Compilation of secondary metabolites from Bidens pilosa L

Bidens pilosa L. is a cosmopolitan annual herb, known for its traditional use in treating various diseases and thus much studied for the biological activity of its extracts, fractions and isolated compounds. Polyacetylenes and flavonoids, typical metabolite classes in the Bidens genus, predominate in the phytochemistry of B. pilosa. These classes of compounds have great taxonomic significance. In the Asteraceae family, the acetylene moiety is widely distributed in the Heliantheae tribe and some representatives, such as 1-phenylhepta-1,3,5-triyne, are noted for their biological activity and strong long-wave UV radiation absorbance. The flavonoids, specifically aurones and chalcones, have been reported as good sub-tribal level markers. Natural products from several other classes have also been isolated from different parts of B. pilosa. This review summarizes the available information on the 198 natural products isolated to date from B. pilosa.     

The cytochalasans: a new class of biologically active microbial metabolites

A series of cytostatically active metabolites have been isolated from microorganisms in recent years. These compounds, which are chemically closely related, are of a new structural type. A highly substituted hydrogenated isoindolone unit is fused to an 11- to 14-membered macrocycle. The large ring may be carbocyclic or heterocyclic (lactone or carbonic diester). The absolute configurations of two cytochalasans (phomin and a cytochalasin D derivative) have been established by X-ray analysis. The biogenesis of phomin (cytochalasin B) is broadly known, and it is probable that all cytochalasans have a common biogenetic scheme. All the compounds of this class have a more or less pronounced specifically cytostatic action.     

Hypolipidemic potential of flowers of Nerium oleander in high fat diet-fed Sprague Dawley rats

Nerium oleander Linn. (NO), an evergreen shrub, is used in folklore medicine as a cardiotonic and exhibits a wide spectrum of bioactivities. Herein, the hypolipidemic potential of the ethanolic extract of flowers of Nerium oleander (ENO) in a minimal dose was assessed. A high fat diet (HFD) resulted in a significant increase in cardiac lipids and lipoproteins and an increase in body weight gain. Simultaneous treatment with ENO significantly lowered the increase in body weight gain, lipid and lipoprotein levels, with a concomitant increase in HDL in the plasma and heart when compared to HFD-fed rats. Likewise, the activities of lipolytic enzymes were also upheld by the ENO treatment in the heart compared to HFD-fed rats. The above findings highlight the possible mechanism of N. oleander as a hypolipidemic agent in its use in folklore medicine as a cardiotonic.     

The structure of a new cardenolide diglycoside and the biological activities of eleven cardenolide diglycosides from Nerium oleander

A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2-11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1-11 was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). Compounds 2-5 were active at an IC(50) value of less than 0.8 μM. The cytotoxicity of compounds 1-11 was evaluated against three human cell lines normal human fibroblast cells (WI-38), malignant tumor cells induced from WI-38 (VA-13), and human liver tumor cells (HepG2). Compound 3 was active toward VA-13 cells, and compounds 2-5 were active toward HepG2 cells at IC(50) values of less than 1.3 μM. The multidrug resistance (MDR)-reversal activity of compounds 1-11 was evaluated on the basis of the amount of calcein in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compounds 1 and 8 showed moderate effects on calcein accumulation.     

Obtaining biologically active substances from Amaranthus caudatus L. seeds in one technological cycle

Nowadays, amaranth is a valuable multipurpose crop and a source of a number of very important biologically active substances. The aim of this study was to develop a comprehensive scheme for obtaining fatty oil, triterpenoids and lectin from the seeds of Amaranthus caudatus L. in one technological cycle. Two variants of the lectin and triterpene compound purification method from amaranth seeds were tested. It was determined that the extraction of triterpene compounds should be carried out after purification of the lectin from degreased seeds. The rationality of this sequence of technological operations is explained by the lability of the lectin and the insolubility in water of triterpene compounds from amaranth seeds. The study also presents a scheme for obtaining squalene from amaranth oil by chromatography on silica gel and proposes a more effective affinity sorbent for purification of the lectin. The use of such a sorbent also opens up the possibility of preserving other water-soluble substances from amaranth seeds. The physicochemical characteristics and carbohydrate specificity of the lectin are described and new data on the results of the interaction of lectin with human and animal erythrocytes are given. The obtained results are discussed in the light of the complex use of raw materials.     

Complexes derived from some biologically active ligands

Complexes derived from ampicillin (L1) and amoxicillin (L2) with (Mg(II), Ca(II), Zn(II), Cu(II), Ni(II), Co(II), Ce(III), Nd(III), UO₂(VI), Th(IV)) were prepared and characterized by elemental analysis, electrical conductivity measurements, magnetic susceptibility, IR, UV/Vis, and thermogravimetry. The formed complexes can be formulated as (ML(H₂O)₃(NO₃) _n ) except for Ce(III) which gave (CeL(H₂O)₃(Cl)₂). The ¹H NMR spectra of the Zn(II) complexes are compared to spectra of the ligands. The shift (δ) gave information about the chelating center of the ligands. The ligands and the synthesized complexes, derived from some alkali earth and transition metal ions, were tested as antibacterial reagents. The formed complexes had enhanced activity.     

Halogenated secondary metabolites from Laurencia obtusa

A new sesquiterpene (1), and a halogenated C15 acetogenin (2), a stereoisomer of neoisoprelaurefucin were isolated from Laurencia obtusa. Four known compounds laurencienyne (3), rogiolenyne B (4), obtusenol (5), and (3E)-dactomelyne (6) were also isolated from this alga. Rogiolenyne B (4) and (3E)-dactomelyne (6) were found for the first from this species. The structures of these compounds were elucidated by spectroscopic methods. The unambiguous assignments of the 1H and 13C NMR spectral data of (5) and 13C NMR data of (6) were also reported for the first time.     

Leaching-out of biologically active elements from enriched granulated phosphogypsum

Leaching-out of biologically active microelements (Mn²⁺, Zn²⁺) from grains of phosphogypsum enriched with macro-and microadditives introduced into its composition before granulation was experimentally studied.     

Synthesis of biologically active pyridazinoquinoxalines

The 2‐(1‐methylhydrazino)quinoxaline 4‐oxides 9a,b were converted into the pyridazino[3,4‐b]‐quinoxalines 10a,b,15a,b,22 and 1,2‐diazepino[3,4‐b]quinoxalines 29a‐c , which were further transformed into the 3‐substituted 1‐methylpyridazino[3,4‐b]quinoxalin‐4(1H)‐ones 5–8 .     

Uncommon secondary metabolites from Etlingera pavieana rhizomes

From the rhizomes of Etlingera pavieana (Pierre ex Gagnep.) R.M. Sm., four phenylpropens, (E)-3-(4-methoxyphenyl)prop-2-en-1-amine (1), (E)-4-methoxycinamaldehyde (2), (E)-4-methoxycinamic acid (3) and (E)-1-methoxy-4-(3-methoxyprop-1-enyl)benzene (4), together with two other compounds, (E)-((E)-3-(4-methoxyphenyl)allyl)3-(4-hydroxyphenyl)acrylate (5) and 4-methoxybenzoic acid (6) were isolated. This is the first report on the presence of all compounds in Etlingera. Compounds 1 and 5 have been previously synthesised, but this is the first report of their isolation from a natural source. Compound 5 exhibited weak activity against Mycobacterium tuberculosis with MIC 50.00 μg/mL and cytotoxic activity against the KB, MCF7 and NCI-H187 cells with IC₅₀ values of 25.11, 20.16 and 34.83 μg/mL, respectively.     

Microbial metabolism of loganin by intestinal bacteria and identification of new metabolites in rat

Loganin is an important constituent of the traditional Chinese medicine Fructus Corni, with several bioactivities. Microbial metabolism of loganin by intestinal bacteria was investigated. Two metabolites (log-1 and log-2) were isolated from anaerobic culture and their structures were identified by means of their ESI-MS, (1)H-NMR, (13)C-NMR and 2D-NMR spectral data. Log-1 was an aglycone of loganin and log-2 was proved to be a new compound. In vivo metabolites of loganin were detected in rat urine, bile and feces after oral administration of loganin and the structures were proved to be identical with that of the microbial metabolites log-1 and log-2 by HPLC-PDA analysis and comparison with the reference standards. Therefore we can prepare metabolites by anaerobic culture with intestinal bacteria.     

Mass spectrometry of biologically active substances

The mass spectra of 2- and 4-iminobarbituric acid derivatives were studied in relation to the mass spectra of their oxygen analogs. It is shown that the pathways of fragmentation of the investigated compounds depend on the type of substituent attached to the C₅ atom, the position of the imino and oxo groups in the ring, and the specific mass-spectral properties. The fragmentation was studied by means of low-voltage mass spectrometry and deuterium labeling.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 813–817, June, 1978.     

Mechanical composites based on biologically active compounds from larch wood

Mechanical composites were prepared by mechanical chemical processing of a mixture of biologically active preparations of arabinogalactan (AG) and dihydroquercetin (DQ) isolated from larch wood. Their properties were studied using HPLC, ¹³C NMR, and IR spectroscopy. It was found that AG and DQ did not react chemically under the studied conditions. According to x-ray phase and thermal analyses, mechanical processing destroyed the DQ crystalline structure and dispersed it into the AG matrix. The resulting mechanical composites had significantly higher (up to 38 times) solubility in water compared with starting DQ and an unprocessed AG/DQ mixture. It was shown that DQ reduces the extent of destruction of polysaccharide macromolecules during mechanical processing.     

Synthesis of new biologically active O-hydrometalatranes

Russian Journal of General Chemistry -     

Silyl modification of biologically active compounds

A series of derivatives of (1,2,3,4-tetrahydro-1-quinolyl)-, (1,2,3,4-tetrahydro-2-isoquinolyl)-, and (1,2,3,4-tetrahydrosila-2-isoquinolyl)acetic acid, which are structural analogs of glycine, were synthesized. The psychotropic activity and the acute toxicity of the compounds were studied.For Communication 3, see [6].Latvian Institute of Organic Synthesis, Riga. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 270–274, February, 1997.     

Electrochemical studies of biologically active indolizines

The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E° values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E° values have been correlated with the Hammett substituent parameters. As expected, low E° values are seen for electron donating substituents and higher E° values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the C-1 position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E° values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the C-1 position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1′ dimers of indolizines as products in good yields. Bulk oxidation of 1-(α-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitrile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-1 position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism.