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
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
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