2023

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13 pages, 9176 KiB

Open AccessArticle

Analysis of Volatile Components in Rosa roxburghii Tratt. and Rosa sterilis Using Headspace–Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry

by Yuhang Deng, Huan Kan, Yonghe Li, Yun Liu and Xu Qiu

Molecules 2023, 28(23), 7879; https://doi.org/10.3390/molecules28237879 - 30 Nov 2023

Viewed by 771

Abstract

Volatile organic compounds (VOCs) and flavor characteristics of Rosa roxburghii Tratt. (RR) and Rosa sterilis (RS) were analyzed using headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME-GC-MS). The flavor network was constructed by combining relative odor activity values (ROAVs), and the signature [...] Read more.

Volatile organic compounds (VOCs) and flavor characteristics of Rosa roxburghii Tratt. (RR) and Rosa sterilis (RS) were analyzed using headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME-GC-MS). The flavor network was constructed by combining relative odor activity values (ROAVs), and the signature differential flavor components were screened using orthogonal partial least squares discriminant analysis (OPLS-DA) and random forest (RF). The results showed that 61 VOCs were detected in both RR and RS: 48 in RR, and 26 in RS. There were six key flavor components (ROAVs ≥ 1) in RR, namely nonanal, ethyl butanoate, ethyl hexanoate, (3Z)-3-hexen-1-yl acetate, ethyl caprylate, and styrene, among which ethyl butanoate had the highest contribution, whereas there were eight key flavor components (ROAVs ≥ 1) in RS, namely 2-nonanol, (E)-2-hexenal, nonanal, methyl salicylate, β-ocimene, caryophyllene, α-ionone, and styrene, among which nonanal contributed the most to RS. The flavor of RR is primarily fruity, sweet, green banana, and waxy, while the flavor of RS is primarily sweet and floral. In addition, OPLS-DA and RF suggested that (E)-2-hexenal, ethyl caprylate, β-ocimene, and ethyl butanoate could be the signature differential flavor components for distinguishing between RR and RS. In this study, the differences in VOCs between RR and RS were analyzed to provide a basis for further development and utilization. Full article

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16 pages, 5743 KiB

Open AccessArticle

Comparative Analysis of the Wood Metabolites of Three Poplar Clones Using UPLC-Triple-TOF-MS

by Liping Li, Yun Liu, Xiaorui Yu, Xiaoqin Yang, Sida Xie, Guolei Zhu and Ping Zhao

Molecules 2023, 28(20), 7024; https://doi.org/10.3390/molecules28207024 - 11 Oct 2023

Viewed by 904

Abstract

Poplar, a woody tree species, is widely used for industrial production and as a protective forest belt. Different clones of poplar exhibit clear variation in terms of morphological and physiological features, however, the impact of the genetic variation on the composition and abundance [...] Read more.

Poplar, a woody tree species, is widely used for industrial production and as a protective forest belt. Different clones of poplar exhibit clear variation in terms of morphological and physiological features, however, the impact of the genetic variation on the composition and abundance of wood metabolite have not been fully determined. In this study, ultra-high pressure liquid chromatography-triple time of flight-mass spectrometer (UPLC-Triple-TOF-MS) was used to explore the metabolite changes in poplar wood from three clones, including Populus deltoides CL. ‘55/65’, P. deltoides CL. ‘Danhong’, and P. nigra CL. ‘N179’. A total of 699 metabolites were identified. Clustering analysis and principal component analysis display that the metabolic differences of wood have allowed distinguishing different species of poplar. Meanwhile, eight significantly different metabolites were screened between P. deltoides and P. nigra, which may be considered as valuable markers for chemotaxonomy. In addition, the highly discriminant 352 metabolites were obtained among the three clones, and those may be closely related to the distinction in unique properties (e.g., growth, rigidity and tolerance) of the poplar wood cultivars. This study provides a foundation for further studies on wood metabolomics in poplar, and offers chemotaxonomic markers that will stimulate the early screening of potentially superior trees. Full article

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32 pages, 9664 KiB

Open AccessArticle

Phytochemical Analysis, Antioxidant and Enzyme-Inhibitory Activities, and Multivariate Analysis of Insect Gall Extracts of Picea koraiensis Nakai

by Yanqiu Wang, Hui Sun, Xu He, Meihua Chen, Hao Zang, Xuekun Liu and Huri Piao

Molecules 2023, 28(16), 6021; https://doi.org/10.3390/molecules28166021 - 11 Aug 2023

Viewed by 970

Abstract

Picea koraiensis Nakai (PK) is an evergreen tree. It plays an important role in landscaping and road greening. Insect galls of PK are formed by parasitism of the adelgid Adelges laricis. Except for phenolics, other chemical constituents and biological activity of insect [...] Read more.

Picea koraiensis Nakai (PK) is an evergreen tree. It plays an important role in landscaping and road greening. Insect galls of PK are formed by parasitism of the adelgid Adelges laricis. Except for phenolics, other chemical constituents and biological activity of insect gall from PK are still unknown. Thus, here, we performed phytochemical and biological activity analyses of PK insect gall extracts, aiming to turn waste into treasure and serve human health. PK insect gall extracts were prepared using seven solvents. Antioxidant activities of the extracts were examined via antioxidant assays (radical and oxidizing substance quenching, metal chelating, and reducing power). The inhibitory activities of the extracts were determined toward the key human-disease-related enzymes α-glucosidase, α-amylase, cholinesterase, tyrosinase, urease, and xanthine oxidase. The content of numerous active constituents was high in the methanol and ethanol extracts of PK insect gall, and these extracts had the highest antioxidant and enzyme-inhibitory activities. They also showed excellent stability and low toxicity. These extracts have potential for use as stabilizers of olive and sunflower seed oils. Full article

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25 pages, 1706 KiB

Open AccessArticle

Stachydrine, a Bioactive Equilibrist for Synephrine, Identified from Four Citrus Chinese Herbs

by Yifei Sun, Xuexue Xia, Ganjun Yuan, Tongke Zhang, Beibei Deng, Xinyu Feng and Qixuan Wang

Molecules 2023, 28(9), 3813; https://doi.org/10.3390/molecules28093813 - 29 Apr 2023

Cited by 2 | Viewed by 1824

Abstract

Four Chinese herbs from the Citrus genus, namely Aurantii Fructus Immaturus (Zhishi), Aurantii Fructus (Zhiqiao), Citri Reticulatae Pericarpium Viride (Qingpi) and Citri Reticulatae Pericarpium (Chenpi), are widely used for treating various cardiovascular and gastrointestinal diseases. [...] Read more.

Four Chinese herbs from the Citrus genus, namely Aurantii Fructus Immaturus (Zhishi), Aurantii Fructus (Zhiqiao), Citri Reticulatae Pericarpium Viride (Qingpi) and Citri Reticulatae Pericarpium (Chenpi), are widely used for treating various cardiovascular and gastrointestinal diseases. Many ingredients have already been identified from these herbs, and their various bioactivities provide some interpretations for the pharmacological functions of these herbs. However, the complex functions of these herbs imply undisclosed cholinergic activity. To discover some ingredients with cholinergic activity and further clarify possible reasons for the complex pharmacological functions presented by these herbs, depending on the extended structure–activity relationships of cholinergic and anti-cholinergic agents, a simple method was established here for quickly discovering possible choline analogs using a specific TLC method, and then stachydrine and choline were first identified from these Citrus herb decoctions based on their NMR and HRMS data. After this, two TLC scanning (TLCS) methods were first established for the quantitative analyses of stachydrine and choline, and the contents of the two ingredients and synephrine in 39 samples were determined using the valid TLCS and HPLC methods, respectively. The results showed that the contents of stachydrine (3.04‰) were 2.4 times greater than those of synephrine (1.25‰) in Zhiqiao and about one-third to two-thirds of those of Zhishi, Qingpi and Chenpi. Simultaneously, the contents of stachydrine, choline and synephrine in these herbs present similar decreasing trends with the delay of harvest time; e.g., those of stachydrine decrease from 5.16‰ (Zhishi) to 3.04‰ (Zhike) and from 1.98‰ (Qingpi) to 1.68‰ (Chenpi). Differently, the contents of synephrine decrease the fastest, while those of stachydrine decrease the slowest. Based on these results, compared with the pharmacological activities and pharmacokinetics reported for stachydrine and synephrine, it is indicated that stachydrine can be considered as a bioactive equilibrist for synephrine, especially in the cardio-cerebrovascular protection from these citrus herbs. Additionally, the results confirmed that stachydrine plays an important role in the pharmacological functions of these citrus herbs, especially in dual-directionally regulating the uterus, and in various beneficial effects on the cardio-cerebrovascular system, kidneys and liver. Full article

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13 pages, 1937 KiB

Open AccessArticle

β-Carboline Alkaloids in Soy Sauce and Inhibition of Monoamine Oxidase (MAO)

by Tomás Herraiz

Molecules 2023, 28(6), 2723; https://doi.org/10.3390/molecules28062723 - 17 Mar 2023

Cited by 4 | Viewed by 1222

Abstract

Monoamine oxidase (MAO) oxidizes neurotransmitters and xenobiotic amines, including vasopressor and neurotoxic amines such as the MPTP neurotoxin. Its inhibitors are useful as antidepressants and neuroprotectants. This work shows that diluted soy sauce (1/3) and soy sauce extracts inhibited human MAO-A and -B [...] Read more.

Monoamine oxidase (MAO) oxidizes neurotransmitters and xenobiotic amines, including vasopressor and neurotoxic amines such as the MPTP neurotoxin. Its inhibitors are useful as antidepressants and neuroprotectants. This work shows that diluted soy sauce (1/3) and soy sauce extracts inhibited human MAO-A and -B isozymes in vitro, which were measured with a chromatographic assay to avoid interferences, and it suggests the presence of MAO inhibitors. Chromatographic and spectrometric studies showed the occurrence of the β-carboline alkaloids harman and norharman in soy sauce extracts inhibiting MAO-A. Harman was isolated from soy sauce, and it was a potent and competitive inhibitor of MAO-A (0.4 µM, 44 % inhibition). The concentrations of harman and norharman were determined in commercial soy sauces, reaching 243 and 52 μg/L, respectively. Subsequently, the alkaloids 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA) were identified and analyzed in soy sauces reaching concentrations of 69 and 448 mg/L, respectively. The results show that MTCA was a precursor of harman under oxidative and heating conditions, and soy sauces increased the amount of harman under those conditions. This work shows that soy sauce contains bioactive β-carbolines and constitutes a dietary source of MAO-A and -B inhibitors. Full article

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16 pages, 2405 KiB

Open AccessArticle

UPLC-MS Analysis, Quantification of Compounds, and Comparison of Bioactivity of Methanol Extract and Its Fractions from Qiai (Artemisia argyi Lévl. et Van.)

by Ting Zhang, Dingrong Wan, Yuanyuan Li, Sisi Wang, Xiuteng Zhou, Fatemeh Sefidkon and Xinzhou Yang

Molecules 2023, 28(5), 2022; https://doi.org/10.3390/molecules28052022 - 21 Feb 2023

Viewed by 1570

Abstract

The Artemisia argyi Lévl. et Van. growing in the surrounding areas of Qichun County in China are called Qiai (QA). Qiai is a crop that can be used both as food and in traditional folk medicine. However, detailed qualitative and quantitative analyses of [...] Read more.

The Artemisia argyi Lévl. et Van. growing in the surrounding areas of Qichun County in China are called Qiai (QA). Qiai is a crop that can be used both as food and in traditional folk medicine. However, detailed qualitative and quantitative analyses of its compounds remain scarce. The process of identifying chemical structures in complex natural products can be streamlined by combining UPLC-Q-TOF/MS data with the UNIFI information management platform and its embedded Traditional Medicine Library. For the first time, 68 compounds in QA were reported by the method in this study. The method of simultaneous quantification of 14 active components in QA using UPLC-TQ-MS/MS was reported for the first time. Following a screening of the activity of QA 70% methanol total extract and its three fractions (petroleum ether, ethyl acetate, and water), it was discovered that the ethyl acetate fraction enriched with flavonoids such as eupatilin and jaceosidin had the strongest anti-inflammatory activity, while the water fraction enriched with chlorogenic acid derivatives such as 3,5-di-O-caffeoylquinic acid had the strongest antioxidant and antibacterial activity. The results provided the theoretical basis for the use of QA in the food and pharmaceutical industries. Full article

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22 pages, 11699 KiB

Open AccessArticle

Resonance Raman and Visible Micro-Spectroscopy for the In-Vivo and In-Vitro Characterization of Anthocyanin-Based Pigments in Blue and Violet Flowers: A Comparison with HPLC-ESI- MS Analysis of the Extracts

by Silvia Bruni, Margherita Longoni, Camilla Minzoni, Martina Basili, Ilaria Zocca, Stefano Pieraccini and Maurizio Sironi

Molecules 2023, 28(4), 1709; https://doi.org/10.3390/molecules28041709 - 10 Feb 2023

Viewed by 1637

Abstract

Microanalysis techniques based on resonance Raman and reflection visible spectroscopy have been applied to the characterization of pigments responsible for the blue or violet coloration in flowers; in particular of Lobelia erinus, Campanula portenschlagiana, Cineraria, Viola tricolor, Anemone coronaria, Agapanthus, [...] Read more.

Microanalysis techniques based on resonance Raman and reflection visible spectroscopy have been applied to the characterization of pigments responsible for the blue or violet coloration in flowers; in particular of Lobelia erinus, Campanula portenschlagiana, Cineraria, Viola tricolor, Anemone coronaria, Agapanthus, Platycodon, Salvia farinacea, Plumbago capensis, Ceratostigma plumbaginoides, Commelina communis and Salvia patens. The spectroscopic methods were applied both in vivo on the flower petals and in vitro on extracts obtained through a procedure based on SPE (solid-phase extraction) optimized for minimal quantities of vegetable raw material. Different patterns obtained for the Raman spectra have been correlated, also on the basis of density functional theory (DFT) calculations, with different schemes of substitution of the benzopyrilium nucleus of the anthocyanins and with various possible forms of copigmentation responsible for the stabilization of the blue color. The results obtained were verified by comparison with the analysis of the extracts by HPLC-ESI-MS (liquid chromatography-electrospray ionization-mass spectrometry). Full article

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2022

Jump to: 2023, 2021, 2020, 2019, 2018

17 pages, 3827 KiB

Open AccessArticle

Post-Harvest Processing Methods Have Critical Roles in the Contents of Active Ingredients of Scutellaria baicalensis Georgi

by Liuwei Zhang, Xuemei Zhang and Zongsuo Liang

Molecules 2022, 27(23), 8302; https://doi.org/10.3390/molecules27238302 - 28 Nov 2022

Cited by 3 | Viewed by 1286

Abstract

To find the best post-harvest processing method for Scutellaria baicalensis Georgi, we explored the effects of fresh and traditional processing on the active ingredients in S. baicalensis and evaluated three drying techniques to determine the optimal post-harvest processing technique. We quantified four active [...] Read more.

To find the best post-harvest processing method for Scutellaria baicalensis Georgi, we explored the effects of fresh and traditional processing on the active ingredients in S. baicalensis and evaluated three drying techniques to determine the optimal post-harvest processing technique. We quantified four active ingredients (baicalin, baicalein, wogonoside, and wogonin) in 16 different processed S. baicalensis samples that were harvested from Tongchuan, Shaanxi province, by HPLC (high-performance liquid chromatography). In addition, we performed a similarity analysis (SA), a hierarchical cluster analysis (HCA), and a principal component analysis (PCA) on the common peaks in S. baicalensis that were identified by the HPLC fingerprints. Compared to the traditional processing method, the fresh processing method could better preserve the four active ingredients in S. baicalensis, meanwhile, the similarity analysis (0.997–1.000) showed that the fresh processing was more similar to the traditional processing, and it did not change the type of 18 active ingredients in S. baicalensis. The cluster analysis results showed that the shade drying and sun drying methods results were more similar to each other, while the oven drying (60 °C) method results were clustered into one category. According to the results of the principal component analysis, S9, S7, and S8 had higher scores, and they were relatively well processed under these processing settings. Fresh processing could be an alternative to traditional processing; the moisture content was reduced to 24.38% under the sun drying condition, and it was the optimal post-harvest processing solution for S. baicalensis. Full article

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18 pages, 2702 KiB

Open AccessArticle

Medicinal Values and Potential Risks Evaluation of Ginkgo biloba Leaf Extract (GBE) Drinks Made from the Leaves in Autumn as Dietary Supplements

by Xiaojia Su, Ruirui Shi, Haiyan Hu, Linfeng Hu, Qichao Wei, Yuanyuan Guan, Jingling Chang and Chengwei Li

Molecules 2022, 27(21), 7479; https://doi.org/10.3390/molecules27217479 - 02 Nov 2022

Cited by 2 | Viewed by 1532

Abstract

Ginkgo tea and ginkgo wine are two familiar Ginkgo biloba leaf extract (GBE) drinks in the form of dietary supplements (DS) used for healthcare in east Asia. Nevertheless, a comprehensive evaluation of their safety and efficacy is still lacking. In this study, GBE [...] Read more.

Ginkgo tea and ginkgo wine are two familiar Ginkgo biloba leaf extract (GBE) drinks in the form of dietary supplements (DS) used for healthcare in east Asia. Nevertheless, a comprehensive evaluation of their safety and efficacy is still lacking. In this study, GBE drinks were prepared from naturally newly senescent yellow leaves (YL) and green leaves (GL) in autumn. Their total flavonoids, antioxidant capacity and prescribed ingredients were investigated. In brief, the proportions of total flavonoids, total flavonol glycosides (TFs), total terpene trilactones (TTLs) and ginkgolic acids in the GBE drinks all did not meet the standards of worldwide pharmacopoeias. Specifically, the levels of TFs in the ginkgo tea prepared from YL were significantly higher than that prepared from GL. Further analyses revealed a substandard ratio of isorhamnetin/quercetin and an accumulation of leaf-age-related compounds, which were both unqualified. The proportions of specific TTLs varied between the ginkgo tea and ginkgo wine, although no significant differences were detected in terms of the total levels of TTLs. Noticeably, numerous biflavones and thousands of times over the limiting concentration of ginkgolic acids, including newly identified types, were only detected in ginkgo wine. Finally, the use of the GBE drinks as DSs was comprehensively evaluated according to the acceptable daily intake. This study showed the limited healthcare effects of GBE drinks despite their powerful antioxidant capacity. Full article

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16 pages, 3647 KiB

Open AccessArticle

Effects of Different Processing Methods Based on Different Drying Conditions on the Active Ingredients of Salvia miltiorrhiza Bunge

by Liuwei Zhang, Xuemei Zhang, Naheeda Begum, Pengguo Xia, Jingling Liu and Zongsuo Liang

Molecules 2022, 27(15), 4860; https://doi.org/10.3390/molecules27154860 - 29 Jul 2022

Cited by 5 | Viewed by 1728

Abstract

Compared to the traditional processing method, fresh processing can significantly enhance the preservation of biologically active ingredients and reduce processing time. This study evaluated the influences of fresh and traditional processing based on different drying conditions (sun drying, oven drying and shade drying) [...] Read more.

Compared to the traditional processing method, fresh processing can significantly enhance the preservation of biologically active ingredients and reduce processing time. This study evaluated the influences of fresh and traditional processing based on different drying conditions (sun drying, oven drying and shade drying) on the active ingredients in the roots and rhizomes of S. miltiorrhiza. High-performance liquid chromatography (HPLC) was utilized to determine the contents of six active ingredients in the roots and rhizomes of S. miltiorrhiza. The data were analyzed by fingerprint similarity evaluation, hierarchical cluster analysis (HCA) and principal component analysis (PCA). The results suggest that compared to the traditional processing method, the fresh processing method may significantly increase the preservation of biologically active ingredients. Furthermore, the findings demonstrated that among the three drying methods under fresh processing conditions, the shade-drying (21.02–26.38%) method is most beneficial for retaining the active ingredients in the roots and rhizomes of S. miltiorrhiza. Moreover, the fingerprint analysis identified 17 common peaks, and the similarity of fingerprints among samples processed by different methods ranged from 0.989 to 1.000. Collectively, these results suggest novel processing methods that may improve the yield of active ingredients for S. miltiorrhiza and may be implemented for industrial production. Full article

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12 pages, 2961 KiB

Open AccessArticle

The Dynamic Accumulation Rules of Chemical Components in Different Medicinal Parts of Angelica sinensis by GC-MS

by Yuying Chen, Qian Li and Daiyu Qiu

Molecules 2022, 27(14), 4617; https://doi.org/10.3390/molecules27144617 - 20 Jul 2022

Cited by 4 | Viewed by 1614

Abstract

The chemical components and medicinal properties of different medicinal parts of Angelica sinensis are often used as medicine after being divided into the head, body and tail of Angelica sinensis. In this study, the chemical components of different medicinal parts in different [...] Read more.

The chemical components and medicinal properties of different medicinal parts of Angelica sinensis are often used as medicine after being divided into the head, body and tail of Angelica sinensis. In this study, the chemical components of different medicinal parts in different periods were analyzed by GC-MS for the first time, and the differences of the accumulation rules of chemical components in different medicinal parts of Angelica sinensis were obtained. This study demonstrated that the differences of composition accumulation in different medicinal parts of Angelica sinensis were mainly reflected in the types and relative contents of compounds. The study found that the number of compounds in different medicinal parts of Angelica sinensis in each period were different and the change rules of the same compound in different medicinal parts were also different. The number of compounds in the tail of Angelica sinensis was the least in April, and the largest in October. The content of ligustilide in the body of Angelica sinensis was higher in April and was the highest in the tail in October. The relative content of butylidenephthalide in the head was the highest in October. The relative contents of senkyunolide A and butylphthalide in the head were decreased in October, while the contents in the body and tail increased, indicating that the compounds that accumulate in the head may transfer to the body and tail in later stages of growth. This study clarified the differences in the accumulation of chemical components in different medicinal parts of Angelica sinensis, which could provide a theoretical basis for the reasons for the differences of chemical components in the different medicinal parts. Full article

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16 pages, 2151 KiB

Open AccessArticle

Chemotaxonomic Classification of Peucedanum japonicum and Its Chemical Correlation with Peucedanum praeruptorum, Angelica decursiva, and Saposhnikovia divaricata by Liquid Chromatography Combined with Chemometrics

by Jung-Hoon Kim, Eui-Jeong Doh and Guemsan Lee

Molecules 2022, 27(5), 1675; https://doi.org/10.3390/molecules27051675 - 03 Mar 2022

Cited by 3 | Viewed by 1665

Abstract

The roots of Peucedanum japonicum (Apiaceae) have been used as an alternative to the roots of Saposhnikovia divaricata (Apiaceae) to treat common cold-related symptoms in Korea. However, a variety of Peucedanum species, including the roots of P. praeruptorum or Angelica decursiva (=P. [...] Read more.

The roots of Peucedanum japonicum (Apiaceae) have been used as an alternative to the roots of Saposhnikovia divaricata (Apiaceae) to treat common cold-related symptoms in Korea. However, a variety of Peucedanum species, including the roots of P. praeruptorum or Angelica decursiva (=P. decursivum), have been used to treat phlegm–heat-induced symptoms in China. Hence, as there are differences in the medicinal application of P. japonicum roots between Korea and China, chemotaxonomic classification of P. japonicum was evaluated. Sixty samples derived from P. japonicum, P. praeruptorum, A. decursiva, and S. divaricata were phylogenetically identified using DNA barcoding tools, and chemotaxonomic correlations among the samples were evaluated using chromatographic profiling with chemometric analyses. P. japonicum samples were phylogenetically grouped into the same cluster as P. praeruptorum samples, followed by S. divaricata samples at the next cluster level, whereas A. decursiva samples were widely separated from the other species. Moreover, P. japonicum samples showed higher chemical correlations with P. praeruptorum samples or A. decursiva samples, but lower or negative chemical correlations with S. divaricata samples. These results demonstrate that P. japonicum is more genetically and chemically relevant to P. praeruptorum or A. decursiva and, accordingly, the medicinal application of P. japonicum might be closer to the therapeutic category of these two species than that of S. divaricata. Full article

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22 pages, 3499 KiB

Open AccessReview

Advances in Chemical Composition, Extraction Techniques, Analytical Methods, and Biological Activity of Astragali Radix

by Xiangna Chang, Xuefeng Chen, Yuxi Guo, Pin Gong, Shuya Pei, Danni Wang, Peipei Wang, Mengrao Wang and Fuxin Chen

Molecules 2022, 27(3), 1058; https://doi.org/10.3390/molecules27031058 - 04 Feb 2022

Cited by 19 | Viewed by 3563

Abstract

Astragali Radix (AR) is one of the well-known traditional Chinese medicines with a long history of medical use and a wide range of clinical applications. AR contains a variety of chemical constituents which can be classified into the following categories: polysaccharides, saponins, flavonoids, [...] Read more.

Astragali Radix (AR) is one of the well-known traditional Chinese medicines with a long history of medical use and a wide range of clinical applications. AR contains a variety of chemical constituents which can be classified into the following categories: polysaccharides, saponins, flavonoids, amino acids, and trace elements. There are several techniques to extract these constituents, of which microwave-assisted, enzymatic, aqueous, ultrasonic and reflux extraction are the most used. Several methods such as spectroscopy, capillary electrophoresis and various chromatographic methods have been developed to identify and analyze AR. Meanwhile, this paper also summarizes the biological activities of AR, such as anti-inflammatory, antioxidant, antitumor and antiviral activities. It is expected to provide theoretical support for the better development and utilization of AR. Full article

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2021

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13 pages, 557 KiB

Open AccessArticle

Açaí (Euterpe oleracea Mart.) Seed Extracts from Different Varieties: A Source of Proanthocyanidins and Eco-Friendly Corrosion Inhibition Activity

by Gabriel Rocha Martins, Douglas Guedes, Urbano Luiz Marques de Paula, Maria do Socorro Padilha de Oliveira, Marcia Teresa Soares Lutterbach, Leila Yone Reznik, Eliana Flávia Camporese Sérvulo, Celuta Sales Alviano, Antonio Jorge Ribeiro da Silva and Daniela Sales Alviano

Molecules 2021, 26(11), 3433; https://doi.org/10.3390/molecules26113433 - 05 Jun 2021

Cited by 13 | Viewed by 2963

Abstract

Euterpe oleracea Mart. (Arecaceae) is an endogenous palm tree from the Amazon region. Its seeds correspond to 85% of the fruit’s weight, a primary solid residue generated from pulp production, the accumulation of which represents a potential source of pollution and environmental problems. [...] Read more.

Euterpe oleracea Mart. (Arecaceae) is an endogenous palm tree from the Amazon region. Its seeds correspond to 85% of the fruit’s weight, a primary solid residue generated from pulp production, the accumulation of which represents a potential source of pollution and environmental problems. As such, this work aimed to quantify and determine the phytochemical composition of E. oleracea Mart. seeds from purple, white, and BRS-Pará açaí varieties using established analytical methods and also to evaluate it as an eco-friendly corrosion inhibitor. The proanthocyanidin quantification (n-butanol/hydrochloric acid assay) between varieties was 6.4–22.4 (w/w)/dry matter. Extract characterization showed that all varieties are composed of B-type procyanidin with a high mean degree of polymerization (mDP ≥ 10) by different analytical methodologies to ensure the results. The purple açaí extract, which presented 22.4% (w/w) proanthocyanidins/dry matter, was tested against corrosion of carbon steel AISI 1020 in neutral pH. The crude extract (1.0 g/L) was effective in controlling corrosion on the metal surface for 24 h. Our results demonstrated that the extracts rich in polymeric procyanidins obtained from industrial açaí waste could be used to inhibit carbon steel AISI 1020 in neutral pH as an abundant, inexpensive, and green source of corrosion inhibitor. Full article

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2020

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25 pages, 1729 KiB

Open AccessReview

Plant Derived Natural Products against Pseudomonas aeruginosa and Staphylococcus aureus: Antibiofilm Activity and Molecular Mechanisms

by Francesca Guzzo, Monica Scognamiglio, Antonio Fiorentino, Elisabetta Buommino and Brigida D’Abrosca

Molecules 2020, 25(21), 5024; https://doi.org/10.3390/molecules25215024 - 29 Oct 2020

Cited by 52 | Viewed by 6510

Abstract

Bacteria are social organisms able to build complex structures, such as biofilms, that are highly organized surface-associated communities of microorganisms, encased within a self- produced extracellular matrix. Biofilm is commonly associated with many health problems since its formation increases resistance to antibiotics and [...] Read more.

Bacteria are social organisms able to build complex structures, such as biofilms, that are highly organized surface-associated communities of microorganisms, encased within a self- produced extracellular matrix. Biofilm is commonly associated with many health problems since its formation increases resistance to antibiotics and antimicrobial agents, as in the case of Pseudomonas aeruginosa and Staphylococcus aureus, two human pathogens causing major concern. P. aeruginosa is responsible for severe nosocomial infections, the most frequent of which is ventilator-associated pneumonia, while S. aureus causes several problems, like skin infections, septic arthritis, and endocarditis, to name just a few. Literature data suggest that natural products from plants, bacteria, fungi, and marine organisms have proven to be effective as anti-biofilm agents, inhibiting the formation of the polymer matrix, suppressing cell adhesion and attachment, and decreasing the virulence factors’ production, thereby blocking the quorum sensing network. Here, we focus on plant derived chemicals, and provide an updated literature review on the anti-biofilm properties of terpenes, flavonoids, alkaloids, and phenolic compounds. Moreover, whenever information is available, we also report the mechanisms of action. Full article

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17 pages, 2211 KiB

Open AccessArticle

Bioactive Flavonoid Glycosides and HPLC and UPLC Quantification of Commercial Astragali Complanati Semen

by Jenny Chun-Ling Kuo, Li-Jie Zhang, Hung-Tse Huang, Chia-Ching Liaw, Zhi-Hu Lin, Min Liu and Yao-Haur Kuo

Molecules 2020, 25(20), 4762; https://doi.org/10.3390/molecules25204762 - 16 Oct 2020

Cited by 10 | Viewed by 2278

Abstract

Eleven compounds, including nine known flavonoid glycosides (1–4, 6–8, and 10–11), one isoflavone glycoside (5), and a glansreginic acid (9), were isolated from the 80% ethanol extract of commercial [...] Read more.

Eleven compounds, including nine known flavonoid glycosides (1–4, 6–8, and 10–11), one isoflavone glycoside (5), and a glansreginic acid (9), were isolated from the 80% ethanol extract of commercial Astragali Complanati Semen (ACS). All chemical structures were determined by spectroscopic analyses, including 1D and 2D NMR. Compounds 2, 4, 5, 6, 9, and 10 were isolated and identified from the title plant for the first time. Biological evaluation revealed that all the isolates showed promising anti-NO production, and 1, 2, 3, and 8 were more potent in antioxidant activity than vitamin E. The major peaks in the UPLC and HPLC profiles identified their chemical structures by comparing their retention time and UV spectra with those of the reference substances. Furthermore, nine of the eleven samples collected from North, Middle, and South regions of Taiwan possessed similar HPLC fingerprints and were identified as Astragali Complanati Semen, whereas the other two samples from southern Taiwan would be the adulterants due to the different fingerprinting patterns. In addition, an HPLC-UV method was employed to determine the content of target compound complanatuside (11) with good linear regression (R² = 0.9998) for ACS in the Taiwanese market. Of the isolates, flavonol glycosides 1 and 3 were the major peaks in HPLC/UPLC, and showed more potent antioxidant and anti-NO production activities than that of 11, revealing that these compounds can be the available agents for the quality control of ACS. Full article

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20 pages, 2452 KiB

Open AccessArticle

Impact of Lipid Sources on Quality Traits of Medical Cannabis-Based Oil Preparations

by Alberto Ramella, Gabriella Roda, Radmila Pavlovic, Michele Dei Cas, Eleonora Casagni, Giacomo Mosconi, Francisco Cecati, Paola Minghetti and Carlo Grizzetti

Molecules 2020, 25(13), 2986; https://doi.org/10.3390/molecules25132986 - 30 Jun 2020

Cited by 9 | Viewed by 6538

Abstract

The feasibility of the use of two lipid sources and their impact on the cannabinoid profile, terpene fingerprint, and degradation products in medical cannabis oil preparations during 3 months of refrigerated storage time were investigated. LCHRMS-Orbitrap^® and HS-SPME coupled to GC-MS for [...] Read more.

The feasibility of the use of two lipid sources and their impact on the cannabinoid profile, terpene fingerprint, and degradation products in medical cannabis oil preparations during 3 months of refrigerated storage time were investigated. LCHRMS-Orbitrap^® and HS-SPME coupled to GC-MS for the investigation of targeted and untargeted cannabinoids, terpenes, and lipid degradation products in Bedrocan^® and Bediol^® macerated oils were used as analytical approaches. As regards the cannabinoid trend during 90 days of storage, there were no differences between PhEur-grade olive oil (OOPH) and medium-chain triglycerides oil (MCT oil) coupled to a good stability of preparations for the first 60 days both in Bedrocan^® and Bediol^® oils. MCT lipid source extracted a significant concentration of terpenes compared to olive oil. Terpenes showed a different scenario since MCT oil displayed the strongest extraction capacity and conservation trend of all compounds during the shelf life. Terpenes remained stable throughout the entire storage period in MCT formulations while a significant decrease after 15 and 30 days in Bediol^® and Bedrocan^® was observed in olive oil. Therefore, MCT oil could be considered a more suitable lipid source compared to olive oil involved in the extraction of medical cannabis for magistral preparations. Full article

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26 pages, 2230 KiB

Open AccessArticle

Chemical Composition and Plant Growth of Centaurea raphanina subsp. mixta Plants Cultivated under Saline Conditions

by Spyridon A. Petropoulos, Ângela Fernandes, Maria Ines Dias, Carla Pereira, Ricardo C. Calhelha, Antonios Chrysargyris, Nikolaos Tzortzakis, Marija Ivanov, Marina D. Sokovic, Lillian Barros and Isabel C. F. R. Ferreira

Molecules 2020, 25(9), 2204; https://doi.org/10.3390/molecules25092204 - 08 May 2020

Cited by 24 | Viewed by 3059

Abstract

The aim of this report was to study the effect of salinity (control: 2dS/m, S1: 4 dS/m and S2: 6 dS/m) and harvest time (first harvest on 9 May 2018 and second harvest on 19 April 2018) on the growth and the chemical [...] Read more.

The aim of this report was to study the effect of salinity (control: 2dS/m, S1: 4 dS/m and S2: 6 dS/m) and harvest time (first harvest on 9 May 2018 and second harvest on 19 April 2018) on the growth and the chemical composition of Centaurea raphanina subsp. mixta plants. The plants of the first harvest were used for the plant growth measurements (fresh weight and moisture content of leaves, rosette diameter, number and thickness of leaves), whereas those of the second harvest were not used for these measurements due to the flowering initiation, which made the leaves unmarketable due to their hard texture. The results of our study showed that C. raphanina subsp. mixta plants can be cultivated under mild salinity (S1 treatment) conditions without severe effects on plant growth and yield, since a more severe loss (27.5%) was observed for the S2 treatment. In addition, harvest time proved to be a cost-effective cultivation practice that allows to regulate the quality of the final product, either in edible form (first harvest) or for nutraceutical and pharmaceutical purposes as well as antimicrobial agents in food products. Therefore, the combination of these two agronomic factors showed interesting results in terms of the quality of the final product. In particular, high salinity (S2 treatment) improved the nutritional value by increasing the fat, proteins and carbohydrates contents in the first harvest, as well as the tocopherols and sugars contents (S1 and S2 treatments, respectively) in the second harvest. In addition, salinity and harvest time affected the oxalic acid content which was the lowest for the S2 treatment at the second harvest. Similarly, the richest fatty acid (α-linolenic acid) increased with increasing salinity at the first harvest. Salinity and harvest time also affected the antimicrobial properties, especially against Staphylococcus aureus, Bacillus cereus and Trichoderma viride, where the extracts from the S1 and S2 treatments showed high effectiveness. In contrast, the highest amounts of flavanones (pinocembrin derivatives) were detected in the control treatment (second harvest), which was also reflected to the highest antioxidant activity (TBARS) for the same treatment. In conclusion, C. raphanina subsp. mixta plants seem to be tolerant to medium salinity stress (S1 treatment) since plant growth was not severely impaired, while salinity and harvesting time affected the nutritional value (fat, proteins, and carbohydrates) and the chemical composition (tocopherols, sugars, oxalic acid, fatty acids), as well as the bioactive properties (cytotoxicity and antimicrobial properties) of the final product. Full article

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15 pages, 271 KiB

Open AccessArticle

Antimicrobial Testing of Schinus molle (L.) Leaf Extracts and Fractions Followed by GC-MS Investigation of Biological Active Fractions

by Giovanni Turchetti, Stefania Garzoli, Valentina Laghezza Masci, Carla Sabia, Ramona Iseppi, Pierluigi Giacomello, Antonio Tiezzi and Elisa Ovidi

Molecules 2020, 25(8), 1977; https://doi.org/10.3390/molecules25081977 - 23 Apr 2020

Cited by 11 | Viewed by 3049

Abstract

Schinus molle (L.) is a dioecious plant of the Anacardiaceae family, originating in South America and currently widespread in many regions throughout the world. In this work leaf extracts and derived low-pressure column chromatography (LPCC) fractions of S. molle L. male and female [...] Read more.

Schinus molle (L.) is a dioecious plant of the Anacardiaceae family, originating in South America and currently widespread in many regions throughout the world. In this work leaf extracts and derived low-pressure column chromatography (LPCC) fractions of S. molle L. male and female plants were investigated for the antimicrobial activity. Leaf extracts were tested on microbes Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Candida albicans and Bacillus subtilis. Furthermore, the extracts showing antimicrobial activity were fractionated by LPCC and the obtained fractions tested on the same microorganism strains. Positive fractions were investigated by gas-chromatography/mass spectrometry (GC-MS) and were seen to be rich in sesquiterpenes, sesquiterpenoids and other terpens. The obtained effects highlighted the antimicrobial properties of S. molle (L.) leaf compounds and revealed their importance as a source of bioactive molecules of potential pharmaceutical interest. To our knowledge, this is the first paper reporting investigations on the chemical composition of the extracts and derived positive fractions from Schinus molle (L.) plants grown in central Italy Full article

16 pages, 3031 KiB

Open AccessArticle

Characterization of Rosa canina Fruits Collected in Urban Areas of Slovakia. Genome Size, iPBS Profiles and Antioxidant and Antimicrobial Activities

by Katarína Rovná, Eva Ivanišová, Jana Žiarovská, Peter Ferus, Margarita Terentjeva, Przemysław Łukasz Kowalczewski and Miroslava Kačániová

Molecules 2020, 25(8), 1888; https://doi.org/10.3390/molecules25081888 - 19 Apr 2020

Cited by 21 | Viewed by 4167

Abstract

The studies of plant bacterial endophytes, colonizing the plant tissues without any signs of diseases, are essential for understanding of ecological interactions. The aim of our study is to detect microbiological contamination and to assess the antimicrobial, antioxidant activity, total phenolic, carotenoid content, [...] Read more.

The studies of plant bacterial endophytes, colonizing the plant tissues without any signs of diseases, are essential for understanding of ecological interactions. The aim of our study is to detect microbiological contamination and to assess the antimicrobial, antioxidant activity, total phenolic, carotenoid content, genome size, and ploidy of non-cultivated Rosa canina sampled from urban areas. Samples of Rosa canina fruits were collected in three locations in Slovakia. The highest total viable count and the Enterobacteriaceae count in fruits were 4.32 log CFU/g and 4.29 log CFU/g, respectively. Counts of the mesophilic anaerobic sporulating bacteria, Pseudomonas spp., and of the microscopic fungi and yeasts were 3.00, 2.15 log CFU/g, 3.65 log CFU/g, and 2.76 log CFU/g, respectively. Regarding the antimicrobial activity, Escherichia coli and Klebsiela oxytoca were the most sensitive species among the assayed microorganisms to the treatment with the ethanolic extracts of Rosa canina fruits. The fruits were rich in bioactive compounds, polyphenols, and carotenoids, that could be related to their antioxidant activity. Genome sizes of analyzed samples ranged from 2.3 to 2.96. DNA-based fingerprinting obtained by iPBS markers of the Rosa canina var. lapidicola Heinr. Braun., was characterized by some distinctive inserted loci. An interdisciplinary study was performed for the dog roses from different parts of Slovakia that resulted in deeper characterization of this species. Full article

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11 pages, 2192 KiB

Open AccessArticle

A2E Distribution in RPE Granules in Human Eyes

by Ziqiang Guan, Yiwen Li, Shuliang Jiao, Nusrat Yeasmin, Philip J. Rosenfeld, Sander R. Dubovy, Byron L. Lam and Rong Wen

Molecules 2020, 25(6), 1413; https://doi.org/10.3390/molecules25061413 - 20 Mar 2020

Cited by 6 | Viewed by 2871

Abstract

A2E (N-retinylidene-N-retinylethanolamine) is a major fluorophore in the RPE (retinal pigment epithelium). To identify and characterize A2E-rich RPE lipofuscin, we fractionated RPE granules from human donor eyes into five fractions (F1–F5 in ascending order of density) by discontinuous sucrose [...] Read more.

A2E (N-retinylidene-N-retinylethanolamine) is a major fluorophore in the RPE (retinal pigment epithelium). To identify and characterize A2E-rich RPE lipofuscin, we fractionated RPE granules from human donor eyes into five fractions (F1–F5 in ascending order of density) by discontinuous sucrose density gradient centrifugation. The dry weight of each fraction was measured and A2E was quantified by liquid chromatography/mass spectrometry (LC/MS) using a synthetic A2E homolog as a standard. Autofluorescence emission was characterized by a customer-built spectro-fluorometer system. A significant A2E level was detected in every fraction, and the highest level was found in F1, a low-density fraction that makes up half of the total weight of all RPE granules, contains 67% of all A2E, and emits 75% of projected autofluorescence by all RPE granules. This group of RPE granules, not described previously, is therefore the most abundant RPE lipofuscin granule population. A progressive decrease in autofluorescence was observed from F2 to F4, whereas no autofluorescence emission was detected from the heavily pigmented F5. The identification of a novel and major RPE lipofuscin population could have significant implications in our understanding of A2E and lipofuscin in human RPE. Full article

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13 pages, 4658 KiB

Open AccessArticle

Anti-Neuraminidase Bioactives from Manggis Hutan (Garcinia celebica L.) Leaves: Partial Purification and Molecular Characterization

by Muchtaridi Muchtaridi, Milyadi Sugijanto, Amirah Mohd Gazzali and Habibah A. Wahab

Molecules 2020, 25(4), 821; https://doi.org/10.3390/molecules25040821 - 13 Feb 2020

Cited by 7 | Viewed by 3085

Abstract

The neuraminidase enzyme (NA) from the influenza virus is responsible for the proliferation and infections of the virus progeny, prompting several efforts to discover and optimize effective neuraminidase inhibitors. The main aim of this study is to discover a new potential neuraminidase inhibitor [...] Read more.

The neuraminidase enzyme (NA) from the influenza virus is responsible for the proliferation and infections of the virus progeny, prompting several efforts to discover and optimize effective neuraminidase inhibitors. The main aim of this study is to discover a new potential neuraminidase inhibitor that comes from Garcinia celebica leaves (GCL). The bioassay-guided isolation method was performed to obtain lead compounds. The binding interaction of the isolated compounds was predicted by using molecular docking studies. Friedeline (GC1, logP > 5.0), two lanastone derivatives (methyl-3α,23-dihydroxy-17,14-friedolanstan-8,14,24-trien-26-oat (GC2) and 24E-3a,9,23-trihydroxy-17,14-friedolanostan-14,24-dien-26-oate (GC3) with LogP > 5.0) and catechin (GC4, LogP = 1.4) were identified. The inhibitory potency of these four compounds on NA from C. perfringens and H₁N₁ was found to be as follows: GC4 > GC2 > GC3 > GC1. All compounds exhibited higher inhibitory activity towards C. perfringens NA compared to H₁N₁ NA. From the molecular docking results, GC4 favorably docked and interacted with Arg118, Arg371, Arg292, Glu276 and Trp178 residues, whilst GC2 interacted with Arg118, Arg371, Arg292, Ile222, Arg224 and Ser246. GC3 interacted with Tyr406 only. GC4 had potent NA inhibition with free energy of binding of −12 kcal/mol. In the enzyme inhibition study, GC4 showed the highest activity with an IC₅₀ of 60.3 µM and 91.0 µM for C. perfringens NA and H₁N₁ NA—respectively. Full article

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2019

Jump to: 2023, 2022, 2021, 2020, 2018

14 pages, 3214 KiB

Open AccessArticle

Chemical Profiles of Cultivated Agarwood Induced by Different Techniques

by Tingting Yan, Sheng Yang, Yuan Chen, Qian Wang and Gaiyun Li

Molecules 2019, 24(10), 1990; https://doi.org/10.3390/molecules24101990 - 24 May 2019

Cited by 26 | Viewed by 4616

Abstract

Agarwood is the resinous wood produced in some Aquilaria species and is highly valued for wide usages in medicine, incense, and perfume. To protect the threatened Aquilaria species, the cultivation of Aquilaria sinensis and artificial agarwood induction techniques have been effectively established in [...] Read more.

Agarwood is the resinous wood produced in some Aquilaria species and is highly valued for wide usages in medicine, incense, and perfume. To protect the threatened Aquilaria species, the cultivation of Aquilaria sinensis and artificial agarwood induction techniques have been effectively established in China. To evaluate the quality of agarwood induced by different techniques, patterns of chemical constituents in artificial agarwood by four methods (wounding using an axe, burning-chisel-drilling, chemical inducer, and biological inoculation) were analyzed and compared by UPLC-ESI-MS/MS and GC-EI-MS in this study. Results of GC-MS gave a panorama of chemical constituents in agarwood, including aromatic compounds, steroids, fatty acids, sesquiterpenoids, and 2-(2-phenlyethyl)-chromones (PECs). Sesquiterpenoids were dominant in agarwood induced by wounding using an axe. PEC comprised over 60% of components in agarwood produced by biological inoculation and chemical inducers. PECs were identified by UPLC-ESI-MS/MS in all artificial agarwood and the relative contents varied in different groups. Tetrahydro-2-(2-phenylethyl)-chromones (THPECs) in wounding by axes induced agarwood were lower while 2-(2-phenylethyl)-chromones (FPECs) were higher than other groups. The results showed that methods used for inducing agarwood formation in Aquilaria sinensis affect the chemical constituents of agarwood. Full article

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10 pages, 1921 KiB

Open AccessArticle

Development of Indirect Competitive ELISA for Lithospermic Acid B of Salvia miltiorrhiza with Its Specific Antibodies Generated via Artificial Oil Bodies

by Yu-En Shih, Chao-Hsiang Chen, Nan-Hei Lin and Jason T.C. Tzen

Molecules 2019, 24(10), 1952; https://doi.org/10.3390/molecules24101952 - 21 May 2019

Cited by 6 | Viewed by 3792

Abstract

Lithospermic acid B (LSB), the major water-soluble ingredient of Salvia miltiorrhiza (Danshen), has been shown to be an active ingredient responsible for the therapeutic effects of this traditional Chinese herb used to treat cardiac disorders. This study aimed to develop an indirect competitive [...] Read more.

Lithospermic acid B (LSB), the major water-soluble ingredient of Salvia miltiorrhiza (Danshen), has been shown to be an active ingredient responsible for the therapeutic effects of this traditional Chinese herb used to treat cardiac disorders. This study aimed to develop an indirect competitive enzyme linked immunosorbent assay (ELISA) for the detection of LSB. Firstly, LSB was chemically conjugated to a modified oil-body protein, lysine-enriched caleosin, recombinantly expressed in Escherichia coli. Antibodies against LSB (Ab-LSB) were successfully generated by immunizing hens with artificial oil bodies constituted with the LSB-conjugated caleosin. Western blotting showed that Ab-LSB specifically recognized LSB, but not the carrier protein, lysine-enriched caleosin. To detect LSB via indirect competitive ELISA, LSB was conjugated with bovine serum albumin (LSB-BSA) and coated on a microplate. The binding between Ab-LSB and LSB-BSA on the microplate was competed dose-dependently in the presence of free LSB with a concentration ranging from 5 to 5 × 10⁴ ng/mL. The IC₅₀ value was approximately determined to be 120 ng/mL for LSB regardless of its complex with a metal ion of Na⁺, K⁺ or Mg²⁺. Full article

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14 pages, 1214 KiB

Open AccessArticle

Chemo-Diversity and Antiradical Potential of Twelve Matricaria chamomilla L. Populations from Iran: Proof of Ecological Effects

by Elahe Piri, Mohammad Mahmoodi Sourestani, Esmaeil Khaleghi, Javad Mottaghipisheh, Zoltán Péter Zomborszki, Judit Hohmann and Dezső Csupor

Molecules 2019, 24(7), 1315; https://doi.org/10.3390/molecules24071315 - 03 Apr 2019

Cited by 30 | Viewed by 3662

Abstract

Matricaria chamomilla L. is a popular medicinal herb that is used for healing various diseases and is widely distributed worldwide in temperate climate zones, and even in the subtropical climate of Southern and Western Iran. This study was aimed at comparing the volatile [...] Read more.

Matricaria chamomilla L. is a popular medicinal herb that is used for healing various diseases and is widely distributed worldwide in temperate climate zones, and even in the subtropical climate of Southern and Western Iran. This study was aimed at comparing the volatile oil constituents, along with antiradical potential and HPLC analysis of methanolic extracts from twelve plant samples growing in Iran. The present research was carried out for the first time on these populations. Among seventeen identified volatile chemicals evaluated by GC/MS and GC/FID, representing 92.73–97.71% of the total oils, α-bisabolone oxide A (45.64–65.41%) was the major constituent, except in case of “Sarableh” as a new chemotype, where (E)- and (Z)-γ-bisabolene (42.76 and 40.08%, respectively) were the predominant components. Oxygenated sesquiterpenes (53.31–74.52%) were the most abundant compounds in the samples excluding “Sarableh” with 91.3% sesquiterpene hydrocarbons. “Sarableh” also exerted the most potent antioxidant capacity with EC₅₀ = 7.76 ± 0.3 µg/mL and 6.51 ± 0.63 mmol TE (Trolox^® equivalents)/g. In addition, populations “Lali” and “Bagh Malek” contained the highest amounts of apigenin and luteolin with 1.19 ± 0.01 mg/g and 2.20 ± 0.0 mg/g of plant material, respectively. Our findings depict a clear correlation between phytochemical profiles and antiradical potential of M. chamomilla and geographical factors. Full article

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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 4409

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

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2018

Jump to: 2023, 2022, 2021, 2020, 2019

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 3756

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

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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 3874

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

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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 11670

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

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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 4595

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

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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 5530

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

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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 4404

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

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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 4821

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

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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 3875

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

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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 6052

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

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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 4576

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

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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 4867

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

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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 4192

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

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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 5109

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

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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 4153

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

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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 3792

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

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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 5777

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

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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 4235

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

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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 3783

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

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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 28880

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

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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 3870

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

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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 3987

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

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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 3705

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

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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 5438

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

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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 6194

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

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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 4054

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

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