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Phytochemicals: Analytical and Medicinal Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 May 2013) | Viewed by 91451

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Guest Editor
State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Macau, China
Interests: allergy and clinical immunology; nephrology; diabetology; toxicology; clinical biochemistry; laboratory medicine; Chinese medicine

Special Issue Information

Dear Colleagues,

Phytochemicals are numerous and have been studied intensely for basic science and applied research. They constitute a wealth of natural resources especially as new drugs or candidate drugs. Phytochemical research encompasses old and new disciplines of plant biology, medicinal chemistry, biochemistry, molecular biology, pharmcogenomics, proteomics, and metabolomics. It utilizes traditional and rapidly advancing analytical methods and instrumentation such as differential solvent extraction, gas or liquid chromatography coupled with tandem mass spectrometry, nuclear magnetic resonance and electron-spin resonance, and gene and protein arrays for fractionation, purification, chemical and genetic fingerprinting, derivatization, modification, synthesis, and clinical trials of photochemicals starting from cell-line to animal and patient studies.

This special issue of Molecules on "Phytochemicals: Analytical and Medicinal Chemistry" welcomes submission of previously unpublished manuscripts from original work on all the above aspects.

Prof. Dr. Christopher W.K. Lam
Guest Editor

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Keywords

  • fractionation and isolation
  • chemical and biological identification
  • chromatography and mass spectrometry
  • pharmacogenomics and metabolomics
  • drug development and formulation
  • cell, animal and patient studies

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Published Papers (8 papers)

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Research

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1538 KiB  
Article
Metabonomic Analysis of Water Extracts from Different Angelica Roots by 1H-Nuclear Magnetic Resonance Spectroscopy
by Pui Hei Chan, Wendy L. Zhang, Chung-Ho Lau, Chi Yuen Cheung, Hector C. Keun, Karl W. K. Tsim and Henry Lam
Molecules 2014, 19(3), 3460-3470; https://doi.org/10.3390/molecules19033460 - 20 Mar 2014
Cited by 14 | Viewed by 9094
Abstract
Angelica Radix, the roots of the genus Angelica, has been used for more than 2,000 years as a traditional medicine in Eastern Asia. The Chinese Pharmacopoeia records more than 100 herbal formulae containing Angelica roots. There are two common sources of Angelica [...] Read more.
Angelica Radix, the roots of the genus Angelica, has been used for more than 2,000 years as a traditional medicine in Eastern Asia. The Chinese Pharmacopoeia records more than 100 herbal formulae containing Angelica roots. There are two common sources of Angelica roots, Angelica sinensis from China and A. gigas from Korea. The two species of Angelica roots differ in their chemical compositions, pharmacological properties and clinical efficacy. 1H-NMR metabolic profiling has recently emerged as a promising quality control method for food and herbal chemistry. We explored the use of 1H-NMR metabolic profiling for the quality control of Angelica Radix. Unlike previous work, we performed the metabolic profiling on hot water extracts, so as to mimic the clinically relevant preparation method. Unsupervised principle component analyses of both the full spectral profile and a selection of targeted molecules revealed a clear differentiation of three types of Angelica roots. In addition, the levels of 13 common metabolites were measured. Statistically significant differences in the levels of glucose, fructose and threonine were found between different sources of Angelica. Ferulic acid, a marker commonly used to evaluate Angelica root, was detected in our samples, but the difference in ferulic acid levels between the samples was not statistically significant. Overall, we successfully applied 1H-NMR metabolic profiling with water extraction to discriminate all three sources of Angelica roots, and obtained quantitative information of many common metabolites. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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571 KiB  
Article
Authentication of Bulbus Fritillariae Cirrhosae by RAPD-Derived DNA Markers
by Gui-Zhong Xin, Yin-Ching Lam, Maitinuer Maiwulanjiang, Gallant K. L. Chan, Kevin Yue Zhu, Wai-Lun Tang, Tina Ting-Xia Dong, Zi-Qi Shi, Ping Li and Karl W. K. Tsim
Molecules 2014, 19(3), 3450-3459; https://doi.org/10.3390/molecules19033450 - 20 Mar 2014
Cited by 31 | Viewed by 9430
Abstract
Bulbus Fritillariae is the most commonly used antitussive herb in China. Eleven species of Fritillaria are recorded as Bulbus Fritillariae in the Chinese Pharmacopoeia. Bulbus Fritillariae Cirrhosae is a group of six Fritillaria species with higher efficiency and lower toxicity derived mainly from [...] Read more.
Bulbus Fritillariae is the most commonly used antitussive herb in China. Eleven species of Fritillaria are recorded as Bulbus Fritillariae in the Chinese Pharmacopoeia. Bulbus Fritillariae Cirrhosae is a group of six Fritillaria species with higher efficiency and lower toxicity derived mainly from wild sources. Because of their higher market price, five other Fritillaria species are often sold deceptively as Bulbus Fritillariae Cirrhosae in the herbal market. To ensure the efficacy and safety of medicinal herbs, the authentication of botanical resources is the first step in quality control. Here, a DNA based identification method was developed to authenticate the commercial sources of Bulbus Fritillariae Cirrhosae. A putative DNA marker (0.65 kb) specific for Bulbus Fritillariae Cirrhosae was identified using the Random Amplified Polymorphic DNA (RAPD) technique. A DNA marker representing a Sequence Characterized Amplified Region (SCAR) was developed from a RAPD amplicon. The SCAR marker was successfully applied to differentiate Bulbus Fritillariae Cirrhosae from different species of Fritillaria. Additionally, the SCAR marker was also useful in identifying the commercial samples of Bulbus Fritillariae Cirrhosae. Our results indicated that the RAPD-SCAR method was rapid, accurate and applicable in identifying Bulbus Fritillariae Cirrhosae at the DNA level. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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791 KiB  
Article
Biosynthesis of Panaxynol and Panaxydol in Panax ginseng
by Nihat Knispel, Elena Ostrozhenkova, Nicholas Schramek, Claudia Huber, Luis M. Peña-Rodríguez, Mercedes Bonfill, Javier Palazón, Gesine Wischmann, Rosa M. Cusidó and Wolfgang Eisenreich
Molecules 2013, 18(7), 7686-7698; https://doi.org/10.3390/molecules18077686 - 2 Jul 2013
Cited by 23 | Viewed by 9543
Abstract
The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. [...] Read more.
The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. ginseng were supplemented with [U-13C6]glucose. The polyynes were isolated from the labeled roots or hairy root cultures, respectively, and analyzed by quantitative NMR spectroscopy. The same mixtures of eight doubly 13C-labeled isotopologues and one single labeled isotopologue were observed in the C17-polyacetylenes obtained from the two experiments. The polyketide-type labeling pattern is in line with the biosynthetic origin of the compounds via decarboxylation of fatty acids, probably of crepenynic acid. The 13C-study now provides experimental evidence for the biosynthesis of panaxynol and related polyacetylenes in P. ginseng under in planta conditions as well as in root cultures. The data also show that 13CO2 experiments under field conditions are useful to elucidate the biosynthetic pathways of metabolites, including those from roots. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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650 KiB  
Article
Characterisation of Phenolic Compounds in South African Plum Fruits (Prunus salicina Lindl.) using HPLC Coupled with Diode-Array, Fluorescence, Mass Spectrometry and On-Line Antioxidant Detection
by Alet Venter, Elizabeth Joubert and Dalene De Beer
Molecules 2013, 18(5), 5072-5090; https://doi.org/10.3390/molecules18055072 - 2 May 2013
Cited by 37 | Viewed by 8603
Abstract
Phenolic compounds are abundant secondary metabolites in plums, with potential health benefits believed to be due to their antioxidant activity, amongst others. Phenolic characterisation of South African Prunus salicina Lindl. plums is necessary to fully evaluate their potential health benefits. An HPLC method [...] Read more.
Phenolic compounds are abundant secondary metabolites in plums, with potential health benefits believed to be due to their antioxidant activity, amongst others. Phenolic characterisation of South African Prunus salicina Lindl. plums is necessary to fully evaluate their potential health benefits. An HPLC method using diode-array detection (DAD) for quantification of phenolic compounds was improved and fluorescence detection (FLD) was added for quantification of flavan-3-ols. Validation of the HPLC-DAD-FLD method showed its suitability for quantification of 18 phenolic compounds, including flavan-3-ols using FLD, and phenolic acids, anthocyanins and flavonols using DAD. The method was suitable for characterisation of the phenolic composition of 11 South African plum cultivars and selections, including various types with yellow and red skin and flesh. The method was used in conjunction with mass spectrometry (MS) to identify 24 phenolic compounds. Neochlorogenic acid and cyanidin-3-O-glucoside were the major compounds in most of the plums, while cyanidin-3-O-glucoside was absent in Sun Breeze plums with yellow skin and flesh. Post-column on-line coupling of the ABTS•+ scavenging assay with HPLC-DAD enabled qualitative evaluation of the relative contribution of individual phenolic compounds to the antioxidant activity. The flavan-3-ols, neochlorogenic acid and cyanidin-3-O-glucoside displayed the largest antioxidant response peaks. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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209 KiB  
Article
Phenolic Constituents, Antioxidant and Preliminary Antimycoplasmic Activities of Leaf Skin and Flowers of Aloe vera (L.) Burm. f. (syn. A. barbadensis Mill.) from the Canary Islands (Spain)
by Aroa López, Miguel Suárez De Tangil, Orestes Vega-Orellana, Ana S. Ramírez and Milagros Rico
Molecules 2013, 18(5), 4942-4954; https://doi.org/10.3390/molecules18054942 - 26 Apr 2013
Cited by 93 | Viewed by 23583
Abstract
The methanol extracts of leaf skins and flowers of Aloe vera from the Canary Islands were analyzed for their phenolic profiles and screened for their antioxidant and antimycoplasmic activities. The use of reversed phase high performance liquid chromatography (RP-HPLC) allowed the identification of [...] Read more.
The methanol extracts of leaf skins and flowers of Aloe vera from the Canary Islands were analyzed for their phenolic profiles and screened for their antioxidant and antimycoplasmic activities. The use of reversed phase high performance liquid chromatography (RP-HPLC) allowed the identification of 18 phenolic constituents. Leaf skin extracts were characterized by the abundance of catechin, sinapic acid and quercitrin. Gentisic acid, epicatechin and quercitrin were the most prominent phenolic compounds of the flowers. The in vitro antioxidant activities determined by using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric antioxidant reducing power (FRAP) assays revealed that both extracts exhibited antioxidant activity, being the leaf skin extract the most active fraction. The leaf skin extract was also found to be active against the microbial strains tested. Therefore, A. vera extracts from leaf skin and flowers can be considered as good natural antioxidant sources. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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468 KiB  
Article
Evaluation of the Biological Activity of Naturally Occurring 5,8-Dihydroxycoumarin
by Gražina Slapšytė, Veronika Dedonytė, Juozas R. Lazutka, Jūratė Mierauskienė, Vaidotas Morkūnas, Rita Kazernavičiūtė, Audrius Pukalskas and Petras Rimantas Venskutonis
Molecules 2013, 18(4), 4419-4436; https://doi.org/10.3390/molecules18044419 - 15 Apr 2013
Cited by 10 | Viewed by 7211
Abstract
5,8-Dihydroxycoumarin (5,8-DHC) was isolated from aerial parts of sweet grass (Hierochloë odorata L.) and screened for antioxidant and genotoxic activities. A clear linear dependency of radical scavenging capacity in DPPH and ABTS•+ assays was determined. 5,8-DHC was very efficient in [...] Read more.
5,8-Dihydroxycoumarin (5,8-DHC) was isolated from aerial parts of sweet grass (Hierochloë odorata L.) and screened for antioxidant and genotoxic activities. A clear linear dependency of radical scavenging capacity in DPPH and ABTS•+ assays was determined. 5,8-DHC was very efficient in retarding rapeseed oil oxidation (Oxipress test). TPC (total phenols content) and FRAP (the ability to reduce ferric ion to ferrous ion) assays revealed a somewhat lower antioxidant capacity of 5,8-DHC as compared with gallic acid. Genotoxic activity was tested using different genetic end-points: chromosome aberrations (CAs) and micronuclei (MN) in Wistar rat bone marrow in vivo, CAs and sister chromatid exchanges (SCEs) in human lymphocytes in vitro, and somatic mutations and recombination in Drosophila melanogaster wing cells in vivo. 5,8-DHC did not increase frequency of CAs in rat bone marrow cells, but induced a significant increase of MN. It was slightly mutagenic in the Drosophila melanogaster assay after 120 h of treatment, but not after 48 h of treatment. 5,8-DHC induced both CAs and SCEs in vitro in human lymphocytes in a clear dose-dependent manner. Thus, 5,8-DHC may be classified as weakly genotoxic both in vivo and in vitro. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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544 KiB  
Article
Effects of Spray-Drying and Choice of Solid Carriers on Concentrations of Labrasol® and Transcutol® in Solid Self-Microemulsifying Drug Delivery Systems (SMEDDS)
by Liang Li, Tao Yi and Christopher Wai-Kei Lam
Molecules 2013, 18(1), 545-560; https://doi.org/10.3390/molecules18010545 - 2 Jan 2013
Cited by 38 | Viewed by 9105
Abstract
Solid self-microemulsifying drug delivery systems (SMEDDS) have been used increasingly for improving the bioavailability of hydrophobic drugs. Labrasol® and Transcutol® are used widely as surfactant and solubilizer in the formulation of solid SMEDDS. We investigated the effects of spray-drying and the [...] Read more.
Solid self-microemulsifying drug delivery systems (SMEDDS) have been used increasingly for improving the bioavailability of hydrophobic drugs. Labrasol® and Transcutol® are used widely as surfactant and solubilizer in the formulation of solid SMEDDS. We investigated the effects of spray-drying and the use of different solid carriers on concentrations of Labrasol® and Transcutol® in solid SMEDDS with scutellarin as the formulated drug. Liquid and gas chromatography tandem mass spectrometry (LC-MS and GC-MS) methods were developed for measuring low concentrations of Labrasol® and Transcutol®. In the preparation of solid SMEDDS, lactose, hydroxypropylmethyl cellulose (HPMC) and microcrystalline cellulose (MCC) were used as solid carriers. Judging from the retention ratios of Labrasol® and Transcutol®, the droplet size of solid SMEDDS increased after spray-drying of liquid SMEDDS, and concentrations of these excipients decreased after the solidifying procedure. In such reduction, Lactose and HPMC were found to preserve Labrasol® and Transcutol® better than MCC during spray-drying, and the resultant droplet sizes were smaller than that of MCC. Labrasol® and Transcutol® showed good thermal stability at 60 °C degree for 10 days. It can be concluded that spray-drying could increase the droplet size of solid SMEDDS and decreased the concentration of Labrasol® and Transcutol® therein, while water-soluble solid carriers could preserve Labrasol® and Transcutol® better than insoluble carriers in the solid SMEDDS. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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Review

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209 KiB  
Review
Herb-Herb Combination for Therapeutic Enhancement and Advancement: Theory, Practice and Future Perspectives
by Chun-Tao Che, Zhi Jun Wang, Moses Sing Sum Chow and Christopher Wai Kei Lam
Molecules 2013, 18(5), 5125-5141; https://doi.org/10.3390/molecules18055125 - 3 May 2013
Cited by 164 | Viewed by 13657
Abstract
Herb-herb combinations have been used in Chinese medicine practice for thousands of years, yet scientific evidence of their therapeutic benefits is lacking. With increasing interest in shifting from the one-drug-one-target paradigm to combination therapy or polypharmacy to achieve therapeutic benefits for a number [...] Read more.
Herb-herb combinations have been used in Chinese medicine practice for thousands of years, yet scientific evidence of their therapeutic benefits is lacking. With increasing interest in shifting from the one-drug-one-target paradigm to combination therapy or polypharmacy to achieve therapeutic benefits for a number of diseases, there is momentum to explore new knowledge by tapping the past empirical experiences of herb-herb combinations. This review presents an overview of the traditional concept and practice of herb-herb combination in Chinese medicine, and highlights the available scientific and clinical evidence to support the combined use of herbs. It is hoped that such information would provide a lead for developing new approaches for future therapeutic advancement and pharmaceutical product development. Very likely modern technologies combined with innovative research for the quality control of herbal products, identification of active components and understanding of the molecular mechanism, followed by well-designed animal and clinical studies would pave the way in advancing the wealth of empirical knowledge from herb-herb combination to new therapeutic modalities. Full article
(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)
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