Separation and identification of steroidal compounds with cytotoxic activity against human gastric cancer cell lines <Emphasis Type="Italic">in vitro</Emphasis> from the rhizomes of <Emphasis Type="Italic">Paris polyphylla</Emphasis> var. <Emphasis Type="Italic">chinensis</Emphasis>

A novel steroidal saponin, along with 12 known steroidal compounds, was isolated from the rhizomes of Paris polyphylla var. chinensis. Spectral data, including two-dimensional NMR, showed that the structure of the novel saponin was 3β,21-dihydroxypregnane-5-en-20S-(22,16)-lactone-1-O-α-L-rhamnopyranosyl(1→2)-[β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside. The isolated steroidal compounds were evaluated for their cytotoxic activity on human gastric cancer cell line HepG₂, SGC7901, BxPC3. Diosgenin-3-O-α-L-rhamnopyranosyl(1→2)[α-L-rabinofuranosyl(1→4)]-β-D-glucopyranoside exhibited the most potent cytotoxic activity among the isolated steroids. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 556–560, November–December, 2007.     

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.     

Antifeedant and antifouling briaranes from the South China Sea gorgonian <Emphasis Type="Italic">Junceella juncea</Emphasis>

A new briarane diterpene, juncin ZII (1), along with three known briaranes (2–4), was isolated from the EtOH/CH₂Cl₂ extracts of the South China Sea gorgonian Junceella juncea. The structure of 1 was established by extensive spectroscopic analysis, including 1D and 2D NMR data. For compounds 1–4 and eight other briaranes (5–12) isolated from J. juncea previously, the antifeedant activity against second-instar larvae of Spodoptera litura and cytotoxicity against S. litura cells were investigated, and it was observed that they all exhibit medium antifeedant activity. Compounds 1, 8, 9, and 12 also showed potent antifouling activity against the larval settlement of barnacle Balanus amphitrite at nontoxic concentrations with EC₅₀ values of 0.004, 0.005, 2.82, and 0.447 μg/mL, respectively, while all compounds did not show obvious cytotoxicity against tumor cell lines K562, A549, Hela, and Hep-2. Their structure-activity relationship was discussed. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–47, January–February, 2009.     

Constituents and biological activity of the chloroform extract and essential oil of <Emphasis Type="Italic">Cupressus sempervirens</Emphasis>

The essential oil of the leaves of Cupressus sempervirens L. was isolated by hydrodistillation and tested against gram positive and gram negative bacteria, showing remarkable antimicrobial activity against Bacillus subtilis with minimum inhibitory concentration (MIC) 75%. The antiviral activity of the essential oil was tested against Herpes simplex virus type 1 (HSV-1), showing antiviral activity with virucidal percentages of 68.0% and 53.2% at concentrations of 1:32 and 1:64, respectively. We firstly reported the isolation of two epi-betulin esters of fatty acids from the CHCl₃ fraction of Cupressus sempervirens L. leaves, which were isolated and purified using HPLC, and identified using PMR and MS. The CHCl₃ fraction showed significant cytotoxicity against HeLa cells. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 265–268, May–June, 2009.     

Characterization of catechol 1,2-dioxygenase from cell extracts of <Emphasis Type="Italic">Sphingomonas xenophaga</Emphasis> QYY

Sphingomonas xenophaga QYY, capable of growing significantly on more than ten kinds of aromatic compounds as sole carbon source, was used to study characterization of catechol 1,2-dioxygenase (C12O) in cell extracts. Characterization of the crude C12O showed that the maximum activity was obtained at 40–70°C and pH 7.8–8.8. Metal ions had different influences on the activity of crude C12O. It was suggested that strain QYY possessed an inducible and ferric-dependent C12O. Kinetic studies showed that the value of V _max and K _m was 0.25 μmol catechol/L/mg protein/min and 52.85 μmol/L, respectively. In addition, the partial purification of C12O was achieved by a HiTrap Q Sepharose column chromatography. Supported by the National Natural Science Foundation of China (Grant No. 50608011) and the 39th Postdoctoral Funds of China (Grant No. 20060390983)     

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.     

<Emphasis Type="Italic">Rhizopus stolonifer</Emphasis> LAU 07: a novel source of fructosyltransferase

Increasing awareness of the importance of fructooligosaccharides (FOS) as ingredients of functional foods has led to intensive search of new sources of fructosyltransferases (FTase), enzymes responsible for the conversion of sucrose to fructooligosaccharides. A local strain of Rhizopus stolonifer isolated from spoilt orange fruit with high fructosyltransferase activity (U _t) of 12.31–45.70 U mL⁻¹ during a fermentation period of 24–120 h is herein reported. It showed low hydrolytic activity (U _h) in the range of 0.86–1.78 U mL⁻¹ during the same period. FOS yield of 34 % (1-kestose, GF₂, nystose, GF₃) was produced by FTase obtained from a 72 h-old culture using 60 g of sucrose per 100 mL of the substrate. When the isolate was grown in a defined submerged medium, its pH dropped sharply from the intial value of 5.5 to 1.0 within 24 h, and this value was maintained throughout the fermentation. The biomass content ranged from 8.8 g L⁻¹ at 24 h of fermentation to reach the maximum of 10 g L⁻¹ at 72 h. It was reduced to 5.6 g L⁻¹ at the end of 120 h of fermentation. This report represents the first reference to a strain of Rhizopus as a source of FTase for the production of FOS. The high U _t/U _h ratio shown by this isolate indicates that it may be a good strain for the industrial and commercial production of FOS. However, there is a need of further optimization of the bioprocess to increase the conversion efficiency of sucrose to FOS by the enzyme.     

Anticoccidial constituents from the stem bark of <Emphasis Type="Italic">Turraeanthus africanus</Emphasis>

In order to study some biological active products, phytochemical investigation of the stem bark of Turraeanthus africanus have led to the isolation of a novel compound 1, a new benzoic acid derivative, named turraeanthin C, and two known compounds sesamin (2) and stigmasterol. The structures of these compounds were established by spectral analysis, including two-dimensional nuclear magnetic resonance. The extract and the isolated compounds 1 and 2 showed noteworthy activity against Toxoplasma gondii intracellular parasite in mammals. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 564–566, November–December, 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.     

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.     

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.     

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.     

Fungicidal lipid-transfer peptide from <Emphasis Type="Italic">Daucus carota sativa</Emphasis> seeds

A non-specific lipid-transfer peptide (nsLTP) with fungicidal activity was isolated from Daucus carota sativa carrot seeds. Peptides were purified by a method including aqueous extraction, anion-exchange chromatography over CM-TSK-650M, and HPLC over a column of 250/8/4 Protein@Peptide C₁₈ using an acetonitrile gradient. The molecular weight of the peptide was determined as 9624 Da by mass spectrometry. The peptide was found to have fungicidal activity against the pathogenic fungus Verticillium dahliae. The partial N-terminal sequence, which was highly homologous to the N-terminal sequences of lipid-transfer peptides from seeds of rice, tobacco, and maize, was determined using Edman automated sequencing. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 371–373, July–August, 2007.     

Research on the strong transglycosylation activity in <Emphasis Type="Italic">Aspergillus niger</Emphasis>

Aspergillus niger M-1 strain shows strong transglycosylation activity. A gene of it was introduced into Escherichia coli, and isomalto-oligosaccharides were isolated by a chemical enzymatic method in order to measure the transglycosylation activity. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 606–607, November–December, 2008.     

New genistein monogalactoside from the aerial part of <Emphasis Type="Italic">Trifolium pratense</Emphasis>

Formononetin, prunetin, genistein, genistin, and a new genistein glycoside genistein-7-O-β-D-galactopyranoside were isolated from the aerial part of Trifolium pratense L. The structures of the isolated compounds were established based on chemical transformations and UV, ¹H, and ¹³C NMR spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 141–143, March–April, 2008.     

Denitrification in presence of benzene,toluene, and <Emphasis Type="Italic">m</Emphasis>-xylene

Denitrification of the electron donors toluene-C(15–100 mg/L), m-xylene-C (15–70 mg/L), benzene-C (5–25 mg/L), and acetate-C as experimental reference (50–140 mg/L) was carried out in batch culture. An initial concentration of 1.1±0.15 g of volatile suspended solids/L of denitrifying sludge without previous exposure to aromatic compounds was used as inoculum. The results showed toluene and nitrate consumption efficiency (E _T and E _N′ respectively) of 100%. Toluene was completely mineralized (oxidized) to CO₂. In all cases, the N₂ (γ_N2) and HCO ₃ ⁻ yields (γ_HCO3) were 0.97±0.01 and 0.8±0.05, respectively. The consumption efficiency (E _x ) of m-xylene (53±5.7%) was partial. The γ_N2 and γ_HCO3 were 0.96±0.01 and 0.86±0.02, respectively. Benzene was not consumed under denitrifying conditions. The specific consumption rates of toluene (q _T ) and m-xylene (q _X ) were lower than that of acetate (q _A ). The differences in specific consumption rates were probably owing to the negative effect of benzene, toluene, and isomers of xylene on the cell membrane.     

A new C-glucoside from <Emphasis Type="Italic">Commelina communis</Emphasis>

A new C-glucoside, 3,4-epoxy-5-hydroxymethyl benzoate 2-C-β-glucoside (1), together with a known alkaloid, 1H-indole-3-carbaldehyde (2), were isolated from the whole plant of Commelina communis L. The structures of these compounds were determined by 1D, 2D NMR and MS techniques. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 51–52, January–February, 2009.     

Synthesis and anti-HIV-1 activity of S-dihydro(alkyloxy)benzyloxypyrimidine derivatives

Several 2-heteroaryl-, 2-heteroarylcarbonylmethyl-, 2-arylcarbonylmethyl, and 2-arylethyl derivatives of S-dihydro(alkyloxy)benzyloxypyrimidines have been synthesized and the anti-HIV activities of these compounds were tested in C8166 cell and against RT enzyme. It was found that some of these compounds showed good activity against HIV-1 (EC ₅₀ = 0.014–0.8 μM) with low toxicity (CC ₅₀ value of 222–564 μM) and high selectivity (SI value of 278–37743). The structure-activity relationships (SAR) of these compounds have also been discussed. First two authors contributed equally to this work Correspondence: Yan-Ping He, Key Laboratory of Medicinal Chemistry for Natural Resource Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People’s Republic of China; Yong-Tang Zheng, Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Chinese Academy of Sciences, Kunming Institute of Zoology, Kunming, Yunnan 650223, People’s Republic of China.     

Three antibacterial compounds from the roots of <Emphasis Type="Italic">Pteris multifida</Emphasis>

A new eudesmane-type sesquiterpenoid, 3β-caffeoxyl-1β,8α-dihydroxyeudesm-4(15)-ene (1), together with two known compounds including ludongnin V (2) and isoneorautenol (3), were isolated from the roots of Pteris multifida. Their structures were determined by spectral and chemical methods, with their antibacterial activities being evaluated by the microdilution technique, respectively. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 41–43, January–February, 2009.