Three Phenolic Glycosides from Gastrodia elata

Chae, Sungwook; Lee, A Yeong; Lee, Hye Won; Yoon, Taesook; Moon, Byeong-Cheol; Choo, Byung-Kil; Kim, Ho-Kyoung

doi:10.3839/jabc.2008.011

Cited by 5 publications

(3 citation statements)

References 10 publications

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“…The UV spectrum showed absorption maxima at 221. . By comparing the above results and the previously reported spectroscopic data [38][39][40]42], compound 10 was identified as tris [4-(β-D-glucopyranosyloxy)benzyl] citrate, namely, parishin or parishin A (Figure 4). Parishin A has only been found in G. elata rhizome [38][39][40]42] and Vanda parishii [43].…”

Section: Isolation and Structure Elucidation Of Parishin-related Comp...supporting

confidence: 61%

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Identification of Novel Parishin Compounds from the Twig of Maclura tricuspidata and Comparative Analysis of Parishin Derivatives in Different Parts

Kim

Gebru

et al. 2022

Molecules

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Parishin compounds are rare polyphenolic glucosides mainly found in the rhizome of the traditional Chinese medicinal plant, Gastrodia elata. These constituents are reported to have several biological and pharmacological activities. In the present study, two novel parishin derivatives not previously reported as plant-based phytochemicals were identified from a twig of Maclura tricuspidata (MT) and two new compounds were elucidated as 1-(4-(β-d-glucopyranosyloxy)benzyl)-3-hydroxy-3-methylpentane-1,5-dioate (named macluraparishin E) and 1,3-bis(4-(β-d-glucopyranosyloxy)benzyl)-3-hydroxy-3-methylpentane- 1,5-dioate (macluraparishin C), based on the experimental data obtained by UV–Visible (UV–Vis) spectroscopy, high performance liquid chromatography–quadrupole time-of-flight mass spectrometry (HPLC-QTOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. Additionally, gastrodin, parishin A and parishin B were positively identified by spectroscopic evidence and the comparison of HPLC retention time with the corresponding authentic standards. Gastrodin, parishin A and parishin B, macluraparishin E and macluraparishin C were found to be the most abundant constituents in the MT twig. The compositions and contents of these constituents were found to vary depending on the different parts of the MT plant. In particular, the contents of parishin A, parishin B, macluraparishin C and macluraparishin E were higher in the twig, bark and root than in the leaves, xylem and fruit.

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Section: Isolation and Structure Elucidation Of Parishin-related Comp...supporting

confidence: 61%

“…4). Parishin B was identified previously in the G. elata rhizome [39][40][41][42]. These results suggest that the MT twig contained large amount of gastrodin, parishin A and parishin B.…”

Section: Isolation and Structure Elucidation Of Parishin-related Comp...supporting

confidence: 55%

Identification of Novel Parishin Compounds from the Twig of Maclura tricuspidata and Comparative Analysis of Parishin Derivatives in Different Parts

Kim

Gebru

et al. 2022

Molecules

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“…13 C NMR (100 MHz, MeOH‐ d 4 , ppm): δ 43.4 (C‐1), 43.7 (C‐3), 60.7 (2C, 2×Glc C‐6), 65.2 (2C, C‐7′, 7′′), 69.7 ((2C, 2×Glc C‐3), 73.2 (2C, 2×Glc C‐2), 73.3 (C‐3), 76.6 (2C, 2×Glc C‐3), 77.0 (2C, 2×Glc C‐5), 100.3 (2C, Glc C‐1), 116.1 (2C, C‐3′, 5′), 116.1 (2C, C‐3′′, 5′′), 129.2 (2C, C‐2′, 6′′), 129.2, 129.3 (C‐2′′, 6′′), 129.3 (C‐1′), 129.5 (C‐1′′), 157.1 (C‐4′), 157.2 (C‐ 4′′), 169.5 (COOR 1 ), 172.9 (COOR 3 ), 173.5 (COOR 2 ). By comparison with reported data, compound 2 was identified as parishin B .…”

Section: Resultsmentioning

confidence: 68%

Effect of inorganic salt on partition of high‐polarity parishins in two‐phase solvent systems and separation by high‐speed counter‐current chromatography from Gastrodia elata Blume

Dong

Yao

Liu

et al. 2019

J of Separation Science

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Parishins are high‐polarity and major bioactive constituents in Gastrodia elata Blume. In this study, the effect of several inorganic salts on the partition of parishins in two‐phase solvent systems was investigated. Adding ammonium sulfate, which has a higher solubility in water, was found to significantly promote the partition of parishins in the upper organic polar solvents. Based on the results, a two‐phase solvent system composed of butyl alcohol/acetonitrile/near‐saturated ammonium sulfate solution/water (1.5:0.5:1.2:1, v/v/v/v) was used for the purification of parishins by high‐speed counter‐current chromatography. Fractions obtained from high‐speed counter‐current chromatography were subjected to semi‐preparative high‐performance liquid chromatography to remove salt and impurities. As a result, parishin E (6.0 mg), parishin B (7.8 mg), parishin C (3.2 mg), gastrodin (15.3 mg), and parishin A (7.3 mg) were isolated from water extract of Gastrodia elata Blume (400 mg). These results demonstrated that adding inorganic salt that has high solubility in water to the two‐phase solvent system in high‐speed counter‐current chromatography was a suitable approach for the purification of high‐polarity compounds.

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Gastrodin Inhibits Glutamate-Induced Apoptosis of PC12 Cells via Inhibition of CaMKII/ASK-1/p38 MAPK/p53 Signaling Cascade

Jiang

et al. 2014

Cell Mol Neurobiol

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Previous research demonstrated that glutamate induces neuronal injury partially by increasing intracellular Ca(2+) concentrations ([Ca(2+)]i), and inducing oxidative stress, leading to a neurodegenerative disorder. However, the mechanism of glutamate-induced injury remains elusive. Gastrodin, a major active component of the traditional herbal agent Gastrodia elata (GE) Blume, has been recognized as a potential neuroprotective drug. In the current study, a classical injury model based on glutamate-induced cell death of rat pheochromocytoma (PC12) cells was used to investigate the neuroprotective effect of gastrodin, and its potential mechanisms involved. In this paper, the presence of gastrodin inhibits glutamate-induced oxidative stress as measured by the formation of reactive oxygen species (ROS), the level of malondialdehyde (MDA), mitochondrial membrane potential (MMP), and superoxide dismutase (SOD); gastrodin also prevents glutamate-induced [Ca(2+)]i influx, blocks the activation of the calmodulin-dependent kinase II (CaMKII) and the apoptosis signaling-regulating kinase-1 (ASK-1), inhibits phosphorylation of p38 mitogen-activated kinase (MAPK). Additionally, gastrodin blocked the expression of p53 phosphorylation, caspase-3 and cytochrome C, reduced bax/bcl-2 ratio induced by glutamate in PC12 cells. All these findings indicate that gastrodin protects PC12 cells from the apoptosis induced by glutamate through a new mechanism of the CaMKII/ASK-1/p38 MAPK/p53-signaling pathway.

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Three Phenolic Glycosides from Gastrodia elata

Cited by 5 publications

References 10 publications

Identification of Novel Parishin Compounds from the Twig of Maclura tricuspidata and Comparative Analysis of Parishin Derivatives in Different Parts

Identification of Novel Parishin Compounds from the Twig of Maclura tricuspidata and Comparative Analysis of Parishin Derivatives in Different Parts

Effect of inorganic salt on partition of high‐polarity parishins in two‐phase solvent systems and separation by high‐speed counter‐current chromatography from Gastrodia elata Blume

Gastrodin Inhibits Glutamate-Induced Apoptosis of PC12 Cells via Inhibition of CaMKII/ASK-1/p38 MAPK/p53 Signaling Cascade

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