Benzofuroxans: their synthesis,properties, and biological activity

The review provides a brief historical background for the establishment of structure of benzofuroxanes. Methods for their synthesis are summarized, and the chemical properties are described, which are splitted into two parts: reactions proceeding with a ring opening of the heterocycle, and those occuring with a participation of the isocyclic moiety. The biological activity of various representatives belonging to the benzofuroxan series is covered in details.

     

Components from the steamed leaves of Acanthopanax koreanum and their effects on PPAR activity in HepG2 cells

Three ent-kaurane diterpenes (1-3), four lupane-triterpene glycosides (4-7), and an oleanane-triterpene glycoside (8) were isolated from the ethyl acetate and water extracts of the steamed leaves of Acanthopanax koreanum using a combination of various column chromatographies. The structures of the isolates were determined by 1H-, 13C-NMR spectroscopy and mass spectrometry. To investigate the biological effects of the eight compounds (1-8) on peroxisome proliferator-activated receptor gamma (PPARgamma), luciferase reporter assays were used. Among the tested compounds, ent-kaur-16-en-19-oic acid (1), 16alpha-hydroxy-ent-kauran-19-oic acid (2), and 17-hydroxy-ent-kaur-15-en-19-oic acid (3) showed considerable effects on PPARgamma activity, compared with the positive control, troglitazone. To evaluate specificity and sensitivity of the active compounds (1-3) in the regulation of transactivation of PPARs, Gal4-PPARs-LBD luciferase reporter assays were examined. In this study, the three ent-kaurane diterpenes (1-3) were found to up-regulate PPARbeta/delta and PPARgamma activities, whereas they did not activate PPARalpha activity.     

Natural arylterpenes and their biological activity

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. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–13, January–February, 2006.     

Investigation of the dynamics of the accumulation of some secondary metabolites of cottonplant leaves

The compositions of the secondary metabolites (SMs) of the leaves and petioles of cotton plants of the deciduous and selection lines L-275, L-470, L-475, and 142-F and the variety Tashkent-1 have been studied. It has been shown that the level of -tocopherol and polyprenols in the leaf blades and petioles changes fairly sharply according to the phases of ontogenesis. The results of an exogenous treatment of the leaves of cotton plants of the control varieties Tashkent-1 and 108-F with the SMs showed an interrelationship of deciduousness and the quantitative composition of the sterols.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, Vol. 33, No. 1, pp. 113–117, January–February, 1997.     

New isolates from leaves of Nicotiana tabacum and their biological activities

Three new isolates (1?3) including one new sterol and two new flavonoids together with three known sterols (4?6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. All compounds were evaluated for their anti-tobacco mosaic virus and cytotoxic activities. The results showed that compounds 2 and 3 exhibited high anti-TMV activity with inhibition rate of 34.2 and 33.4%, respectively, which were roughly equivalent to that of positive control. The cytotoxicities of compounds 1 and 4–6 against five human tumour cell lines were also tested, and tested compounds showed weak inhibitory activities against some tested human tumour cell lines.     

Volatiles from steam-distilled leaves of some plant species from Madagascar and New Zealand and evaluation of their biological activity

Steam-distilled aerial parts of Ravensara aromatica and Cinnamomum camphora from Madagascar and Leptospermum scoparium from New Zealand have been subjected to qualitative and quantitative analysis by means of GC techniques. This allowed the elucidation of conflicting data present in the available literature for these species. Also, the biological activity in vitro was evaluated by measuring MICs and GIZs.     

Action of cottonplant glycoproteins on the proliferative activity of cells

A mitogenic action of the total (LLPs) and lactose-specific (LLPs-1) lectin-like proteins on the proliferation of lymphocytes and of myeloma cells in culture has been found. A dose-dependent influence of the LLPs and extensin-like proteins (ELPs) on the inclusion of³H proteins in the myeloma cells, including an antimitotic effect of the ELPs with an increase in the protein dose, has been shown; the ELPs exert an analogous action on K–562 tumor cells of human erythroblasts. The nature of the biological action of the LLPs and ELPs is discussed in connection with features of the structure of the carbohydrate fragments of the composition of the glycoproteins.A. S. Sadykov Institute of Bioorganic Chemistry of the Academy of Sciences, Republic of Uzbekistan, Tashkent, fax (3712) 62 70 71. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 912–915, November–December, 1996. Original article submitted May 20, 1996.     

Influence of some ions on the activity of cottonplant phytase

The activity of the phytase from cottonplant shoots has been studied. It has been shown that Ca²⁺ and Mg²⁺ ions in low concentrations weakly stimulate the activity of the phytase, while Fe³⁺, Zn²⁺, and Cu²⁺ ions are inhibitors. It is suggested that the Fe³⁺ and Cu²⁺ ions accumulating in the aleurone grains may fulfill the function of phytase inhibitors during the dormancy of the seeds.Tashkent Mirzo Ulugbek State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–342, May–June, 1998.     

Bisquaternary derivatives of cyclobuxine-D and their biological activity

Six new bisquaternary derivatives of cyclobuxine-D have been obtained, and their biological activities have been studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 742–744, September–October, 1997.     

Qingqianliusus A-N, 3,4-seco-dammarane triterpenoids from the leaves of Cyclocarya paliurus and their biological activities

Fourteen previously unreported 3,4-seco-dammarane triterpenoids named Qingqianliusus A-N (1–14), along with four known 3,4-seco-dammarane triterpenoid derivatives (15–18) were isolated from the 95 % ethanol extract of the Cyclocarya paliurus leaves. Compounds 1 and 2 possess a rare 3,11-heptacyclic lactone as natural product, and several pairs of the 3,4-seco-dammarane triterpenoid epimers with R/S configuration at C-24 were investigated and determined in detail for the first time. Compounds 8, 11, and 14 showed good α-glucosidase inhibitory effects with IC₅₀ values of 4.97 ± 0.63, 7.08 ± 0.53, and 3.76 ± 0.77 μM, respectively. Meanwhile, compound 11 was also found potent inhibition rate of 35.83 % against COX-2, as compared with the positive control celecoxib (70.28 %). In addition, compounds 3, 7, 10, and 13 exhibited outstanding cytotoxicities against human gastric cancer cell lines (BGC-823) with IC₅₀ values of 7.69 ± 0.21, 8.47 ± 0.41, 9.04 ± 0.61, and 8.86 ± 0.38 μM, respectively. Compounds 13 and 3 had modest activities on human colon cancer cell lines (HCT-116) with IC₅₀ values of 8.80 ± 0.36 and 9.45 ± 0.93 μM, respectively.     

New semisynthetic cardiac glycosides and their biological activity

Digitoxigenin, digitoxin, D-xylose and L-rhamnose have been used as the starting materials for the synthesis of the new cardiac glycosides: digitoxigenin 3-O-β-D-xylopyranoside and digitoxin 4‴-O-α-L-rhamnopyranoside. It has been established that the compounds obtained possess comparatively high biological activities. All-Union Scientific-Research Institute of Drug Chemistry and Technology. Khar'kov Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 776–779, November–December, 1990.     

New semisynthetic cardiac glycosides and their biological activity

Digitoxigenin, digitoxin, D-xylose and L-rhamnose have been used as the starting materials for the synthesis of the new cardiac glycosides: digitoxigenin 3-O--D-xylopyranoside and digitoxin 4-O--L-rhamnopyranoside. It has been established that the compounds obtained possess comparatively high biological activities.All-Union Scientific-Research Institute of Drug Chemistry and Technology. Khar'kov Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 776–779, November–December, 1990.     

Components and insecticidal activity against the maize weevils of Zanthoxylum schinifolium fruits and leaves

In our screening program for new agrochemicals from Chinese medicinal herbs and wild plants, Zanthoxylum schinifolium essential oils were found to possess strong insecticidal activity against the maize weevil Sitophilus zeamais. The essential oils of Z. schinifolium fruits and leaves were extracted via hydrodistillation and investigated by GC and GC-MS. Estragole (69.52%) was the major compound of the essential oil of fresh fruits, followed by linalool (8.63%) and limonene (4.34%) and 94.33% of the total components were monoterpenoids. The main components of the essential oil of fresh leaves were linalool (12.94%), ar-tumerone (8.95%), limonene (6.45%) and elixene (5.43%) and only 50.62% were monoterpenoids. However, the essential oil from purchased fruits contained linalool (33.42%), limonene (13.66%) and sabinene (5.72%), followed by estragole (4.67%), nerol (4.56%) and 4-terpineol (4.27%). Estragole, linalool and sabinene were separated and purified by silica gel column chromatography and preparative thin layer chromatography, and further identified by means of physicochemical and spectrometric analysis. The essential oil from the fresh fruits (LD?? = 15.93 μg/adult) possessed two times more toxicity to the insects compared with that of fresh leaves (LD?? = 35.31 μg/adult). Estragole, linalool and sabinene exhibited contact activity against S. zeamais with LD?? values of 17.63, 13.90 and 23.98 μg/adult, respectively. The essential oils of Z. schinifolium possessed strong fumigant toxicity against S. zeamais adults with LC?? values of 13.19 mg/L (fresh fruits), 24.04 mg/L (fresh leaves) and 17.63 mg/L (purchased fruits). Estragole, linalool and sabinene also exhibited strong fumigant toxicity against the maize weevils with LC?? values of 14.10, 10.46 and 9.12 mg/L, respectively.     

聚异戊二烯基三胺的合成及生理活性评价

设计、合成了一系列聚异戊二烯基三胺化合物,目标化合物结构均经过核磁共振谱、质谱及元素分析确认;利用MTT法测试了目标化合物对人白血病细胞K562和人肝癌细胞Bel-7402的体外抗肿瘤活性.结果表明,目标化合物对两种肿瘤细胞的生长均有较强的抑制活性.     

Novel synthesis of zerumbone-pendant derivatives and their biological activity

Zerumbone 1, having powerful latent reactivity and containing two conjugated double bonds and a double conjugated carbonyl group is the major component of the essential oil of wild ginger, Zingiber zerumbet Smith. The conjugation system plays an important role in the expression of biological activity. N-Bromosuccinimide (NBS) reaction of 1 gave high reactive intermediate 2 with an exo-methylene group, which was obtained from 1 quantitatively. Treatment of 2 with nucleophiles gave various zerumbone-pendant derivatives, including C–H, C–O, C–N, and C–C bond formation, maintaining the conjugation system through S_N2′-type reaction. Almost all zerumbone-pendant derivatives showed a good value of IC₅₀ against the suppressive effect of NO generation. Among them, amine derivative 5, binding with 2 mol of zerumbone, showed the strongest activity (IC₅₀: 0.24 μM).     

Constituents from the leaves of Phellodendron amurense and their antioxidant activity

Three new coumarins, phellodenols F-H (1-3) and a new glutaric acid derivative, phellodendric acid-A (4) were isolated from the leaves of Phellodendron amurense together with twenty-nine known compounds. Extensive 1D and 2D NMR experiments and other spectroscopic studies were employed to determine the structures of 1-4. The isolated compounds were screened for their antioxidant activity through DPPH (alpha,alpha-diphenyl-beta-picrylhydrazyl) radical scavenging assay. Compounds quercetin, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-D-galactoside and kaempferol-3-O-beta-D-glucoside demonstrated significant radical scavenging activity comparable to vitamin E.