A chemosystematic study of the phenolics of Sonchus

Thirty-three Sonchus, one Embergeria, one Babcockia and five Taeckholmia species were surveyed for their phenolic constituents. The coumarins scopoletin and aesculetin were found as major constituents of Embergeria, Babcockia and Taeckholmia species, and in lesser amount in some Sonchus species. Six flavone glycosides were identified: apigenin 7-glucuronide, apigenin 7-rutinoside, luteolin 7-glucoside, luteolin 7-glucuronide, luteolin 7-rutinoside and luteolin 7-glucosylglucuronide and the systematic significance of their distribution is discussed.     

A chemosystematic investigation on Ipomopsis

The diminutive North American desert annual species of Ipomopsis, Section Microgilia, I. depressa and I. polycladon, agree with other members of the genus in having a flavonoid syndrome based upon 6-methoxyflavonols. Patuletin is the predominant aglycone present but traces of eupatolitin and eupalitin were detected. In I. polycladon, four glycosides of patuletin and one of eupalitin were isolated and identified.     

Flavone glycosides of some Launaea species

Eight flavone glycosides were isolated from Launaea nudicaulis and identified as apigenin 7-glucoside and 7-gentiobioside, luteolin 7-glucoside, 7-     

Floral anthocyanins of some malesian Hibiscus species

In 14 Malesian species of Hibiscus (sensu lato) the most common floral anthocyanin was cyanidin 3-sambubioside. Cyanidin 3-glucoside was found     

A chemosystematic study of Veronica: Iridoid glucosides

Caffeoyl-catalpol, isoferuloyl-catalpol, protocatechuoyl-catalpol, benzoyl-catalpol, p-hydroxybenzoyl catalpol (catalposide), vanilloyl-catalpol and cinnamoyl-aucubin have been isolated from several Veronica species (Scrophulariaceae) in a more or less pure state. The first four compounds have never been recorded in plants before. A PC survey of forty-three species of the genus sensu lato has shown a general presence of aucubin and catalpol. They are accompanied in many of the species by a complex mixture of esters, especially esters of catalpol with aromatic acids. In only one species have aucubin esters been found. Loganin has been identified in five species, this being the first time that this compound has been found in the Scrophulariaceae. Loganin is accompanied by unidentified loganin esters in the same five species. From the systematic point of view the complex mixtures of esters of catalpol in Veronica seem to be noteworthy. Species of Globularia, Erinus, Scrophularia Verbascum, Wulfenia, Catalpa and Plantago investigated either totally lacked ester glucosides in leaves or contained mainly different types of esters. The possible systematic meaning of these results is briefly discussed.     

A chemosystematic survey of the fern genus Bommeria

A phytochemical survey of the species of Bommeria showed that foliage of the members of this genus contains a variety of flavonol and flavone glycosides. The distributions of chemical and morphological characters in Bommeria correlated to circumscribe infrageneric affinities: B. hispida and B. subpalaecea comprise one evolutionary line, while B. pedata and B. ehrenbergiana form a second. Flavonoid data may also be applied in concert with spore morphology in defining intergeneric species groups within Bommeria and Hemionitis.     

Flavonoids in Parahebe and Veronica: a chemosystematic study

Flavone glycosides are the main flavonoid leaf constituents in the related genera Parahebe and Veronica (Scrophulariaceae), in agreement with former chemical studies of the family. In Parahebe there are groups of species in which there are mainly luteolin glycosides, and groups in which 6-hydroxyluteolin dominates. Small amounts of apigenin occur in many taxa. Glycosylation is usually in the 7-position but 4′- and 5-glycosides were also found. In Veronica a larger variety of flavone aglycones was found: e.g. luteolin, apigenin, chrysoeriol, tricin and three different 6-hydroxyflavones. They are often present in the plants in the form of glucuronides. Glycosylation is in the 7-or-5-position. Most species of both genera have a distinctive pattern of flavonoid glycosides in their leaves which can be used for identification. Populations of P. catarractae are an exception in showing three different patterns, but here the variety in flavone profiles corresponds to the pattern of morphological and geographic variation within this taxon. Anthocyanins are responsible for the blue, mauve and pink colours of the flowers in the two genera. In Veronica they are based on delphinidin, whereas in Parahebe catarractae on both delphinidin and cyanidin.     

Prasinoxanthin—a chemosystematic marker for algae

A new coccoid marine alga (clone Ω 48-23) contained chlorophylls a and b and carotenoids consisting of β,β-carotene (3% of total), β,ε-carotene (1%), zeaxanthin (2%), neoxanthin (21%), two minor unknowns (2 + 2%) and prasinoxanthin (69%). Prasinoxanthin is identical with xanthophyll K, previously considered characteristic of prasinophytes. From spectroscopic and chemical evidence prasinoxanthin is assigned the structure (3′R,-6′R)-3,6,3′ trihydroxy-7,8-dihydro-γ,ε-caroten-8-one, with tentative 3R,6R chirality from biogenetic considerations, thus representing the first algal carotenoid with a γ-end group. The structural relationship between prasinoxanthin and siphonaxanthin (ex Prasinophyceae and Siphonales) is discussed in chemosystematic terms.     

High pressure liquid chromatographic analysis of flavonoid chemical markers in petals from Gerbera flowers as an adjunct for cultivar and germplasm identification

Flavonoids present in petals from Gerbera flowers were resolved and quantitated by high pressure liquid chromatography (HPLC). The anthocyanins isolated from 18 cultivars, ranging in color from orange through lavender, were pelargonidin and cyanidin 3-malonylglucosides accompanied by smaller amounts of pelargonidin and cyanidin 3-glucosides. Related flavonoid copigments were apigenin and luteolin 4′-glucosides and 7-glucosides, apigenin 7-malonylglucoside, kaempferol and quercetin 3-glucosides, 4′-glucosides and 3-malonylglucosides. Both qualitative and quantitative differences in these flavonoid chemical markers distinguished cultivars with very similar colors. Malonyl esters of anthocyanins are easily degraded by HCl and conventional extraction and purification procedures were adjusted to preserve their natural state.     

Flavonoid glycosides of Tribulus pentandrus and T. Terrestris

Twenty-five flavonoid glycosides were detected in Tribulus pentandrus and T. terrestris. The glycosides belong to the common flavonols, kaempferol, quercetin and isorhamnetin, with the 3-gentiobiosides as the major glycosides. Traces of a flavone (tricin) glycoside was also present in T. pentandrus. The separation of Tribulaceae as a distinct family from Zygophyllaceae is discussed.     

The effect of water stress on the life cycles of Erodium crinitum Carolin and Erodium cicutarium (L.) L'Hérit. ex Alton (Geraniaceae)

Abstract Erodium cicutarium (L.) L'Hérit. ex Aiton (Geraniaceae) from temperate Mediterranean Eurasia is naturalized across large areas of arid and semi-arid Australia to which Erodium crinitum Carolin is native. plant size, leaf and bud numbers and fruit/plant biomass ratio were significantly lower under drought, flower and fruit number, fruit size and total mass were unaffected. In contrast, E. crinitum was largely unaffected by the drought conditions, showing only an increase in the fruit/plant biomass ratio.     

Phenolic glycosides from Solanum glaucophyllum: A new quercetin triglycoside containing D- apiose

Eight phenolic glycosides have been isolated from the leaves of S. glaucophyllum, one of them being quercetin-3-O-(2^G-β-D-apiosylrutinoside).     

Flavonoid glycosides and the chemosystematics of Eucalyptus camaldulensisis

Leaf flavonoid glycosides of Eucalyptus camaldulensis were identified as kaempferol 3-glucoside and 3-glucuronide; quercetin 3-glucoside, 3-glucuronide, 3-rhamnoside, 3-rutinoside and 7-glucoside, apigenin 7-glucuronide and luteolin 7-glucoside and 7-glucuronide. Two chemical races were observed based on the flavonoid glycosides. These races correspond to the northern and southern populations of species growing in Australia. The Middle Eastern species examined were found to belong to the southern Australian chemical race. The major glycosides of E. occidentalis proved to be quercetin and myricetin 3-glucuronide.     

A comparative study of the flavonoids of Medicago radiata with other Medicago and related Trigonella species

The flavonoid glycosides of Medicago radiata as well as M. arabica, M. polymorpha, M. sativa, Trigonella coerulescens, T. foenum-graecum and T. spicata were studied in detail. Major glycosides identified were the 7-glucuronides of apigenin, luteolin, chrysoeriol and tricin, as well as lesser amounts of di- and triglucuronides of chrysoeriol and tricin. Also identified were the 3-robinobioside and 3,7-diglucoside of kaempferol, along with lesser amounts of quercetin-3,7-diglucoside, 4′,7-dihydroxyflavone, 3′,4′,7-trihydroxyflavone, formononetin and daidzein. Twelve other Medicago and Trigonella species were also studied for their flavonoid aglycones. The systematic position of M. radiata is discussed.     

Flavonoids of three local Senecio species

Two isorhamnetin glycosides and two sulphated derivatives are reported for the first time in the genus Senecio.     

Occurrence of 1,5-dimethylcyclodeca-1,5,7-triene (Pregeijerene) in Pimpinella species and chemosystematic implications

The essential oils from fresh roots of 66 species, representing 39 general of the Apiaceae (Umbelliferae), subfamily Apioideae, were surveyed for pregeijerene. Of all plants examined, only the 11 species of the genus Pimpinella were shown to contain pregeijerene. According to its extremely restricted occurrence in the Apiaceae, its possible taxonomic value with regard to the definition of the genus Pimpinella is discussed.     

First Extensive Polyphenolic Profile of Erodium cicutarium with Novel Insights to Elemental Composition and Antioxidant Activity

Erodium cicutarium is known for its total polyphenolic content, but this work reveals the first highly detailed profile of E. cicutarium, obtained with UHPLC‐LTQ OrbiTrap MS⁴ and UHPLC‐QqQ‐MS/MS techniques. A total of 85 phenolic compounds were identified and 17 constituents were quantified. Overall, 25 new compounds were found, which have not yet been reported for the Erodium genera, or the family Geraniaceae. Along with methanolic extracts, the so far poorly investigated water extracts exhibited in vitro antioxidant activity according to all performed assays, including the ferric reducing/antioxidant power assay (FRAP), 2,2‐diphenyl‐1‐picrylhydrazyl assay (DPPH), 2,2′‐azinobis(3‐ethylbenzthiazoline‐6‐sulfonic acid) assay (ABTS) and cupric ion reducing antioxidant capacity assay (CUPRAC). Elemental composition analysis performed with inductively coupled plasma atomic emission spectrometry (ICP‐AES) and, additionally, hydride generation atomic absorption spectrometry (HydrEA‐ETAAS) showed six most abundant elements to be decreasing as follows: Mg>Ca>K>S>P>Na, and gave first data regarding inorganic arsenic content (109.3–248.4 ng g^?1). These results suggest E. cicutarium to be a valuable source of various phenolic compounds with substantial potential for further bioactivity testing.     

The distribution of geraniin and mallotusinic acid in the order geraniales

The distribution of geraniin and mallotusinic acid in Geraniaceae, Euphorbiaceae and other families in the Geraniales were investigated by HPLC. Geraniin composes the main part of the tannin in all of the investigated species of Geranium, but not in species of Pelargonium. The species of Geraniaceae lack mallotusinic acid. Geraniin was also detected in most of the species in the subfamily Euphorbioideae of Euphorbiaceae, although the amount was generally smaller than in Geranium, except for some woody species. Several species of Euphorbioideae contained mallotusinic acid. Characteristic of the subfamily Phyllanthoideae is the absence of mallotusinic acid and poor distribution of geraniin. Geraniin and mallotusinic acid were not detected in most of the species of other families in the Geraniales, except in Erythroxylum coca. Hyperin was found to be the main flavonol glycoside in most species of Geranium.     

La variation flavonique chez les sous-especes de l'Anthyllis vulneraria

Nine infraspecific taxa of Anthyllis vulneraria have been investigated for leaf flavonoids. The distribution of 35 flavonol glycosides within 26 populations, indicated the presence of four chemical taxa, each based on different glycosides of 7-methylkaempferol.     

Negatively charged flavones and tricin as chemosystematic markers in the palmae

A survey of 125 species of the Palmae revealed a complex pattern of flavonoids in the leaf. C-Glycosylflavones, leucoanthocyanins and tricin, luteolin and quercetin glycosides were common, being present in 84, 66, 51, 30 and 24% of the species respectively. Apigenin and kaempferol were recorded in only a few species and isorhamnetin only once. Eighteen flavonoids were identified: the 7-glucoside, 7-diglucoside and 7-rutinoside of both luteolin and tricin, tricin 5-glucoside, apigenin 7-rutinoside, quercetin 3-rutinoside-7-galactoside, isorhamnetin 7-rutinoside, orientin, iso-orientin, vitexin, isovitexin and vitexin 7-O-glucoside. Many of the C- and O-flavonoid glycosides were present as the potassium bisulphate salts and negatively charged compounds were detected in 50% of the species. The distribution patterns are correlated with the taxonomy of the family in several ways. Thus, the Phoenicoideae and Caryotoideae have distinctive flavonoid patterns, there is evidence to support the separation of the subfamilies Phytelephantoideae and Nypoideae, and tricin is a useful marker at tribal level. At the generic level, Cocos is clearly separated from Butia, and other Cocoseae and Mascarena and Chamaedorea form well defined groups within the Arecoideae. A numerical analysis of these biochemical data, together with morphological characters, produces a new classification which suggests that the flavonoid data may have more systematic value than is indicated when they are applied to the traditional classification.