Chemical constituents from Glehnia littoralis and their chemotaxonomic significance

Abstract

Phytochemical investigation of the roots of Glehnia littoralis Fr. Schmidt. ex Miq. led to the isolation of 16 known compounds, including three β-carboline alkaloids (1-3), four phenylpropanoids (4-7), five phenolic acids (8-12), three polyacetylenes (13-15) and one fatty acid ( 16). The structures of these compounds were elucidated on the basis of spectral analysis and comparison with those reported in literatures. To the best of knowledge, the report of the first β-carboline alkaloid in the Umbelliferae family. Additionally, compounds 1-5, 9, 10 and 16 have not been reported from any species in Umbelliferae family, compounds 7, 8 and 12 were isolated from the genus Glehnia for the first time and could be of the chemotaxinomic significance and serve as valuable chemotaxonomic makers for G. littoralis. The chemotaxonomic significance of the isolated compounds was summarised.

Ethnopharmacology, Phytochemistry, and Pharmacology of the GenusGlehnia: A Systematic Review

“…e results showed that the total content of these three coumarins was the highest in fruit (0.6364 mg•g − 1 ), which was 8.24 times higher than that of roots and 42.15 times higher than that of leaves [75]. In another study, Xin et al (2009) compared the coumarin content in the roots of G. littoralis in four different harvesting periods (September 15, September 30, October Evidence-Based Complementary and Alternative Medicine 4 Evidence-Based Complementary and Alternative Medicine 6 Evidence-Based Complementary and Alternative Medicine Dried roots [19] (S)-Phenyllactic acid methyl ester (2) Dried roots [19] Caffeic acid 3Dried root, dried underground parts [38,39] Chlorogenic acid (4) Dried root, dried underground parts [38,39] Ferulic acid (5) Dried root, dried underground parts [38][39][40] 3-Methoxy-4-β-D-glucopyranosyloxypropiophenone (6) Dried underground parts, dried roots bark [39,41] 4…”

“…So far, ten phenylpropanoids, including six phenylpropionic acid (1-5, 10), three phenylpropanal (6)(7)(8), and one phenylpropanol (9) were isolated from G. littoralis. Furthermore, Zhang et al isolated and identified two simple phenyllactic acid compounds (S)-phenyllactic acid (1) and (S)-phenyllactic acid methyl ester (2) via spectral analysis of ethanol extract from the root of G. littoralis [19]. It is worth noting that these compounds were isolated from the plant for the second time when studying their taxonomic significance, suggesting that these compounds may be useful chemical taxonomic markers for G. littoralis.…”

“…More than 90% of coumarins contain either a hydroxyl or an ether group at C7 position [53,74]. To date, totally 67 coumarins have been isolated and identified from G. littoralis, of which seventeen are simple coumarins (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27), six are pyranocoumarins (28)(29)(30)(31)(32)(33), and forty-four are furanocoumarins . Among these coumarins, eight new coumarin glycosides, (S)-peucedanol 7 (59), and 5″-hydroxyimperatorin 5″-O-β-D-glucopyranoside (60), were isolated from the methanolic extract of the root and rhizome of G. littoralis by Kitajima et al [53].…”

“…Dried root, dried underground parts [39,42] 2-Methoxy-4-(1-propionyl) phenyl β-D-glucopyranoside (8) Fresh root and rhizome [43] Syringin 9Dried root, dried roots bark [41,44] Glehnilate 10Dried underground parts [45] Evidence-Based Complementary and Alternative Medicine Dried roots, dried roots and rhizomes [46][47][48] Esculetin (12) Dried root [49] Umbelliferone 7-O-β-D-glucopyranoside (13) Fresh fruit, dried root [38,50] Scopoletin 14Dried root and rhizome, dried root, dried underground parts [38, 39, 46-48, 51, 52] Scopolin (15) Dried root [38,49] Scopoletin-apiosylglucoside (16) Dried root [38] Osthenol 7-O-β-D-gentibioside (17) Fresh fruit [50] 6-(3,3-Dimethylallyl)-7-hydroxycoumarin (18) Dried root [38] 6-(3,3-Dimethylallyl)-7-hydroxycoumarin-apiosyl-glucoside (19) Dried root [38] 6-(3,3-Dimethylallyl)-7-hydroxycoumarindiglucoside (20) Dried root [38] 7-O-(3,3-Dimethylallyl) scopoletin (21) Dried root and rhizome [52] (S)-Peucedanol 7-O-β-D-glucopyranoside (22)…”

“…e systematic review on G. littoralis serves as a comprehensive overview of past and current studies of traditional practices and activities, and we found that all of during the last fifty years (from 1969 to 2019) available information on G. littoralis focuses on the botany, phytochemistry, pharmacological activities, clinical application, and cultivation of G. littoralis, while there are few research studies on the traditional uses and toxicity. ere are seven reviews in Chinese and one review in English on G. littoralis, of which the reviews in Chinese are mainly about its phytochemical and pharmacological research, and the review in English is only about the phytochemical research on G. littoralis [8,[15][16][17][18][19][20][21]. is review is currently the most advanced systematic review on the botany, traditional uses, ethnopharmacology, phytochemistry, pharmacological activities, and toxicity of Glehnia littoralis and provides an indepth analysis to explore its therapeutic potential for improving human health.…”