Components and antioxidant activity of fruits of Cirsium palustre and C. rivulare

In the hexane extract of C. palustre and C. rivulare fruits, fatty acids, sterols, triterpenes, and volatile compounds were analyzed by the GC-MS-FID method. In the methanolic extracts, total phenol content was estimated. The antioxidant activity of both extracts was measured with DPPH assay and expressed in % scavenged DPPH.     

Die Glykoside der Wurzeln von Glossostelma carsoni (N. E. BR.) BULLOCK. Glykoside und Aglykone, 297. Mitteilung

Pentacyclic triterpenes, sterols, cardenolides and pregnane derivatives could be identified in extracts from roots of Glossostelma carsoni (N.E. BR .) Bullock. From the first group, the following substances could be isolated in crystalline form: β-amyrin, lupeol, their 3-O-acetyl derivatives, and 3-O-isovaleryl-β-amyrin. The sterols were isolated in the form of two mixed but crystalline fractions. The less polar fraction was shown to be a mixture of β-sitosterol, campesterol, stigmasterol, and cholesterol (stereoisomers are not excluded); the more polar fraction is probably a mixture of monohydroxy derivatives of the four above mentioned sterols.     

Highly selective Markovnikov hydration of Δ24-sterols and triterpenes by oxymercuration–hydrodemercuration

The reaction of mercuric acetate with unsaturated sterols and tetracyclic triterpenes (oxymercuration), followed by reduction with sodium borohydride/sodium hydroxide in water (hydrodemercuration), is highly selective for the side-chain double bonds 24-methylene or 24 (25). The nuclear double bonds, or those on other positions in the side-chain, do not react. The specificity of mercuration is therefore not directly correlated to the degree of substitution of the double bond, but rather to its steric accessibility. This sequence, which has been tested on some 30 sterols and related tetracyclic triterpenes, can be used to separate conveniently some of the constituents of the often-complex mixtures of sterols and of their tetracyclic triterpene precursors present in the unsaponifiable fraction of plant lipids. To cite this article: L. Elkihel et al., C. R. Chimie 6 (2003) 000–000.     

Lipids from leaves ofEphedra equizetina

The content and composition by class and fatty acid of neutral (NL), glyco- (GL), and phospholipids (PL) in leaves ofEphedra equizetina Bunge (Ephedraceae) are determined. The acid composition of NL, GL, and PL includes saturated 12∶0–32∶0 acids and unsaturated 15∶1, 16∶1, 18∶1, 18∶2, and 18∶3 acids. Unsaponified components of the total lipids also contained biologically active substances such as α-tocopherol, carotenoids, high-molecular-weight fatty alcohols, triterpenes, and sterols. Academician S. Yu. Yunusov Institute of the Chemistry of Plant Substances. Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 718–721, November–December, 1999.     

Synthesis of Cholest-5-en-24-oxo-3b, 19-Diacetate

Two biologically active 19-hydroxylated sterols, 24-methylenecholesta-3b, 5a, 6b, 19- tetrol 1, 24-methylenecholesta-5-ene-3b, 7b, 19-triol 2, were isolated from the soft corals, Nephthea albida and Nepthea tiexieral verseveldt by L. M. Zeng1,2. 1 showed strong anti-inflamatory activity comparable with dexamethone and 2 showed potent anti-leukemic activity (IC50 0.01 mg/mL). We have designed a synthetic route for the synthesis of 1 and 2 as shown in Scheme 1. In this route, cholest-5-en-…     

Enzymatic synthesis of cyclic triterpenes

This review covers recent advances in the chemistry and enzymology of squalene cyclase and oxidosqualene cyclase. The enzymatic cyclizations of squalene and oxidosqualene are the most remarkable steps in the biosynthesis of sterols and triterpenes. The polyenes are converted to various polycyclic triterpenes by different enzyme systems employing only small modification of the active-site. Recent crystallographic and structure-based mutagenesis studies as well as utilization of chemically synthesized active-site probes have begun to reveal intimate structural details of the enzyme-templated cyclization reactions. 126 References are cited.     

Anti-Escherichia coli activity of extracts from Schinus terebinthifolius fruits and leaves

Ethanol extracts obtained from Schinus terebinthifolius Raddi fruits and leaves were active against Escherichia coli with MIC of 78 μg mL^?1 for both extracts. Phytochemical analyses revealed a major presence of phenolic acids, tannins, fatty acids and acid triterpenes in the leaves and phenolic acids, fatty acids, acid triterpenes and biflavonoids in the fruits. Major compounds isolated from the plant, such as the acid triterpene schinol, the phenolic acid derivative ethyl gallate and the biflavonoids agathisflavone and tetrahydroamentoflavone, showed very little activity against E. coli. Bioautography of the ethanol extracts on silica gel plate showed inhibition zones for E. coli. They were removed from the plate and the compounds identified as a mixture of myristic, pentadecanoic, palmitic, heptadecanoic, stearic, nonadecanoic, eicosanoic, heneicosanoic and behenic fatty acids.     

Complete 1H and 13C NMR spectral assignment of 17-hydroxy epimeric sterols with planar A or A and B rings

Complete 1H and 13C spectral assignments of 17beta- and 17alpha-hydroxy epimers of three biologically active sterols (boldenone, 3-methoxyestradiol and 3-methoxydihydroequilenin) were achieved making use of one- and two-dimensional NMR techniques (1D-HOHAHA, DEPT, COSY, NOESY, TOCSY, HSQC and COLOC).     

Lipids and Lipophilic Components of the Aerial Part of Daucus sativus

The benzene extract of the aerial part ofDaucus sativusis analyzed. Sterols, aliphatic alcohols and their esters, triterpenes, and isoprenes make up >50%% of the extract mass. Carotenoids, -tocopherol, and other biologically active substances are also observed     

Combination of active components enhances the efficacy of Prunella in prevention and treatment of lung cancer

The efficacy of Prunella extracts in the prevention and treatment of lung cancer has been attributed to different components. In this study, an "active components combination model" hypothesis was proposed to explain the anti-tumor activity of Prunella. The efficacy of Prunella extracts from different regions was compared in vitro and in vivo, and the TNF-α activity in serum of tumor-bearing mice was also evaluated. High performance liquid chromatography (HPLC) was used to analyze the extracts and identify 26 common peaks. Prunella samples from different regions were classified by the cluster analysis method; both P. vulgaris L. from Bozhou and P. asiatica Nakai from Nanjing, which had the highest activities, were further divided into different classes. Six peaks from the HPLC analysis were very similar, and were identified as caffeic acid, rosmarinic acid, rutin, quercetin, oleanolic acid and ursolic acid. The total ratio of these compounds in Prunella from Bozhou and Nanjing were 1.0:14.7:3.9:1.0:4.4:1.4 and 1.0:14.8:4.0:0.8:5.6:1.8, respectively. Total triterpenes and total phenols in Prunella were separated by macroporous resin purification for activity studies. The results showed that total triterpenes and total phenols had anti-lung cancer activity and their combination significantly enhanced the activity. In addition, the combination also significantly increased the TNF-α content compared to total triterpenes or total phenols. The results indicated that the efficacy of Prunella against lung cancer was attributable to multiple components acting at an optimal ratio.     

Chemical constituents and bioactivities of the plants of genus flemingia roxb. Et ait. (Leguminosae)

The genus Flemingia Roxb. et Ait. (Leguminosae) has been used for disease prevention and therapy in China since ancient times. So the material basis of the pharmacological activity in the genus Flemingia should be clear for how to use this kind of traditional Chinese medicines more reasonably in pharmacology. Therefore, this review gives an account of the current knowledge on the chemical constituents, biological activities and pharmacological properties of the plants of the genus. Several different classes of compounds were previously isolated, which the main groups are flavones, particularly prenylated flavones, and triterpenes accompanied with sterols, anthraquinones, and others. The names and structures of the chemical constituents are given in this review. In addition, the pharmacological effects of the extracts and individual compounds (mainly for flavones) derived from the genus plants have been found, including neuroprotection, anti-inflammation, anti-oxidation, cytotoxicity, hormone-like effects, antimicrobial activities, and so on.     

Polyoxygenated Sterols from Freshwater Clam

Two new biologically active polyoxygenated sterols, 3,5,9‐trihydroxycholest‐7‐en‐6‐one ( 1 ) and cholest‐7‐ene‐3,6,9‐triol ( 3 ), together with one known sterone, topsentisterol D3 ( 2 ), were isolated from freshwater clam (Corbicula fluminea Muller ; an important cultured edible shellfish in Taiwan). The structure elucidation of sterols 1 – 3 were accomplished by ¹H‐ and ¹³C‐NMR, HMQC, and HMBC, and MS analyses. The sterols 1 – 3 displayed cytotoxicities against the human hepatoma Hep G2 cells (IC₅₀: 6.04±0.07, 40.78±4.28, and 10.57±0.51 μg/ml, resp.).     

Color versus bioactivity in the flowers of Bougainvillea spectabilis (Nyctaginaceae)

The methanolic extracts of Bougainvillea spectabilis (Nyctaginaceae) flowers (five different colors) were screened biologically by performing four bioassays: antibacterial, antifungal, brine shrimp lethality and phytotoxicity. It was observed that the methanolic extract of white flowers was the most biologically active among all tested extracts. The extracts of white, orange and shocking pink flowers inhibit, while the extracts of red and violet flowers promote, the growth of Lemna plants. The extract of white flowers also exhibits toxicity against shrimp larvae with a LD50 value of 33.5627 microg/mL. However, none of the tested samples gave positive responses against any tested fungi.     

Phytochemical Analysis of Phenolics,Sterols, and Terpenes in Colored Wheat Grains by Liquid Chromatography with Tandem Mass Spectrometry

The colored grain of wheat (Triticum aestivum L.) contains a large number of polyphenolic compounds that are biologically active ingredients. The purpose of this work was a comparative metabolomic study of extracts from anthocyaninless (control), blue, and deep purple (referred to here as black) grains of seven genetically related wheat lines developed for the grain anthocyanin pigmentation trait. To identify target analytes in ethanol extracts, high-performance liquid chromatography was used in combination with Bruker Daltonics ion trap mass spectrometry. The results showed the presence of 125 biologically active compounds of a phenolic (85) and nonphenolic (40) nature in the grains of T. aestivum (seven lines). Among them, a number of phenolic compounds affiliated with anthocyanins, coumarins, dihydrochalcones, flavan-3-ols, flavanone, flavones, flavonols, hydroxybenzoic acids, hydroxycinnamic acids, isoflavone, lignans, other phenolic acids, stilbenes, and nonphenolic compounds affiliated with alkaloids, carboxylic acids, carotenoids, diterpenoids, essential amino acids, triterpenoids, sterols, nonessential amino acids, phytohormones, purines, and thromboxane receptor antagonists were found in T. aestivum grains for the first time. A comparative analysis of the diversity of the compounds revealed that the lines do not differ from each other in the proportion of phenolic (53.3% to 70.3% of the total number of identified compounds) and nonphenolic compounds (46.7% to 29.7%), but diversity of the compounds was significantly lower in grains of the control line. Even though the lines are genetically closely related and possess similar chemical profiles, some line-specific individual compounds were identified that constitute unique chemical fingerprints and allow to distinguish each line from the six others. Finally, the influence of the genotype on the chemical profiles of the wheat grains is discussed.     

Studies on anti-allergic constituents in the leaves and stems of Anchientia salutaris var. martiana (Violaceae).

The anti-allergic active fractionation of hexane extracts of the leaves and stems of Anchietia salutaris var. martiana (family Violaceae) was performed by monitoring their activities with an in vitro bioassay system measuring the inhibitory effects on induced histamine release from guinea pig lung cells. Three known pentacyclic triterpenes (friedelin, alpha-amyrin, beta-amyrin) were isolated, but these compounds were inactive. Aliphatic hydrocarbons and methyl esters of fatty acids (palmitic, oleic, linoleic, linolenic acids) were detected in active fractions. All compounds isolated were detected for the first time in this medicinal plant.     

Study of the composition of biologically active compounds in chaga meal. Perspectives of application of chaga meal in pharmaceutical industry

Methods of utilization of chaga meal are reviewed. Extraction of chaga meal with ethanol, chloroform, and tert-butyl methyl ether gives compounds possessing a high antioxidant activity. A wide spectrum of other biologically active compounds was found in these extracts. These compounds can be used for production of drugs and biologically active additives.     

Haberlea rhodopensis: pharmaceutical and medical potential as a food additive

This review discusses the potential of Haberlea rhodopensis as a food additive. The following are described: plant distribution, reproduction, cultivation, propagation and resurrection properties; extraction, isolation and screening of biologically active compounds; metabolite changes during dehydration; phytotherapy-related properties such as antioxidant potential and free radical-scavenging activities, antioxidant skin effect, antibacterial activity, cytotoxic activity and cancer-modulating effect, radioprotective effect, chemoprotective effect, immunologic effect; present use in homoeopathy and cosmetics, pharmacological and economical importance; perspectives based on the ethnobotanical data for medicinal, cosmetic or ritual attributes. H. rhodopensis showed unique medical and pharmaceutical potential, related to antioxidant, antimicrobial, antimutagenic, anticancer, radioprotective, chemoprotective and immunological properties. H. rhodopensis extracts lack any cytotoxic activity and could be used in phytotherapy. The metabolic profiling of H. rhodopensis extracts revealed the presence of biologically active compounds, possessing antiradical and other physiological activities, useful for design of in vitro synthesised analogues and drugs.     

Identification of short‐chain poly‐3‐hydroxybutyrates in Saiga horn extracts using LC–MS/MS

Saiga horn extracts were analyzed with the goal of obtaining new information about compounds present in it. The purpose of this study is to find synthetic alternatives to Saiga horn extract, which is used in traditional Chinese medicine, by identifying potentially biologically active compounds in the extracts. Using high‐performance liquid chromatography coupled with high‐resolution mass spectrometry, we have been able to identify a series of short‐chain polyhydroxybutyrates in alcoholic extracts of Saiga horn. Optimized high‐performance liquid chromatography coupled with tandem mass spectrometry methods for analysis of short‐chain poly‐3‐hydroxybutyrates were developed and subsequently applied to investigate Saiga horn extract for the presence of these compounds, which might explain its biological actions, particularly for its antipyretic and procoagulant properties.     

Studies on differentiation-inducing activities of triterpenes.

Differentiation-inducing activity of over 180 extracts of crude drugs and plants was tested using mouse myeloid leukemia cell line (M1). The methanol extracts of clove (Syzygium aromaticum Merrill et Perry, Myrtaceae) showed remarkable induction of differentiation of M1 cells into macrophage-like cells. From the extract, oleanolic acid (1) and crategolic acid (2) were isolated as the active components. We also tested other triterpenes, such as oleananes, ursanes and dammaranes, to investigate the structure-activity relationship. Some triterpene aglycones showed differentiation-inducing activity, but triterpene glycosides showed little activity. Furthermore, the differentiation-inducing activity of these triterpene compounds was tested against human acute promyelocytic leukemia cell line (HL-60).