Novel <Emphasis Type="Italic">S</Emphasis>-containing lactones from monoterpene oxides

A new type of S-containing terpene lactones was produced by the reactions of limonene-1,2-oxide and β-pinene-α-oxide with mercaptoacetic acid. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 220–223, May–June, 2007.     

Synthesis of 4<Emphasis Type="Italic">E</Emphasis>,7<Emphasis Type="Italic">Z</Emphasis>-tridecadien-1-ylacetate,a component of the <Emphasis Type="Italic">Phthorimaea opercucella</Emphasis> sex pheromone

A new synthetic approach to 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella (Zeller) potato moth sex pheromone, was developed using a highly stereoselective Claisen rearrangement and Wittig reaction. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 235–236, May–June, 2007.     

Influence of inhibitory compounds and minor sugars on xylitol production by <Emphasis Type="Italic">Debaryomyces hansenii</Emphasis>

To obtain in-depth information on the overall metabolic behavior of the new good xylitol producer Debaryomyces hansenii UFV-170, batch bioconversions were carried out using semisynthetic media with compositions simulating those of typical acidic hemicellulose hydrolysates of sugarcane bagasse. For this purpose, we used media containing glucose (4.3–6.5 g/L), xylose (60.1–92.1 g/L), or arabinose (5.9–9.2 g/L), or binary or ternary mixtures of them in either the presence or absence of typical inhibitors of acidic hydrolysates, such as furfural (1.0–5.0 g/L), hydroxymethylfurfural (0.01–0.30 g/L), acetic acid (0.5–3.0 g/L), and vanillin (0.5–3.0 g/L). D. hansenii exhibited a good tolerance to high sugar concentrations as well as to the presence of inhibiting compounds in the fermentation media. It was able to produce xylitol only from xylose, arabitol from arabinose, and no glucitol from glucose. Arabinose metabolization was incomplete, while ethanol was mainly produced from glucose and, to a lesser less extent, from xylose and arabinose. The results suggest potential application of this strain in xyloseto-xylitol bioconversion from complex xylose media from lignocellulosic materials.     

Reaction of frangula-emodin with <Emphasis Type="Italic">α</Emphasis>-bromoalkylmethylketones

The alkylation of 1,6,8-trihydroxy-3-methylanthraquinone (frangula-emodin) by α-bromoalkylmethylketones was investigated. Hydroxyls in the 1-and 8-positions of the β-derivatives were O-acylated. The compositions and structures of the prepared compounds were confirmed by elemental analysis and UV, IR, PMR, and ¹³C NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 324–326, July–August, 2007.     

Conpropine,a new alkaloid from the aerial part of <Emphasis Type="Italic">Convolvulus subhirsutus</Emphasis> from Uzbekistan

The known alkaloid convolvidine and a new base conpropine, for which the structure N-propylconvolvine was proposed, were isolated from total alkaloids from the aerial part of Convolvulus subhirsutus. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 601–602, November–December, 2008.     

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.     

Structure of a new xanthone from <Emphasis Type="Italic">Securidaca inappendiculata</Emphasis>

A new xanthone (1, 1,7-dihydroxy-2-methoxyxanthone), in addition to the known metabolites 1,7-dihydroxyxanthone (2), 24(R)-stigmast-7,22 (E)-dien-3α-ol (3), and 1,7-dimethoxyxanthone (4), was isolated from the roots of Securidaca inappendiculata. Compounds 1–4 were evaluated by anti-HIV assay and 1–3 showed anti-HIV-1inhibitory activity in vitro. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 348–349, July–August, 2008.     

Minor polyphenols from <Emphasis Type="Italic">Maackia amurensis</Emphasis> wood

The rare α,4,2′,4′-tetrahydroxydihydrochalcone, flavanones liquiritigenin and naringenin, isoflavones calycosin and 5-methoxydaidzein, and reduced stilbene dihydroresveratrol were isolated for the first time from Maackia amurensis wood. The structures of the pure compounds were established using 2D NMR COSY, NOE, HMBC, and HSQC experiments. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 575–577, November–December, 2008.     

Essential Oil Composition of Four <Emphasis Type="Italic">Achillea</Emphasis> Species from the Balkans and Its Chemotaxonomic Significance

The chemical composition of the essential oils of Achillea clavennae L., Achillea holosericea Sibth. & Sm., Achillea lingulata W. & K., and Achillea millefolium L. from the Balkans was determined by GC and GC/MS analyses. The main components were 1,8-cineole in A. holosericea, camphor in A. clavennae, β-pinene in A. millefolium, and τ-cadinol in A. lingulata. A detailed chemotaxonomic discussion is presented. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 555–558, November–December, 2005.     

Alpinine,A New Norditerpene Alkaloid from <Emphasis Type="Italic">Delphinium alpinum</Emphasis>

The known alkaloids deltaline, methyllycaconitine, elasine, and the new norditerpene alkaloid alpinine were isolated from the aerial part of Delphinium alpinum. The structure of the last was proposed as 1α,6β, 16β-trimethoxy-7-hydroxy-8-ethoxy-14α-propionyloxy-4β-(2″-methyl)succinylanthranoyloxymethyl-N-ethylaconitane on the basis of PMR, ¹³C NMR, IR, and mass spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 469–471, September–October, 2005.     

Lamiaceae carbohydrates. VI. Water-soluble polysaccharides from <Emphasis Type="Italic">Lophanthus chinensis</Emphasis>

The composition of water-soluble polysaccharides from the aerial part of Lophanthus chinensis Benth. (Lamiaceae) was studied. The dominant polymer LCW_H-2, which was a partially acetylated glucoarabinogalactan, the main chain of which was constructed of α-(1→6)-bonded galactopyranose, was isolated and characterized. Atoms C-2 and C-3 of the main chain had branches of single glucopyranose and arabinopyranose units and short chains of (1→3)-bonded arabinose. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 258–260, May–June, 2009.     

Antioxidant flavonoids from <Emphasis Type="Italic">Tamus communis</Emphasis> ssp. <Emphasis Type="Italic">cretica</Emphasis>

A new flavonoid, kaempferol-3,4′-di-O-α-L-rhamnopyranoside (1), and three known flavonoids (2–4) were isolated from the aerial parts of T. communis L. The structure of the new compound was elucidated on the basis of spectroscopic data. Compounds 1 and 2 showed significant antioxidant activity (IC₅₀ 187.151 ± 0.821 μM, and 92.079±0.513 μM, respectively), whereas compounds 3 and 4 showed moderate activity in DPPH free radical scavenging assays. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 295–297, May–June, 2009.     

Composition of essential oils from <Emphasis Type="Italic">Salvia anatolica</Emphasis>, a new species endemic from Turkey

The component composition of essential oils produced by steam distillation from flower heads, leaves, and stems of Salvia anatolica (Lamiaceae), a recently described new species endemic from Turkey, was studied by GC/FID and GC/MS. A total of 127 volatile components representing 96% of the oil was identified in essential oil from flower heads and leaves. It was found that the principal oil components of flower heads and leaves were α-pinene (10.9%), β-pinene (6.7%), α-copaene (6.3%), heptacosane (6.2%), and hexadecanoic acid (5.0%). A total of 109 volatile compounds representing 87.9% of the oil was characterized in essential oil isolated from stems. The principal oil components of stems were identified as hexadecanoic acid (27.2%), tetradecanoic acid (15.2%), dodecanoic acid (5.5%), and α-copaene (5.0%). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 552–555, November–December, 2007.     

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.     

Bacillomycin D from the Marine Isolate of <Emphasis Type="Italic">Bacillus subtilis</Emphasis> KMM 1922

Strain KMM 1922 of Bacillus subtilis, a producer of the antifungal iturin peptide antibiotic bacillomycin D, was isolated from a specimen of the Kuril sponge Stelletta validissima. The structure of the compound was proved using two-dimensional NMR spectroscopy, tandem electrospray mass spectrometry, and literature data. The peptide was shown to exhibit a pH-dependent cytotoxic activity. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 373–375, July–August, 2005.     

Glycosides from <Emphasis Type="Italic">Stevia rebaudiana</Emphasis>

A new laboratory method for isolating the glycosides stevioside and rebaudiosides A and C from leaves of Stevia rebaudiana was proposed. According to HPLC, the glycoside contents in plants grown in Russia (Voronezh Oblast’) and Ukraine (Crimea) were 5–6% (stevioside) and 0.3–1.3% (rebaudiosides A and C). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 68–71, January–February, 2007     

Xanthothone,a new nematicidal N-compound from <Emphasis Type="Italic">Coprinus xanthothrix</Emphasis>

Coprinus xanthothrix was found to have nematicidal activity. Xanthothone was isolated from culture extract guided by activity assay, which was identified as a novel natural product. Two other compounds were also isolated. These compounds showed nematicidal activity, with LD₅₀ value of 125–250 ppm both against Panagrellus redivivus and Meloidogyne incognita. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 161–162, March–April, 2008.     

Two new isoflavonoid monogalactosides from <Emphasis Type="Italic">Trifolium pratense</Emphasis> roots

Formononetin and the new isoflavonoid glycosides formononetin-7-O-β-D-galactopyranoside and inermin-3-O-β-D-galactopyranoside were isolated from Trifolium pratense L. roots. The structures of the isolated compounds were proved using chemical transformations and UV, PMR, and ¹³C NMR spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 21–23, January–February, 2008.     

Synthesis of isomeric 2-oxazolidinones from (1<Emphasis Type="Italic">R</Emphasis>,2<Emphasis Type="Italic">R</Emphasis>)-and (1<Emphasis Type="Italic">S</Emphasis>,2<Emphasis Type="Italic">S</Emphasis>)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

A synthesis is reported for (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-ones and (1′R,4R)-and (1′S,4S)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-ones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols. The effect of the experimental conditions on the formation of these compounds was studied. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1562–1570, October, 2007.     

Balanoinvolin,a new steroid derivative from <Emphasis Type="Italic">Balanophora involucrate</Emphasis>

A new compound, β-sitosterylglucoside-3′-O-linoleate, named balanoinvolin, and three known compounds coniferin, methylconiferin, and 4-O-β-D-glucopyranosylconiferyl aldehyde, were isolated from Balanophora involucrate Hook. f. and their structures were determined by MS and 1D/2D NMR spectra. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 315–317, May–June, 2009.