Hydrolyzable Tannins, Flavonol Glycosides, and Phenolic Acids Show Seasonal and Ontogenic Variation in Geranium sylvaticum

The seasonal variation of polyphenols in the aboveground organs and roots of Geranium sylvaticum in four populations was studied using UPLC-DAD-ESI-QqQ-MS/MS. The content of the main compound, geraniin, was highest (16% of dry weight) in the basal leaves after the flowering period but stayed rather constant throughout the growing season. Compound-specific mass spectrometric methods revealed the different seasonal patterns in minor polyphenols. Maximum contents of galloylglucoses and flavonol glycosides were detected in the small leaves in May, whereas the contents of further modified ellagitannins, such as ascorgeraniin and chebulagic acid, increased during the growing season. In flower organs, the polyphenol contents differed significantly between ontogenic phases so that maximum amounts were typically found in the bud phase, except in pistils the amount of gallotannins increased significantly in the fruit phase. These results can be used in evaluating the role of polyphenols in plant–herbivore interactions or in planning the best collection times of G. sylvaticum for compound isolation purposes

Appendix A. Relationship between leaf damage and total seed predator abundance.

Relationship between leaf damage and total seed predator abundance

Appendix C. Percentage of seeds consumed on induced vs. control plants by each seed predator.

Percentage of seeds consumed on induced vs. control plants by each seed predator

Analysis of Hydrolyzable Tannins and Other Phenolic Compounds in Emblic Leafflower (<i>Phyllanthus emblica</i> L.) Fruits by High Performance Liquid Chromatography–Electrospray Ionization Mass Spectrometry

Phenolic compounds were extracted from dried emblic leafflower (<i>Phyllanthus emblica</i> L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid glycosides, quercetin glycosides, and eriodictyol coumaroyl glycosides in the fruits. The study provides a systematic report of the retention data and characteristics of UV, MS, and MS/MS spectra of the phenolic compounds in the fruits of emblic leafflower. The fruits of two varieties (Ping Dan No 1 and Fruity) from Guangxi Province differed from those of wild Tian Chuan emblic leafflower from Fujian Province in the content and profile of phenolic compounds

Analysis of Hydrolyzable Tannins and Other Phenolic Compounds in Emblic Leafflower (<i>Phyllanthus emblica</i> L.) Fruits by High Performance Liquid Chromatography–Electrospray Ionization Mass Spectrometry

Phenolic compounds were extracted from dried emblic leafflower (<i>Phyllanthus emblica</i> L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid glycosides, quercetin glycosides, and eriodictyol coumaroyl glycosides in the fruits. The study provides a systematic report of the retention data and characteristics of UV, MS, and MS/MS spectra of the phenolic compounds in the fruits of emblic leafflower. The fruits of two varieties (Ping Dan No 1 and Fruity) from Guangxi Province differed from those of wild Tian Chuan emblic leafflower from Fujian Province in the content and profile of phenolic compounds

Mean (± S.E.) concentrations of five chemical compounds in the leaves of <i>Vincetoxicum hirundinaria</i> from three populations.

<p>All concentrations are presented as mg/g dry weight. Overall, the concentrations differ significantly among the populations (MANOVA, Pillai's trace F_10,48 = 2.84, <i>p</i> = 0.007). The <i>F</i>- and <i>p</i>- values represent the results of one-way ANOVAs for differences among the populations for each compound separately. The letters indicate significant difference (<i>p</i><0.05) in the amount of each chemical compound between plant populations.</p

Effects of chlorogenic acid content on pupal mass of <i>Abrostola asclepiadis</i> from three populations.

<p>Effects of chlorogenic acid content on pupal mass of <i>Abrostola asclepiadis</i> from three populations.</p

Appendix D. Correlations between leaf herbivory and leaf chemical compounds.

Correlations between leaf herbivory and leaf chemical compounds

Appendix C. Characteristics of the studied Vincetoxicum hirundinaria populations.

Characteristics of the studied Vincetoxicum hirundinaria populations

Mean (± S.E.) pupal mass of <i>Abrostola asclepiadis</i> in a reciprocal feeding trial.

<p>In a reciprocal feeding trial, <i>A. asclepiadis</i> larvae from three sites (Herbivore population) were grown on plants from the same three sites (Plant population). S denotes sympatric combinations of plant and herbivore populations. The asterisk and “ns” indicate statistical significance (<i>P</i><0.05 or <i>P</i>>0.05, respectively) of contrasts comparing pupal mass of herbivores feeding on sympatric host plants to that on allopatric host plants from the two other populations.</p