiling of Fruit Powders of Twenty Sorbus L. Cultivars

by Kristina Zymone, Lina Raudone, Raimondas Raudonis, Mindaugas Marksa, Liudas Ivanauskas and Valdimaras Janulis

Molecules 2018, 23(10), 2593; https://doi.org/10.3390/molecules23102593 - 10 Oct 2018

Cited by 35 | Viewed by 4832

Abstract

Rowanberries have been traditionally used in various processed foods. Scientific research demonstrates the pharmacological effects of Sorbus L. fruits are determined by their unique composition of biologically active compounds. The aim of this study was to determine the composition of flavonoids, phenolic acids, [...] Read more.

Rowanberries have been traditionally used in various processed foods. Scientific research demonstrates the pharmacological effects of Sorbus L. fruits are determined by their unique composition of biologically active compounds. The aim of this study was to determine the composition of flavonoids, phenolic acids, anthocyanins, carotenoids, organic acids and sugars as well as the total antioxidant activity in fruit powders of 20 Sorbus cultivars. Chemical profiles of rowanberry fruit powders vary significantly. Cultivars ‘Burka’, ‘Likernaja’, ‘Dodong’, and ‘Fructo Lutea’ distinguish themselves with exclusive phytochemical composition and high antioxidant activity. Fruit powders from ‘Burka’, ‘Likernaja’ contain the highest contents of anthocyanins while fruit powder samples from ‘Fructo Lutea’ and ‘Dodong’ contain the highest levels of phenolic acids, ascorbic acid and the lowest levels of fructose. Fruit powder samples from ‘Dodong’ also contain the highest levels of β-carotene and sorbitol and the lowest levels of malic acid. Cultivars ‘Burka’, ‘Likernaja’, ‘Dodong’, and ‘Fructo Lutea’ could be selected as eligible raw materials for the preparation of rowanberry fruit powders. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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18 pages, 2318 KiB

Open AccessArticle

Establishing the Phenolic Composition of Olea europaea L. Leaves from Cultivars Grown in Morocco as a Crucial Step Towards Their Subsequent Exploitation

by Lucía Olmo-García, Aadil Bajoub, Sara Benlamaalam, Elena Hurtado-Fernández, María Gracia Bagur-González, Mohammed Chigr, Mohamed Mbarki, Alberto Fernández-Gutiérrez and Alegría Carrasco-Pancorbo

Molecules 2018, 23(10), 2524; https://doi.org/10.3390/molecules23102524 - 02 Oct 2018

Cited by 26 | Viewed by 3882

Abstract

In Morocco, the recovery of olive agro-industrial by-products as potential sources of high-added value substances has been underestimated so far. A comprehensive quantitative characterization of olive leaves’ bioactive compounds is crucial for any attempt to change this situation and to implement the valorization [...] Read more.

In Morocco, the recovery of olive agro-industrial by-products as potential sources of high-added value substances has been underestimated so far. A comprehensive quantitative characterization of olive leaves’ bioactive compounds is crucial for any attempt to change this situation and to implement the valorization concept in emerging countries. Thus, the phenolic fraction of olive leaves of 11 varieties (‘Arbequina’, ‘Hojiblanca’, ‘Frantoio’, ‘Koroneiki’, ‘Lechín’, ‘Lucque’, ‘Manzanilla’, ‘Picholine de Languedoc’, ‘Picholine Marocaine’, ‘Picual’ and ‘Verdal’), cultivated in the Moroccan Meknès region, was investigated. Thirty eight phenolic or related compounds (including 16 secoiridoids, nine flavonoids in their aglycone form, seven flavonoids in glycosylated form, four simple phenols, one phenolic acid and one lignan) were determined in a total of 55 samples by using ultrasonic-assisted extraction and liquid chromatography coupled to electrospray ionization-ion trap mass spectrometry (LC-ESI-IT MS). Very remarkable quantitative differences were observed among the profiles of the studied cultivars. ‘Picholine Marocaine’ variety exhibited the highest total phenolic content (around 44 g/kg dry weight (DW)), and logically showed the highest concentration in terms of various individual compounds. In addition, chemometrics (principal components analysis (PCA) and stepwise-linear discriminant analysis (s-LDA)) were applied to the quantitative phenolic compound data, allowing good discrimination of the selected samples according to their varietal origin. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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16 pages, 1501 KiB

Open AccessFeature PaperArticle

Unravelling the Distribution of Secondary Metabolites in Olea europaea L.: Exhaustive Characterization of Eight Olive-Tree Derived Matrices by Complementary Platforms (LC-ESI/APCI-MS and GC-APCI-MS)

by Lucía Olmo-García, Nikolas Kessler, Heiko Neuweger, Karin Wendt, José María Olmo-Peinado, Alberto Fernández-Gutiérrez, Carsten Baessmann and Alegría Carrasco-Pancorbo

Molecules 2018, 23(10), 2419; https://doi.org/10.3390/molecules23102419 - 20 Sep 2018

Cited by 59 | Viewed by 6056

Abstract

In order to understand the distribution of the main secondary metabolites found in Olea europaea L., eight different samples (olive leaf, stem, seed, fruit skin and pulp, as well as virgin olive oil, olive oil obtained from stoned and dehydrated fruits and olive [...] Read more.

In order to understand the distribution of the main secondary metabolites found in Olea europaea L., eight different samples (olive leaf, stem, seed, fruit skin and pulp, as well as virgin olive oil, olive oil obtained from stoned and dehydrated fruits and olive seed oil) coming from a Picudo cv. olive tree were analyzed. All the experimental conditions were selected so as to assure the maximum coverage of the metabolome of the samples under study within a single run. The use of LC and GC with high resolution MS (through different ionization sources, ESI and APCI) and the annotation strategies within MetaboScape 3.0 software allowed the identification of around 150 compounds in the profiles, showing great complementarity between the evaluated methodologies. The identified metabolites belonged to different chemical classes: triterpenic acids and dialcohols, tocopherols, sterols, free fatty acids, and several sub-types of phenolic compounds. The suitability of each platform and polarity (negative and positive) to determine each family of metabolites was evaluated in-depth, finding, for instance, that LC-ESI-MS (+) was the most efficient choice to ionize phenolic acids, secoiridoids, flavonoids and lignans and LC-APCI-MS was very appropriate for pentacyclic triterpenic acids (MS (−)) and sterols and tocopherols (MS (+)). Afterwards, a semi-quantitative comparison of the selected matrices was carried out, establishing their typical features (e.g., fruit skin was pointed out as the matrix with the highest relative amounts of phenolic acids, triterpenic compounds and hydroxylated fatty acids, and seed oil was distinctive for its high relative levels of acetoxypinoresinol and tocopherols). Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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12 pages, 677 KiB

Open AccessArticle

Natural Scaffolds with Multi-Target Activity for the Potential Treatment of Alzheimer’s Disease

by Luca Piemontese, Gabriele Vitucci, Marco Catto, Antonio Laghezza, Filippo Maria Perna, Mariagrazia Rullo, Fulvio Loiodice, Vito Capriati and Michele Solfrizzo

Molecules 2018, 23(9), 2182; https://doi.org/10.3390/molecules23092182 - 29 Aug 2018

Cited by 24 | Viewed by 4663

Abstract

A few symptomatic drugs are currently available for Alzheimer’s Disease (AD) therapy, but these molecules are only able to temporary improve the cognitive capacity of the patients if administered in the first stages of the pathology. Recently, important advances have been achieved about [...] Read more.

A few symptomatic drugs are currently available for Alzheimer’s Disease (AD) therapy, but these molecules are only able to temporary improve the cognitive capacity of the patients if administered in the first stages of the pathology. Recently, important advances have been achieved about the knowledge of this complex condition, which is now considered a multi-factorial disease. Researchers are, thus, more oriented toward the preparation of molecules being able to contemporaneously act on different pathological features. To date, the inhibition of acetylcholinesterase (AChE) and of β-amyloid (Aβ) aggregation as well as the antioxidant activity and the removal and/or redistribution of metal ions at the level of the nervous system are the most common investigated targets for the treatment of AD. Since many natural compounds show multiple biological properties, a series of secondary metabolites of plants or fungi with suitable structural characteristics have been selected and assayed in order to evaluate their potential role in the preparation of multi-target agents. Out of six compounds evaluated, 1 showed the best activity as an antioxidant (EC₅₀ = 2.6 ± 0.2 μmol/µmol of DPPH) while compound 2 proved to be effective in the inhibition of AChE (IC₅₀ = 6.86 ± 0.67 μM) and Aβ_1–40 aggregation (IC₅₀ = 74 ± 1 μM). Furthermore, compound 6 inhibited BChE (IC₅₀ = 1.75 ± 0.59 μM) with a good selectivity toward AChE (IC₅₀ = 86.0 ± 15.0 μM). Moreover, preliminary tests on metal chelation suggested a possible interaction between compounds 1, 3 and 4 and copper (II). Molecules with the best multi-target profiles will be used as starting hit compounds to appropriately address future studies of Structure-Activity Relationships (SARs). Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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16 pages, 1800 KiB

Open AccessArticle

UHPLC Analysis of Saffron (Crocus sativus L.): Optimization of Separation Using Chemometrics and Detection of Minor Crocetin Esters

by Angelo Antonio D’Archivio, Francesca Di Donato, Martina Foschi, Maria Anna Maggi and Fabrizio Ruggieri

Molecules 2018, 23(8), 1851; https://doi.org/10.3390/molecules23081851 - 25 Jul 2018

Cited by 22 | Viewed by 4874

Abstract

Ultra-high performance liquid chromatography (UHPLC) coupled with diode array detection (DAD) was applied to improve separation and detection of mono- and bis-glucosyl esters of crocetin (crocins), the main red-colored constituents of saffron (Crocus sativus L.), and other polar components. Response surface methodology [...] Read more.

Ultra-high performance liquid chromatography (UHPLC) coupled with diode array detection (DAD) was applied to improve separation and detection of mono- and bis-glucosyl esters of crocetin (crocins), the main red-colored constituents of saffron (Crocus sativus L.), and other polar components. Response surface methodology (RSM) was used to optimise the chromatographic resolution on the Kinetex C18 (Phenomenex) column taking into account of the combined effect of the column temperature, the eluent flow rate and the slope of a linear eluent concentration gradient. A three-level full-factorial design of experiments was adopted to identify suitable combinations of the above factors. The influence of the separation conditions on the resolutions of 22 adjacent peaks was simultaneously modelled by a multi-layer artificial neural network (ANN) in which a bit string representation was used to identify the target analytes. The chromatogram collected under the optimal separation conditions revealed a higher number of crocetin esters than those already characterised by means of mass-spectrometry data and usually detected by HPLC. Ultra-high performance liquid chromatography analyses carried out on the novel Luna Omega Polar C18 (Phenomenex) column confirmed the large number of crocetin derivatives. Further work is in progress to acquire mass-spectrometry data and to clarify the chemical structure to the newly found saffron components. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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18 pages, 2599 KiB

Open AccessArticle

Stereoselective and Simultaneous Analysis of Ginsenosides from Ginseng Berry Extract in Rat Plasma by UPLC-MS/MS: Application to a Pharmacokinetic Study of Ginseng Berry Extract

by Seong Yon Han, Min Goo Bae and Young Hee Choi

Molecules 2018, 23(7), 1835; https://doi.org/10.3390/molecules23071835 - 23 Jul 2018

Cited by 7 | Viewed by 4198

Abstract

The role of ginseng berry extract (GBE) has been attributed to its anti-hyperglycemic effect in humans. However, the pharmacokinetic characteristics of GBE constitutes after oral GBE administration have not been established yet. In this study, stereoselective and simultaneous analytical methods for 10 ginsenosides [...] Read more.

The role of ginseng berry extract (GBE) has been attributed to its anti-hyperglycemic effect in humans. However, the pharmacokinetic characteristics of GBE constitutes after oral GBE administration have not been established yet. In this study, stereoselective and simultaneous analytical methods for 10 ginsenosides (ginsenoside Rb1, Rb2, Rc, Rd, Re, Rg1, S-Rg2, R-Rg2, S-Rg3, and R-Rg3) were developed using ultra-performance liquid chromatography, coupled with electrospray ionization triple quadrupole tandem mass spectrometry (UPLC-MS/MS), for the pharmacokinetic study of GBE. Furthermore, the pharmacokinetic profiles of 10 ginsenosides after oral GBE were evaluated in rats. All analytes were detected with a linear concentration range of 0.01–10 µg/mL. Lower limits of detection (LLOD) and quantification (LLOQ) were 0.003 and 0.01 µg/mL, respectively, for all 10 ginsenosides. This established method was adequately validated in linearity, sensitivity, intra- and inter-day precision, accuracy, recovery, matrix effect, and stability. Relative standard deviations for all intra- and inter-precision of the 10 ginsenosides were below 11.5% and accuracies were 85.3–111%, which were sufficient to evaluate the pharmacokinetic study of oral GBE in rats. We propose that Rb1, Rb2, Rc, Rd, Re, Rg1, S-Rg2, R-Rg2 and/or S-Rg3 were appropriate pharmacokinetic markers of systemic exposure following oral GBE administration. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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12 pages, 1312 KiB

Open AccessArticle

Phytochemical Analysis of Podospermum and Scorzonera n-Hexane Extracts and the HPLC Quantitation of Triterpenes

by Özlem Bahadır-Acıkara, Serkan Özbilgin, Gülcin Saltan-İşcan, Stefano Dall’Acqua, Veronika Rjašková, Fevzi Özgökçe, Václav Suchý and Karel Šmejkal

Molecules 2018, 23(7), 1813; https://doi.org/10.3390/molecules23071813 - 21 Jul 2018

Cited by 16 | Viewed by 5113

Abstract

Previously tested n-hexane extracts of the Scorzonera latifolia showed promising bioactivity in vivo. Because triterpenes could account for this activity, n-hexane extracts were analyzed by HPLC to identify and quantify the triterpenes as the most abundant constituents. Other Scorzonera and Podospermum [...] Read more.

Previously tested n-hexane extracts of the Scorzonera latifolia showed promising bioactivity in vivo. Because triterpenes could account for this activity, n-hexane extracts were analyzed by HPLC to identify and quantify the triterpenes as the most abundant constituents. Other Scorzonera and Podospermum species, potentially containing triterpenic aglycones, were included in the study. An HPLC method for simultaneous determination of triterpene aglycones was therefore developed for analysis of Podospermum and Scorzonera species. n-Hexane extracts of root and aerial parts of S. latifolia, ten other Scorzonera species and two Podospermum species were studied to compare the content of triterpenes. HPLC was used for the qualitative and quantitative analysis of α-amyrin, lupeol, lupeol acetate, taraxasteryl acetate, 3-β-hydroxy-fern-7-en-6-one acetate, urs-12-en-11-one-3-acetyl, 3-β-hydroxy-fern-8-en-7-one acetate, and olean-12-en-11-one-3-acetyl. Limits of detection and quantification were determined for each compound. HPLC fingerprinting of n-hexane extracts of Podospermum and Scorzonera species revealed relatively large amounts of triterpenes in a majority of investigated taxa. Lupeol, lupeol acetate, and taraxasteryl acetate were found in a majority of the species, except S. acuminata. The presence of α-amyrin, 3β-hydroxy-fern-7-en-6-one-acetate, urs-12-en-11-one-3-acetyl, 3β-hydroxy-fern-8-en-7-one-acetate, and olean-12-en-11-one-3-acetyl was detected in varying amounts. The triterpene content could correlate with the analgesic and anti-inflammatory activity of Scorzonera, which was previously observed and Scorzonera species that have been determined to contain triterpenes in large amounts and have not yet been tested for their analgesic activity should be tested for their potential analgesic and anti-inflammatory potential. The presented HPLC method can be used for analysis of triterpene aglycones, for example dedicated to chemosystematic studies of the Scorzonerinae. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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13 pages, 573 KiB

Open AccessArticle

A UPLC-ESI-MS/MS Method for Simultaneous Quantitation of Chlorogenic Acid, Scutellarin, and Scutellarein in Rat Plasma: Application to a Comparative Pharmacokinetic Study in Sham-Operated and MCAO Rats after Oral Administration of Erigeron breviscapus Extract

by Siying Chen, Mei Li, Yueting Li, Hejia Hu, Ying Li, Yong Huang, Lin Zheng, Yuan Lu, Jie Hu, Yanyu Lan, Aimin Wang, Yongjun Li, Zipeng Gong and Yonglin Wang

Molecules 2018, 23(7), 1808; https://doi.org/10.3390/molecules23071808 - 21 Jul 2018

Cited by 12 | Viewed by 4156

Abstract

Erigeron breviscapus, a traditional Chinese medicine, is clinically used for the treatment of occlusive cerebral vascular diseases. We developed a sensitive and reliable ultra-performance liquid chromatography-electrospray-tandem mass spectrometry (UPLC-ESI-MS/MS) method for simultaneous quantitation of chlorogenic acid, scutellarin, and scutellarein, the main active [...] Read more.

Erigeron breviscapus, a traditional Chinese medicine, is clinically used for the treatment of occlusive cerebral vascular diseases. We developed a sensitive and reliable ultra-performance liquid chromatography-electrospray-tandem mass spectrometry (UPLC-ESI-MS/MS) method for simultaneous quantitation of chlorogenic acid, scutellarin, and scutellarein, the main active constituents in Erigeron breviscapus, and compared the pharmacokinetics of these active ingredients in sham-operated and middle cerebral artery occlusion (MCAO) rats orally administrated with Erigeron breviscapus extract. Plasma samples were collected at 15 time points after oral administration of the Erigeron breviscapus extract. The levels of chlorogenic acid, scutellarin, and scutellarein in rat plasma at various time points were determined by a UPLC-ESI-MS/MS method, and the drug concentration versus time plots were constructed to estimate pharmacokinetic parameters. The concentration of chlorogenic acid in the plasma reached the maximum plasma drug concentration in about 15 min and was below the limit of detection after 4 h. Scutellarin and scutellarein showed the phenomenon of multiple absorption peaks in sham-operated and MCAO rats, respectively. Compared with the sham-operated rats, the terminal elimination half-life of scutellarein in the MCAO rats was prolonged by more than two times and the area under the curve of each component in the MCAO rats was significantly increased. The results showed chlorogenic acid, scutellarin, and scutellarein in MCAO rats had higher drug exposure than that in sham-operated rats, which provided a reference for the development of innovative drugs, optimal dosing regimens, and clinical rational drug use. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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10 pages, 2103 KiB

Open AccessArticle

Analysis of the Active Constituents and Evaluation of the Biological Effects of Quercus acuta Thunb. (Fagaceae) Extracts

by Mi-Hyeon Kim, Dae-Hun Park, Min-Suk Bae, Seung-Hui Song, Hyung-Ju Seo, Dong-Gyun Han, Deuk-Sil Oh, Sung-Tae Jung, Young-Chang Cho, Kyung-Mok Park, Chun-Sik Bae, In-Soo Yoon and Seung-Sik Cho

Molecules 2018, 23(7), 1772; https://doi.org/10.3390/molecules23071772 - 19 Jul 2018

Cited by 10 | Viewed by 3800

Abstract

We evaluated the antioxidant and antibacterial activity of hexnane, ethyl acetate, acetone, methanol, ethanol, and water extracts of the Quercus acuta leaf. The antioxidant properties were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity, reducing power, and total phenolic content. Antibacterial activity was [...] Read more.

We evaluated the antioxidant and antibacterial activity of hexnane, ethyl acetate, acetone, methanol, ethanol, and water extracts of the Quercus acuta leaf. The antioxidant properties were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity, reducing power, and total phenolic content. Antibacterial activity was assessed against general infectious pathogens, including antibiotic-resistant clinical isolates. The methanolic extract showed the highest DPPH radical scavenging activity and total phenolic content, while the reducing power was the highest in the water extract. The ethyl acetate extract showed the best antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains. Additionally, it displayed antibacterial activity against Staphylococcus aureus KCTC1928, Micrococcus luteus ATCC 9341, Salmonella typhimurium KCTC 1925, Escherichia coli KCTC 1923, and eight MRSA strains. These results present basic information for the possible uses of the ethanolic and ethyl acetate extracts from Q. acuta leaf in the treatment of diseases that are caused by oxidative imbalance and antibiotic-resistant bacterial infections. Six active compounds, including vitamin E, which are known to possess antioxidant and antibacterial activity, were identified from the extracts. To the best of our knowledge, this is the first study that reports the chemical profiling and antibacterial effects of the various QA leaf extracts, suggesting their potential use in food therapy or alternative medicine. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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9 pages, 588 KiB

Open AccessArticle

Simultaneous Quantification of Three Curcuminoids and Three Volatile Components of Curcuma longa Using Pressurized Liquid Extraction and High-Performance Liquid Chromatography

by In-Cheng Chao, Chun-Ming Wang, Shao-Ping Li, Li-Gen Lin, Wen-Cai Ye and Qing-Wen Zhang

Molecules 2018, 23(7), 1568; https://doi.org/10.3390/molecules23071568 - 28 Jun 2018

Cited by 50 | Viewed by 5827

Abstract

A high-performance liquid chromatography (HPLC) method was investigated for the simultaneous quantification of two chemical types of bioactive compounds in the rhizome of Curcuma longa Linn. (turmeric), including three curcuminoids: Curcumin, bisdemethoxycurcumin, and demethoxycurcumin; and three volatile components: ar-turmerone, β-turmerone, and [...] Read more.

A high-performance liquid chromatography (HPLC) method was investigated for the simultaneous quantification of two chemical types of bioactive compounds in the rhizome of Curcuma longa Linn. (turmeric), including three curcuminoids: Curcumin, bisdemethoxycurcumin, and demethoxycurcumin; and three volatile components: ar-turmerone, β-turmerone, and α-turmerone. In the present study, the sample extraction system was optimized by a pressurized liquid extraction (PLE) process for further HPLC analysis. The established HPLC analysis conditions were achieved using a Zorbax SB-C18 column (250 mm × 4.6 mm i.d., 5 μm) and a gradient mobile phase comprised of acetonitrile and 0.4% (v/v) aqueous acetic acid with an eluting rate of 1.0 mL/min. The curcuminoids and volatile components were detected at 430 nm and 240 nm, respectively. Moreover, the method was validated in terms of linearity, sensitivity, precision, stability and accuracy. The validated method was successfully applied to evaluate the quality of twelve commercial turmeric samples. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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11 pages, 23061 KiB

Open AccessArticle

Aleuritolic Acid Impaired Autophagic Flux and Induced Apoptosis in Hepatocellular Carcinoma HepG2 Cells

by Hua Yi, Kun Wang, Biaoyan Du, Lina He, Hiuting HO, Maosong Qiu, Yidan Zou, Qiao Li, Junfeng Jin, Yujuan Zhan, Zhongxiang Zhao and Xiaodong Liu

Molecules 2018, 23(6), 1338; https://doi.org/10.3390/molecules23061338 - 02 Jun 2018

Cited by 9 | Viewed by 4244

Abstract

Aleuritolic acid (AA) is a triterpene that is isolated from the root of Croton crassifolius Geisel. In the present study, the cytotoxic effects of AA on hepatocellular carcinoma cells were evaluated. AA exerted dose- and time-dependent cytotoxicity by inducing mitochondria-dependent apoptosis in the [...] Read more.

Aleuritolic acid (AA) is a triterpene that is isolated from the root of Croton crassifolius Geisel. In the present study, the cytotoxic effects of AA on hepatocellular carcinoma cells were evaluated. AA exerted dose- and time-dependent cytotoxicity by inducing mitochondria-dependent apoptosis in the hepatocellular carcinoma cell line, HepG2. Meanwhile, treatment with AA also caused dysregulation of autophagy, as evidenced by enhanced conversion of LC3-I to LC3-II, p62 accumulation, and co-localization of GFP and mCherry-tagged LC3 puncta. Notably, blockage of autophagosome formation by ATG5 knockdown or inhibitors of phosphatidylinositol 3-kinase (3-MA or Ly294002), significantly reversed AA-mediated cytotoxicity. These data indicated that AA retarded the clearance of autophagic cargos, resulting in the production of cytotoxic factors and led to apoptosis in hepatocellular carcinoma cells. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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13 pages, 1041 KiB

Open AccessArticle

Hydrophobic Amino Acid Content in Onions as Potential Fingerprints of Geographical Origin: The Case of Rossa da Inverno sel. Rojo Duro

by Federica Ianni, Antonella Lisanti, Maura Marinozzi, Emidio Camaioni, Lucia Pucciarini, Andrea Massoli, Roccaldo Sardella, Luciano Concezzi and Benedetto Natalini

Molecules 2018, 23(6), 1259; https://doi.org/10.3390/molecules23061259 - 25 May 2018

Cited by 11 | Viewed by 3786

Abstract

In this study, we were interested in comparing the amino acid profile in a specific variety of onion, Rossa da inverno sel. Rojo Duro, produced in two different Italian sites: the Cannara (Umbria region) and Imola (Emilia Romagna region) sites. Onions were [...] Read more.

In this study, we were interested in comparing the amino acid profile in a specific variety of onion, Rossa da inverno sel. Rojo Duro, produced in two different Italian sites: the Cannara (Umbria region) and Imola (Emilia Romagna region) sites. Onions were cultivated in a comparable manner, mostly in terms of the mineral fertilization, seeding, and harvesting stages, as well as good weed control. Furthermore, in both regions, the plants were irrigated by the water sprinkler method and subjected to similar temperature and weather conditions. A further group of Cannara onions that were grown by micro-irrigation was also evaluated. After the extraction of the free amino acid mixture, an ion-pairing reversed-phase (IP-RP) HPLC method allowed for the separation and the evaporative light scattering detection of almost all the standard proteinogenic amino acids. However, only the peaks corresponding to leucine (Leu), phenylalanine (Phe), and tryptophan (Trp), were present in all the investigated samples and they were unaffected from the matrix interfering peaks. The use of the beeswarm/box plots revealed that the content of Leu and Phe were markedly influenced by the geographical origin of the onions (with *** p << 0.001 for Phe), but not by the irrigation procedure. The applied HPLC method was validated in terms of the specificity, the linearity (a logarithm transformation was applied for the method linearization), the limit of detection (LOD) and limit of quantification (LOQ), the accuracy (≥90% for inter-day Recovery percentage), and the precision (≤10.51 for the inter-day RSD percentage), before the quantitative assay of Leu, Phe, and Trp in the onion samples. These preliminary findings are a good starting point for considering the quantity of the specific amino acids in the Rossa da inverno sel. Rojo Duro variety as a fingerprint of its geographical origin. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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22 pages, 1865 KiB

Open AccessArticle

Quality Traits of “Cannabidiol Oils”: Cannabinoids Content, Terpene Fingerprint and Oxidation Stability of European Commercially Available Preparations

by Radmila Pavlovic, Giorgio Nenna, Lorenzo Calvi, Sara Panseri, Gigliola Borgonovo, Luca Giupponi, Giuseppe Cannazza and Annamaria Giorgi

Molecules 2018, 23(5), 1230; https://doi.org/10.3390/molecules23051230 - 20 May 2018

Cited by 140 | Viewed by 28927

Abstract

Cannabidiol (CBD)-based oil preparations are becoming extremely popular, as CBD has been shown to have beneficial effects on human health. CBD-based oil preparations are not unambiguously regulated under the European legislation, as CBD is not considered as a controlled substance. This means that [...] Read more.

Cannabidiol (CBD)-based oil preparations are becoming extremely popular, as CBD has been shown to have beneficial effects on human health. CBD-based oil preparations are not unambiguously regulated under the European legislation, as CBD is not considered as a controlled substance. This means that companies can produce and distribute CBD products derived from non-psychoactive hemp varieties, providing an easy access to this extremely advantageous cannabinoid. This leaves consumers with no legal quality guarantees. The objective of this project was to assess the quality of 14 CBD oils commercially available in European countries. An in-depth chemical profiling of cannabinoids, terpenes and oxidation products was conducted by means of GC-MS and HPLC-Q-Exactive-Orbitrap-MS in order to improve knowledge regarding the characteristics of CBD oils. Nine out of the 14 samples studied had concentrations that differed notably from the declared amount, while the remaining five preserved CBD within optimal limits. Our results highlighted a wide variability in cannabinoids profile that justifies the need for strict and standardized regulations. In addition, the terpenes fingerprint may serve as an indicator of the quality of hemp varieties, while the lipid oxidation products profile could contribute in evaluation of the stability of the oil used as milieu for CBD rich extracts. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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13 pages, 1174 KiB

Open AccessArticle

Rapid Characterization of Components in Bolbostemma paniculatum by UPLC/LTQ-Orbitrap MSⁿ Analysis and Multivariate Statistical Analysis for Herb Discrimination

by Yanling Zeng, Yang Lu, Zhao Chen, Jiawei Tan, Jie Bai, Pengyue Li, Zhixin Wang and Shouying Du

Molecules 2018, 23(5), 1155; https://doi.org/10.3390/molecules23051155 - 11 May 2018

Cited by 28 | Viewed by 3874

Abstract

Bolbostemma paniculatum is a traditional Chinese medicine (TCM) showed various therapeutic effects. Owing to its complex chemical composition, few investigations have acquired a comprehensive cognition for the chemical profiles of this herb and explicated the differences between samples collected from different places. In [...] Read more.

Bolbostemma paniculatum is a traditional Chinese medicine (TCM) showed various therapeutic effects. Owing to its complex chemical composition, few investigations have acquired a comprehensive cognition for the chemical profiles of this herb and explicated the differences between samples collected from different places. In this study, a strategy based on UPLC tandem LTQ-Orbitrap MSⁿ was established for characterizing chemical components of B. paniculatum. Through a systematic identification strategy, a total of 60 components in B. paniculatum were rapidly separated in 30 min and identified. Then based on peak intensities of all the characterized components, principle component analysis (PCA) and hierarchical cluster analysis (HCA) were employed to classify 18 batches of B. paniculatum into four groups, which were highly consistent with the four climate types of their original places. And five compounds were finally screened out as chemical markers to discriminate the internal quality of B. paniculatum. As the first study to systematically characterize the chemical components of B. paniculatum by UPLC-MSⁿ, the above results could offer essential data for its pharmacological research. And the current strategy could provide useful reference for future investigations on discovery of important chemical constituents in TCM, as well as establishment of quality control and evaluation method. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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14 pages, 921 KiB

Open AccessArticle

A Preliminary Study of Aroma Composition and Impact Odorants of Cabernet Franc Wines under Different Terrain Conditions of the Loess Plateau Region (China)

by Bao Jiang and Zhen-Wen Zhang

Molecules 2018, 23(5), 1096; https://doi.org/10.3390/molecules23051096 - 05 May 2018

Cited by 12 | Viewed by 3997

Abstract

Due to its appropriate climate characteristics, the Loess Plateau region is considered to be one of the biggest optimal regions for producing high-quality mountain wine in China. However, the complex landform conditions of vineyards are conducive to the formation of mountainous microclimates, which [...] Read more.

Due to its appropriate climate characteristics, the Loess Plateau region is considered to be one of the biggest optimal regions for producing high-quality mountain wine in China. However, the complex landform conditions of vineyards are conducive to the formation of mountainous microclimates, which ultimately influence the wine quality. This study aimed to elucidate the influences of three terrain conditions of the Loess Plateau region on the aroma compounds of Cabernet Franc wines by using solid phase microextraction (SPME) with gas chromatography-mass spectrometry (GC-MS). A total of 40, 36 and 35 volatiles were identified and quantified from the flat, lower slope and higher slope vineyards, respectively. Esters were the largest group of volatiles, accounting for 54.6–56.6% of total volatiles, followed by alcohols. Wines from the slope lands had the higher levels of aroma compounds than that from flat land. According to their aroma-active values (OAVs), ethyl hexanoate, ethyl octanoate and isoamyl acetate were the most powerful compounds among the eight impact odorants, showing only quantitative but not qualitative differences between the three terrain wines. The shapes of the OAVs for three terrain wines were very similar. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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12 pages, 2125 KiB

Open AccessArticle

Chromatogram-Bioactivity Correlation-Based Discovery and Identification of Three Bioactive Compounds Affecting Endothelial Function in Ginkgo Biloba Extract

by Hong Liu, Li-ping Tan, Xin Huang, Yi-qiu Liao, Wei-jian Zhang, Pei-bo Li, Yong-gang Wang, Wei Peng, Zhong Wu, Wei-wei Su and Hong-liang Yao

Molecules 2018, 23(5), 1071; https://doi.org/10.3390/molecules23051071 - 03 May 2018

Cited by 4 | Viewed by 3707

Abstract

Discovery and identification of three bioactive compounds affecting endothelial function in Ginkgo biloba Extract (GBE) based on chromatogram-bioactivity correlation analysis. Three portions were separated from GBE via D101 macroporous resin and then re-combined to prepare nine GBE samples. 21 compounds in GBE samples [...] Read more.

Discovery and identification of three bioactive compounds affecting endothelial function in Ginkgo biloba Extract (GBE) based on chromatogram-bioactivity correlation analysis. Three portions were separated from GBE via D101 macroporous resin and then re-combined to prepare nine GBE samples. 21 compounds in GBE samples were identified through UFLC-DAD-Q-TOF-MS/MS. Correlation analysis between compounds differences and endothelin-1 (ET-1) in vivo in nine GBE samples was conducted. The analysis results indicated that three bioactive compounds had close relevance to ET-1: Kaempferol-3-O-α-l-glucoside, 3-O-{2-O-{6-O-[P-OH-trans-cinnamoyl]-β-d-glucosyl}-α-rhamnosyl} Quercetin isomers, and 3-O-{2-O-{6-O-[P-OH-trans-cinnamoyl]-β-d-glucosyl}-α-rhamnosyl} Kaempferide. The discovery of bioactive compounds could provide references for the quality control and novel pharmaceuticals development of GRE. The present work proposes a feasible chromatogram-bioactivity correlation based approach to discover the compounds and define their bioactivities for the complex multi-component systems. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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14 pages, 1834 KiB

Open AccessArticle

Simultaneous Determination of Decursin, Decursinol Angelate, Nodakenin, and Decursinol of Angelica gigas Nakai in Human Plasma by UHPLC-MS/MS: Application to Pharmacokinetic Study

by Sook-Jin Kim, Se-Mi Ko, Eun-Jeong Choi, Seong-Ho Ham, Young-Dal Kwon, Yong-Bok Lee and Hea-Young Cho

Molecules 2018, 23(5), 1019; https://doi.org/10.3390/molecules23051019 - 26 Apr 2018

Cited by 13 | Viewed by 5445

Abstract

Coumarins in Cham-dang-gwi, the dried root of Angelica gigas Nakai (AGN), possess pharmacological effects on anemia, pain, infection, and articular rheumatism. The AGN root containes decursin (D), decursinol angelate (DA), nodakenin, and decursinol (DOH), a major metabolite of D and DA. The aim [...] Read more.

Coumarins in Cham-dang-gwi, the dried root of Angelica gigas Nakai (AGN), possess pharmacological effects on anemia, pain, infection, and articular rheumatism. The AGN root containes decursin (D), decursinol angelate (DA), nodakenin, and decursinol (DOH), a major metabolite of D and DA. The aim of this study was to develop a simultaneous determination method for these four coumarins in human plasma using ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Chromatographic separation was performed on dual columns (Kinetex^® C₁₈ column and Capcell core C₁₈ column) with mobile phase consisting of water and acetonitrile at a flow rate of 0.3 mL/min using gradient elution. Multiple reaction monitoring was operated in positive ion mode with precursors to product ion transition values of m/z 328.9→228.8, 328.9→228.9, 409.4→248.8, and 246.8→212.9 to measure D, DA, nodakenin, and DOH, respectively. Linear calibration curves were fitted over concentration range of 0.05–50 ng/mL for these four components, with correlation coefficient greater than 0.995. Inter- and intra-day accuracies were between 90.60% and 108.24%. These precisions were within 11.19% for all components. The established method was then applied to a pharmacokinetic study for the four coumarins after usual dosing in Korean subjects. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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12 pages, 2461 KiB

Open AccessArticle

Isolation of High Purity Anthocyanin Monomers from Red Cabbage with Recycling Preparative Liquid Chromatography and Their Photostability

by Yijun Chen, Zikun Wang, Hanghang Zhang, Yuan Liu, Shuai Zhang, Qingyan Meng and Wenjie Liu

Molecules 2018, 23(5), 991; https://doi.org/10.3390/molecules23050991 - 24 Apr 2018

Cited by 20 | Viewed by 6200

Abstract

Anthocyanins from red cabbage are of great importance for their applications in the food industry as natural colorants and their beneficial effects on human wellness as natural antioxidants. This study aimed to develop an effective method for the isolation of anthocyanins with the [...] Read more.

Anthocyanins from red cabbage are of great importance for their applications in the food industry as natural colorants and their beneficial effects on human wellness as natural antioxidants. This study aimed to develop an effective method for the isolation of anthocyanins with the help of a combination of alternate recycling and direct recycling preparative liquid chromatography. Ten major components of anthocyanins from red cabbage were isolated and their structures were identified by HPLC-MS/MS. Meanwhile, the stability of the isolated anthocyanins under various light conditions was also investigated so as to provide data for their storage. In sum, the results showed that twin column recycling preparative chromatography is an effective method for the isolation of anthocyanin monomers with similar structures. Besides, the stability of various anthocyanins from red cabbage was related to the number of acylated groups and mainly affected by illumination. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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9 pages, 1394 KiB

Open AccessArticle

Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces pinophilus

by Maria Michela Salvatore, Marina DellaGreca, Rosario Nicoletti, Francesco Salvatore, Francesco Vinale, Daniele Naviglio and Anna Andolfi

Molecules 2018, 23(4), 950; https://doi.org/10.3390/molecules23040950 - 19 Apr 2018

Cited by 17 | Viewed by 4062

Abstract

Talarodiolide, a new 12-membered macrodiolide, was isolated and characterized from the culture filtrate of strain LT6 of Talaromyces pinophilus. The structure of (Z)-4,10-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione was assigned essentially based on NMR and MS data. Furthermore, several known compounds were isolated and identified in the [...] Read more.

Talarodiolide, a new 12-membered macrodiolide, was isolated and characterized from the culture filtrate of strain LT6 of Talaromyces pinophilus. The structure of (Z)-4,10-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione was assigned essentially based on NMR and MS data. Furthermore, several known compounds were isolated and identified in the crude extract of the culture filtrate and mycelium of this strain. EI mass spectrum at 70 eV of all isolated metabolites was acquired and compiled in a custom GC/MS library to be employed to detect metabolites in the crude extracts. Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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Review

Jump to: Research

20 pages, 1153 KiB

Open AccessReview

Extraction and Analysis of Phenolic Compounds in Rice: A Review

by Marco Ciulu, Maria de la Luz Cádiz-Gurrea and Antonio Segura-Carretero

Molecules 2018, 23(11), 2890; https://doi.org/10.3390/molecules23112890 - 06 Nov 2018

Cited by 73 | Viewed by 11689

Abstract

Rice represents the main source of calorie intake in many world countries and about 60% of the world population include rice in their staple diet. Whole grain rice, also called brown rice, represent the unpolished version of the more common white rice including [...] Read more.

Rice represents the main source of calorie intake in many world countries and about 60% of the world population include rice in their staple diet. Whole grain rice, also called brown rice, represent the unpolished version of the more common white rice including bran, germ, and endosperm. Many health-promoting properties have been associated to the consumption of whole grain rice and, for this reason, great attention has been paid by the scientific community towards the identification and the quantification of bioactive compounds in this food item. In this contribution, the last five years progresses in the quali-quantitative determination of phenolic compounds in rice have been highlighted. Special attention has been devoted to the most recent strategies for the extraction of the target compounds from rice along with the analytical approaches adopted for the separation, identification and quantification of phenolic acids, flavonoids, anthocyanins, and proanthocyanidins. More specifically, the main features of the “traditional” extraction methods (i.e., maceration, ultrasound-assisted extraction) have been described, as well as the more innovative protocols involving advanced extraction techniques, such as MAE (microwave-assisted extraction). The predominant role of HPLC in the definition of the phenolic profile has been examined also presenting the most recent results obtained by using mass spectrometry-based detection systems. In addition, the most common procedures aimed to the quantification of the total amount of the cited classes of phenolic compounds have been described together with the spectrophotometric protocols aimed to the evaluation of the antioxidant properties of rice phenolic extracts (i.e., FRAP, DPPH, ABTS and ORAC). Full article

(This article belongs to the Special Issue Qualitative and Quantitative Analysis of Bioactive Natural Products 2018)

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