Entwicklungsgeschichte der Prothallien von Equisetum silvaticum L. und Equisetum palustre L.

Ohne ZusammenfassungMit 29 Textabbildungen und Tafel I–X.     

Kaempferol glycosides from Hosta ventricosa.

Leaves of Hosta ventricosa yielded eight kaempferol glycosides, of which six: the 3-(2G-glucosylrutinoside)-7-glucoside, 3-sophoroside-7-glucoside, 3-rutinoside-7-glucoside, 3-(2G-glucosylrutinoside), 3-sophoroside, 3-rutinoside were fully characterized and two: the 3-xylosylrutinoside-7-glucoside and 3-xylosylrutinoside were tentatively identified. Investigations included 1H-1H COSY and 1H-1H 2D J NMR analysis.     

Kaempferol glycosides from Siparuna apiosyce

The kaempferol derivative 3,7-di-O-methyl-4'-O-beta-[alpha rhamnosyl (1 --> 6)]-glucopyranoside (siparunoside) was isolated from the leaves of Sparuna apiosyce. Its structure was established by extensive NMR studies. The alkaloids reticuline and liriodenine were also isolated from the leaves along with the kaempferol derivative tiliroside. Benzylisoquinoline alkaloids were isolated from the wood (liriodenine) and wood bark (liriodenine, laurotetanine, N-methyl-laurotetanine, reticuline), together with a mixture of cis and trans-N-feruloyltyramines. 3,7,4'-tri-O-methylkaempferol was isolated from all organs.     

Galium silvaticum L. in Ungarn

Ohne Zusammenfassung     

Sterol Composition of the Strobilus of Equisetum arvense L.

“Process whey protein” was prepared by heating bovine milk whey protein isolate solution at neutral pH under salt-free conditions. The process whey protein solution, being clear, was heated at various pHs (2.0 to 11.0) and NaCl concentrations (0 to 200 mM), and the turbidity and gel properties of the products were then examined. For comparison, the properties of the whey protein isolate treated under the same conditions were measured. The whey protein isolate formed a transparent gel or sol below pH 3 and above pH 7 at low NaCl concentration after heating, but the process whey protein formed transparent gels and sols over a wider range of pH and NaCl concentrations than those of the whey protein isolate. More elastic, firmer, and denser gels were obtained from the process whey protein than from the whey protein isolate. The process whey protein provides a novel food material with useful properties.     

槐果皮中的黄酮醇及其苷类成分

槐 (ＳｏｐｈｏｒａｊａｐｏｎｉｃａＬ .)又名豆槐 ,白槐。槐角为槐的果实 ,药用历史悠久 ,化学成分已有报道[1～ 3 ] 。作者首次对槐的果皮进行化学成分研究 ,从中分离得到 3个黄酮醇和 4个黄酮醇苷类成分 ,经波谱和化学方法确定了结构。其中化合物Ⅰ、Ⅳ和Ⅶ为首次从该植物中分离得到。为槐角的开发利用奠定基础。1　实验部分1.1　药材、仪器与试剂药材采自南京市中国药科大学本部校园内 ,原植物由中国药科大学龚祝南博士鉴定。熔点测定用ＸＴ4双目体视显微熔点测定仪 (温度未经校正 ) ;红外光谱测定用ＮｉｃｏｌｅｔＩｍｐａｃｔ 410型…     

Sieve-Element Ontogeny in the Aerial Shoot of Equisetum hyemale L.

The aerial shoots of Equisetum hyemale L. var. affine (Engelm.)A. A. Eat. were examined with the electron microscope as partof a continuing study of sieveelement development in the lowervascular plants. Young E. hyemale sieve elements are distinguishablefrom all other cell types within the vascular system by thepresence of refractive spherules, proteinaceous bodies whichdevelop within dilated portions of the endoplasmic reticulum(ER). Details of cell wall thickening differ between protophloemand metaphloem sieve elements. Following cell wall thickeningthe ER increases in quantity and aggregates into stacks. Shortlythereafter, nuclear degeneration is initiated. During the periodof nuclear degeneration some cytoplasmic components-dictyosomes,microtubules and ribosomes-degenerate and disappear, while organellessuch as mitochondria and plastids persist. The latter undergostructural modifications and become parietal in distribution.Eventually the massive quantities of ER are reduced, leavingthe lumen of the cell clear in appearance. At maturity the plasmalemma-linedsieve element contains a parietal network of tubular ER, aswell as mitochondria, plastids, and refractive sphemh At thistime many of the spherules are discharged into the region ofthe wall. Sieveelement pores occur in both lateral and end walls.At maturity many pores are traversed by large numbers of ERmembranes. The metaphloem sieve elements of the mid-internodalregions apparently are sieve-tube members. The connections betweenmature protophloem sieve elements and pericycle cells are associatedwith massive wall thickenings on the pericyclecell side.     

Die Chondriosomen in der Gonogenese bei Equisetum palustre L.

Ohne ZusammenfassungDer Name Gonogenese wird hier im Anschlu\ an die schon eingebürgerte Terminologie vonLotsy eingeführt. Alle Zellen, die infolge zweier meiotischer Teilungen hervorgehen, ungeachtet ihrer morphologischen Bedeutung, nennt er Gonen. Zum ersten Male wurde die hier vorgeschlagene neue Bezeichnung in meinem Buche Die stofflichen Grundlagen der Vererbung (Russisch 1924) gebraucht.     

Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L

Chemical investigation of the pollen grain collected from male plants of Cannabis sativa L. resulted in the isolation for the first time of two flavonol glycosides from the methanol extract, and the identification of 16 cannabinoids in the hexane extract. The two glycosides were identified as kaempferol 3-O-sophoroside and quercetin 3-O-sophoroside by spectroscopic methods including high-field two-dimensional NMR experiments. The characterisation of each cannabinoid was performed by GC-FID and GC-MS analyses and by comparison with both available reference cannabinoids and reported data. The identified cannabinoids were delta9-tetrahydrocannabiorcol, cannabidivarin, cannabicitran, delta9-tetrahydrocannabivarin, cannabicyclol, cannabidiol, cannabichromene, delta9-tetrahydrocannabinol, cannabigerol, cannabinol, dihydrocannabinol, cannabielsoin, 6a, 7, 10a-trihydroxytetrahydrocannabinol, 9, 10-epoxycannabitriol, 10-O-ethylcannabitriol, and 7, 8-dehydro-10-O-ethylcannabitriol.     

Influence of shade timing on an Equisetum arvense L. population

Equisetum arvense L. is a perennial pteridophyte that grows in open sites. In Tokyo, the plant has photosynthetic shoots from late March to November. However, in some populations, these shoots are lost before summer because of shading by taller plants. To investigate the contribution of shoots that remain on the plant for a certain duration, in terms of the maintenance of the E.arvense population, tubers were cultivated under different light conditions and the dry weight of growth, photosynthetic rates and respiration rates were measured. Individual growth was simulated on the basis of matter production and its partitioning. Biomass at the start of the next growing season (the initial size) was seriously decreased by shading before July. However, shading after July had little effect on the initial size of the next season plants. Thus, E.arvense can maintain its population if its shoots are retained until summer.     

Autofluorescence of intact Equisetum arvense L. spores during their development

The autofluorescence of horsetail Equisetum arvense spores excited with UV-light of 360-380 nm was studied by microspectrofluorimetry during their development from an individual cell to the formation of a multicellular thallus with the generative organs. The investigation involved the registration of the fluorescence spectra of individual intact developing cells and the measurement of the ratio of cell fluorescence intensities in the blue and red regions of the spectrum. Dry blue-fluorescing microspores showed the maxima at 460 and 530 nm and a small maximum at 680 nm. Thirty minutes after moistening in water, red-fluorescing cells arose among blue-fluorescing microspores, indicating the onset of development. Red fluorescence with a maximum at 680 nm enhanced as cells put off their cover, which brightly fluoresced in the blue region of the spectrum with the main maximum at 460 nm. By estimating the ratio of autofluorescence intensities in the blue region of the spectrum to red lightening of microspores at the first stages of development up to 24 h (in particular, their first division, the formation of nonfluorescencing rhizoid, etc.), nonviable (only blue-lightening) cells were distinguished from viable cells, in which red fluorescence began to prevail. After 25-40 days of development, the gametophyte fluorescing mainly at 680 nm formed male organs, antheridia, with blue-green-fluorescing spermatozoids. Then female generative organs archegonia with the egg cell appeared, which fluoresced blue, whereas the surrounding cells fluoresced red. It was supposed that the lightening in the blue and green regions of the spectrum is due to the presence of phenols, terpenoids, and azulenes, whereas the emission in the red region is associated with the presence of chlorophyll and azulenes. The observation of autofluorescence makes it possible to easily distinguish generative cells without additional staining.     

Gas Exchange between Equisetum limosum and its Environment

Equisetum limosum grows in standing water. Its perennating rhizomesramify in the bottom mud, which is a markedly oxygen-deficientmedium. During the summer months aerial shoots are present andextend above the surface of the water to a height of about 1m. The concentration of oxygen in the internal atmosphere ofplants in the field decreases progressively from the stem tothe perennating rhizomes. There is a reverse gradient of carbondioxide concentrations. The structure of the nodal diaphragms of the aerial stem isdescribed and the progressive occlusion of the pores of thediaphragms between May and November is demonstrated. This occlusionof the diaphragms has been correlated with a reduction in thecase of gaseous diffusion along lengths of aerial stems. Oxygen is present in the rhizomes throughout the winter, despitethe fact that the dead aerial stems have broken off and thestumps have been submerged by the rise in water level, thusisolating the rhizome from atmospheric oxygen. The results are discussed in relation to the ability of theplant to grow in an oxygen-deficient environment.     

Furostanol saponins and quercetin glycosides from the leaves of Helleborus viridis L

Phytochemical analysis of the polar extracts of the leaves of Helleborus viridis (Ranunculaceae) resulted in the isolation of two new furostanol saponins (25R)-26-[(alpha-L-rhamnopyranosyl)oxy]-22alpha-methoxyfurost-5-en-3beta-yl O-beta-D-glucopyranosyl-(1-->3)-O-[6-acetyl-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranoside (1) and (25R)-26-[(alpha-L-rhamnopyranosyl)oxy]-22alpha-methoxyfurost-5-en-3beta-yl O-beta-D-glucopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->3)-O-beta-D-glucopyranoside (2) and three new quercetin glycosides, quercetin 3-O-(2-E-caffeoyl)-alpha-L-arabinopyranosyl-(1-->2)-beta-D-galactopyranoside-7-O-beta-d-glucopyranoside (3), quercetin 3-O-(2-E-caffeoyl)-alpha-L-arabinopyranosyl-(1-->2)-beta-D-galactopyranoside (4), and quercetin 3-O-alpha-L-arabinopyranosyl-(1-->2)-beta-D-galactopyranoside (5). The structures of the new compounds were determined by spectroscopic analysis, including 2D NMR data and mass spectrometry.     

Acylated apigenin glycosides from alfalfa (Medicago sativa L.) var. Artal.

Three flavones, including 4'-O-[2'-O-E-feruloyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin, 7-O-beta-D-glucuronopyranosyl-4'-O-[2'-O-E-feruloyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin and 7-O-beta-D-glucuronopyranosyl-4'-O-[2'-O-p-E-coumaroyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin have been identified in alfalfa var. Artal. The known flavone 7-O-[2-O-E-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucurono-pyranoside] apigenin was also isolated. The structures of these compounds were deduced on the basis of their spectral data.     

A study of the migration and degradation of oil in an upland bog peat soil in the Khanty-Mansi autonomous district during biotesting

Water migration and the degradation of Shaim oil in soils of upland bogs in the Khanty-Mansi Autonomous District were studied under laboratory conditions and the toxicity of consecutive samples of water extracts was investigated using Ceriodaphnia affinis, Paramecium caudatum, and Allium sera as test objects. It was found that oil (up to 2 g/kg) is retained by the humic matrix of peat and does not pass into water. The biotesting method permits one to fix the toxic effect of leachate from oil-contaminated peat, even in cases when petroleum products are not detected by means of IR spectrometry.     

Flavonol glycosides from Asplenium foreziense and its five related taxa and A. incisum

The flavonoids of Asplenium foreziense, A. fontanum subsp. fontanum and subsp. pseudofontanum, A. obovatum subsp. obovatum var. obovatum and var. protobillotii, A. obovatum subsp. lanceolatum, and A. incisum were isolated and identified for chemotaxonomic survey. A major constituent of all taxa was kaempferol 3-O-gentiobioside. As minor compounds, kaempferol 3,7-O-glycoside and/or kaempferol 3-O-glycoside were found in A. fontanum, A. obovatum and A. foreziense, and kaempferol 3-O-gentiobioside-4'-O-glucoside, kaempferol 3-O-glucoside and quercetin 3-O-diglucoside in A. incisum. It was suggested that A. foreziense, A. fontanum including subsp. pseudofontanum and A. obovatum including subsp. lanceolatum are not only morphologically but also chemotaxonomically related. The East Asian A. incisum was chemically and geographically different from these taxa.     

Three 2-oxoglutarate-dependent dioxygenase activities of Equisetum arvense L. forming flavone and flavonol from (2S)-naringenin

Equisetum arvense L. (Equisetaceae-horsetail) accumulates various flavones and flavonols in infertile shoot. Enzyme assays conducted with crude extracts of the green tissue revealed chalcone synthase activity and also three further activities assigned to flavonoid biosynthesis and identified as flavone synthase I, flavanone 3β-hydroxylase and flavonol synthase. The latter three activities were characterized as soluble, 2-oxoglutarate-dependent dioxygenases by their typical cofactor requirements and peculiar inhibition. Notably, this is the first report of flavone synthase I which had been considered to be restricted solely to species of the Apiaceae from a distant plant taxon.     

Six new C21 steroidal glycosides from Asclepias curassavica L

Six new C₂₁ steroidal glycosides, named curassavosides A–F (3–8), were obtained from the aerial parts of Asclepias curassavica (Asclepiadaceae), along with two known oxypregnanes, 12-O-benzoyldeacylmetaplexigenin (1) and 12-O-benzoylsarcostin (2). By spectroscopic methods, the structures of the six new compounds were determined as 12-O-benzoyldeacylmetaplexigenin 3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (3), 12-O-benzoylsarcostin 3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (4), sarcostin 3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (5), sarcostin 3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (6), 12-O-benzoyldeacylmetaplexigenin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (7), and 12-O-benzoylsarcostin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (8), respectively. All compounds (1–8) were tested for in vitro cytotoxicity; only compound 3 showed weak inhibitory activity against Raji and AGZY cell lines.     

Biosynthesis of oleanolic acid glycosides in protoplasts isolated from Calendula officinalis L. roots

Many medicinal plants contain oleanane saponins in roots, however, only scarce data on their biosynthesis in this organ are available so far, including our previous results concerning Calendula officinalis plant. Thus, the purpose of the present work was to confirm the presumable biosynthetic pathway of oleanolic acid glycosides in roots of young C. officinalis plants. First of all, the effective method of isolation of protoplasts from C. officinalis roots was established. Then, isolated root protoplasts were supplied with radioactive precursors, [2-¹⁴C] mevalonate (MVA) and [3-³H] oleanolic acid (OL) and their transformations were studied with comparison to results obtained with excised roots. The penetration of both precursors into protoplasts was more rapid and effective than in the case of excised roots. The labeling of sterols and OL during the incubation with MVA showed that the isoprenoid pathway leading to triterpenoids was operative in excised roots as well as isolated root protoplasts. Moreover, the transformations of OL into two series of its glycosides, i.e. glucosides and glucuronides were investigated. It has been shown that both series of OL glycosides are synthesized in isolated root protoplasts in the same way as in excised roots of young marigold plants.