Synthesis of 20-hydroxyecdysone 6-chloronicotinates

New esters 2-5 that contain 6-chloropyridine groups characteristic of the alkaloid epibatidine were prepared by acylation of 20-hydroxyecdysone (1) by 6-chloronicotinoylchloride. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 328–331, May–June, 2009.     

Phytoecdysteroids from <Emphasis Type="Italic">Serratula komarovii</Emphasis>

Integristerone A and 2-deoxy-20-hydroxyecdysone were observed for the first time in the aerial and subterrean organs of the eastern Asian plant Serratula komarovii Iljin. -Ecdysone was not found in the plants. The dynamics of phytoecdysteroid content (integristerone A, 20-hydroxyecdysone, and 2-deoxy-20- hydroxyecdysone) in the vegetative and generative organs of this species were investigated.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 404–406, September–October, 2004.     

Naupliolide, a sesquiterpene lactone with a novel tetracyclic skeleton from Nauplius graveolens subsp. odorus

The aerial parts of Nauplius graveolens subsp. odorus (Schousb) Wikl. afforded a novel sesquiterpene lactone (1) named naupliolide together with the known 6,7,9,10-tetradehydroasteriscanolide 2 and asteriscunolides A-D 3a-d. The structure of compound 1 corresponds to a novel skeleton of 14,15-dimethyl-7,13-dioxotricyclic[6.4.0.0^9,11]dodeca-12,13-olide, and was established on the basis of spectroscopic methods including 2D-NMR. The coexistence of naupliolide 1 together with the structurally related sesquiterpene lactones asterisculolides A-D (3a-d) and 6,7,9,10-tetradehydroasteriscanolide 2, seems to indicate their biosynthetic relationship.     

Ecdysteroids from Silene claviformis

The ecdysteroid content ofSilene claviformishas been analyzed and the four major compounds have been identified as 20-hydroxyecdysone, 2-deoxy-20-hydroxyecdysone, 2-deoxyecdysone, and integristerone A. Two new minor compounds have also been identified An erratum to this article can be found at     

Influence of different extraction methods on the yield and linalool content of the extracts of Eugenia uniflora L

This work has been developed using a sylvestral fruit tree, native to the Brazilian forest, the Eugenia uniflora L., one of the Mirtaceae family. The main goal of the analytical study was focused on extraction methods themselves. The method development pointed to the Clevenger extraction as the best yield in relation to SFE and Soxhlet. The SFE method presented a good yield but showed a big amount of components in the final extract, demonstrating low selectivity. The essential oil extracted was analyzed by GC/FID showing a large range of polarity and boiling point compounds, where linalool, a widely used compound, was identified. Furthermore, an analytical solid phase extraction method was used to clean it up and obtain separated classes of compounds that were fractionated and studied by GC/FID and GC/MS.     

Synthesis of 20S-protopanaxadiol 20-O-β-D-glucopyranoside, a metabolite of Panax ginseng glycosides, and compounds related to it

A preparative semi-synthetic method was developed to prepare 20S-protopanaxadiol 20-O-β-Dglucopyranoside (1), a metabolite of Panax ginseng glycosides. The 20-O-•-D-glucopyranosides of 20S-hydroxydammar-24-en-3,12-dione, 3β,20S-dihydroxydammar-24-en-12-one, and 3β,12α, 20S-trihydroxydammar-24-ene were synthesized for the first time. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 364–369, July–August, 2006.     

Study of alkaloids of the Siberian and Altai flora. 10. Synthesis of N(20)-deethyllappaconitine derivatives

Efficient procedures were developed for N-deethylation of lappaconitine to give N(20)-deethyllappaconitine. Alkyl derivatives of N(20)-deethyllappaconitine, including labeled lappaconitine, and N(20)-acetoxy-N(20)-deethyllappaconitine were prepared for the first time. The assignments of the signals for the carbon atoms in the ¹³C NMR spectra of lappaconitine and related lappaconine were refined using ¹³C—¹³C 2D INADEQUATE and 2D ¹³C—¹H correlation experiments.     

Biologically Active Substances from Cacalia hastate Leaves. 1. Carbohydrates from Leaves and Their Hypoglycemic Activity

Leaves of Cacalia hastate L. (Asteraceae) were composed of free sugars, water-soluble polysaccharides (arabinogalactan type), pectinic substances, hemicelluloses, and cellulose. The hypoglycemic activity was determined for the water-soluble polysaccharides and pectinic substances.     

Glucofructans from <Emphasis Type="Italic">Taraxacum officinale</Emphasis> roots

The structure of glucofructans from Taraxacum officinale roots growing in Buryatia was studied by chemical, chromatographic, and spectral methods. It was found that fructose,glucose, saccharose, 1-kestose, and nystose were present in the free state. The structures of the two dominant polymeric compounds, TGf-1 (5.7 kDa) and TGf-2 (2.6 kDa), which were linear inulin-type macromolecules consisting of fructofuranose units bonded through β-(2→1)-bonds, were studied. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 125–127, March–April, 2009.     

A new component from <Emphasis Type="Italic">Eupatorium cannabinum</Emphasis>

A new compound of formula C₂₈H₄₈O with mp 179-180°C (aqueous ethanol) that was called eucanbin was isolated pure by column chromatography of the ethanol extract of the aerial part of Eupatorium cannabinum L. The structure 24α-methylcholest-20(21)-en-3β-ol was assigned based on chemical and spectral data. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 318–320, May–June, 2009.     

The chemical composition of fruits of <Emphasis Type="Italic">Pistacia atlantica</Emphasis> desf. subsp. <Emphasis Type="Italic">atlantica</Emphasis> from Algeria

The chemical composition of the fruits of the north algerian ecotype Pistacia atlantica subsp. atlantica was determined and compared to other fruits of different species in the genus growing in south Algeria and other Mediterranean regions. These fruits were analyzed for their dry matter, protein, crude oil, ash, fatty acids, and phytosterol content. The main fatty acids identified by gas chromatography were oleic (54.15%), linoleic (28.84%), and palmitic (12.21%) acids. The fruits of the north ecotype were found to be rich in protein, oil, fiber, and unsaturated fatty acids, suggesting that they may be valuable for food uses. The sterols isolated were campesterol, stigmasterol, β-sitosterol, and Δ⁵-avenasterol with β-sitosterol as the major constituent (85%±0.85). The biochemical data indicated an elevated MUFA rate (∼56%) in pistacia oil which may be important against certain pathologies for its nutritional and preventive virtues. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 103–105, March–April, 2007.     

Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus

A method for preparative production of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT₈ was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (3) under Koenigs—Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D-glucopyranoside if equimolar amounts of (2) and (3) were used. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–48, January–February, 2006.     

Triterpene glycosides from Kalopanax septemlobum. VII. Minor glycosides from stems of Kalopanax septemlobum var. maximowiczii and Kalopanax septemlobum var. typicum

Sixteen triterpene glycosides, three of which were new, hederagenin 28-O-β-D-glucuronopyranosyl ester and 28-O-β-D-gentiobiosyl ester and oleanolic acid 3-O-α-L-arabinopyranoside, were isolated from stem bark of Kalopanax septemlobum. The glycoside contents in stem bark of two varieties, maximowiczii and typicum, were compared. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 49–53, January–February, 2006.     

Alkaloids from Plants of the Nitraria Genus. Structure of Sibiridine

The new alkaloid sibiridine was isolated from the aerial parts of Nitraria sibirica and N. schoberi. Its structure was established using spectral data and chemical transformations. Its synthesis was carried out.     

2-Phenoxychromone flavonoid glycoside from <Emphasis Type="Italic">Artemisia rupestris</Emphasis>

A new 2-phenoxychromone glycoside was isolated from the n-butanol extract of Artemisia rupestris. Its structure was established as 6-demethoxy-4′-O-methylcapillarisin-7-O-β-glucoside based on spectral data.     

Determination of the volatile constituents and total phenolic contents of some endemic Stachys taxa from Turkey

The total phenolic contents and the essential oil compositions of the previously unknown Stachys taxa (Labiatae), including Stachys pinardii Boiss, Stachys cretica L. subsp. mersinaea (Boiss.) Rech., and Stachys aleurites Boiss. & Heldr., all endemic to Turkey, were studied. Their essential oil compositions were investigated by GC-MS. It was found that the main constituents were α-curcumene (34.10%) for S. cretica, cedrandiol (25.26%) and caryophyllene dioxide (22.15%) for S. pinardii, and (Z)-β-caryophyllene (31.60%) for S. aleurites. The total phenolic contents, by the Folin-Ciocalteu colorimetric method, of the S. pinardii, S. cretica subsp. mersinaea, and S. aleurites methanolic extract were found to be 600.74±0.23, 1200.94±0.11, and 900.61±0.06 mg gallic acid equivalent (GAE)/100 g in dried herb, respectively. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 141–143, March–April, 2006.     

Antimalarial 20-membered macrolides from Streptomyces sp. BCC33756

Two new natural products, samroiyotmycins A (1) and B (2), along with two naturally new novclobiocin 101 (3) and 4-hydroxy-3-(3-methylbut-2-enyl)benzamide (5), and five known substances including neoantimycin, clorobiocin (4), 29-O-methylabierixin, daidzein, and 1-(3-indolyl)-2,3-dihydroxypropan-1-one have been isolated from Streptomyces sp. BCC33756. Their chemical structures were determined based on NMR spectral information and the relative stereochemistry of compound 1 was determined by X-ray crystallographic data. Both samroiyotmycins A and B exhibited antimalarial activity against Plasmodium falciparum K1—multi-drug resistant strain, with IC₅₀ values of 3.65 and 3.16 μg/mL, respectively. Compound 1 was inactive against both cancerous (MCF-7, KB) and non-cancerous (Vero) cells, while compound 2 displayed cytotoxicity against Vero cell with IC₅₀ value of 29.57 μg/mL.     

Essential oil composition of aerial parts from Algerian Anacyclus monanthos subsp. cyrtolepidioides (Pomel) Humphries

The chemical composition of the essential oil from the aerial parts of Anacyclus monanthos subsp. cyrtolepidioides (Pomel) Humphries (Asteraceae) growing in a semi-arid region of Algeria was investigated for the first time. The essential oil was obtained by hydrodistillation and fully characterized by gas chromatography-mass spectrometry (GC-MS). A total of 97 compounds were identified. The essential oil was found to be rich in trans-chrysanthenyl acetate (9.8 ± 2.0%), (E)-β-farnesene (7.4 ± 1.5%), germacrene D (6.9 ± 1.3%) and myristicin (4.8 ± 0.8%).     

Partial characterization of an inducible amylase produced byPseudomonas cellulosa

Applied Biochemistry and Biotechnology - The products secreted byPseudomonas cellulosa were examined to determine if this bacterium could be used in a fluidized-bed bioreactor system to produce...