Two flavone C-glycosides as quality control markers for the manufacturing process of ephedrine alkaloids-free Ephedra Herb extract (EFE) as a crude drug preparation

Oshima, Naohiro; Maruyama, Toru; Yamashita, Tadatoshi; Uchiyama, Nahoko; Amakura, Yoshiaki; Hyuga, Sumiko; Hyuga, Masashi; Nakamori, Shunsuke; Takemoto, Hiroaki; Kobayashi, Yoshinori; Hakamatsuka, Takashi; Odaguchi, Hiroshi; Hanawa, Toshihiko; Goda, Yukihiro

doi:10.1007/s11418-017-1111-8

Cited by 12 publications

(9 citation statements)

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“…Molecules 2020, 25, x; doi: FOR PEER REVIEW www.mdpi.com/journal/molecules the sweating generated by the ingest of E. sinica Stapf that could be attributed to compounds such as mahuannins B ( 93) and F (97), and also to ephedrannin A ( 98) [92]. In this context, vicenin 2 (66), isovitexin 2"-O-rhamnoside (64) and apigenin (52) have been evaluated as quality control markers for the manufacturing process of Ephedra Herb extract (EHE) [93].…”

Section: Amino Acid Derivativesmentioning

confidence: 99%

“…Likewise, several EFE extracts from plants grown in different habitats and collected over a 12 year period of time were analyzed trough liquid chromatography coupled to high resolution mass spectrometry (LC/HRMS), showing two common notable corresponding to the flavone C-glycosides: vicenin 2 (66) and isovitexin 2"-O-rhamnoside (64). Therefore, they then served as quantitative markers for the quality control of the manufacturing process of the extract [93].…”

Section: Marker Compounds For the Quality Control Of The Manufacturing Process Of Ephedrine Alkaloids-free Ephedra Herb Extracts (Efe's)mentioning

confidence: 99%

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A Review of the Ephedra genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties

et al. 2020

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Ephedra is one of the largest genera of the Ephedraceae family, which is distributed in arid and semiarid regions of the world. In the traditional medicine from several countries some species from the genus are commonly used to treat asthma, cold, flu, chills, fever, headache, nasal congestion, and cough. The chemical constituents of Ephedra species have been of research interest for decades due to their contents of ephedrine-type alkaloids and its pharmacological properties. Other chemical constituents such as phenolic and amino acid derivatives also have resulted attractive and have provided evidence-based supporting of the ethnomedical uses of the Ephedra species. In recent years, research has been expanded to explore the endophytic fungal diversity associated to Ephedra species, as well as, the chemical constituents derived from these fungi and their pharmacological bioprospecting. Two additional aspects that illustrate the chemical diversity of Ephedra genus are the chemotaxonomy approaches and the use of ephedrine-type alkaloids as building blocks in organic synthesis. American Ephedra species, especially those that exist in Mexico, are considered to lack ephedrine type alkaloids. In this sense, the phytochemical study of Mexican Ephedra species is a promising area of research to corroborate their ephedrine-type alkaloids content and, in turn, discover new chemical compounds with potential biological activity. Therefore, the present review represents a key compilation of all the relevant information for the Ephedra genus, in particular the American species, the species distribution, their ecological interactions, its ethnobotany, its phytochemistry and their pharmacological activities and toxicities, in order to promote clear directions for future research.

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Section: Amino Acid Derivativesmentioning

confidence: 99%

Section: Marker Compounds For the Quality Control Of The Manufacturing Process Of Ephedrine Alkaloids-free Ephedra Herb Extracts (Efe's)mentioning

confidence: 99%

A Review of the Ephedra genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties

et al. 2020

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“…However, ephedrine alkaloids, 6-hydroxykynurenic acid, and 6-methoxykynurenic acid were not present in the EFE chromatogram. Later, in 2018, Oshima et al [108] analyzed Ephedra herb extracts grown in different habitats and collection years in Japan by liquid chromatography/high-resolution mass spectrometry (LC/HRMS). ese authors detected two notable peaks common to each extract.…”

Section: Recent Applications Of High-resolution Mass Spectrometry For Ephedra Extract Characterizationmentioning

confidence: 99%

“…Quantitative analyses using the isocratic condition of LC/MS showed that the content percentages of 1 and 2 in EFE were 0.140-0.146% and 0.350-0.411%, respectively. Furthermore, Oshima et al [108] analyzed apigenin (3), an aglycon common to 1 and 2. In 2016, Mei et al [110] reported that the HPLC analysis determined five activity components of Ephedra-Gypsum extract.…”

Section: Recent Applications Of High-resolution Mass Spectrometry For Ephedra Extract Characterizationmentioning

confidence: 99%

A Review on Worldwide Ephedra History and Story: From Fossils to Natural Products Mass Spectroscopy Characterization and Biopharmacotherapy Potential

Elhadef

Smaoui

Fourati

et al. 2020

Evidence-Based Complementary and Alternative Medicine

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Growing worldwide, the genus Ephedra (family Ephedraceae) had a medicinal, ecological, and economic value. The extraordinary morphological diversity suggests that Ephedra was survivor of an ancient group, and its antiquity is also supported by fossil data. It has recently been suggested that Ephedra appeared 8–32 million years ago, and a few megafossils document its presence in the Early Cretaceous. Recently, the high analytical power provided by the new mass spectrometry (MS) instruments is making the characterization of Ephedra metabolites more feasible, such as ephedrine series. In this regard, the chemical compounds isolated from crude extracts, fractions, and few isolated compounds of Ephedra species were characterized by MS-based techniques (LC-MS, LC-ESI-MS, HPLC-PDA-ESI/MS, LC-DAD-ESI/MSn, LC/Orbitrap MS, etc.). Moreover, we carry out an exhaustive review of the scientific literature on biomedicine and pharmacotherapy (anticancer, antiproliferative, anti-inflammatory, antidiabetic, antihyperlipidemic, antiarthritic, and anti-influenza activities; proapoptotic and cytotoxic potential; and so on). Equally, antimicrobial and antioxidant activities were discussed. This review is focused on all these topics, along with current studies published in the last 5 years (2015–2019) providing in-depth information for readers.

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“…For example, vicenin-2 is a flavone C -glycoside found in diverse plants including Orchidaceae ( Figure 1 a) [ 7 , 8 , 9 ] and has shown various biological activities, including anticancer [ 10 ], anti-inflammatory [ 11 ], and antioxidant effects [ 12 ]. As a result, recent studies on vicenin-2 have focused on various aspects from the quality control of herbal medicine [ 13 ] to organic synthesis [ 14 , 15 ] to the treatment [ 10 ] or prevention [ 16 ] of prostate cancer.…”

Section: Introductionmentioning

confidence: 99%

Identification of Major Flavone C-Glycosides and Their Optimized Extraction from Cymbidium kanran Using Deep Eutectic Solvents

et al. 2017

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Cymbidium kanran, an orchid exclusively distributed in Northeast Asia, has been highly valued as a decorative plant and traditional herbal medicine. Here, C. kanran extracts were prepared in 70% aqueous methanol using ultrasound-assisted extraction (UAE) and subjected to liquid chromatography-photodiode array detection and ultra-high performance liquid chromatography-quadrupole-time-of-flight-mass spectrometry analysis, which were used for quantitative and qualitative analysis, respectively. It was found that the extracts were rich in flavone C-glycosides including vicenin-2, vicenin-3, schaftoside, vitexin, and isovitexin. Ten deep eutectic solvents (DESs) were synthesized by combining choline chloride (hydrogen bond acceptor) with various polyols and diols (hydrogen bond donors) and were tested as a medium for the efficient production of extracts enriched with potentially bioactive flavone C-glycosides from C. kanran. A DES named ChCl:DPG, composed of choline chloride and dipropylene glycol at a 1:4 molar ratio, exhibited the best extraction yields. Then, the effects of extraction conditions on the extraction efficiency were investigated by response surface methodology. Lower water content in the extraction solvent and longer extraction time during UAE were desirable for higher extraction yields. Under the statistically optimized conditions, in which 100 mg of C. kanran powder were extracted in 0.53 mL of a mixture of ChCl:DPG and water (74:26, w/w) for 86 min, a total of 3.441 mg g−1 flavone C-glycosides including 1.933 mg g−1 vicenin-2 was obtained. This total yield was 196%, 131%, and 71% more than those obtained using 100% methanol, water, and 70% methanol, respectively.

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Two flavone C-glycosides as quality control markers for the manufacturing process of ephedrine alkaloids-free Ephedra Herb extract (EFE) as a crude drug preparation

Cited by 12 publications

References 5 publications

A Review of the Ephedra genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties

A Review of the Ephedra genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties

A Review on Worldwide Ephedra History and Story: From Fossils to Natural Products Mass Spectroscopy Characterization and Biopharmacotherapy Potential

Identification of Major Flavone C-Glycosides and Their Optimized Extraction from Cymbidium kanran Using Deep Eutectic Solvents

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