Molecular structure of the alkaloid solasodine

An x-ray structural study of the monohydrate of the alkaloid solasodine has been made. Rings A, C, and F have the chair conformation, ring B half-chair, and rings D and E envelope conformations. The linkages of rings B/C and C/D are trans and that of rings D/E cis. It has been shown that solasodine is a diastereomer of the alkaloid tomatidenol.A. N. Nesmeyanov Institute of Heteroorganic Compounds, Moscow. Institute of Organic Synthesis and Coal Chemistry of the Kazakh SSR Academy of Sciences, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 86–88, January–February, 1989.     

Salinity stress enhances production of solasodine in Solanum nigrum L

Various in vitro grown tissues (non-regenerative callus, regenerative callus and microshoot derived leaves) of Solanum nigrum L. were cultured under salinity stress (0-150 mM NaCl) for enhanced production of solasodine, a steroidal alkaloid and an alternative to diosgenin, which is used as a precursor for the commercial production of steroidal drugs. The role of plant growth regulators and various concentrations of NaCl during in vitro production of solasodine was studied. The in vitro yield was compared with the yield from leaves of field grown plant. Solasodine content was maximum (2.39 mg/g dry wt.) in regenerative callus when grown on medium added with 150 mM NaCl; followed by in vitro raised leaf of microshoot. Quantitative estimation of solasodine was carried out using a new HPTLC method, which is validated for its recovery and precession. The proposed HPTLC method showed a good linear relationship (r(2)=0.994) in 50-2000 ng/spot concentration ranges. The data demonstrate that the solasodine production in cultures was growth dependent.     

Transformations of hetarylideneoxazolones

Hetarylideneoxazolones are converted to hetarylideneamino acid esters by methanolysis in the presence of sodium. Alkaline hydrolysis in aqueous alcohol gives the corresponding amino acids. Hydrazinolysis of pyranylideneoxazolone gives pyranylideneamino acid hydrazide. Complete hydrolysis of oxazolone gives formylpyran, the methylation of which gives the methoxymethylpyrylium salt. Benzamidomethyl-substituted pyrylium salts were obtained by treatment of the hetarylideneamino acids with perchloric acid.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 757–763, June, 1976.     

Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives

<正>Solasodine 11 is a steroidal alkaloid with various biological activities.Herein,8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro.Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs.In particular,19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line(IC_(50) = 3.91μmol/L).     

A facile and efficient method for the synthesis of solasodine from diosgenin

A facile and high-yielding route for the synthesis of solasodine from diosgenin is devised. Ring opening of steroidal spiroketal under mild conditions with trifluoroacetyl trifluoromethanesulfonate (TFAT) provides an applicable protocol to prepare key intermediates 4 or 3-Ac-solasodine, which can potentially serve as a platform for the selective functionalization of C(3)-OH and N-H of solasodine. The simple operations without purification by column chromatography make this method suitable to scale up.     

Determination of solasodine in cell cultures of Solanum laciniatum by high-performance liquid chromatography

A method is proposed for the quantitative determination of solasodine by HPLC on a Millikhrom domestic microcolumn chromatograph. The amounts of solasodine in various cell lines ofSolanum laciniatum have been determined. It has been shown that the genetic transformation leads to a substantial increase in the amount of solasodine in the biomass. Amounts of solasodine in multishoot cultures are comparable with its amount in normal mature plants. M. A. Aitkhozhina Institute of Molecular Biology and Biochemistry, Academy of Sciences of the Kazakh SSR, Alma-Ata. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 538–541, July–August, 1991.     

Oxidative Transformations of Polyprenols

Oxidative transformationsinvolving the hydroxylsand -methylsof polyprenolsisolated from birch greenery (7-9 isoprene units in the chain) were used to produce ,-diols, diesters, aldehydoalcohols, and hydroxyacids. The products are of interest as potential anti-inflammatory, antiulcer, hepatoprotective, and cardio-active preparations.     

Electric-Field-Induced Organic Transformations

Experiments showed that the existence of electric fields in non-redox processes may alter the catalytic activity, rate enhancement, and selection of organic reactions. It is expected that the interaction between electric fields and chemical reactions will create new avenues for producing materials with desired properties in several chemical disciplines, including synthetic organic chemistry, catalysis, nanotechnology, membrane technology, and enzyme catalysis. Specifically, in this review, we discuss the elegant experimental investigations carried out using the scanning tunneling microscope, the interfacial electric field, and designed local electric fields. The results of these studies are remarkable, leading to new information on the function of electric fields in controlling chemical reactivity and selectivity in different reactions and offering a glimpse of the great potential of electrostatic fields. This article not only presents the core concepts of field-induced chemical transformations but also illustrates the potential use of electric field catalysis in chemistry and other fields.     

Transformations of 2-formyl-n-nitroarylimidazoles

Esters of-1-aryl--2-imidazolylacrylic acid were synthesized by the Wittig reaction from 2-formyl-1-arylimidazoles. The reaction of these aldehydes with arylamines and 1,2-dianilinoethane was examined.Considering the method used to prepare the esters, the trans structure can be assigned to them [9].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 788–790, June, 1973.     

Thermal Transformations of Polyoxadiazoles

Changes of the structural characteristics and electrical properties of fibers based on polyoxadiazole (Arselon) upon a low-temperature thermal treatment in an inert atmosphere were studied. Extremal dependences of the conductivity of the fibers on treatment temperature were observed and a mechanism of this process was suggested. The X-ray diffraction parameters of the Arselon fibers were determined for the extreme states and practical recommendations were made for using a preliminary heating of the fibers.     

Asymmetric Electrochemical Transformations

The field of electrochemical synthesis has developed rapidly over the last decade and has provided alternative synthetic methods with the absence of stoichiometric amounts of chemical oxidants or reductants. Although sustainable electrosynthetic procedures have been developed, relatively few examples of highly enantioselective catalytic electrosynthesis have been reported to date. The development of general strategies for electrochemical enantiocontrol has thus proven to be a considerable challenge. This Minireview highlights the current knowledge and recent advances in the synthetic utility of electrochemical transformations for asymmetric synthesis. Specifically, three major types of catalytic enantioselective strategy in electrosynthesis are outlined, including electrochemical activation of chiral catalyst‐bound substrates, asymmetric cascade electrochemical processes, and chemically modified chiral electrodes.     

Transformations in quasimelting

The structural fluctuations in small particles in the presence of an electron beam has been investigated using real time video recordings. The acquired images have been analyzed frame by frame in order to probe the exact nature of the quasimolten state. This analysis demonstrates that quasimelting, as experimentally observed in a high resolution microscope is a mixture of rapid rotations of the particle and much slower structural transformations. In addition, no evidence is found for an amorphous state.     

Interesting Transformations of Thiocamphor

Thiocamphor has been found to furnish bornane, camphor, isoborneol, isobornylthiol, bornylthiol, tetrahydro-bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-disulfide, and three isomeric bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-dithiols when treated with NaBH₄ either in dry THF or dry diethylene glycol diethyl ether. The origins of the above interesting compounds and their mass spectral characterization are presented in this article.