4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata

Acta Pharmaceutica Sinica B

Liu

et al. 2017

Six new indole alkaloid sulfonic acids (1–6), together with two analogues (7 and 8) that were previously reported as synthetic products, were isolated from an aqueous extract of the Isatis indigotica root. Their structures including the absolute configurations were determined by spectroscopic data analysis, combined with enzyme hydrolysis and comparison of experimental circular dichroism and calculated electronic circular dichroism spectra. In the preliminary assay, compounds 2 and 4 showed antiviral activity against Coxsackie virus B3 and influenza virus A/Hanfang/359/95 (H3N2), respectively.

Section: Introductionmentioning

confidence: 99%

Indole alkaloid sulfonic acids from an aqueous extract of Isatis indigotica roots and their antiviral activity

Meng

Acta Pharmaceutica Sinica B

Liu

et al. 2017

“…However, the previous studies were mainly focused on ethanol or methanol extracts, which is not in agreement with practical application of the herbal medicine by decocting with water. Therefore, an aqueous decoction of “ban lan gen” was investigated as part of our program to systematically study the chemical and biological diversity of several Chinese traditional medicines10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22. From the decoction, 43 new alkaloids and 54 known compounds, including a pair of indole alkaloid enantiomers containing dihydrothiopyran and 1,2,4-thiadiazole rings, a pair of bisindole alkaloid enantiomers, four stereoisomers of 3,5-bis(2-hydroxybut-3-en-1-yl)-1,2,4-thiadiazole, and twelve glycosidic indole alkaloids, as well as their antiviral and/or hepatocyte-protective activities, were characterized23, 24, 25, 26, 27, 28, 29, 30.…”

Section: Introductionmentioning

confidence: 99%

Aromatic compounds from an aqueous extract of “ban lan gen” and their antiviral activities

Liu

Chen

Acta Pharmaceutica Sinica B

et al. 2017

A pair of new diphenyl glycerol ether enantiomers (−)-1 and (+)-1 and two new methyl benzamidobenzoates 2 and 3, named (−)-(R)- and (+)-(S)-isatindigotrioic acid [(−)-1 and (+)-1] and isatindigoticamides A (2) and B (3), respectively, were isolated from an aqueous decoction of the roots of Isatis indigotica (ban lan gen). Their structures were elucidated by spectroscopic data analysis including 2D NMR experiments. The absolute configurations of (−)-1 and (+)-1 were assigned based on the CD exciton chirality method. Compounds 2 and 3 exhibited antiviral activities against HSV-1 with IC50 values of 4.87 and 25.87 μmol/L, respectively. Compound 2 was also found active against Coxsackie virus B3 and LPS-induced NO production.

“…All isolated compounds were evaluated using preliminary in vitro assays, including neuroprotective activity against serum deprivation-induced PC12 cell damage [53], H 2 O 2and L-glutamate-induced SK-N-SH cell injury [54,55], inflammation inhibitory activity against TNF-α production in RAW264.7 cells [56], antioxidant activity against Fe 2+ / cysteine-induced liver microsomal lipid peroxidation [53], cytotoxicity against human cancer cell lines [57], and antiviral activity against HIV-1 replication [57], but inactive at a concentration of 10 μM.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, we systematically studied the chemical constituents of an aqueous extract of "tian ma" to unravel the chemical and biological diversity of certain traditional Chinese medicines [26][27][28][29][30][31][32][33][34][35][36][37]. We previously reported on 51 compounds from the aqueous extract, including seven new p-hydroxybenzyl-substituted amino acids, seven new p-hydroxybenzyl-substituted glutathione derivatives, one new N,N-bis(p-hydroxybenzyl)-substituted ergothioneine, and one new bis(p-hydroxybenzyl)-substituted 9,9′-neolignan with a novel carbon skeleton [38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Gastrodin Derivatives from Gastrodia elata

Chen

Nat. Prod. Bioprospect.

Wang

et al. 2019

Self Cite

Nine new gastrodin derivatives, including seven p-hydroxybenzyl-modified gastrodin ethers (1-7), 6′-O-acetylgastrodin (8), and 4-[α-d-glucopyranosyl-(1 →6)-β-d-glucopyranosyloxy]benzyl alcohol (9), together with seven known derivatives, were isolated from an aqueous extract of Gastrodia elata ("tian ma") rhizomes. Their structures were determined by spectroscopic and chemical methods as well as single crystal X-ray diffraction. Compounds 1-4, 7, 10, and 11 were also isolated from a reaction mixture by refluxing gastrodin and p-hydroxybenzyl alcohol in H 2 O. As both gastrodin and p-hydroxybenzyl alcohol exist in the plant, the reaction results provide evidence for the production and increase/decrease of potential effective/toxic components when "tian ma" is decocted solely or together with ingredients in Chinese traditional medicine formulations, though the isolates were inactive in the preliminarily cell-based assays at concentrations of 10 μM. Moreover, using ultraperformance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS), 4, 7, 10, and 11, as well as component variations, were detectable in the freshly prepared extracts of different types of samples, including the freeze-dried fresh G. elata rhizomes.