Ten diterpenoids, named macrorilone A-B, macroripremyrsinone A, macrorilathyrone A-B, macrorieuphorone A-B and macroricasbalone A-C, together with ten known diterpenoids, jatrophalone, sikkimenoids A-D, jatrophodione A, latilagascenes F, jolkinol B, 15β-O-benzoyl-5α-hydroxyisolathyrol and jatrophalactone were isolated from the whole plant of Euphorbia macrorrhiza C.A. Mey. These diterpenoids belong to six skeleton-types, including jatropholane, premyrsinane, lathyrane, euphoractin, casbene and rhamnofolane diterpenoids. Their structures were elucidated by extensive analysis of 1D, 2D NMR and HRESIMS spectroscopic data. The absolute configurations of macrorilone B, macroripremyrsinone A and macrorilathyrone A were established by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Several of the isolated compounds exhibited weak cytotoxicity against the KB and KBv200 cell lines with IC50 values ranging from 21.19 to 47.87μM. Some also showed multidrug resistance (MDR) reversal activity, among which macrorilathyrone B exhibited a remarkable inhibitory effect on P-gp-mediated drug exclusion.

The known compounds cappariloside A and stachydrin, an adenosine nucleoside, and for the first time from plants of the Capparidaceae family the known compounds hypoxanthine and uracil were isolated from Capparis spinosa (Capparidaceae) fruit.Capparis spinosa (Capparidaceae) is widely distributed throughout the whole world. Information on alkaloids, flavonoids, and glycosides [1][2][3][4][5] in addition to lipids and carbohydrates [6] from this plant has been published.Herein we report a study of alkaloids from fruit of C. spinosa growing in Xinjiang Autonomy Region of China. The alcohol extract of ground and defatted ripe fruit of C. spinosa produced total extracted substances containing also water-soluble alkaloids of the betaine type. The lipophilic components were removed by washing the acidic solution of extracted substances with ether. The total alkaloids were obtained by treatment of the acidic solution with conc. ammonia to adjust the pH to 9 and extraction with n-butanol (fraction A). The dried alkaloidal fraction A was chromatographed over a silica-gel column with elution by CHCl 3 , CHCl 3 :CH 3 OH, and CH 3 OH. Work up with CH 3 OH of the CHCl 3 :CH 3 OH (12:1) fractions isolated amorphous hypoxanthine (1) and uracil (2) [7,8], which were identified using PMR and 13 C NMR spectral data and authentic samples (spectral properties are given in Experimental).Crystalline 3, mp 228-229°C, was isolated from CHCl 3 :CH 3 OH (10:1) fractions. The UV spectrum of 3 had absorption maxima at 206.4 and 259.6 nm. The IR spectrum had absorption bands for active H at 3425, 3370 (NH 2 ), 3320, and 3143 (OH) cm −1 ; lactone ring (tetrahydrofuran), 1680; ether, 1100 and 1030; and tri-and disubstituted aromatic rings, 1600, 1577, 870, 822, 795, and 765. The mass spectrum of 3 gave a peak for the molecular ion with m/z 267 and fragments with m/z 148 and 119 produced by cleavage of the tetrahydrofuran ring. Peaks for ions with m/z 134 and 133 corresponded to fragments formed by cleavage of the C-N bond between the main part of the molecule and the tetrahydrofuran ring. NMR data ( 1 H and 13 C) are given in Experimental.The spectral data (UV, IR, mass, NMR) were reminiscent of those of adenosine (3) [9]. However, the lack of an authentic sample prohibited reliable identification of 3 as adenosine. As a result, a single-crystal x-ray structure analysis (XSA) of 3 showed that the isolated base was in fact the known nucleoside adenosine (C 10 H 13 N 5 O 4 ), which is constructed from D-ribose and a purine base in which the N-9 atom of the purine base adenine is bonded to C-1 of D-ribose [10][11][12][13]. Adenosine

We have previously studied the chemical composition of essential oil (EO) from seeds of Anethum graveolens from Xinjiang Autonomous District in the PRC [1]. The component composition of essential oils is known to depend on the habitat. It seemed interesting to compare the composition and biological activity of EO from dill seeds growing in China and Uzbekistan. We used GC-MS to establish the structures of the isolated compounds.EO from seeds of A. graveolens (2007 harvest) that were collected in Tashkent Oblast was isolated by steam distillation in 4.2% yield. The chemical composition of the EO was studied using a Perkin-Elmer Turbo GC-MS. The component content of the oil was calculated using areas of GC peaks of total ion current without correlation coefficients. EO components were identified by comparing retention times and mass spectra of the component obtained in mass scanning mode and by using mass-spectral library data for standard oil components and pure compounds. A total of 22 chemical compounds was identified in EO of A. graveolens seeds growing in Uzbekistan. Table 1 lists the chemical composition of the EO.The principal EO components from dill seed growing in Uzbekistan were carvone (73.61%), limonene (14.69), cis-dihydrocarvone (5.87), diplaniol (1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene) (2.16), and 1,2-diethoxyethane (1.43%), which together made up 99.2% of the total EO component composition. The principal components of EO from dill seed growing in China were n-pentacosane (27.96%), dioctylester of 1,2-phenyldicarboxylic acid (25.10), octacosane (13.81), tricosane (9.14), and n-nonacosane (6.85%) [1]. A comparison of our data with that obtained earlier indicated that both the qualitative and quantitative composition of the principal EO components of A. graveolens growing in different geographic zones differed considerably. The high content in the studied EO of carvone, which is widely used as a growth inhibitor of bacteria [2-4] and certain fungi [5] and as a repellent [6] is noteworthy. Both S-(+)-carvone and R-(-)-carvone are used in the food industry to produce flavors [4] and in agriculture. For example, S-(+)-carvone is used in the Netherlands to prevent premature sprouting of potato tubers and tulip bulbs during storage [7,8]. Carvone is an available and inexpensive reagent for organic synthesis in both enantiomeric forms. This makes it attractive for asymmetric synthesis of natural compounds [9].Antimicrobial activity of EO fractions toward Candida albican and Staphylococcus aureus was estimated using the Barry method to determine the minimal inhibiting concentration (MIC) [10]. Growth of microorganisms decreased markedly upon addition of EO to nutrient medium. The experimental results are given below:Complicated mixtures of monoterpenes and sesquiterpenes from A. graveolens EO possessed pronounced antimicrobial and fungicidal activities and were a strong barrier against penetration of bacterial and fungal infection in plant seeds during their storage and sprouting. Furthermore, a comp...

Dill, Anethum graveolens L. (Apiaceae), is an annual plant with a strong spicy odor [1]. Dill has been known since antiquity as an agent for increasing the stomach tonus and has been used for aches in the stomach and intestines, dispepsia, bladder inflammation, liver diseases, headaches, cramps, and insomnia [2]. The essential oil (EO) of dill seeds contains biologically active compounds [3,4].We used EO from dill seeds collected in the Xinjiang-Uigur Autonomous Region of China. EO was extracted from dill seeds (50 g) by steam distillation for 4 h and extracted from the aqueous phase by diethylether. The ether extract was dried with Na 2 SO 4 . Solvent was removed overnight. The yield of EO was 3.8% of the seed mass. EO of dill was an oily light yellow liquid with a unique odor and a density of 0.925 g/cm 3 .The chemical composition of the EO was studied by GC-MS on a Perkin-Elmer Turbo Mass Aid System XL gas chromatograph with a quadrupole mass spectrometer as the detector. We used a 30-m PE-5MS capillary quartz column (copolymer 5% phenylmethylsilicone) with internal diameter 0.25 mm and stationary-phase film thickness 25 µm, flow rate 35 mL/min, He carrier gas with temperature programming. The column was held for 2 min at 75°C, heated to 100°C at 2°C/min, to 160°C at 4°C/min, to 220°C at 2°C/min, and held for 2 min at that temperature. The final isothermal duration was 20 min at 230°C. Samples (0.2 µL) were injected. The evaporator temperature was 180°C; detector, 220°C; ionization potential, 70 eV, m/z, 30-550. The contents of oil components were calculated using the areas of the GC peaks without correction coefficients. Quantitative analysis was based on comparison of retention times and complete mass spectra with those of standard oil components, pure compounds, and mass spectrometric libraries of NBS, NIST, and Wiley.