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Chemistry of Natural Compounds (v.42, #1)

Natural arylterpenes and their biological activity by O. S. Kukovinets; R. A. Zainullin; M. I. Kislitsyn (pp. 1-15).
Information on naturally occurring aromatic mono-, sesqui-, and diterpenes was systematized. The types of their biological activity and possible practical applications were described. Possible synthetic pathways to the most important terpenes were examined.

Keywords: aromatic terpenes; diterpenes; sesquiterpenes; isolation from natural sources; biological activity; synthesis

A 2-phenoxychromone from Artemisia rupestris by Haji Akber Aisa; Yun Zhao; Chengxiang He (pp. 16-18).
A 2-phenoxychromone, 6-demethoxy-4′-O-methylcapillarisin, was isolated from Artemisia rupestris L. The structure of this compound was established by analysis of the spectroscopic data. A single-crystal diffraction analysis was performed in order to confirm the proposed structure.

Keywords: 2-phenoxychromone; 6-demethoxy-4′-O-methylcapillarisin; single-crystal diffraction analysis

Essential oil variation of Salvia officinalis aerial parts during its phenological cycle by Mohammad Hossein Mirjalili; Peyman Salehi; Ali Sonboli; Masood Mohammadi Vala (pp. 19-23).
In this paper the variation in the quantity and quality of the essential oil of Salvia officinalis during its life cycle stages is reported. The oils were obtained by hydrodistillation of air-dried samples. The yield of essential oil (w/w %) in different stages was in the order: floral budding (0.9%) > vegetative (0.7%) > flowering (0.5%) > immature fruit (0.4%) > ripen fruit (0.2%). The essential oils were analyzed by GC and GC-MS. In total, 36, 41, 40, 38, and 41 constituents were identified and quantified in the subsequent stages, respectively. Oxygenated monoterpenes were the main group of compounds in the fruiting set (56.9%), vegetative (48.5%), flowering (47.7%), and floral budding (45.3%) stage. 1,8-cineole as one of the major constituents of all samples was lower in the vegetative stage and gradually increased in subsequent harvesting times to reach a maximum in flowering and then decreased in the fruiting set. In contrast, the globulol content was higher in the first stage and decreased drastically during fruit maturation.

Keywords: Salvia officinalis L; Lamiaceae; phenological cycle; essential oil variation

Composition of the essential oils of Lycium barbarum and L. ruthenicum fruits by A. Altintas; M. Kosar; N. Kirimer; K. H. C. Baser; B. Demirci (pp. 24-25).
Water-distilled essential oils from the fruits of Lycium barbarum and L. ruthenicum were analyzed by GCMS. The main components in the oil of L. barbarum were found to be hexadecanoic acid (47.5%), linoleic acid (9.1%), β-elemene (5.4%), myristic acid (4.2%), and ethyl hexadecanoate (4.0%). The essential oil of L. ruthenicum has heptacosane (14.3%), ethyl linoleate (10.0%), hexacosane (7.0%), nonacosane (6.2%), and ethyl hexadecanoate (5.8%) as the main compounds.

Keywords: Lycium barbarum; Lycium ruthenicum; essential oil; GC/MS; Solanaceae

Study of the essential oil composition of Pinus sylvestris from Turkey by O. Ustun; E. Sezik; M. Kurkcuoglu; K. H. C. Baser (pp. 26-31).
The needle oils of Pinus sylvestris L. were analyzed by GC and GC-MS. The results showed some qualitative and quantitative variations. Forty-three components were identified in the oils of P. sylvestris. All the samples of essential oils contained α-pinene, camphene, and β-pinene as major constituents. Chemical variations of P. sylvestris samples were discussed.

Keywords: Pinus sylvestris L; essential oils; α-pinene; germacrene-D, β-pinene, β-caryophyllene

Substrate requirements of phospholipase D from Streptomyces netropsis in the transphosphatidylation synthesis of phospolipids by L. L. Birichevskaya; L. A. Eroshevskaya; M. A. Kisel’; A. I. Zinchenko (pp. 32-35).
The effect of the structure of the phospholipid substrate on the yield of phosphatidyl-5′-thymidine by transphosphatidylation catalyzed by phospholipase D from Streptomyces netropsis was studied. The reaction and product yield depended on the structures of the polar and nonpolar parts, the hydrophobic-hydrophilic balance, and the degree of unsaturation of the fatty-acids in the phospholipid substrate.

Keywords: phospholipase D; phospholipids; transphosphatidylation; thymidine; Streptomyces netropsis

Structure and biological activity of α-santonin chloro-derivatives by S. A. Ivasenko; T. T. Edil’baeva; A. T. Kulyyasov; G. A. Atazhanova; A. I. Drab; K. M. Turdybekov; V. A. Raldugin; S. M. Adekenov (pp. 36-40).
2-Chloro-4,5α-epoxy-α-santonin and 2-chloro-α-santonin, the molecular structure of which was confirmed by an XSA, were produced by reacting α-santonin and chlorine in aqueous acetonitrile. It was found that 2-chloro-α-santonin is highly effective against trichomonas.

Keywords: sesquiterpene lactones; α-santonin; chlorination; XSA; NMR

Buddledin C from Pulicaria prostrata and selective synthesis of its epoxy derivative by D. T. Sadyrbekov; G. A. Atazhanova; A. T. Kulyyasov; V. A. Raldugin; Yu. V. Gatilov; M. M. Shakirov; T. T. Edil’baeva; K. M. Turdybekov; S. M. Adekenov (pp. 41-45).
The structure of the sesquiterpene ketone buddledin C isolated from Pulicaria prostrata (Gilib.) Aschers., was confirmed by XSA. The stereochemistry of its epoxide, which was formed selectively by treating it with hydrogen peroxide in alkaline solution, was proposed based on quantum-chemical and molecular-mechanical calculations.

Keywords: Pulicaria prostrata; buddledin C; caryophyllane-type sesquiterpene; XSA; epoxidation; quantum-chemical calculations

Isolation of ent-labdane (+)-12,15-epoxylabda-8(17), 12,14-trien-16-yl acetate from the seeds of Turraeanthus africanus and its cytostatic/cytotoxic effect on the growth of cancer cells in vitro by F. S. Tayman; V. Y. Atsu Barku; Y. Opoku-Boahen; K. Seifert; D. Grote (pp. 46-48).
(+)-12,15-Epoxylabda-8(17),12,14-trien-16-yl acetate has been isolated from the seed kernels of Turraeanthus africanus (Nelw. ex DC). The stereo structure was confirmed by 1D-and 2D-NMR spectroscopy. Cytostatic/cytotoxic test of (I) on the growth of cancer cells in vitro gave positive results.

Keywords: Cytostatic; cytotoxic; Turraeanthus africanus; limonoid; Meliaceae

Triterpene glycosides from Kalopanax septemlobum. VI. Glycosides from leaves of Kalopanax septemlobum var. typicum introduced to crimea by D. A. Panov; V. I. Grishkovets; V. V. Kachala; A. S. Shashkov (pp. 49-54).
Thirteen known glycosides of hederagenin and oleanolic acid and the three new triterpene glycosides of oleanolic acid-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→ 3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and the 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and 3-O-β-D-glucopyranosyl-(1→4)-O-β-Dxylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→ 2)-O-α-L-arabinopyranoside of oleanolic acid were isolated from leaves of Kalopanax septemlobum var. typicum introduced to Crimea.

Keywords: Kalopanax septemlobum var. typicum ; Araliaceae; triterpene glycosides; oleanolic acid and hederagenin glycosides

Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus by L. N. Atopkina; V. A. Denisenko (pp. 55-60).
A method for preparative production of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT8 was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (3) under Koenigs—Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D-glucopyranoside if equimolar amounts of (2) and (3) were used.

Keywords: dammarane triterpenoids; 12-keto-20S-protopanaxadiol; 3β-20S-dihydroxydammar-24-en-12-one; chikusetsusaponin-LT8 ; Betula; Panax japonicus

Triterpene glycosides from Kalopanax septemlobum. VII. Minor glycosides from stems of Kalopanax septemlobum var. maximowiczii and Kalopanax septemlobum var. typicum by D. A. Panov; V. I. Grishkovets; V. V. Kachala; A. S. Shashkov (pp. 61-66).
Sixteen triterpene glycosides, three of which were new, hederagenin 28-O-β-D-glucuronopyranosyl ester and 28-O-β-D-gentiobiosyl ester and oleanolic acid 3-O-α-L-arabinopyranoside, were isolated from stem bark of Kalopanax septemlobum. The glycoside contents in stem bark of two varieties, maximowiczii and typicum, were compared.

Keywords: Kalopanax septemlobum var. maximowiczii ; Kalopanax septemlobum var. typicum ; Araliaceae; triterpene glycosides; hederagenin glycosides; oleanolic and echinocystic acid glycosides

Synthesis of N-glycoconjugates of glycyrrhetic acid by S. R. Mustafina; L. A. Baltina Jr.; R. M. Kondratenko; L. A. Baltina; F. Z. Galin; G. A. Tolstikov (pp. 67-70).
New N-glycoconjugates that are analogs of glycyrrhizic acid were synthesized by condensation of α-L-rhamnopyranosylamine and β-D-lactosylamine with acid succinate and phthalate of glycyrrhetic acid methyl ester using N,N′-dicyclohexylcarbodiimide (DCC) or DCC-N-hydroxybenzotriazole.

Keywords: glycosylamines; N-glycoconjugates; glycyrrhetic acid

Alkaloid accumulation dynamics in Veratrum lobelianum growing in Georgia and biological activity of Jervine by T. Sh. Suladze; V. Yu. Vachnadze; D. M. Tsakadze; M. D. Gedevanishvili; L. E. Tsutsunava; N. A. Malazoniya (pp. 71-74).
The alkaloid accumulation dymanics in Veratrum lobelianum were investigated. Jervine was found from 0.02 to 0.11% in the subterranean part at all vegetation stages. The jervine content was greatest in subterranean plant organs, reaching a maximum (0.3%) during natural dying off of aerial organs. Jervine, a natural analog of serotonin, can be used as a specific fibroblast growth factor.

Keywords: Veratrum lobelianum; alkaloid accumulation dynamics; jervine; biological activity

Diterpenoid alkaloids of Delphinium schmalhausenii by S. Suzgec; L. Bitis; S. Pirildar; H. Ozcelik; J. Zapp; H. Becker; F. Mericli; A. H. Mericli (pp. 75-77).
From the aerial parts of Delphinium schmalhausenii six norditerpenoid alkaloids gigactonine, lycoctonine, anthranoyllycoctonine, delsemine A, delsemine B, N-acetyldelectine and a diterpenoid alkaloid septatisine were isolated.

Keywords: Delphinium schmalhausenii; Ranunculaceae; diterpenoid alkaloids

UV-stability and UV-protective activity of alkaloids from the marine sponge Zyzzya fuliginosa by A. E. Makarchenko; N. K. Utkina (pp. 78-81).
Alkaloids from the marine sponge Zyzzya fuliginosa damirones A (1) and B (2); makaluvamines H (3), C (4), G (5), and L (6); and zyzzyanones A (8) and B (9) were investigated for the ability to protect egg-cell membranes of the sea urchin Strongylocentrotus nudus from UV-radiation. Damirones, zyzzyanones, and tricyclic makaluvamines C (4) and H (3) exhibited the greatest membrane-protective activity. It was shown that makaluvamines G (5) and L (6) were converted by UV-irradiation into damirones A (1), B (2), tricyclic makaluvamines H (3), C (4), and zyzzyanones A (8) and B (9), respectively.

Keywords: marine metabolites; alkaloids; makaluvamines; damirones; zyzzyanones; UV-protectors; photolysis; marine sponge

Biologically active compounds from Lake Baikal streptomycetes by M. P. Sobolevskaya; I. A. Terkina; L. S. Buzoleva; I. A. Li; M. I. Kusaikin; N. S. Verigina; A. N. Mazeika; L. S. Shevchenko; Yu. V. Burtseva; T. N. Zvyagintseva; V. V. Parfenova; T. A. Kuznetsova (pp. 82-87).
Data on the biological activity of ethylacetate extracts of Lake Baikal streptomycetes were obtained for the first time. The extracts of isolated actinobacteria of the genus Streptomyces were tested for the presence of compounds that inhibit the growth of pathogenic and conditionally pathogenic microorganisms and that exhibit a cytotoxic effect on Erlich carcinoma tumor cells. The ability of streptomycetes to produce inhibitors of enzymes isolated from marine organisms was also investigated. The production of bioactive compounds as a function of medium composition was given.

Keywords: actinomycetes; Streptomyces; biological activity; Lake Baikal

Modification of hydrolyzed lignin in acidic and basic media by G. N. Dalimova (pp. 88-91).
The content of reactive groups such as OH, CO, and COOH was increased by modifying hydrolyzed lignin with sulfuric acid and sodium hydroxide. The increase was confirmed by IR spectral analysis. The sorptive capacity of the resulting hydrolyzed lignin derivatives was increased sharply by base activation.

Keywords: hydrolyzed lignin; modification; acid and base activation; sorption isotherm; polymolecular adsorption; IR spectra; functional composition

Synthesis of 3S-methylundec-1-ylbromide, a key synthon in the synthesis of (S,S,S)-diprionylacetate, from L-(-)-menthol by G. Yu. Ishmuratov; M. P. Yakovleva; V. A. Ganieva; R. Ya. Kharisov; R. R. Gazetdinov; A. M. Abulkaramova; G. A. Tolstikov (pp. 92-95).
Three new approaches to the synthesis of 1-bromo-3S-methylundecane, a key synthon in the synthesis of (S,S,S)-diprionylacetate, a sex pheromone of pine sawflies of the genera Diprion and Neodiprion, were proposed based on chemo-and stereoselective transformations of L-(-)-menthol derivatives.

Keywords: L-(-)-menthol; 3R-dimethyloctan-6S-olide (mentholactone); 4R-menthenone; 1-bromo-3S-methylundecane; 2S-acetoxy-3S,7S-dimethylpentadecane [(S,S,S)-diprionylacetate]; synthon; pheromone; synthesis

α-Tocopherol from Italian hazelnut germplasm by G. Sivakumar; L. Bacchetta (pp. 96-97).
Lipids from leaves of Hippophae rhamnoides by N. K. Yuldasheva; N. T. Ul’chenko; T. V. Chernenko; A. I. Glushenkova (pp. 98-99).
Lipids and carbohydrates from Capparis spinosa roots by A. Yili; Wu Tao; B. T. Sagdullaev; H. A. Aisa; N. T. Ul’chenko; A. I. Glushenkova; R. K. Rakhmanberdyeva (pp. 100-101).
Furocoumarins from Prangos ferulacea by K. A. Eshbakova; A. I. Saidkhodzhaev; K. H. C. Baser; H. Duman; A. D. Vdovin; N. D. Abdullaev (pp. 102-103).
Flavonoid glycosides from Pituranthos chloranthus by A. Touil; S. Rhouati; J. Creche (pp. 104-105).
Luteolin diglucuronide from Perilla nankinensis by D. T. Berashvili; M. D. Alaniya; A. D. Bakuridze; D. K. Kuchukhidze; L. N. Gvazava; G. Balansard; R. Elias (pp. 106-107).
Flavonoids from Sophora griffithii and Goebelia pachycarpa by B. A. Muminova; E. Kh. Batirov; M. P. Yuldashev; Z. G. Inamova (pp. 108-109).
Kaempferol glycosides from Allium cepa and Raphanus sativus by B. A. Muminova; E. Kh. Batirov; M. P. Yuldashev; Z. G. Inamova (pp. 110-111).
Flavanes from Limonium gmelinii. II. by G. E. Zhusupova; S. A. Abil’kaeva (pp. 112-113).
Alkaloids from Sophora alopecuroides growing in Azerbaijan. 1. Sophocarpine by I. S. Movsumov; E. A. Garaev; M. I. Isaev (pp. 116-117).
Salts of spiro-derivatives of benzo[f]quinoline and several natural carboxylic acids by E. A. Dikusar; A. P. Kadutskii; N. G. Kozlov; A. P. Yuvchenko; L. A. Mel’nichuk (pp. 118-120).
Degree of protein denaturation in waste from natural silk processing in a high-frequency field by I. A. Nabieva; K. E. Ergashev; L. G. Mezhlumyan (pp. 121-122).
Amino-acid composition of flowers, leaves, and extract of Sambucus nigra flowers by V. S. Kislichenko; V. V. Vel’ma (pp. 125-126).
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