Sedum acre

N.A. Sedum acre L. Sedacrine, n-methyl anabasine, sedinine, sedacryptine, flavanol glycosides.102-294 Insomnia, depressant, hemorrhoidal pain, treat excessive menstrual flow during menopause. 

Apocynum androsaemifolium, Caesalpinia ascendens, C. bonducella, C. sylvatica, Cydonia oblonga, Cyperus esculentus, C. brevifolius, Euphorbia lathyrus, Momordica charantia, Trillium erectum Rhodiola rosea, Sedum acre Populus alba... 

A synthesis of arecoline (17) from acetaldehyde has been described.17 Sederine (18) is a minor base occurring in Sedum acre-, its structure has been settled by spectral and chemical study, but its stereochemistry has yet to be established.18 A new total synthesis of racemic solenopsin A (19) (fire-ant venom) has been published the pathway is outlined in Scheme 2.19... 

Mcotiana tabacum (tobacco), JV. spp. (Solanaceae) also in Asclepias syriaca (Asclepiadaceae), Sedum acre (Crassulaceae), Lycopodium spp., Equisetum arvmse (Equisetaceae) tobacco smoking introduced to England from America by Sir Walter Raleigh (subsequently beheaded)... 

Proner has proved the presence of sedoheptulose in Sedum acre L., S. boloniense Lois., and reflexum L. Bennet-Clark reported its presence in S. praealtum A. de C. Nordal ° identified sedoheptulose conclusively in S. acre, L., S. album L., S. roseum (L.) Scop., S. spurium M.-B., and S. Telephium L., and concluded from qualitative color reactions that sedoheptulose is widely distributed within the family Crassu-laceae, but it is not always present. The experiments of Wolf have made it appear highly probable that sedoheptulose occurs in Bryophyllum calycinum Salisb. and Sempervivum glaucum Tenore. 

Further experiments with [6- H,6- C]-DL-lysine have been carried out on the origins of pipecolic acid (12) in Sedum acre, bean plants Phaseolus vulgaris), a lysine-less mutant of Neurospora crassa, and intact rats. In each case, the original ratio was maintained in the pipecolic acid isolated. This is... 

Hydroxysedamine (172) and (+)-4-hydroxyallosedamine (173) were isolated from Sedum acre using countercurrent distribution and preparative chromatography [448]. Their structures were determined using MS, and 13c NMR of 172, 173, and their diacetyl derivatives, and by synthesis via tetrahydro 1,3-oxazines of known absolute configuration. Conversion of these oxazines to 172 and 173 via a UAIH4 reduction established the absolute configuration of the new alkaloids [448],... 

Hydroxysedamine (174), 3-hydroxyallosedamine (175) and 3-hydroxynorallosedamine (176) were isolated from Sedum acre and their structures were determined by MS, IR, lH and 13c NMR and chemical transformations [449]. Treatment of 176 with aqueous HCHO/KOH gave a tetrahydro 1,3-oxazine. Spectroscopic analysis of the oxazine and application of Horeau s method provided the relative and absolute configurations of 176, respectively [449]. 

Structures were proposed for the new Sedum acre alkloids sediene (229) and sediendione (230) based on GC-MS analysis [507], The structure of 230 was further investigated using UV, IR and GC-MS [508]. An extract of S. acre containing 229, 171, and hydroxysedamine at 0.02% (w/v) displayed antimicrobial activity [508]. 

Homosedinone (233) and dihomosedinone (234), along with their C(6) epimers, were isolated in small amounts from Sedum acre. Support for the proposed structures and the absolute configurations was supplied by the synthesis of 233 and 234 from a derivative of (-)-norsedamine using anodic oxidation to allow addition of the side chains [511],... 

Lobelanidine glycoside (239) was isolated from Sedum acre. Its structure was determined using MS and by X-ray crystallography of the pentaacetate derivative [537],... 

Further work56 has now disproved this pathway, at least for sedamine. When [2-3H,6-14C]lysine was administered to Sedum acre the alkaloid incorporated both labels with an unchanged isotopic ratio. Thus, the hydrogen at C(2) of lysine is not lost in the biosynthesis as would be required for pathway a. An alternative sequence, path b (Scheme 16) satisfactorily accommodates the fresh evidence. Decarboxylation at C-2 now precedes rather than follows the oxidation step. To avoid the generation of a symmetrical diamine, the amino-group at C(6) is differentiated by methylation in the first step. 

Two species of Sedum have been examined for alkaloids, i.e., Sedum acre L. and Sedum sarmentomm Bunge. The first yielded the alkaloids sedamine (83) and sedridine (84, 85), whereas the other contained IV-methyl isopelletierine and its dihydro derivative (86). 

The pH dependence of the synthesis of pelletierine from J -piperideine and acetoacetic acid has been investigated (17,18). Pelletierine has been synthesized from cadaverine and acetoacetic acid in the presence of diamine oxidase (19). Pelletierine has recently been isolated from Duboisia myoporoides R.Br. (20), Sedum acre L. (21), and Withania somnifera Dunal (22). 

Proner has proved the presence of sedoheptulose in Sedum acre L.,... 

The conversion of lysine into piperidine alkaloids involves retention of hydrogen isotope at C-2/° The sequence is suggested to be that shown in Scheme 1, and catalysis of the reaction may be attributed to L-lysine decarboxylase. This enzyme, from the micro-organism Bacillus cadaveris, has been found to carry out the conversion of L-lysine into cadaverine with retention of configuration. Decarboxylation of L-[2- H]lysine by this enzyme then affords [15- H]-cadaverine. When this material is converted into alkaloids, e.g. iV-methyl-pelletierine (4 R = Me), the tritium attached to what becomes C-2 is lost cf. refs. 5 and 6. On the other hand, conversion of lysine into sedamine (27) in Sedum acre results in retention of the tritium originally present at C-2. The simplest explanation is that protonation of (26) in the micro-organism and plant proceeds with opposite stereochemistry. This is at variance, however, with current ideas on the stereochemistry of reactions that are catalysed by pyridoxal phosphate. ... 

Sedum alcaloids. C-2 monosubstituted piperidine alkaloids from Sedum species (Crassulaceae). Seda-mine is responsible for the hot taste of the wall pepper (Sedum acre). 

CAS 90106-69-7 EINECS/ELINCS 290-293-3 Definition Extract of the herb of the stonecrop, Sedum acre... 

Sandalwood (Santalum album) extract Sarsaparilla (Smilax aristolochiaefolla) extract . Sassafras (Sassafras officinale) extract . Seabuckthorn (Hippophae rhamnoides) extract Sedum acre extract... 

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