Parishins B and C from rhizomes of Gastrodia elata

Lin, Jer-Huei; Liu, Yi-Chu; Hau, J.‐P.; Wen, Kuo‐Ching

doi:10.1016/0031-9422(95)00955-8

Cited by 49 publications

(2 citation statements)

References 2 publications

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“…Additionally, eight known parishins 8 – 15 , parishin A ( 8 ), B ( 9 ), C ( 10 ), E ( 11 ), G ( 12 ), J ( 13 ), K ( 14 ), and Y ( 15 ), were assigned by comparison with NMR data from the literature. It should be noted that parishin K was initially reported and named in 2015, while other publications referred to a different structure without providing concrete evidence to support it …”

Section: Resultsmentioning

confidence: 99%

Isolation, Bioactivity, and Molecular Docking of a Rare Gastrodin Isocitrate and Diverse Parishin Derivatives from Gastrodia elata Blume

Zhou,

Chen,

Gong

et al. 2024

ACS Omega

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Gastrodia elata Blume (G. elata) is a well-known medicine food homology plant widely used in treating neurological disorders such as Alzheimer's disease (AD). Here, undiscovered gastrodin derivatives were systematically studied. Seven novel gastrodin derivatives (1−7), including a unique gastrodin isocitrate (1) and six differently substituted parishin derivatives (2−7), were isolated. Structural identification was mainly based on 1D and 2D NMR data, high-resolution ESI-MS data, and HPLC analysis. Notably, the stereochemistry of 1 was further elucidated by ECD calculations. Compounds 1 and 6 showed neuroprotective effects on the H 2 O 2 -induced PC12 cell injury model. Molecular docking analysis exhibited that 1 and 6 had good affinities with three popular AD-related targets. These findings not only enriched the chemical diversity but also revealed potential active components in G. elata.

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Section: Resultsmentioning

confidence: 99%

Isolation, Bioactivity, and Molecular Docking of a Rare Gastrodin Isocitrate and Diverse Parishin Derivatives from Gastrodia elata Blume

Zhou,

Chen,

Gong

et al. 2024

ACS Omega

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“…After purification, all isolated compounds were fully characterized by extensive 2D NMR experiments, which complemented the HRMS 2 results. Compounds 1 – 3 and 7 – 11 , were identified as plantainoside B ( 1 ), monnieraside III ( 2 ), monnieraside II ( 3 ) [48], 4-hydroxybenzoyl glucose ( 7 ) [56], 3,4-dihydroxyphenethyl glucoside ( 8 ) [57], parishin C ( 9 ), parishin A ( 10 ) and parishin B ( 11 ) [58], respectively, by comparing their spectral data with literature. Compounds 4 – 6 were isolated for the first time and identified as new phenylethanoid glycosides: monnieraside IV ( 4 ), monnieraside V ( 5 ), and monnieraside VI ( 6 ).…”

Section: Resultsmentioning

confidence: 99%

Discovery of Lipid Peroxidation Inhibitors from Bacopa Species Prioritized through Multivariate Data Analysis and Multi-Informative Molecular Networking

et al. 2019

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A major goal in the discovery of bioactive natural products is to rapidly identify active compound(s) and dereplicate known molecules from complex biological extracts. The conventional bioassay-guided fractionation process can be time consuming and often requires multi-step procedures. Herein, we apply a metabolomic strategy merging multivariate data analysis and multi-informative molecular maps to rapidly prioritize bioactive molecules directly from crude plant extracts. The strategy was applied to 59 extracts of three Bacopa species (B. monnieri, B. caroliniana and B. floribunda), which were profiled by UHPLC-HRMS2 and screened for anti-lipid peroxidation activity. Using this approach, six lipid peroxidation inhibitors 1‒6 of three Bacopa spp. were discovered, three of them being new compounds: monnieraside IV (4), monnieraside V (5) and monnieraside VI (6). The results demonstrate that this combined approach could efficiently guide the discovery of new bioactive natural products. Furthermore, the approach allowed to evidence that main semi-quantitative changes in composition linked to the anti-lipid peroxidation activity were also correlated to seasonal effects notably for B. monnieri.

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Analysis of the metabolic profile of parishin by ultra‐performance liquid chromatography/quadrupole‐time of flight mass spectrometry

Tang

Wang

et al. 2015

Biomedical Chromatography

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Parishin is a dominant active ingredient originating from Gastrodia elata Blume, and has good neuroprotective effects against brain disorders. In the present study, the metabolic profile of parishin by in vitro and in vivo experiments was investigated using ultra-high performance liquid chromatography coupled with quadrupole-time of flight mass spectrometry (UHPLC/Q-TOF MS) combined with an automated MS(E) technique. By comparison with reference compounds, accurate mass measurement, the characteristic fragmentation patterns of the parent drug parishin and gastrodin and relevant bio-transformation knowledge, 14 metabolites (seven hydrolyzates and seven derivatives of gastrodin) were detected and identified in rat plasma and urine after intragastric administration of parishin, including processes of hydrolyzation, oxidation, sulfation and glucuronidation. According to the proposed metabolic pathways of parishin, in vitro hydrolytic experiments and metabolic study of gastrodin in rat plasma, it can be inferred that parishin mainly functions as a prodrug and undergoes hydrolysis before being absorbed into the blood. The hydrolyzate, mainly gastrodin, was involved in further metabolism, which was responsible for pharmacological activities of parishin. In conclusion, this work provides valuable information on parishin metabolism using a rapid and reliable UHPLC/Q-TOF MS method, which could be widely used for the metabolic investigation of natural product.

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Parishins B and C from rhizomes of Gastrodia elata

Cited by 49 publications

References 2 publications

Isolation, Bioactivity, and Molecular Docking of a Rare Gastrodin Isocitrate and Diverse Parishin Derivatives from Gastrodia elata Blume

Isolation, Bioactivity, and Molecular Docking of a Rare Gastrodin Isocitrate and Diverse Parishin Derivatives from Gastrodia elata Blume

Discovery of Lipid Peroxidation Inhibitors from Bacopa Species Prioritized through Multivariate Data Analysis and Multi-Informative Molecular Networking

Analysis of the metabolic profile of parishin by ultra‐performance liquid chromatography/quadrupole‐time of flight mass spectrometry

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