Flavonoids of Helichrysum chasmolycicum and its antioxidant and antimicrobial activities

From the aerial parts of Helichrysum chasmolycicum P.H Davis, which is an endemic species in Turkey, the flavonoids apigenin, luteolin, kaempferol, 3,5-dihydroxy-6,7,8-trimethoxyflavone, 3,5-dihydroxy-6,7,8,4′-tetramethoxyflavone, apigenin 7-O-glucoside, apigenin 4′-O-glucoside, luteolin 4′-O-glucoside, luteolin 4′,7-O-diglucoside, kaempferol 3-O-glucoside, kaempferol 7-O-glucoside and quercetin 3-O-glucoside were isolated. The methanol extract of the aerial parts of H. chasmolycicum showed antioxidant activity by DPPH method (IC₅₀ 0.92 mg/mL). Antimicrobial activity test was performed on the B, D, E extracts and also 3,5-dihydroxy-6,7,8-trimethoxyflavone and kaempferol 3-O-glucoside which were the major flavonoid compounds obtained from aerial parts of H. chasmolycicum by microbroth dilutions technique. The E (ethanol-ethyl acetate) extract showed moderate antimicrobial activity against Pseudomonas aeruginosa, B (petroleum ether-60% ethanol-chloroform) extract and 3,5-dihydroxy-6,7,8-trimethoxyflavone showed moderate antifungal activity against Candida albicans.     

Species-specific kaempferol derivatives in ferns of the appalachian Asplenium complex

A series of kaempferol derivatives have been identified in fronds of three parental species of the Appalachian Asplenium complex. Asplenium platyneuron is characterised by the presence of the 7-glucoside of kaempferol 3,4′-dimethyl ether and also contains kaempferol 3,7-diglucoside, free and with an aliphatic acyl attachment. By contrast, A. rhizophyllum contains a remarkable caffeoyl complex of kaempferol glycosides, which appears to be chromatographically homogenous. However, on deacylation, the complex yields caffeic acid and the 7-glucoside, 3,7-diglucoside, 3-sophoroside-7-glucoside and 7,4′-diglucoside of kaempferol. Asplenium montanum, in addition to having previously characterised glycosylxanthones, has two further kaempferol derivatives. It has been confirmed that these various species specific flavonoids are inherited in an additive fashion in three interspecific hybrids.     

Distribution of charged flavones and caffeylshikimic acid in Palmae

Identification of the phenolic constituents in flowers of nine palm species has revealed that charged C-glycosylflavones and caffeylshikimic acid are characteristically present. Flavonol glycosides are also common; the 3-glucosides, 3-rutinosides and 3,4′-diglucosides of quercetin and isorhamnetin and the 7-glucoside and 3,7-diglucoside of quercetin are all variously present. Tricin 7-glucoside, luteolin 7-rutinoside and several unchanged C-glycosylflavones were also detected. Male flowers of Phoenix canariensis differ from female flowers in having flavonol glycosides. As expected, in most species studied, flavonoid patterns in the flowers vary considerably from those found in the leaves.     

Flavonol glycosides from Asplenium bulbiferum

From aerial parts of the fern Asplenium bulbiferum, besides kaempferol 3,7-diglucoside and kaempferol 3-O-rhamnoside- 7-O-glucoside, the new glycoside kaempferol 3-O-β-glucoside-7-O-β-galactoside has been characterized.     

Acylated anthocyanins in a hybrid Vitis variety

The anthocyanin skin pigments of the hybrid grape variety Royalty have been reexamined using isolation and chromatographic techniques designed to avoid degradation of the more labile pigments. Acetic acid has been identified as an acylating acid in acylated anthocyanin-3,5-diglucosides. The position of acylation of the malvidin-3,5-digucoside p-coumarate has been shown to be on the C-6 OH of the 3-0 glucose moiety.     

EVOLUTION IN THE GENUS RUELLIA (ACANTHACEAE): A DISCUSSION BASED ON FLORAL FLAVONOIDS

A clear dichotomy exists in the genus Ruellia, separating the blue from the red flowered species. Flavonoids differ in a qualitative rather than a quantitative way. Apigenin 7-glucuronide and malvidin 3,5-diglucoside are common to all the blue flowered species, whereas chalcononaringenin 2'-glucoside (isosalipurposide) and pelargonidin 3,5-diglucoside are shared by the red flowered ones. The blue flowered species are linked with the red via apigenin 7-glucuronide and 3,5-diglucosylation of their respective anthocyanins. Both groups are involved in flavonoid race formation. All examined species (and some populations within species) differ in flavonoid content. The patterns of variability displayed provide a basis upon which an evolutionary scheme is constructed. Genetic drift is hypothesized as the effector of race formation in the blue flowered group.     

Flavonoid glucosides from licorice

Two new flavanone glycosides, liquiritigenin 4′-apiosyl(1 → 2)-glucoside and liquiritigenin 7,4′-diglucoside together with a known flavone, apigenin 6,8-di-C-glucoside, have been isolated from licorice.     

Impact of specific environmental characteristics of the site of origin (shady,sunny) on anthocyanin and flavonol contents of replanted plants at common cyclamen (<Emphasis Type="Italic">Cyclamen purpurascens</Emphasis> Mill.)

The value of plant provenance (plant origin) is well-known phenomena in woody plants, but less is known in herbaceous plants (perennials). This study with common cyclamen (Cyclamen purpurascens Mill.) was conducted to reveal the importance of specific environmental site properties of plant origin for plant growth and plant quality in the next years. The plants were observed in years 2013 and 2014, more than 10 years after removing and replanting them from the original sites. Morphological characteristics of plants were evaluated by measuring the length and the width of plant rosettes, whereby plants originated from different sites did not show any significant differences. Additionally, the pigment composition, flavonol and anthocyanin content of plant leaves were evaluated. Plants removed from sunny sites showed significantly lower chlorophyll values (total chlorophyll, chlorophyll a) in the both observed years; lower carotenoid and total pigment values were measured only in year 2013. The prevailing anthocyanin in cyclamen leaves was malvidin-3,5-diglucoside with 57.28 µg l^?1 FW in the year 2013 and with 103.68 µg l^?1 FW in the year 2014. Plants originated from the sunny sites accumulated in 2013 significantly more malvidin-3,5-diglucoside in comparison with plants from shady sites of origin. The major substances from the flavonol group were quercetin-3-O-rutinoside and quercetin-dirhamnosyl-glucoside in both analysed years. The cyclamen leaves originated from sunny sites contained in 2013 significant more quercetin-dirhamnosyl-glucoside than cyclamen leaves from shady sites. The results of the study show that different stress parameters (irradiation and water supply in specific year) have a significant impact on the morphological and also internal parameters of cyclamen leaves.     

Streptococcal oxidation of malvin: The role peroxidogenic bacteria can play in decolorization

The possible use of microorganisms which yield substantial levels of hydrogen peroxide in treatments for decolorization of a natural pigment (malvidin-3,5-diglucoside) was studied. Streptococcus durans S-76 was able to oxidize about 38% malvin implicating biogenic hydrogen peroxide in a buffered solution. Malvin by-products and the coumarinic derivative have identical properties and high-performance liquid chromatographic patterns.     

Two distinctive anthocyanin patterns in the commelinaceae

A survey of lead and flower anthocyanins in a representative sample (28 spp./10 genera) of the Commelinaceae has shown that the dominant anthocyanin is cyanidin 3,7,3′-triglucoside, acylated with caffeic acid. Acylation with other hydroxycinnamic acids also occurs. As a flower pigment, this anthocyanin is stabilized at the pH of the cell sap by the presence of the three acyl substituents attached through glucose. In Gibasis, the related delphinidin triglucoside is also present. By contrast, the genus Commelina is distinguished by uniformly containing p-coumaroyl-delphinidin 3,5-diglucoside, which is stabilized in flowers as a copigment complex with glycoflavone. There are thus two distinctive sources of blue flower colour in the family. Furthermore, the presence of these rare acylated glucosides clearly separates the Commelinaceae from all other monocotyledonous groups.     

Chemotaxonomic Studies on Equisetaceous Plants in China

The present paper deals mainly with the chemical contents of the family Equisetaceae in China. The taxonomic value of the flavonol in this family is discussed. The results of chemical investigation show that kaempferol-3,7-diglucoside and kaempferol are the characteristic components of the family; kaempferol-3-diglucoside is characteristic of the genus Hippochaete and quercetin is characteristic of the genus Equisetum. Described in this paper are isolation of 11 compounds and identification of 7 compounds in this experiment, among which kaempferol-3-diglucoside and succinic acid are isolated from Hippochaete hiemale for the first time.     

Design,synthesis and antimycobacterial activity of 3,5-dinitrobenzamide derivatives containing fused ring moieties

We report herein the design, synthesis and antimycobacterial activity of 3,5-dinitrobenzamide derivatives containing fused ring moieties. Results reveal that many of the target compounds have considerable in vitro antitubercular activity. Especially, N-((2-(4-fluorophenyl)/N-((2-(3-fluorobenzyl)-1,2,3,4-tetrahydroisoquilin-6-yl)methyl)-3,5-dinitrobenzamides 18a and 20e exhibit potent MIC values of 0.056–0.078?μg/mL against both drug-sensitive Mycobacterium tuberculosis (MTB) H37Rv strain and two clinically isolated multidrug-resistant MTB (MDR-MTB) strains, opening a new direction for further SAR studies.     

Aloeresin c,a bitter c,o-diglucoside from cape aloe

A new bitter C,O-diglucoside, aloeresin C, was isolated from commercial Cape aloe. Its structure, 2-acetonyl-7-O-β-D-glucopyranosyl-8-C-β-D-[2′-O-(E)-p-coumaroyl]glucopyranosyl-5-methylchromone, was established by spectral and chemical methods.     

Phenols bromes d'une algue rouge, Halopytis incurvus: Acides carboxyliques

Extracts of Halopytis incurvus yielded, after methylation, the esters of 3,5-dibromo-4-methoxy-phenylacetic acid and 2-methoxy-3-(3′,5′-dibromo-4′-methoxyphenyl)acrylic acid.     

Characterization of 5-O-glucosyltransferase involved in anthocyanin biosynthesis in Cyclamen purpurascens

Wild cyclamen (Cyclamen purpurascens) is considered as a precious breeding material for the development of new cultivars. Malvidin 3,5-diglucoside is the main anthocyanin in the petals of C. purpurascens, whereas the F1 progeny of the C. persicum × C. purpurascens cultivars cross contains 3,5-diglucoside-type anthocyanins as the main pigment. The anthocyanin 5-O-glucosyltransferase (A5GT) enzyme is responsible for the glycosylation of the A ring of anthocyanin at the 5-O-position, which implies that the expression of A5GT is dominant in the petals of C. purpurascens × C. persicum cultivars. Here, we isolated the complete open reading frame of the A5GT gene from C. purpurascens (Cpur5GT). Results of qRT-PCR revealed that Cpur5GT shows tissue-specific expression, with strong expression in fully opened petals and weak expression in young petals. In vitro enzyme assay showed that when uridine diphosphate glucose was used as the sugar donor, recombinant Cpur5GT could catalyze the glycosylation of 3-glucoside-type anthocyanidins at the 5-O-position, but when uridine diphosphate galactose was served as glycosyl donor, the reaction could not be performed. These results demonstrate that Cpur5GT exhibits valid anthocyanin glucosylation activity and could be used to analyze the mechanism of A5GT-mediated flower coloration in cyclamen in future studies.     

The effect of hydrogen fluoride on two pigments in coleus

Coleus blumei Benth. cv. ‘12th Man’ was fumigated with hydrogen fluoride gas. The treatment caused the development of lesions which originally involved the mesophyll but spread to and eventually included the epidermis. An anthocyanin, cyanidin-3,5-diglucoside acylated with p-coumaric acid, was destroyed and it was postulated that the flavanonol, dihydrokaempferol, was converted to the flavone, apigenin. The anthocyanin destruction and pigment conversion occurred following membrane injury and mixing of the cellular constituents.     

Short communication. Do anthocyanins play a role in UV protection of the red juvenile leaves of Syzygium?

The biological function of juvenile leaves pigmented with anthocyanin is poorly understood. The role anthocyanins play in UV protection was assessed in juvenile leaves of two Syzygium species (S. luehmannii and S. wilsonii) which contain high anthocyanin concentrations. HPLC was used to separate UV-absorbing anthocyanins from other soluble UV-absorbing phenolic compounds. The isolated anthocyanins (predominantly malvidin-3,5-diglucoside) contributed little to the total absorbance of UV-A and UV-8 radiation. This was because the non-acylated anthocyanins only effectively absorbed shortwave UV-B radiation and the strong absorbance by other compounds. These results suggest that the UV protection hypothesis is not valid for anthocyanins in juvenile Syzygium leaves.     

Morphology of Cell Wall Pore Channels in the Genus <Emphasis Type="Italic">Euastrum</Emphasis> Ralfs (Desmidiales)

The study of the cell wall structure was performed for ten species of Euastrum: E. ansatum (Ehrenb.) Ralfs, E. bidentatum Näg., E. binale (Turp.) Ehrenb. ex Ralfs, E. dubium Näg., E. elegans (Bréb.) Kütz. ex Ralfs, E. germanicum (Schmidle) W. Krieger, E. oblongum (Grev.) Ralfs ex Ralfs, E. pectinatum Bréb. ex Bréb. in Ralfs, E. validum West et G.S.West, E. verrucosum (Ehrenb.) ex Ralfs. The investigation of the cell wall ultrastructure has established for the first time that the pore canal in 6 of 10 species always has a coiled form to some degree. Three species (E. germanicum, E. pectinatum, and E. verrucosum) have both coiled and straight canals, and E. ansatum has only straight ones. A new type of pores (P7), typical only for representatives of the genus Euastrum, was also noted. In addition, a simple and effective method of preparing desmidium algal cells for investigation with transmission electron microscope has been developed.     

A new photoactivatable support for protein immobilization: Fixation of β-d-galactosidase on modified chitosan

A new photoactivatable matrix has been obtained by arylation of chitosan, a widespread natural polymer, with 4-azido,3,5-dichloro-2,6-difluoropyridine. The potential of this matrix has been tested with Escherichia coli β-d-galactosidase (β-d-galactoside galactohydrolase, EC 3.2.1.23) as enzyme.     

A bromophenol in the red alga Halopitys incurvus

A new dibromophenol has been isolated from the acidified ethanolic extracts of the red alga Halopitys incurvus, and is shown to be 2,6-dibromo-3,5-dihydroxyphenylacetic acid, probably derived from a disulfate dipotassium salt.