The ether extract of small everlasting (Antennaria microphylla Rydb.) was phytotoxic to lettuce seed root growth and leafy spurge (Euphorbia esula L. # EPHES) root elongation and cell culture growth. Three phenolic compounds (hydroquinone, arbutin, and caffeic acid) were chromatographically isolated and characterized from the ether extract. Arbutin and caffeic acid were moderately phytotoxic to leafy spurge root growth at 300 ppm (w/v), and hydroquinone was strongly phytotoxic to leafy spurge root growth at 50 ppm (w/v). The observed phytotoxicity of hydroquinone and the high-yield natural occurrence of arbutin, a water soluble, easily hydrolyzed monoglucoside of hydroquinone, in small everlasting is consistent with the participation of these two compounds in the observed allelopathy of small everlasting against leafy spurge.

Lutein is assumed to protect the human retina from blue light and oxidative stress and diminish the incidence of age-related macular degeneration. This antioxidant is commonly ingested with other dietary antioxidants. The aim of the present study was to assess whether the main dietary antioxidants, i.e. carotenoids, polyphenols and vitamins C and E, affect lutein absorption. We measured the effect of adding a mixture of antioxidants (500 mg vitamin C, 67 mg (100 IU) vitamin E and 1 g polyphenols) to a lutein-containing meal (18 mg) on the postprandial lutein response in the chylomicron-rich fraction in eight healthy men. Lutein response was weakest ( − 23 %; P = 0·07) after ingestion of the meal containing antioxidants (21·9 (sem 4·6) v. 28·4 (sem 7·2) nmol × h/l). To assess the effect of each class of antioxidants and potential interactions, we subsequently evaluated the effect of various combinations of antioxidants on lutein uptake by human intestinal Caco-2 TC-7 cells. A full factorial design showed that both a mixture of polyphenols (gallic acid, caffeic acid, (+)-catechin and naringenin) and a mixture of carotenoids (lycopene plus β-carotene) significantly (P < 0·05) impaired lutein uptake by ( − 10 to − 30 %), while vitamins C and E had no significant effect. Subsequent experiments showed that the aglycone flavanone naringenin was the only polyphenol responsible for the effect of the polyphenol mixture, and that the carotenoid effect was not carotenoid species-dependent. Taken together, the present results suggest that lutein absorption is not markedly affected by physiological concentrations of vitamins C and E but can be impaired by carotenoids and naringenin.

The absorption and metabolism in the small intestine of chlorogenic acid (5-0-caffeoylquinic acid), the main phenolic acid in the human diet, and of caffeic acid were studied in rats in order to determine whether chlorogenic acid is directly absorbed or hydrolysed in the small intestine. Chlorogenic and caffeic acids were perfused into a segment of ileum plus jejunum during 45;min (50;μm, 0·75sp;ml/min) using an in situ intestinal perfusion rat model with cannulation of the biliary duct, and were quantified together with their metabolites in perfusion effluent, bile and plasma. The net absorption (influent flux minus effluent flux of phenolic acids and their metabolites) accounted for 19·5% and 8% of the perfused caffeic and chlorogenic acids, respectively. A minor fraction of the perfused caffeic acid was metabolized in the intestinal wall and secreted back into the gut lumen in the form of ferulic acid (0·5% of the perfused flux). Part of the chlorogenic acid (1·2% of the perfused flux) was recovered in the gut effluent as caffeic acid, showing the presence of trace esterase activity in the gut mucosa. No chlorogenic acid was detected in either plasma or bile, and only low amounts of phenolic acids (less than 0·4%) were secreted in the bile. The present results show that chlorogenic acid is absorbed and hydrolysed in the small intestine. In contrast to numerous flavonoids, absorbed phenolic acids are poorly excreted in the bile or gut lumen. Their bioavailability therefore appears to be governed largely by their uptake into the gut mucosa.

The effect on the larval development of Helicoverpa armigera of caffeoylquinic acids and their structural units, caffeic acid and quinic acid, was evaluated. 5-Caffeoylquinic acid (5CQA) (syn. chlorogenic acid) significantly retarded larval development and increased the number of days to pupation at a concentration of 9 mM in an artificial diet, although final pupal weights were not severely affected. Caffeic acid and quinic acid also inhibited larval development although their effect was less marked. In all cases the effect of the compounds was dose-dependent. A mixture containing 5CQA, 3-caffeoylquinic acid (3CQA) and the novel compound, 1-caffeoyl-4-deosyquinic acid (ICdQA), which were extracted from the wild groundnut species, Arachis paraguariensis (Chod et Hassl.) was also evaluated at a concentration equivalent to that found in the plant (9 mM). This mixture was a potent inhibitor of larval development and more potent than 5CQA alone at the same concentration. The potential role of these substances in host plant resistance of groundnuts and their interaction with other components of pest management strategies are discussed.