Flavonoid and Galloyl Glycosides Isolated from <i>Saxifraga spinulosa</i> and Their Antioxidative and Inhibitory Activities against Species That Cause Piroplasmosis

Badral, Duger; Odonbayar, Batsukh; Murata, Toshihiro; Munkhjargal, Tserendorj; Tuvshintulga, Bumduuren; Igarashi, Ikuo; Suganuma, Keisuke; Inoue, Noboru; Brantner, Adelheid; Gendaram, Odontuya; Sasaki, Kenroh; Batkhuu, Javzan

doi:10.1021/acs.jnatprod.7b00142

Cited by 29 publications

(20 citation statements)

References 31 publications

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“…We performed screening to identify SS -derived virucidal components. The first evaluation focused on the virucidal activities of the aqueous extract and Fr 1A–F ( Figure S1 ) [ 15 ] against IAV, FCV, and MNV. Fr 1A–F were fractionated from aqueous extract ( Figure S1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Extraction and isolation of plant materials as well as structural determination procedures were as described in a previous report [ 15 ]. The compounds isolated from each fraction and their respective yields are included in Table 1 .…”

Section: Methodsmentioning

confidence: 99%

“…Saxifraga spinulosa ( SS ) Adams (family, Saxifragaceae) is a perennial herbaceous plant that is distributed widely in eastern continental Asia. Flavonoids, phenolic acids, terpenoids, and phytosterols have all been reported as chemical constituents of Saxifraga plants; compounds that feature a pyrogallol B-ring as well as galloyl moieties have been identified as constituents of SS -derived extracts [ 15 ]. Furthermore, many of the compounds isolated from SS have DPPH (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging activities and/or can inhibit Babesia and Theileria parasites [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

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Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2

Takeda

Murata

Jamsransuren

et al. 2020

Viruses

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Novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), influenza A virus (IAV), and norovirus (NV) are highly contagious pathogens that threaten human health. Here we focused on the antiviral potential of the medicinal herb, Saxifraga spinulosa (SS). Water-soluble extracts of SS were prepared, and their virus-inactivating activity was evaluated against the human virus pathogens SARS-CoV-2 and IAV; we also examined virucidal activity against feline calicivirus and murine norovirus, which are surrogates for human NV. Among our findings, we found that SS-derived gallocatechin gallate compounds were capable of inactivating all viruses tested. Interestingly, a pyrogallol-enriched fraction (Fr 1C) inactivated all viruses more rapidly and effectively than did any of the component compounds used alone. We found that 25 µg/mL of Fr 1C inactivated >99.6% of SARS-CoV-2 within 10 s (reduction of ≥2.33 log10 TCID50/mL). Fr 1C resulted in the disruption of viral genomes and proteins as determined by gel electrophoresis, electron microscopy, and reverse transcription–PCR. Taken together, our results reveal the potential of Fr 1C for development as a novel antiviral disinfectant.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2

Takeda

Murata

Jamsransuren

et al. 2020

Viruses

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“…In general, conventional methods, such as gel and silicagel column chromatography, are still utilized to isolate and purify phenols from plants in the Saxifragaceae family [8][9][10]; these techniques require only simple equipment and are easy to perform. However, owing to their inferior separation reproducibility and the absence of online detection, S. tangutica phenols cannot be isolated easily.…”

Section: Introductionmentioning

confidence: 99%

Preparative isolation of arylbutanoid‐type phenol [(‐)‐rhododendrin] with peak tailing on conventional C18 column using middle chromatogram isolated gel column coupled with reversed‐phase liquid chromatography

Dang

Wang

et al. 2020

J of Separation Science

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Reversed‐phase liquid chromatography coupled with middle chromatogram isolated gel column was employed for the efficient preparative separation of the arylbutanoid‐type phenol [(‐)‐rhododendrin] from Saxifraga tangutica. Universal C18 (XTerra C18) and XCharge C18 columns were compared for (‐)‐rhododendrin fraction analysis and preparation. Although tailing and overloading occurred on the XTerra C18 column, the positively charged reversed‐phase C18 column (XCharge C18) overcame these drawbacks, allowing for favorable separation resolution, even when loading at a on a preparative scale (3.69 mg per injection). The general separation process was as follows. First, 365.0 mg of crude (‐)‐rhododendrin was enriched from 165 g Saxifraga tangutica extract via a middle chromatogram isolated gel column. Second, separation was performed on an XTerra C18 preparative column, from which 73.8 mg of the target fraction was easily obtained. Finally, the 24.0 mg tailing peak of (‐)‐rhododendrin on XTerra C18 column was selectively purified on the XCharge C18 analytical column. These results demonstrate that the tailing nonalkaloid peaks can be effectively used for preparative isolation on XCharge C18 columns.

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“…It has been recorded in "Zhong Yao Ci Hai" and used for the treatment of hepatitis, Article Related Abbreviations: MCI, middle chromatogram isolated gel; prep-HPLC, preparative high-performance liquid chromatography cholecystitis, and influenza [2,3]. Flavonoids, one of the vital active ingredients of Saxifraga plants, possess a number of pharmacological activities [4]; however, only four flavonoids have been isolated from S. tangutica to date [5]. For quality control and bioactivity assessment, it is essential to develop a productive technique to isolate and purify flavonoids from S. tangutica.…”

Section: Introductionmentioning

confidence: 99%

Target separation of flavonoids from Saxifraga tangutica using two‐dimensional hydrophilic interaction chromatography/reversed‐phase liquid chromatography

Dang

Zhang

Wang

et al. 2018

J of Separation Science

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An orthogonally (80.3%) preparative two‐dimensional hydrophilic interaction chromatography/reversed‐phase liquid chromatography method has been established for the isolation and purification of flavonoids from Saxifraga tangutica. Initially, flavonoids were enriched by means of a middle‐pressure chromatographic tower (containing middle chromatogram isolated gel). In the first dimension, a XION preparative column was used to separate the flavonoid fractions under the guidance of characteristic ultraviolet absorption spectra of flavonoids and nine flavonoid fractions were obtained. Then, the coeluted flavonoid fractions were selected for further purification via reversed‐phase liquid chromatography with the parent ion peak of quercetin (303), kaempferol (287), or isorhamnetin (317). Several flavonoids could be separated from each hydrophilic interaction chromatography fraction; furthermore, flavonoids with poor resolution in one‐dimensional liquid chromatography were isolated in two‐dimensional liquid chromatography due to the orthogonality. In addition, this technique was valuable for trace flavonoids, which were concentrated in the first stage and separated in the second stage. In total, 18 flavonoids with either quercetin, kaempferol, or isorhamnetin parent nuclei were targetedly obtained, and 15 flavonoids were obtained for the first time from S. tangutica. These results established that the off‐line two‐dimensional hydrophilic interaction chromatography/reversed‐phase liquid chromatography technique was efficient for the isolation of flavonoids from Saxifraga tangutica.

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Flavonoid and Galloyl Glycosides Isolated from Saxifraga spinulosa and Their Antioxidative and Inhibitory Activities against Species That Cause Piroplasmosis

Cited by 29 publications

References 31 publications

Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2

Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2

Preparative isolation of arylbutanoid‐type phenol [(‐)‐rhododendrin] with peak tailing on conventional C18 column using middle chromatogram isolated gel column coupled with reversed‐phase liquid chromatography

Target separation of flavonoids from Saxifraga tangutica using two‐dimensional hydrophilic interaction chromatography/reversed‐phase liquid chromatography

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