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Chemistry of Natural Compounds (v.43, #3)

Alkylation of pyrocatechol and resorcinol by camphene by I. Yu. Chukicheva; I. V. Timusheva; L. V. Spirikhin; A. V. Kuchin (pp. 245-249).
Alkylation of pyrocatechol and resorcinol by camphene in the presence of the organoaluminum catalysts aluminum phenoxide and aluminum isopropoxide was studied.

Keywords: pyrocatechol; resorcinol; camphene; organoaluminum catalysts; alkylation

Mercaptan addition to 1-O-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose by N. N. Sidamonidze; R. O. Vardiashvili; M. O. Isakadze; E. I. Chachua (pp. 250-252).
Addition of ethyl-, propyl-, and n-butylmercaptans to 1-O-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose in the presence of benzoyl peroxide catalyst was studied for the first time. The products were 1-O-(3-ethylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose, 1-O-(3-propylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose, and 1-O-(3-butylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose. Deacetylation of 1-O-(3-ethylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose produced 1-O-(3-ethylthiopropyl)-β-D-galactopyranose.

Keywords: mercaptan addition; allylgalactopyranoside; mercaptans; S-containing glycosides; benzoyl peroxide; deacetylation

Chemical investigation of Callisia fragrans by T. V. Chernenko; N. T. Ul’chenko; A. I. Glushenkova; D. Redzhepov (pp. 253-255).
Lipids of leaves, runners, and stems of Callisia fragrans were investigated. Classes of neutral, glyco-, and phospholipids and their fatty-acid compositions were determined. The contents of ascorbic acid and organic acids and chlorophyll and carotinoid pigments in various plant organs were established.

Keywords: Callisia fragrans; neutral lipids; glyco- and phospholipids; fatty acids; pigments

New long-chained feruloyl ester from the bark of Cedrelinga catenaeformis by H. R. El-Seedi (pp. 256-258).
Tetradecyl ferulate and a new n-alkyl ester of 3-hydroxy-4-methoxy-trans-cinnamate (hexacosanylisoferulate) have been isolated from Cedrelinga catenaeformis Duke (Leguminoseae). The structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, chemical transformations and finally from unambiguous synthesis. This is the first report of long chained cinnamic acid ester derivative from the genus.

Keywords: Cedrelinga catenaeformis; Leguminoseae; accelerating gradient chromatography; NMR and MS spectrometry

Determination of some polyphenolic compounds in buds of Alnus and Corylus species by HPLC by C. I. Peev; L. Vlase; D. S. Antal; C. A. Dehelean; Z. Szabadai (pp. 259-262).
The presence of 19 polyphenolic compounds was simultaneously assessed through a HPLC method in the buds of three species: Alnus glutinosa, Alnus incana, and Corylus avellana. The pattern of phenol carboxylic acids indicates that compounds like gentisic acid, sinapic acid, and the esters of tartaric acid (cichoric acid, caftaric acid) do not exist in buds, although they have been detected in mature organs. Buds only contain esters of quinic acid. Ferulic acid is a common compound in buds, being observed in all genus investigated. In the case of the flavonoid profile, young tissues of Alnus sp. and Corylus avellana only contain glycosides of quercetin. The preferred sugar for glycosylation is galactose, as the major flavonoid glycoside is in all cases hyperoside. The buds of A. glutinosa display the highest content in phenol carboxylic acids; this situation justifies their main prescription in the treatment of hepatic disorders.

Keywords: polyphenolic compounds; buds; Alnus glutinosa; Alnus incana; Corylus avellana; HPLC-DAD

Novel S-containing lactones from monoterpene oxides by L. E. Nikitina; V. A. Startseva; V. V. Plemenkov; S. A. Dieva; O. A. Lodochnikova; I. A. Litvinov (pp. 263-267).
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.

Keywords: limonene-1,2-oxide; β-pinene-α-oxide; mercaptoacetic acid; S-containing lactones

Superacid cyclization of (2E,6E,10E,14E)-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether by V. Kulcitki; M. Grin’ko; A. Barba; N. Ungur; P. F. Vlad (pp. 268-273).
A mixture of (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol tetrahydropyranyl ether (8) and (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol (9) was formed by superacid low-temperature cyclization of exclusively trans-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether (1). The structures of 8 and 9 were established using spectral data. The optically active form of 9 was also confirmed by retrosynthesis from (+)-sclareolide (10).

Keywords: superacid cyclization; sesquiterpenoids; terpenylphenylsulfones; synthesis

Crystal structure of hinokiol isolated from Isodon henryi by Bao-Lin Li; Guang-hui Tian; Zhen-guo Zhang; Bo Liang; Wei Wang (pp. 274-276).
Hinokiol was isolated for the first time from Isodon henryi and the structure was elucidated on the basis of IR and NMR spectra analysis. Its molecular configuration, conformation, and crystal structure were also characterized by X-ray structure analysis. The infrequent H-π stacking and hydrogen bonding assemble the molecules of hinokiol into a three-dimensional network structure.

Keywords: hinokiol; Isodon henryi; X-ray structure analysis; H-π stacking

Synthesis from geraniol of (2E,6E,10E,14E)-16-hydroxygeranylgeraniol and some of its derivatives by M. Grin’ko; V. Kulcitki; N. Ungur; A. Barba; K. Delyanu; P. F. Vlad (pp. 277-281).
Several α,ω-bifunctional derivatives of E,E,E-geranylgeraniol were prepared via convergent synthesis starting with geraniol (8), which was converted in three steps into the tetrahydropyranyl ether of 8-chlorogeraniol (9) and 8-hydroxygeranylphenylsulfone (10). Combination of synthons 9 and 10 with subsequent reductive removal of the phenylsulfonyl group produced the tetrahydropyranyl ether of ω-hydroxygeranylgeraniol (5), hydrolysis of which gave exclusively trans-ω-hydroxygeranylgeraniol (1). Derivatives 5–7 of geranylgeraniol were synthesized using standard methods.

Keywords: aliphatic diterpenoids; natural compounds; synthesis; combination reaction; alcohols

Synthesis of 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella sex pheromone by R. R. Vakhidov; I. N. Musina (pp. 282-284).
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.

Keywords: Phthorimaea opercucella; 4E,7Z-tridecadien-1-ylacetate; synthesis

Aminomethylation of cytisine by 3-hetaryl-7-hydroxychromones by M. S. Frasinyuk; A. V. Turov; V. I. Vinogradova; V. P. Khilya (pp. 285-290).
8-Aminomethyl derivatives of 7-hydroxychromones were prepared by reaction of methylene-bis-cytisine with substituted 7-hydroxychromones. The structures of the synthesized compounds were investigated using NMR spectroscopy.

Keywords: cytisine; alkylation; 3-hetaryl-7-hydroxychromones; aminomethylation; Mannich bases

Alkaloids of Convolvulus subhirsutus from Uzbekistan by A. M. Gapparov; N. A. Razzakov; S. F. Aripova (pp. 291-292).
Convolvine, convolamine, convolidine, phyllalbine, and the new alkaloid phyllalbine N-oxide and the aminoalcohol nortropine were isolated from the total alkaloids of Convolvulus subhirsutus and for the first time from this plant.

Keywords: Convolvulus subhirsutus; alkaloids; isolation; phyllalbine; N-oxide; nortropine

Synthesis and structure of N-(2-(1-adamantyl)-2-hydroxyethyl)cytisine diastereomers by D. V. Shishkin; E. R. Mukhamed’yarova; N. Z. Baibulatova; V. A. Dokichev; Yu. V. Tomilov (pp. 293-297).
Diastereomers of N-(2-(1-adamantyl)-2-hydroxyethyl)cytisine were synthesized by reduction of N-(2-(1-adamantyl)-2-oxoethyl)cytisine with NaBH4. Their structures were established using x-ray structure analysis.

Keywords: synthesis; cytisine derivatives; diastereomers; 15(R)- and 15(S)-N-(2-(1-adamantyl)-2-hydroxyethyl)cytisine; x-ray structure analysis; PMR; 13C NMR

Shawurensine, a new C19-diterpenoid alkaloid from Delphinium shawurense by D. Y. Gu; H. A. Aisa; S. K. Usmanova (pp. 298-301).
The new norditerpenoid alkaloid shawurensine in addition to β-sitosterol and the known alkaloids elatin, delbrulin, and methyllycaconitine were isolated from Delphinium shawurense. A structure for shawurensine was proposed based on spectral data.

Keywords: Delphinium shawurense; Ranunculaceae; C19-norditerpenoid alkaloid; shawurensine

Structural modification of potato starch by solutions of nitrogen(IV) oxide in CCl4 by S. M. Butrim; T. D. Bil’dyukevich; N. S. Butrim; T. L. Yurkshtovich (pp. 302-305).
Structural transformations of potato starch by solutions of nitrogen(IV) oxide in CCl4 were studied as a function of oxidant concentration, starch moisture content, reaction time, and molar ratio of reactants. Oxidized starches with various numbers of carboxylic acids were studied by x-ray phase analysis, 13C NMR, and IR spectroscopy. It was found that carboxylic acids were formed primarily on C6 in starch oxidation products that were x-ray amorphous. The number of carboxyls increased slightly with increased oxidation time and oxidant concentration. It was shown that moisture must be present in the starch for oxidation by nitrogen(IV) oxide to be effective.

Keywords: potato starch; oxidation; nitrogen(IV) oxide; functional composition; carboxylic and carbonyl groups; structure; 13C NMR and IR spectra

Carbohydrates from Lepidium sativum by T. V. Orlovskaya; V. A. Chelombit’ko (pp. 306-307).
Oligo- and polysaccharides from Cousinia umbrosa by K. Turdumambetov; D. A. Rakhimov; M. Kh. Malikova (pp. 308-309).
Determination of folic acid level in some foodstuffs by F. Karatas; A. Cansiz; H. Cifci; Z. Serbetci (pp. 310-312).
Analysis of the fatty oil of Pistacia eurycarpa nuts by gas chromatography/mass spectrometry by E. Kafkas; M. Kurkcuoglu; S. Kafkas; K. H. C. Baser (pp. 313-314).
Lipids from Sterculia platanifolia and Hamamelis virginiana seeds by N. S. Khatiashvili; L. N. Gogilashvili; E. A. Yarosh; E. P. Kemertelidze (pp. 315-316).
Coumarins from the bark of Daphne marginata by Wei Zhang; YunHeng Shen; RunHui Liu; Chuan Zhang; HaiSheng Chen; Peng Fu; Lei Shan; WeiDong Zhang (pp. 317-318).
Flavonol glycosides from Centaurea furfuracea. Antiplasmodial and cytotoxic activities by S. Akkal; F. Benayache; K. Medjroubi; F. Tillequin (pp. 319-320).
Flavonoids from Thymus algeriensis by R. Benkiniouar; S. Rhouati; A. Touil; E. Seguin; E. Chosson (pp. 321-322).
Phenolic compounds from Lepidium sativum by T. V. Orlovskaya; V. A. Chelombit’ko (pp. 323-323).
Flavonoids from Scutellaria phyllostachya roots by G. U. Siddikov; M. P. Yuldashev; Sh. V. Abdullaev (pp. 324-325).
Catechins and proanthocyanidines from Alhagi pseudoalhagi by D. F. Alimova; Z. A. Kuliev; A. D. Vdovin (pp. 326-327).
Composition of essential oil from seeds of Metasequoia glyptostroboides growing in China by X. L. Mou; C. Fu; H. K. Wu; B. B. Abduazimov; Y. Yang (pp. 334-335).
Volatile compositions and some fruit characteristics of table apricot varieties from Turkey by E. Kafkas; L. Son; M. Kurkcuoglu; K. H. C. Baser (pp. 344-346).
Chemical study of Artemisia filatovae by R. I. Jalmakhanbetova; S. M. Adekenov (pp. 347-348).
Chemical constituents from the ascomycetous fungus Tuber indicum by An-Ling Zhang; X.-N. Zhao; Hui Chen; La-Ping Liu; Yasuo Konishi; Jin-Ming Gao (pp. 349-350).
Pentacyclic triterpenes from Plumeria inodora by M. Grignon-Dubois; B. Rezzonico (pp. 351-352).
Formation of glycyrrhizin by in vitro cultures of Glycyrrhiza glabra by M. Shams-Ardakani; A. Mohagheghzadeh; A. Ghannadi; A. Barati (pp. 353-354).
Chemical constituents of Bacopa monnieri by Y. Zhou; Y.-H. Shen; C. Zhang; W.-D. Zhang (pp. 355-357).
Cycloartanes from Astragalus flexus by T. Kh. Naubeev; K. K. Uteniyazov; V. V. Kachala; A. S. Shashkov (pp. 360-360).
Cyclocephalogenin and cyclogalegigenin from Astragalus caucasicus by M. D. Alaniya; T. I. Gigoshvili; N. Sh. Kavtaradze; Serge Lavoi; Andre Pichette; V. D. Mshvildadze (pp. 361-362).
Triterpene glycosides from Clematis orientalis by N. A. Tabatadze; B. V. Tabidze; V. D. Mshvildadze; R. Elias; G. E. Dekanosidze; G. Balansard (pp. 363-363).
Norditerpenoid alkaloids from Delphinium cinereum by A. H. Mericli; M. Ulusoylu Dumlu; F. Mericli; H. Ozcelik; J. Zapp; H. Becker (pp. 364-366).
Amino acid and mineral composition of Nepeta grandiflora by F. S. Ortobaeva; V. A. Chelombit’ko (pp. 367-368).
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