Polybenzyls from Gastrodia elata, their agonistic effects on melatonin receptors and structure-activity relationships

Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata

“…The HMBC spectrum of 10 exhibited the correlations (Fig. 2 18) [84], gastropolybenzylol A ( 19) [8], gastrol A ( 20) [85]. The structure of 11 was previously determined only by UPLC/Q-TOF MS analysis [81] and identified in this study by comprehensive analysis of the spectroscopic data including 2D NMR experiments (Fig.…”

“…To satisfy medicinal utilization and to protect the wildly endangered species and ecological environment, starting in the late 1950′s, tremendous efforts were made and succeeded in agricultural cultivation of this plant by Chinese scientists [3,4]. Meanwhile, considerable chemical and pharmacological studies of the raw material and the processed "tian ma" led to isolation and identification of around 100 constituents with diverse chemical structures and biological activities from extracts of this herbal medicine [2,[5][6][7][8]. Most the constituents feature characteristic structures deriving from or modified by p-hydroxybenzyl alcohol [2,[5][6][7][8].…”

“…Meanwhile, considerable chemical and pharmacological studies of the raw material and the processed "tian ma" led to isolation and identification of around 100 constituents with diverse chemical structures and biological activities from extracts of this herbal medicine [2,[5][6][7][8]. Most the constituents feature characteristic structures deriving from or modified by p-hydroxybenzyl alcohol [2,[5][6][7][8]. Notably, vanillyl alcohol and vanillin exhibited antiepileptic and anticonvulsant activities similar to that of the water extract of G. elata rhizomes, which promoted the clinic application of vanillin as an antiepileptic drug in China [9][10][11][12][13] 3 .…”

“…The occurrence of antiepileptic vanillin in "tian ma" was questioned until 2006 [48,49]. Meanwhile, new constituents from "tian ma" and their bioactivities were frequently discovered [2,[5][6][7][8].…”

“…Thus, there are important secrets of medicinal chemistry hiding behind processing and/or decocting protocols in TCM though these are yet to be confirmed in many cases including "tian ma" [50][51][52][53][54][55][56][57][58]. Because the previous phytochemical studies of "tian ma" were performed mostly by extracting the drug material with ethanol or methanol [2,[5][6][7][8], the extracting protocol completely differed from that of conventional application by decocting with water. Therefore, an aqueous extract of "tian ma" (the steamed and dried G. elata rhizomes [50][51][52][53][54][55][56][57][58]) was investigated as part of our project to investigate chemical diversity and biological activities of several commonly used TCM [59][60][61][62][63][64][65][66][67][68][69][70].…”