A novel sesquiterpenoid from the leaves of <Emphasis Type="Italic">Cinnamomum subavenium</Emphasis>

A novel sesquiterpenoid, subamol ((3-methoxy-5H-9,10-dihydroxybenzo[3,4]cyclohepta[1,2-f])inden-7-yl)methanol)) (1), along with six compounds, including one ionone: (+)-abscisic acid (2); and five benzenoids: syringaldehyde (3), trans-coumaric acid (4), cis-coumaric acid (5), vanillic acid (6), and p-hydroxybenzoic acid (7), were isolated from the leaves of Cinnamomum subavenium Miq (Lauraceae). These compounds were identified and characterized by physical and spectral evidence.     

A new <Emphasis Type="Italic">N</Emphasis>-containing cucurbitacin from <Emphasis Type="Italic">Hemsleya endecaphylla</Emphasis>

A new cucurbitacin, endecaphyllacin C, was isolated from the tubers of Hemsleya endecaphylla. The structure was elucidated as 2β,16α,20β,25-tetrahydroxy-24-acetylaminocucurbita-5-en-3,11,22-trione (1) on the basis of extensive 1D and 2D NMR techniques, including COSY, HMBC, HMQC, and NOESY correlations, as well as HR-FAB-MS analysis.     

Chemical constituents from the leaves of <Emphasis Type="Italic">Cinnamomum reticulatum</Emphasis>

Reticuol, a novel Cinnamomum sesquiterpenoid, has been isolated from Cinnamomum reticulatum Hay (Lauraceae), together with eight known compounds, p-hydroxybenzoic acid, isoanwulignan, 2,6-dimethyl1,7-octadiene-3,6-diol, a-tocopheryl quinone, kaempferol-3-O-(2″,4″-di-E-p-coumaroyl)-α-L-rhamnopyranoside, kaempferol-3-O-(3″,4″-di-E-p-coumaroyl)-α-L-rhamnopyranoside, pheophorbide a, and aristophyll C. The structure of reticuol was determined on the basis of spectroscopic analysis.     

<Emphasis Type="Italic">Z</Emphasis>-and <Emphasis Type="Italic">E</Emphasis>-conformers of <Emphasis Type="Italic">N</Emphasis>-chloroacetylcytisine

N-Chloroacetylcytisine was synthesized by acylation of (–)-cytisine. Stable Z- and E-conformers with respect to rotational isomerism around the N-12–CO bond were found in PMR spectra at room temperature. The point at which PMR resonances of the Z- and E-conformers coalesced upon heating was measured. The transition barrier between the conformers was estimated.     

A new 3,4-dihydroisocoumarin isolated from <Emphasis Type="Italic">Botryosphaeria</Emphasis> sp<Emphasis Type="Italic">.</Emphasis> F00741

A new 3,4-dihydroisocoumarin, named botryoisocoumarin A (1), was obtained from the fermentation culture of Botryosphaeria sp. F00741, together with two known ones, 3,8-dihydroxy-3-methylisochroman-1-one (2) and 4,8-dihydroxy-3-methylisochroman-1-one (3). Their structures were elucidated by spectroscopic analyses, including 1D and 2D NMR experiments and ESI mass spectrometry, and by comparison with those reported. Compound 1 was evaluated for its antitumor and antimicrobial activities in vitro.     

A new stilbene glycoside from the <Emphasis Type="Italic">n</Emphasis>-butanol fraction of <Emphasis Type="Italic">Veratrum dahuricum</Emphasis>

A new stilbene glycoside, 5-methylresveratrol-3,4′-O-β-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-β-D-glycoside (2), 4′-methylresveratrol-3-O-β-D-glycoside (3), oxyresveratrol-4′-O-β-D-glycoside (4), oxyresveratrol-3-O-β-D-glycoside (5), and oxyresveratrol-3,4′-O-β-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of 1D and 2D NMR data. Compounds 1–6 showed platelet aggregation inhibition, and compound 1 had an IC₅₀ value of 383.6 μM against platelet aggregation induced by AA. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 279–282, May–June, 2009.     

Molecular properties of the copolymers of <Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-diallyl-<Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-dimethylammonium chloride and maleic acid

The hydrodynamic and conformational properties of molecules of poly(N,N-diallyl-N,N-dimethylammonium chloride) and N,N-diallyl-N,N-dimethylammonium chloride-maleic acid copolymers of different compositions in solutions with various ionic-strength and pH values, as well as of the polyelectrolyte complex based on the copolymer with dodecyl sulfate anions in chloroform, are studied. For poly(N,N-diallyl-N,N-dimethylammonium chloride) molecules in a 1 M NaCl solution, the Kuhn segment length and the hydrodynamic diameter of the chain are estimated as A = 3.9 nm and d = 0.48 nm, respectively. In acidic solutions with pH 3.5, the copolymers demonstrate behavior typical for polyelectrolytes. In an alkaline solution with pH 13, when 1 M NaCl is added to the solution of the copolymer containing 29 mol % maleic acid units, there is an antipolyelectrolyte effect that manifests itself as an increase in the intrinsic viscosity of the copolymer and in the hydrodynamic radius of its molecules. It is found that an increase in the fraction of maleic acid units in the copolymer from 12 to 42 mol % brings about a reduction in the equilibrium rigidity of its macromolecules from 4.1 to 2.2 nm. The equilibrium rigidity of polyelectrolyte-complex molecules is higher than that of initial copolymer molecules owing to steric interactions arising between the aliphatic chains of dodecyl sulfate anions. In an electric field, the molecules of the complex are oriented owing to the induced dipole moment resulting from the displacement of dodecyl sulfate anions along the chain contour.     

A new ten-membered lactone from <Emphasis Type="Italic">Tubercularia</Emphasis> sp<Emphasis Type="Italic">.</Emphasis> TF5, an endophytic fungus of <Emphasis Type="Italic">Taxus mairei</Emphasis>

One new ten-membered lactone (1) named (Z)-4,6,9-trihydroxy-10-nonyl-3,4,5,6,9,10-hexahydrooxecin-2-one along with 5-methoxycarbonylmellein (2) and cytochalasin D (3) were isolated from the culture of the endophytic fungus strain Tubercularia sp. TF5, originally separated from the inner bark of Taxus mairei obtained in Fujian Province, Southeast China. The structures of compounds 1–3 were elucidated by spectroscopic methods. The antimicrobial and cytotoxic activities of 1 were analyzed but it showed no significant activities.     

A new cerebrogalactoside from <Emphasis Type="Italic">Juglans mandshurica</Emphasis>

A new cerebrogalactoside, Juglans cerebroside A (1), together with five known compounds, quercetin-3-O-β-D-galactopyranoside (2), myricetin-3-O-β-D-galactopyranoside (3), 2″E-quercetin-3-O-β-D-(6″″-O-[3″(4′″-hydroxyphenyl) propylene acyl]) glucopyranoside (4), gallic acid (5), and 2-methyl-1-hexadecanol (6) were isolated from the leaves of Juglans mandshurica Maxim. The structures of these compounds were determined by 1D, 2D NMR, and MS techniques.     

A new 18,19-secoursane triterpene from the leaves of <Emphasis Type="Italic">Diospyros kaki</Emphasis>

A new 18,19-secoursane triterpene together with five known compounds were isolated from the leaves of Diospyros kaki. The structure of the new compound was elucidated as 18,19-seco-3β-hydroxy-urs-12-en-18-one on the basis of spectroscopic methods.     

A new alloside from <Emphasis Type="Italic">Neocheiropteris palmatopedata</Emphasis>

A new compound, 2,4,6-trihydroxybenzoic acid 4-O-β-D-allopyranoside (1), together with four known compounds, sucrose (2), fructose (3), ecdysterone (4), and β-sitosterol (5) was isolated from the roots of Neocheiropteris palmatopedata (Baker) Christ. The new compound was identified based on extensive spectroscopic studies including HR-ESI-MS, FAB-MS, ¹H NMR, ¹³C NMR, DEPT, ¹H–¹H COSY, HSQC, HMBC, and NOESY spectra, and the known compounds were identified by their spectroscopic data analysis, comparison with reports in the literature, and co-chromatography with authentic standards. Compounds 2, 3, and 5 were obtained from the Neocheiropteris genus for the first time, and 4 was originally isolated from the plant.     

A new nortriterpenoid from <Emphasis Type="Italic">Phlomis umbrosa</Emphasis>

A new nortriterpenoid (1), together with five known compounds, was isolated from Phlomis umbrosa. The structure of 1 was elucidated by spectroscopic evidence.     

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.     

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.     

Lipids from <Emphasis Type="Italic">Halostachys caspica</Emphasis> and <Emphasis Type="Italic">Halocharis hispida</Emphasis>

The composition of lipids from the aerial parts of two species of halophytes from the family Chenopodiaceae, Halostachys caspica C. A. Mey. and Halocharis hispida Bge. was determined. Neutral lipids (NL, 62.1 and 54.2%, respectively) dominated the total lipids (TL) of these plants. More than a third of the NL were esters of aliphatic alcohols and phytosterols (FAE). Fatty acids 16:0, 18:1, and 18:2 dominated the acids of FAE; 16:0, 18:1, and 18:3, the phospholipids. The principal fatty acids of glycolipids were unsaturated acids (68.3 and 75.1%) with linolenic acid dominating (44.9 and 43.5%). Presented at the 7th International Symposium on the Chemistry of Natural Compounds, Tashkent, October 16–18, 2007. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 276–278, May–June, 2009.     

A new sesquiterpenoid from <Emphasis Type="Italic">Mallotus apelta</Emphasis>

A new sesquiterpenoid, malloapelin D (1), and a known schizandriside (2) were isolated from the roots of Mallotus apelta. Their structures were elucidated on the basis of spectroscopic methods including IR, MS, and 1D and 2D NMR.     

A new flavonoid from <Emphasis Type="Italic">Macrothelypteris torresiana</Emphasis>

A new flavonoid, 5,7-dihydroxy-2-(1-hydroxy-2,6-dimethoxy-4-oxo-cyclohex)-chromen-4-one (1), was isolated from the roots of Macrothelypteris torresiana (Gaud.) Ching. (Thelypteridaceae). The structure of the product was identified on the basis of detailed spectral analysis, including X-ray structure analysis.