This paper reviews the chemistry, pharmacology and clinical properties of Echinacea species used medicinally. The Echinacea species Echinacea angustifolia, Echinacea pallida and Echinacea purpurea have a long history of medicinal use for a variety of conditions, particularly infections, and today echinacea products are among the best-selling herbal preparations in several developed countries. Modern interest in echinacea is focused on its immunomodulatory effects, particularly in the prevention and treatment of upper respiratory tract infections. The chemistry of Echinacea species is well documented, and several groups of constituents, including alkamides and caffeic acid derivatives, are considered important for activity. There are, however, differences in the constituent profile of the three species. Commercial echinacea samples and marketed echinacea products may contain one or more of the three species, and analysis of samples of raw material and products has shown that some do not meet recognized standards for pharmaceutical quality. Evidence from preclinical studies supports some of the traditional and modern uses for echinacea, particularly the reputed immunostimulant (or immunomodulatory) properties. Several, but not all, clinical trials of echinacea preparations have reported effects superior to those of placebo in the prevention and treatment of upper respiratory tract infections. However, evidence of efficacy is not definitive as studies have included different patient groups and tested various different preparations and dosage regimens of echinacea. On the basis of the available limited safety data, echinacea appears to be well tolerated. However, further investigation and surveillance are required to establish the safety profiles of different echinacea preparations. Safety issues include the possibility of allergic reactions, the use of echinacea by patients with autoimmune diseases and the potential for echinacea preparations to interact with conventional medicines.

Echinacea species (Echinacea angustifolia (DC.) hell., Echinacea pallida (nutt.) nutt., Echinacea purpurea (L.) Moench) : a review of their chemistry, pharmacology and clinical properties

https://pubs.rsc.org/en/content/articlepdf/2013/np/c3np20106f

Natural product isolation – how to get from biological material to pure compounds

https://www.ars.usda.gov/ARSUserFiles/37108/PDF/2009/2009FoodChem115_650_656.pdf

Chicoric acid found in basil (Ocimum basilicum L.) leaves

Fresh aerial parts of different chicory varieties: green chicory (c.v. "Catalogna"), two red chicory varieties ("radicchio rosso di Chioggia" and "radicchio rosso di Treviso"), and Witloof or Belgian endive were analyzed by HPLC/DAD/MS. The chromatographic fingerprint was diagnostic for each variety. A monocaffeoyl tartaric acid, chlorogenic acid, and chicoric acid were detected in all the varieties, while cyanidin 3-O-glucoside, delphinidin 3-O-(6'' malonyl) glucoside, and cyanidin 3-O-(6'' malonyl) glucoside were the main phenolic compounds in the red varieties. The flavonoidic compounds, quercetin 3-O-glucuronide and luteolin 7-O-glucuronide, were absent in the Witloof sample. The phenolic compounds from total leaves were the same as those obtained from only the colored parts; nevertheless, the total amount was remarkably lower with a decrease of up to 80% for Belgian endive. Chemical stability at high temperature was observed for the phenolic fraction from the green variety after decoction at 100 degrees C for 30 min.

Evaluation of the Phenolic Content in the Aerial Parts of Different Varieties of Cichorium intybus L.

Quantitative phytochemical variation was determined from roots and inflorescences of native plant populations in the genus Echinacea. Specimens were collected in situ throughout the natural range of each putative taxon and transplanted to greenhouse cultivation. Ethanolic extracts from individual plants were separated by reversed-phase HPLC to quantify the alkamides, polyenes/ynes, and phenolics, and then grouped by age and taxonomically, according to a recent morphometric taxonomic revision of the genus. Canonical discriminant analysis revealed that cichoric acid, the diene alkamides 1−3 and 7, and ketoalkene 24 were the best taxonomic markers. Mean content for each of 26 phytochemicals revealed useful agronomic information, such as those varieties and organs with the highest accumulations, as well as the optimal age and growth conditions for each variety. The highest amounts of cichoric acid were measured from the older, wild inflorescences of E. pallida var. sanguinea, whereas the highest quantities of...

Phytochemical Variation in Echinacea from Roots and Flowerheads of Wild and Cultivated Populations

Cichoric acid (2R,3R-O-dicaffeoyltartaric acid) (1) is highly susceptible to enzymatic degradation during the preparation of Echinacea purpurea products. Degradation of 1 and other caffeic acid derivatives can be inhibited by antioxidants added to the extraction solvent or in buffered protein extracts saturated with nitrogen. Inhibitor studies conducted with protein extracts prepared from dried overground parts of E. purpurea revealed that polyphenol oxidases (PPO) but not peroxidases are responsible for the oxidative degradation of exogenous and endogenous caffeic acid derivatives. With a view to stabilizing aqueous extracts with respect to their content of 1, the effects of ascorbic acid and ethanol were tested. Compound 1 was not stable under conditions where oxidative processes could almost be excluded. It was found that an esterase hydrolyzing the ester bonds between tartaric acid and caffeic acid is still active under PPO inhibitory conditions. Finally, addition of 40% ethanol and 50 mM ascorbic acid to aqueous extracts of "Echinaceae purpureae herba" resulted in a constant amount of cichoric acid over four weeks.

Birgit Nüsslein

Papers

Enzymatic degradation of cichoric acid in Echinacea purpurea preparations.