Sedum Acre Research Articles

Alkaloids of the herb sedum acre L. Part II: Separation by countercurrent distribution

Component alkaloids of Sedum acre L. (stonecrop) were partly separated on preparative scale by countercurrent distribution, using selective solvent systems of the type chloroform/buffer solution and benzene/buffer solution, the optimal pH of the aqueous phase being estimated from paper chromatographic data. Good agreement between predicted and experimental separations was observed.

Alkaloids of the herb sedum acre L. Part I. Chromatographic analysis

Alkaloid extracts from the herb Sedum acre L. (stonecrop) were analysed by the “moist buffered paper” technique in solvent systems of the type nonpolar or weakly polar solvent-aqueous buffer solution, which were found to be much more selective than one-phse systems or liquid-solid systems. In addition to six previously known Sedum alkaloids, three new alkaloids in the extract were demonstrated.

Biosynthesis of the piperidine nucleus metabolism of dl-ϵ- N-METHYL- 3H-lysine-2- 14c by Sedum acre

dl-ϵ- N-Methyl- 3H-lysine-2- 14C was prepared and administered to excised shoots of Sedum acre from which dl-sedamine was isolated. The ϵ- N-methyllysine was not incorporated without degradation and, therefore, it is probably not a direct precursor of the piperidine ring of sedamine.

ChemInform Abstract: NEUE FLAVONOIDE VERBINDUNGEN AUS DER SEDUM ACRE L. (CRASSULACEAE)

Chemischer InformationsdienstVolume 3, Issue 39 Isocyclic Compounds ChemInform Abstract: NEUE FLAVONOIDE VERBINDUNGEN AUS DER SEDUM ACRE L. (CRASSULACEAE) MARIA KROLIKOWSKA, MARIA KROLIKOWSKASearch for more papers by this author MARIA KROLIKOWSKA, MARIA KROLIKOWSKASearch for more papers by this author First published: September 26, 1972 https://doi.org/10.1002/chin.197239429AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume3, Issue39September 26, 1972 RelatedInformation

CYTOLOGICAL AND MORPHOLOGICAL VARIATION IN SEDUM ACRE L. IN WESTERN EUROPE

SUMMARY Within Sedum acre L. s.l. a polyploid series occurs with the chromosome numbers 2n= 40, 2n= 60, 2n= 80, 2n= 100 and 2n= 120. The plants with 2n= 40 and 2n= 80 chromosomes have different areas. When cultivated under uniform conditions the cytotypes 2n= 40, 2n= 60 and 2n= 80 show differences in some morphological characters. It seems likely that these three cytotypes correspond with Sedum acre L. subsp. neglectum Ten., var. majus Masters, and subsp. acre, respectively.

Biosynthesis of the piperidine nucleus: The occurrence of two pathways from lysine

2- 3H,6- 14C- dl-Lysine was administered to the intact rat, to intact bean plants ( Phaseolus vulgaris) and to excised shoots of Sedum acre. Pipecolic acid (IV), which was isolated from each of these tissues, contained 14C but was free of tritium. Since incorporation of label from 6- 3H,6- 14C- dl-lysine into pipecolic acid had previously been shown 1 to take place specifically and to occur without change in 3H: 14C ratio in each of these systems, the evidence is now complete that conversion of lysine (I) into pipecolic acid (IV) proceeds via ϵ-amino-α-ketocaproic acid (II) and Δ 1-piperideine-2-carboxylic acid (III) and not via α-aminoadipic-δ-semialdehyde (VI) and Δ 1-piperideine-6-carboxylic acid (V). In S. acre, 2- 3H,6- 14C- dl-lysine was incorporated into sedamine (X) without change in 3H: 14C ratio. It follows that ϵ-amino-α-ketocaproic acid (II) cannot be an intermediate in the biosynthesis of sedamine from lysine, as had been previously suggested. Specific conversion of 6- 3H,6- 14C- dl-lysine into sedamine without change in 3H: 14C ratio had been demonstrated earlier. This and other evidence had been interpreted to show that α-aminoadipic-δ-semialdehyde (VI) is not an intermediate on the route from lysine to sedamine and other piperidine alkaloids. An alternative pathway, which invokes neither ϵ-amino-α-ketocaproic acid nor α-aminoadipic-δ-semialdehyde as intermediate, is now suggested.

Environment-induced changes in peroxidase zymograms in the stems of deciduous and evergreen plants

Summary Stems of four plants ( Sedum acre L., Mitchella repens L., Cornus stolonifera Michx., and Salix fragilis L.) representing a range of plant types were extracted and analyzed for peroxidase isozyme components. In all four species, the peroxidase components from the stems of winter-acclimated plants differed from the components found in tender, nonacclimated plants. This and other studies indicate that plant peroxidase metabolism is strongly influenced by the environment in which the plants are grown.

Biosynthesis of the Piperidine Nucleus: The mode of incorporation of lysine into pipecolic acid and into piperidine alkaloids

Abstract 6-3H,6-14C-dl-Lysine was administered in metabolite overloading experiments to the intact rat, to a lysine-less mutant of Neurospora crassa, to intact bean plants (Phaseolus vulgaris), and to excised shoots of Sedum acre. Pipecolic acid was then isolated from the tissues. In each case the pipecolic acid showed a 3H:14C ratio which was similar to that of the administered precursor. It follows that, in each case, the conversion of lysine into pipecolic acid proceeds via e-amino-α-ketocaproic acid. α-Aminoadipic-δ-semialdehyde cannot be an intermediate. These results complement earlier findings that, in the rat, the nitrogen atom of pipecolic acid is supplied by the e-amino group of lysine; they provide evidence for a similar route in N. crassa and in higher plants. They conflict with reports that, in higher plants, it is the α-amino group of lysine which supplies the nitrogen atom of pipecolic acid. In S. acre, the doubly labeled lysine was incorporated into sedamine without change in 3H:14C ratio.

The biosynthesis of sedamine

The biosynthesis of sedamine (IX) was studied in excised shoots of Sedum acre L. Phenyl-alanine serves as the precursor of the C6 – C2side chain. The piperidine nucleus is derived from lysine, which is incorporated by way of a nonsymmetrical intermediate. These findings are consistent with Robinson's classical biogenetic hypothesis. They are incompatible with a polyacyl origin of the sedamine skeleton.

The complete configuration of sedridine and of pelletierine

Abstract(+)‐Sedridine from Sedum acre L. is shown to be (2S)‐1‐[(2′S)‐2′‐piperidyl]‐propan‐2‐ol.Oxidation of unnatural (‐)‐sedridine yielded D‐pipecolic acid, from which follows the absolute configuration of the piperidine asymmetric centre. Oxidation of unnatural (+)‐pelletierine sulfate gave L‐pipecolic acid.This also confirms a previous deduction of the absolute configuration of (‐)‐pelletierine from Punica granatum L.; this is R‐1‐(2‐piperidyl)propan‐2‐one.Racemic sedridine and allosedridine were condensed with p‐substituted benzaldehydes to 1‐(4‐substituted‐phenyl)‐3‐methylhexahydro‐1H,3H‐pyrido‐[1,2‐c]oxazines. The relative configurations followed from conformational analysis and proton magnetic resonance spectra: sedridine is threoid and allosedridine is erythroid.

An Experimental Approach to Part of the Calcicole Problem

The correlation of certain plant distributions with the presence or absence of calcium carbonate in the soil is well known. Hope-Simpson (1938) has defined as calcicoles 'species affecting the more important types of calcareous soil and rare on, or absent from, acid soils, and calcifuges as the reverse'. Other pairs of terms are also in use to describe the same observations. There is some danger that the semantic similarity of the terms may be taken to imply a reciprocally related explanation for each of the calcicole and calcifuge distribution types. With this reservation, the terms are useful as field descriptions, much as fever in medicine describes a class of symptoms with many underlying causes. The experiments to be described have been concerned only with 'the calcicole problem'. Much work has been done on this subject and numerous summaries have been produced, e.g. by Black (1957), Grime (1960), Hartwell & Pember (1918), Hewitt (1952), Jensen (1952), Lundergardh (1931), Rorison (1956), Russell (1961), Salisbury (1920), Schmehl et al. (1950), Steele (1955), Webb & Hart (1945), Wilde (1954) and Zlatnik (1928). To add another would serve no useful purpose. There are, however, four complicating factors, the importance of which has not been generally recognized. These affect the design of experiments, and must therefore be mentioned first of all. First, as was pointed out by Salisbury (1920), most calcareous soils are well drained. He suggested that the calcicoles Fagus sylvatica, Juniperus communis, Clematis vitalba, Buxus sempervirens, Helleborus foetidus and the moss Pleurochaete squarrosa are really plants of well-drained soils. The calcicole status of beech and juniper is questionable (for example in the New Forest and Rothiemurchus Forest respectively) and the restriction of box to calcareous slopes may be related to the instability of these areas (Pigott & Walters 1953), but the possibility of such an explanation must be borne in mind, since most of the plants used to investigate the calcicole problem have been chalk downland plants. Secondly, a number of plant taxa are calcicole only at the limits of their range. They may be called 'marginal calcicoles'. Praeger (1950) considered Stellaria palustris, Arenaria verna, Sedum acre, Origanum vulgare and Primula veris as calcicole in Ireland but not in Britain. A survey of the soil preferences of the plants used in earlier investigations of the calcicole problem is given in Table 1. The information has been condensed from accounts in various Floras. It seems therefore that about two-thirds of these plants are calcicole in Britain in special circumstances; at the limit of their range, in well-drained soils, or as 'ruderals and weeds' in open disturbed ground. The experiments of Webb & Hart, and Steele

Studies on sedum alkaloids V. Synthesis and optical resolution of sedamine and sedridine

AbstractThe synthesis of the racemates of the alkaloids sedamine and sedridine, the separation of the racemates, and their resolution into optical antipodes are described, with the exception of the resolution of (±)‐allosedridine and so far as no earlier information about these subjects has been given by us.The results are compared with data about the natural products obtained from Sedum acre and Lobelia inflata.

Ueber die Isolierung und Strukturaufklärung eines neuen Alkaloids aus Sedum acre L: (Vorläufige Mitteilung)

AbstractExtracts of Sedum acre L. were analysed by chromatography on paper. Sedamine and nicotine reported to occur in S. acre could not be found, but several spots marked the presence of other alkaloids.One of these alkaloids — was isolated and is shown to be the dextro‐rotatory component of the racemate with m.p. 75° of 1‐(2‐piperidyl)‐2‐propanol (III, “dihydroisopelletierine”, ( + )‐sedridine). Some (±)‐sedridine was also found.Possible implications of these findings are indicated.

THE ALKALOIDS OF SEDUM ACRE L.

Two alkaloids have been isolated from Sedum acre L. (Crassulaceae). One is the previously reported sedamine and the other is nicotine, the occurrence of which in this plant is now reported for the first time.

Studies on the Host Range of Sclerotium delphinii Welch

In a note published previously (8) the writer mentioned that A. J. Mix had made an isolation of Sclerotium delphinii Welch from Ajuga reptans. The organism was observed in a rock garden where in addition to Ajuga it was parasitizing Sedum acre and Lysimachia nummularia. This marked the first time this species had been isolated in Kansas, although Sclerotium rolfsii Sacc., a closely related species, is listed by Bartholomew (1) as occurring in the state. Figure 1, left, is a photograph of the strain of S. delphinii isolated from Ajuga, and, right, a typical culture of S. rolfsii growing on potato dextrose agar slants. In the course of a general study of this isolate from Ajuga it was decided to investigate the host range and make a few comparisons with S. rolfsii. The latter, because of its wide geographical distribution and economic importance as a plant pathogene, has received considerable mention in the literature and is known to be parasitic on nearly two hundred hosts. Sclerotium delphinii, on the other hand, has been reported on only about forty species. These have been compiled and are listed in Table I. Unfortunately some workers gave only the common names for some of the hosts, and where there was doubt as to the correct scientific name, either just the genus name or common name is listed.

Sedum acre X mite (Sedum Füreri K. Wein) nov. hybr

Repertorium novarum specierum regni vegetabilisVolume 11, Issue 4-8 p. 83-84 Article Sedum acre X mite (Sedum Füreri K. Wein) nov. hybr K. Wein, K. WeinSearch for more papers by this author K. Wein, K. WeinSearch for more papers by this author First published: 1912 https://doi.org/10.1002/fedr.19120110409AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume11, Issue4-81912Pages 83-84 RelatedInformation