Cichoriin

Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities.[Pubmed:31906487]

Biomolecules. 2020 Jan 2;10(1). pii: biom10010074.

The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin (1), fraxetin (2), esculetin (3), Cichoriin (4), euphorbetin (5), kaempferol-3-O-beta-rutinoside (6), oleuropein (7), linoleic acid (8), methyl linoleate (9), and beta-sitosterol (10). Structures of the isolated constituents were characterized by (1)H NMR, (13)C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC50 values of 0.31 +/- 0.01 mmol/L, 10.50 +/- 0.02 mmol/L, and 0.40 +/- 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC50 values of 0.74 +/- 0.01 mmol/L, 1.78 +/- 0.01 mmol/L and 1.41 +/- 0.00 mmol/L. Herbicidal activity tests showed that compounds 8-10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC50 values of 1.16 +/- 0.23 mmol/L, 1.28 +/- 0.58 mmol/L and 1.33 +/- 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC50 values of 1.56 +/- 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria (Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum).

Inhibitory activity of Podospermum canum and its active components on collagenase, elastase and hyaluronidase enzymes.[Pubmed:31614286]

Bioorg Chem. 2019 Dec;93:103330.

Present study is aimed to investigate in vitro inhibitory effects of the extract prepared from the aerial parts of Podospermum canum (syn: Scorzonera cana var. jacquiniana) (Asteraceae) on hyaluronidase, collagenase, and elastase enzymes using a bioassay-guided fractionation. Inhibitory effects of the extract, sub-extracts, fractions obtained by column chromatography, and isolated compounds on collagenase, elastase, and hyaluronidase were performed by using in vitro enzyme inhibitory assays based on spectrophotometric evaluation. The methanolic extract obtained from P. canum exhibited strong inhibitory activities on elastase and collagenase while the insignificant activity was observed on hyaluronidase. Through bioactivity-guided fractionation, the ethyl acetate and remaining water sub-extracts obtained from the methanolic extract displayed significant inhibitory activities on collagenase and elastase, while petroleum ether and chloroform extracts did not show any inhibitory activity. Eleven known compounds: arbutin, 6-O-caffeoylarbutin, Cichoriin, 3,5-dicaffeoylquinic acid methyl ester, apigenin 7-O-beta-glucoside, luteolin 7-O-beta-glucoside, apigenin 7-O-beta-rutinoside, isoorientin, orientin, vitexin, procatechuic acid, and new compound 4-hydroxy-benzoic acid 4-(6-O-alpha-rhamnopyranosyl-beta-glucopyranosyl) benzyl ester have been obtained from ethyl acetate sub-extract. Results of the present study have revealed that apigenin 7-O-beta-glucoside, luteolin 7-O-beta-glucoside, apigenin 7-O-beta-rutinoside, and isoorientin showed potent enzyme inhibitory activities. However, methanolic extract of P. canum displayed a greater inhibitory activity than fractions and isolated compounds both on collagenase and elastase.

Phytochemical Investigations on Chemical Constituents of Taraxacum bessarabicum (Hornem.) Hand.-Mazz. subsp. bessarabicum (Hornem.) Hand.-Mazz.[Pubmed:31089374]

Iran J Pharm Res. 2019 Winter;18(1):400-405.

Plants of the genus Taraxacum Wigg., have long been used as medicinal herbs. A phytochemical investigation of the aerial parts of Taraxacum bessarabicum (Hornem.) Hand.-Mazz. subsp. bessarabicum (Hornem.) Hand.-Mazz. (Asteraceae) yielded two coumarins [esculetin (1), Cichoriin (2)], three flavonoids [ luteolin (3), luteolin 7-O-beta-D-glucoside (4), gossypetin (5)] and six phenolic acids and their derivatives [ p-coumaric acid (6), caffeic acid (7), ferulic acid (8), chlorogenic acid methyl ester (9), 3,5-di-O-caffeoylquinic acid (10), 3,5-di-O-caffeoylquinic acid methyl ester (11)]. Their structures were established conclusively by UV, ESI-MS, 1-D and 2-D NMR spectra analyses and comparison with literature data. The presence of these compounds has been shown for the first time from this species. This is the first report of the isolation of compound 5 from the genus Taraxacum.

Ethnobotany of the genus Taraxacum-Phytochemicals and antimicrobial activity.[Pubmed:30039597]

Phytother Res. 2018 Nov;32(11):2131-2145.

Plants belonging to the genus Taraxacum have been used in traditional healthcare to treat infectious diseases including food-borne infections. This review aims to summarize the available information on Taraxacum spp., focusing on plant cultivation, ethnomedicinal uses, bioactive phytochemicals, and antimicrobial properties. Phytochemicals present in Taraxacum spp. include sesquiterpene lactones, such as taraxacin, mongolicumin B, and taraxinic acid derivatives; triterpenoids, such as taraxasterol, taraxerol, and officinatrione; and phenolic derivatives, such as hydroxycinnamic acids (chlorogenic, chicoric, and caffeoyltartaric acids), coumarins (aesculin and Cichoriin), lignans (mongolicumin A), and taraxacosides. Aqueous and organic extracts of different plant parts exhibit promising in vitro antimicrobial activity relevant for controlling fungi and Gram-positive and Gram-negative bacteria. Therefore, this genus represents a potential source of bioactive phytochemicals with broad-spectrum antimicrobial activity. However, so far, preclinical evidence for these activities has not been fully substantiated by clinical studies. Indeed, clinical evidence for the activity of Taraxacum bioactive compounds is still scant, at least for infectious diseases, and there is limited information on oral bioavailability, pharmacological activities, and safety of Taraxacum products in humans, though their traditional uses would suggest that these plants are safe.

Isolation of major phenolics from Launaea spinosa and their protective effect on HepG2 cells damaged with t-BHP.[Pubmed:26052623]

Pharm Biol. 2016;54(3):536-41.

CONTEXT: Some Launaea species (Asteraceae) are used traditionally to treat liver oxidative stress. OBJECTIVE: The present study investigates the protective effects of isolated compounds from Launaea spinosa Sch. Bip. (Asteraceae) against oxidative stress on t-BHP-induced HepG2 cells. MATERIALS AND METHODS: Major phenolic content from flowering aerial parts of L. spinosa was isolated and identified. The protective effects of isolated compounds (10 and 20 muM) against oxidative stress induced by tert-butyl hydroperoxide (t-BHP) in HepG2 cells were investigated through the measurement of aspartate aminotransferase (AST), alanine transaminase (ALT), and superoxide dismutase (SOD) levels. RESULTS: A new phenolic compound identified as 2,3-diferulyl R,R-(+) methyl tartrate (6), in addition to five known metabolites, esculetin (1), esculetin-7-O-d-glucoside (Cichoriin) (2), fertaric acid (3), acacetin-7-O-d-glucoside (4), and acacetin-7-O-d-glucuronic acid (5), were isolated. Oxidant-induced damage by 200 muM t-BHP in HepG2 cells was inhibited by compounds 1, 4, and 5 (10 and 20 muM), or quercetin (10 muM; positive control). The protective effects of compounds 1, 4, and 5 were associated with decreasing in AST, ALT, and SOD levels. Compound 4 (20 muM) decreased the AST level from 128.5 +/- 13.9 to 7.9 +/-1.8 U/mL. Meanwhile, compound 1 (20 muM) decreased ALT activity from 20.3 +/- 7.0 to 7.6 +/- 2.4 U/mL, while compound 5 decreased SOD levels from 41.6 +/- 9.0 to 28.3 +/- 3.4 mU/mg. CONCLUSION: The major phenolic compounds isolated from L. spinosa displayed a significant cytoprotective effect against oxidative stress, leading to maintenance of the normal redox status of the cell.

Introducing Cichorium Pumilum as a potential therapeutical agent against drug-induced benign breast tumor in rats.[Pubmed:22812448]

Electromagn Biol Med. 2012 Dec;31(4):299-309.

Cichorium Pumilum (chicory) is could be a promising cancer treatment in which a photosensitizing drug concentrates in benign tumor cells and activated by quanta at certain wavelength. Such activated extracts could lead to cell death and tumor ablation. Previous studies have shown that Cichorium Pumilum (chicory) contains photosensitive compounds such as Cichoriin, anthocyanins, lactucin, and Lactucopicrin. In the present study, the protective effect of sun light-activated Cichorium against the dimethylbenz[a]anthracene (DMBA) induced benign breast tumors to female Sprague-Dawley rats was investigated. Chicory's extract has significantly increase P.carbonyl (PC) and malondialdehyde (MDA) and decreases the hepatic levels of total antioxidant capacity (TAC) and superoxide dismutase (SOD) in benign breast tumors-induced group compared to control. It also significantly decrease the number of estrogen receptors ER-positive cells in tumor masses. These results suggest that chicory extracts could be used as herbal photosensitizing agent in treating benign breast tumor in rats.

Furofuran lignans from a callus culture of Cichorium intybus.[Pubmed:15809887]

Plant Cell Rep. 2005 Jun;24(4):246-9.

Three new and one known furofuran lignans--syringaresinol derivatives--along with the known phenylpropanoids Cichoriin and syringin were isolated from a callus tissue of Cichorium intybus. The compounds were characterised by spectral methods. This is the first report on the presence of furofuran lignans in Cichorium species.

A new coumarin glucoside ester from Cichorium intybus.[Pubmed:12385886]

Fitoterapia. 2002 Oct;73(6):544-6.

Cichoriin-6'-p-hydroxyphenyl acetate, a new natural product, was isolated from chicory leaves.

Glycosidic fraction of flue-cured tobacco leaves: its separation and component analysis.[Pubmed:10803957]

Biosci Biotechnol Biochem. 2000 Mar;64(3):584-7.

The fraction containing glycosidic components was separated from flue-cured tobacco (Nicotiana tabacum L.) leaves by a facile method. Some components of the fraction were isolated and elucidated to be syringin, coniferin, Cichoriin, benzyl-beta-D-glucoside, Blumenol A-beta-D-glucoside, and 5,6-epoxy-5,6-dihydro-3-hydroxy-beta-ionyl-beta-D-glucoside. Syringin and coniferin were detected in the Nicotiana species for the first time.

Flavonoids, cinnamic acids and coumarins from the different tissues and medicinal preparations of Taraxacum officinale.[Pubmed:8728061]

Phytochemistry. 1996 May;42(1):121-7.

Three flavonoid glycosides: luteolin 7-glucoside and two luteolin 7-diglucosides were isolated from dandelion flowers and leaves together with free luteolin and chrysoeriol in the flower tissue. The hydroxycinnamic acids, chicoric acid, monocaffeyltartaric acid and chlorogenic acid were found throughout the plant and the coumarins, Cichoriin and aesculin were identified in the leaf extracts. This represents the first report of free chrysoeriol (luteolin 3'-methyl ether) in Taraxacum officinale agg. An earlier provisional identification of chicoric acid, chlorogenic acid, Cichoriin and aesculin in a phenolic survey of the tribe Cichorieae is confirmed. Chicoric acid and the related monocaffeyltartaric acid were found to be the major phenolic constituents in flowers, roots, leaves and involucral bracts and also in the medicinal preparations tested.