Chemistry of Natural Compounds (v.44, #2)

Neutral lipids from seeds of Asteraceae plants by N. T. Ul’chenko; N. P. Bekker; A. I. Glushenkova (147-150).
Lipids from seeds of three plants of the Asteraceae family, Cousinia franchetii, Arctium leiospermum, and Rhaponticum integrifolium, were studied. The principal constituents of lipids from the three plants were shown to be acylglycerides of ordinary fatty acids and oxygenated fatty acids using chemical and chromatographic analyses. The composition of the ordinary unoxidized and epoxy acids was determined by GC.
Keywords: Asteraceae; Cousinia franchetii; Arctium leiospermum; Rhaponticum integrifolium; neutral lipids; fatty acids; epoxy-and hydroxyacids

Physicochemical properties and fatty acid composition of Juglans regia cultivars grown in Serbia by B. Rabrenovic; K. Picuric-Jovanovic; S. Sobajic (151-154).
Tree cultivars (Jupiter, Sejnov, and Elit) of walnut (Juglans regia L.) were collected during the 2004 harvest from Cacak, Central Serbia. The chemical composition, including moisture, total oil content, crude protein, ash, and carbohydrates, was determined. Afterwards, two techniques of oil extraction were implemented: cold pressing extraction and organic solvent extraction. Iodine value, saponification value, acid value, and peroxide value of obtained walnut oils were analyzed. The fatty acid composition of the walnut oils was determined using gas chromatography with flame ionization detector. The oleic acid content of the oils ranged from 15.9–23.7% of the total acids, while linoleic acid content ranged from 57.2–65.1% and the linolenic acid from 9.1–13.6%. The process of oil extraction had no significant effect on content and composition of fatty acids.
Keywords: walnut oil; cold pressing extraction; solvent extraction; physical and chemical constants; fatty acid composition

The effect of methanol on the change of phospholipid composition of germinating cotton seeds was studied. It was shown that adding methanol to the germination medium caused the formation of the new phospholipid phosphatidylmethanol.
Keywords: phospholipids; germination; methanol; phosphatidylmethanol

Quantitative study of antioxidant properties of phenolcarboxylic acids from Larix sibirica bark by V. R. Khairullina; G. G. Garifullina; A. Ya. Gerchikov; L. A. Ostroukhova; V. A. Babkin (158-162).
Antioxidant properties of caffeic, ferulic, vanillic, and 4-hydroxybenzoic acids isolated from Larix sibirica Ledeb. bark were studied using model radical-chain reactions for oxidation of propan-2-ol and 1,4-dioxane under kinetic control. Quantitative characteristics of the antioxidant activities were determined as effective rate constants fkIn for oxidation chain termination of the phenolcarboxylic acids. It was found that caffeic acid had the highest antioxidant activity among the investigated natural compounds.
Keywords: phenolcarboxylic acids; antioxidants; radical-chain reactions; initiated oxidation; inhibition rate constant

A new biphenyl derivative from an unidentified marine fungus E33 by Chunyuan Li; Weijiang Ding; Zhigang She; Yongcheng Lin (163-165).
A new biphenyl derivative 3,5′-dihydroxy-4′,5-dimethoxy-2′-methyl-[1,1′-biphenyl]-2-carboxylic acid methyl ester (1), was isolated from the culture broth of a fungus isolated from the rhizosphere soil of mangrove root on the South China Sea. The structure of 1 was determined by comprehensive spectroscopic methods, primarily 2D NMR techniques.
Keywords: mangrove; marine fungus; biphenyl

Two new linear furanocoumarin glycosides from Angelica dahurica by Xiaodong Jia; Xu Feng; Xingzeng Zhao; Yunfa Dong; Youyi Zhao; Hao Sun (166-168).
Two new linear furanocoumarin glycosides, tert-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosyl-oxypeucedanin hydrate (1) and sec-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosyl-oxypeucedanin hydrate (2), were isolated from the fresh roots of Angelica dahurica. The structures of new compounds were elucidated on the basis of spectral analysis.
Keywords: Angelica dahurica; linear furanocoumarin glycosides; structure elucidate

Lavandoside from Lavandula spica flowers by V. A. Kurkin; M. Lamrini; S. G. Klochkov (169-170).
The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was established using UV, NMR, and mass spectra and chemical transformations.
Keywords: phenylpropanoids; cinnamic acids; ferulic acid glucoside; lavandoside; Lavandula spica L

New flavonoid-C-glycosides from Triticum aestivum by Xu Feng; Dong Jiang; Yu Shan; Tingbo Dai; Yunfa Dong; Weixing Cao (171-173).
Two new flavonoid-C-glycosides named triticuside A (1a) and triticuside B (1b) were isolated from bran of Triticum aestivum L. The structures of the two new compounds were elucidated by spectral techniques including 1H NMR, 13C NMR as well as HSQC, HMBC, and COSY.
Keywords: Triticum aestivum L; triticuside A; triticuside B; flavonoid-C-glycoside; structure elucidation

Tricetin 4′-O-α-L-rhamnopyranoside: A new flavonoid from the aerial parts of Erica arborea by H. Nazemiyeh; F. Bahadori; A. Delazar; M. Ay; G. Topcu; U. Kolak; L. Nahar; A. A. Auzie; S. D. Sarker (174-177).
Reversed-phase preparative HPLC purification of the methanol (MeOH) extract of the aerial parts of Erica arborea resulted in the isolation of a new flavonoid glycoside, tricetin 4′-O-α-L-rhamnopyranoside, together with the known flavonoid, isorhamnetin 3-O-α-L-rhamnopyranoside. The structures of these compounds were determined by spectroscopic means. The antioxidant properties of these compounds were assessed by the DPPH assay.
Keywords: Erica arborea; Ericaceae; flavonol; tricetin; glycoside; antioxidant activity; DPPH; chemical taxonomy

New genistein monogalactoside from the aerial part of Trifolium pratense by A. A. Drenin; E. Kh. Botirov; E. V. Petrulyak (178-181).
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.
Keywords: Trifolium pratense L; isoflavonoids; formononetin; prunetin; genistein; genistin; genistein-7-O-β-D-galactopyranoside; inermin-3--D-galactopyranoside

Aqueous alkaline depolymerization of technical hydrolysis lignin (THL) was carried out with a 5% NaOH solution at a temperature of 180°C for 6 hours, the ratio between the biomass and depolymerizing agent being 1:8. The poplar wood sawdust was treated under the same conditions for 2 hours, where anthraquinone was added as a catalyst (0.5 wt %). The poplar wood bark was treated for 4 hours, without anthraquinone. Compounds contained in the aqueous phase were extracted three times by means of toluene for a ratio between the organic and aqueous phases equal to 1:5, 1:5 and 1:5. The compounds 2-methoxyphenol, 2,6-dimethoxyphenol, 4-hydroxy-3-methoxybenzaldehyde, 1-(4-hydroxy-3-methoxyphenyl)ethanone, 4-hydroxy-3,5-dimethoxybenzaldehyde, etc., were identified through GC-MS analysis in obtained extracts.
Keywords: lignin; poplar wood; alkaline treatment; extraction; low-molecular phenol compounds

Brugnanin (1), a neolignan dioate, was isolated from a mangrove plant Bruguiera gymnorrhiza. Based on spectroscopic interpretation of MS, IR, and NMR data, 1 was elucidated as (7R*,8S*,E)-3-hydroxy-5,5′-dimethoxy-7-O-4′,8-3′-neolignan-7′-ene-9,9′-dioic acid dioctadecyl ester. MTT assay showed that 1 had weak inhibitory activity against growth of CNE-1 nasopharyngeal carcinoma cell line.
Keywords: brugnanin; mangrove; Bruguiera gymnorrhiza; MTT; CNE-1

Cichoric acid and caftaric acid are the main phenolic compounds in Echinacea purpurea tops. The level of these phenolic compounds in E. purpurea extracts is affected by different factors such as seasonal variations, drying methods, extraction methods, and growing location of the plant. HPLC analysis of caffeic acid derivatives in extracts of Echinacea purpurea (Cultivar) aerial parts, produced by boiling water extraction and ethanol-water extraction methods, showed various levels of the derivatives. Our findings revealed that the Iranian cultivated E. purpurea had a high level of cichoric acid (3.5–5.7 %). Caftaric acid was also the main phenolic compound in E. purpurea tops (3.1–4.5 %). After 2 h of boiling water extraction, the level of cichoric acid was 5.7 %, whereas the level of this acid in 60:40 ethanol-water extraction did not exceed 3.9 %.
Keywords: Echinacea purpurea; aerial parts; caftaric acid; cichoric acid; HPLC; extraction methods

Synthesis of glycyrrhetic acid derivatives by J.-P. Yong; J.-W. Wang; H. A. Aisa; L.-J. Liu (194-196).
11-Deoxyglycyrrhetinic acid (DGA) (2) was produced by Clemmensen reduction of the C-11 carbonyl of 18β-glycyrrhetic acid (GA) (1). Four derivatives of GA and DGA (3a–3d) were synthesized. Their structures were elucidated using spectral data (IR, mass, 1H, 13C NMR).
Keywords: synthesis; glycyrrhetic acid; 11-deoxyglycyrrhetinic acid; derivatives

Synthesis and biological activity of amination products of the alkaloid securinine by S. G. Klochkov; S. V. Afanas’eva; V. V. Grigor’ev (197-202).
A method for stereospecific synthesis of allomargaritarin and other amination products of the natural alkaloid securinine was developed. Stereoselective nucleophilic addition of an amine at the double bond of the azobicyclooctane moiety of securinin was achieved by using ytterbium triflate as the catalyst. The biological activity of securining caused by adding pharmacophores to the molecule was shown to change experimentally.
Keywords: alkaloids; securinine; allomargaritarin; ytterbium triflate; stereospecific synthesis

Xanthothone, a new nematicidal N-compound from Coprinus xanthothrix by Ya Jun Liu; Yi Liu; Ke Qin Zhang (203-205).
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.
Keywords: Coprinus xanthothrix; nematicidal activity; N-compounds; xanthothone

Triterpenoid alkaloids from Buxus rugulosa by H. Guo; X. H. Cai (206-207).
A new triterpenoid alkaloid, buxrugulosamine (1), together with four known, ones was isolated from the ethanolic extract of the leaves and twigs of Buxus rugulosa. Their structures were determined by analysis of spectral data or comparing them with authentic samples.
Keywords: Buxus rugulosa; triterpenoid alkaloids

Molecular structure of N-(o-and p-hydroxybenzyl)cytisine by U. S. Makhmudov; Sh. B. Rakhimov; B. Tashkhodzhaev; M. G. Levkovich; V. I. Vinogradova (208-212).
The molecular structures of N-(o-and p-hydroxybenzyl)cytisine were investigated by NMR spectroscopy, x-ray structure analysis, and molecular modeling. It was found that NMR resonances of the OH and aromatic protons in N-(o-hydroxybenzyl)cytisine were doubled because of the presence of two conformers in solution.
Keywords: cytisine derivatives; NMR spectroscopy; x-ray structure analysis

A thermostable xylose isomerase (D-xylose ketol-isomerase; EC.5.3.1.5) was isolated from the cladodes of xerophytic Cereus pterogonus. The enzyme was purified to homogeneity. SDS-PAGE analysis estimated the molecular mass of the enzyme protein at 66 kDa. The enzyme exhibited temperature optima at 60 and 80°C. Though the enzyme activity was optimum at pH 7.0, the enzyme was found to be stable in both acidic and basic pH ranges in the presence of divalent ions Mn2+, Co2+, and Mg2+. This enzyme may find potential use in the food and beverage industry.
Keywords: xylose isomerase; Cereus pterogonus; thermophilic; pH dependence

Chitin-binding antifungal protein from Ficus carica latex by G. T. Mavlonov; Kh. A. Ubaidullaeva; M. I. Rakhmanov; I. Yu. Abdurakhmonov; A. Abdukarimov (216-219).
A low-molecular-weight protein with antifungal activity was isolated from freshly collected latex of the Inzhir tree (Ficus carica L.) by successive affinity chromatography over chitin, cation-exchange chromatography over SP-Sephadex C-50, and reversed-phase HPLC. The molecular weight of 6481 and the partial N-terminus sequence of the protein were determined (MALDI-TOFMS).
Keywords: chitin-binding protein; antifungal protein

Synthesis of graft copolymers of wood and N-vinylpyrrolidone by N. N. Chopabaeva; E. E. Ergozhin (220-223).
Lignocellulose copolymers with grafted lactam rings were prepared by graft copolymerization of wood with N-vinylpyrrolidone initiated by Fe2+-H2O2. The principal features of their formation were investigated as functions of reactant concentrations, temperature, and polymerization time.
Keywords: wood; N-vinylpyrrolidone; graft copolymer

11-Tetradecen-1-ol acetate is a mixture of geometric isomers with the Z/E-conformations in a 94:6 ratio that is used as an attractant to trap corn pests. It has a powerful attractive action similar to that of an isomeric mixture of 11-tetradecenyl acetate with the Z/E-conformation in a 95:5 ratio that was extracted from the peritoneal cavity of male Ostrinia nubilalis Hubner in Xinjing (PRC).
Keywords: Ostrinia nubilalis Hubner; sex pheromone; (Z/E)-11-tetradecen-1-ol acetate; synthesis

Polysaccharides from Zingiber officinale by T. V. Orlovskaya (229-230).

Fatty acids of Acinos alpinus and A. hungaricus by T. Jovanovic; R. Palic; D. Kitic; M. Ristic; B. Zlatkovic (231-233).

Flavonoid aglycones from Centaurea sphaerocephala by A. Bentamene; M. Baz; R. Boucheham; S. Benayache; J. Creche; F. Benayache (234-235).

Chemical constituents from the aquatic weed Pistia stratiotes by Han-Wei Liu; Li-Ying He; Jing-Ming Gao; Yun-Bao Ma; Xue-Mei Zhang; Hua Peng; Ji-Jun Chen (236-238).

New antioxidant phytopreparation from Rumex thyrsiflorus roots. III by Yu. A. Litvinenko; R. A. Muzychkina (239-240).

Composition of the essential oil of Indigofera microcarpa from the Northeast of Brazil by A. M. C. Arriaga; M. Andrade-Neto; G. T. Malcher; T. B. M. Gomes; J. N. Vasconcelos; A. C. P. Rodrigues; M. C. F. de Oliveira; G. M. P. Santiago (245-246).

Phytochemical study and antiradical activity of Artemisia coerulescens from Abruzzo by L. Menghini; F. Epifano; F. Tammaro; B. Tirillini (247-249).

Composition and biological activities of Lippia aff. gracilis essential oil by M. da Conceicao; L. Lima; T. L. G. Lemos; O. D. L. Pessoa; G. M. P. Santiago; F. J. A. Matos; A. M. C. Arriaga; J. P. P. de Oliveira; A. E. G. Sant’ana (254-256).

Component composition of essential oil from Artemisia taurica by G. V. Khodakov; I. V. Kotikov (261-262).

Component composition and antimicrobial activity of essential oil from Artemisia kasakorum by E. M. Suleimenov; T. Ozek; F. Demirci; B. Demirci; K. H. C. Baser; S. M. Adekenov (263-265).

Alkaloids from Convolvulus lineatus and C. olgae growing in Uzbekistan by A. M. Gapparov; N. A. Razzakov; S. M. Abdullabekov; S. F. Aripova (270-271).

Auxin treatment improves indigo biosynthesis in hairy root cultures of Polygonum tinctorium by S. U. Park; Y. K. Kim; H. G. Jang; J. N. Kim; H. W. Ryu (272-273).

Mutagenized phenylalanine ammonia-lyase from yeast by Yan Su; Gui-Guang Chen; Bin Xiong; Zhi-Qun Liang (274-276).