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.     

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.     

Alkaloids from <Emphasis Type="Italic">Nitraria schoberi</Emphasis>. O-acetylnitraraine

The new alkaloid O-acetylnitraraine was isolated from the aerial part of Nitraria schoberi. Its structure was established using spectral data and chemical transformations. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 472–473, September–October, 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     

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.     

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.     

Flavonoids from the aerial part of <Emphasis Type="Italic">Vicia subvillosa</Emphasis>

The new flavone glucoside viscioside, luteolin-4′-O-β-D-galactopyranoside, in addition to the known flavonoids apigenin, luteolin, quercetin, cinaroside, luteolin-4′-O-β-D-glucoside, and isoquercitrin were isolated from the aerial part of Vicia subvillosa. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 30–31, January–February, 2007.     

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.     

Chemotypical Variability of Leaf Oils in <Emphasis Type="Italic">Elephantopus scaber</Emphasis> from 12 Locations in China

The chemical constituents of leaf oils of Elephantopus scaber L. from 12 locations in Southern China, including three provinces and Hong Kong, were investigated using GC/MS. A total of 24 compounds were detected, of which 20 were identified by their mass spectra fragmentation patterns. The major compounds include hexadecanoic acid (8.19–39.22%), octadecadienoic acid (trace - 29.22%), five alkane homologues, i.e., n-tetradecane (1.19–5.26%), n-pentadecane (3.22–12.05%), n-hexadecane (2.38–16.26%), n-heptadecane (2.48–15.32%), and n-octadecane (1.39–9.59%), as well as tetramethylhexadecenol (2.06–4.31%). Hierarchical cluster analysis classified the leaf oils into two groups. Two main chemotypes of leaf oils in E. scaber were thus identified, one rich in hexadecanoic acid and octadecadienoic acid, and the other rich in the five alkane homologues. __________ Published in Kimiya Prirodnikh Soedinenii No. 5, pp. 403–404, September–October, 2005.     

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.     

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.     

Low-molecular-weight phenolic compounds from <Emphasis Type="Italic">Hedysarum theinum</Emphasis> roots

Isoflavonoids (−)-medicarpin, (−)-vestitol, formononetin, 8-hydroxydaidzein, and 6″-O-acetylononin were isolated for the first time in addition to (−)-catechin, (−)-epicatechin, protocatechoic acid, raspberry ketone, and rhododendrol from the alcohol extract of Hedysarum theinum roots. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 26–28, January–February, 2008.     

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.     

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.     

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.     

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.     

Phenylethanoid glycosides from the bark of <Emphasis Type="Italic">Fraxinus mandschurica</Emphasis>

The new phenylethanoid glycoside calceolarioside A-2′-α-L-rhamnopyranoside and calceolarioside A and calceolarioside B were isolated from the bark of Fraxinus mandschurica Rupr. for the first time by column chromatography. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 283–284, May–June, 2009.     

New acyl derivatives of <Emphasis Type="Italic">N</Emphasis>-deacetyllappaconitine

New N-acylates of the norditerpenoid alkaloid N-deacetyllappaconitine that were modified in the aromatic ring and are interesting as potential pharmacologically valuable compounds were prepared. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 275–279, May–June, 2008.     

<Emphasis Type="Italic">O</Emphasis>-nitrates of hydroxyamino acids serine and threonine

The synthesis of O-nitrates of natural hydroxyamino acids serine and threonine was described for the first time. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 52–53, January–February, 2008.