In recent years, caffeic acid and its derivatives have received increasing attention due to their obvious physiological activities and wide distribution in nature. In this paper, to clarify the status of research on plant-derived caffeic acid and its derivatives, nuclear magnetic resonance spectroscopy data and possible biosynthetic pathways of these compounds were collected from scientific databases (SciFinder, PubMed and China Knowledge). According to different types of substituents, 17 caffeic acid and its derivatives can be divided into the following classes: caffeoyl ester derivatives, caffeyltartaric acid, caffeic acid amide derivatives, caffeoyl shikimic acid, caffeoyl quinic acid, caffeoyl danshens and caffeoyl glycoside. Generalization of their ¹³C-NMR and ¹H-NMR data revealed that acylation with caffeic acid to form esters involves acylation shifts, which increase the chemical shift values of the corresponding carbons and decrease the chemical shift values of the corresponding carbons of caffeoyl. Once the hydroxyl group is ester, the hydrogen signal connected to the same carbon shifts to the low field (1.1~1.6). The biosynthetic pathways were summarized, and it was found that caffeic acid and its derivatives are first synthesized in plants through the shikimic acid pathway, in which phenylalanine is deaminated to cinnamic acid and then transformed into caffeic acid and its derivatives. The purpose of this review is to provide a reference for further research on the rapid structural identification and biofabrication of caffeic acid and its derivatives.

Background: To promote herbal medicine depends largely on its quality. Chromatographic fingerprint is a frequent approach for quality assessment of herbs however with challenges on robust and reproducibility. To develop rapid, cheap and comprehensive measurements as complementary tools for herbal quality control are still urgently needed. Moreover, biological activities are essential for herbal quality, and should be taken into consideration with emphasized in quality control.Methods: In this research, HPLC fingerprint and delayed luminescence (DL, a rapid and systematic tool) were used to measure the rhubarb samples of multiple species. Statistics were explored to classify these rhubarb samples using data obtained from two analytic methods. In addition, DL properties were linked to specific chemical components which may reflect bioactivities of rhubarb using Spearman’s rank correlation. Moreover, mice model was used to evaluate the cathartic effect between rhubarb samples stratifying by two analytic methods.Results: We found that there was no significant difference of chemical fingerprints and DL signals among the different species of medicinal rhubarb. However, our results show a high similarity between HPLC fingerprint analysis and DL measurements in classification of these rhubarb samples into two sub-groups. In addition, the two sub-groups of rhubarb samples that may have different cathartic activities.Conclusion: This approach provides new leads for development of herbal quality assessment based on bioactivity. In conclusion, integrated assessment by measuring HPLC fingerprint and DL with emphasized on bioactivity may provide novel strategy for herbal quality control.

A novel series of biscoumarin (1–4) and dihydropyran (5–13) derivatives were synthesized via a one-pot multicomponent condensation reaction and evaluated for antibacterial and antitumor activity in vitro. The X-ray crystal structure analysis of four representative compounds, 3, 7, 9 and 11, confirmed the structures of these compounds. Compounds 1–4 showed the most potent antitumor activity among the total 13 derivatives; especially for compounds 1 and 2, they also emerged as promising antibacterial members with better antibacterial activity. In addition, the results of density functional theory (DFT) showed that compared with compounds 3 and 4, biscoumarins 1 and 2 had lower intramolecular hydrogen bonds (HB) energy in their structures.