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Timofey V. Malyarenko Olesya S. Malyarenko Alla A. Kicha Anatoly I. Kalinovsky Pavel S. Dmitrenok Natalia V. Ivanchina 《Marine drugs》2022,20(3)
Sea stars or starfish (class Asteroidea) and holothurians or sea cucumbers (class Holothuroidea), belonging to the phylum Echinodermata (echinoderms), are characterized by different sets of glycosidic metabolites: the steroid type in starfish and the triterpene type in holothurians. However, herein we report the isolation of eight new triterpene glycosides, pacificusosides D–K (1–3, 5–9) along with the known cucumarioside D (4), from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The isolated new compounds are closely related to the metabolites of sea cucumbers, and their structures of 1–3 and 5–9 were determined by extensive NMR and ESIMS techniques. Compounds 2, 5, and 8 have a new type of tetrasaccharide chain with a terminal non-methylated monosaccharide unit. Compounds 3, 6, and 9 contain another new type of tetrasaccharide chain, having 6-O-SO3-Glc as one of the sugar units. The cytotoxic activity of 1–9 against non-cancerous mouse epidermal cells JB6 Cl41 and human melanoma cell lines SK-MEL-2, SK-MEL-28, and RPMI-7951 was determined by MTS assay. Compounds 1, 3, 4, 6, and 9 showed potent cytotoxicity against these cell lines, but the cancer selectivity (SI > 9) was observed only against the SK-MEL-2 cell line. Compounds 1, 3, 4, 6, and 9 at the non-toxic concentration of 0.1 μM significantly inhibited neoplastic cell transformation of JB6 Cl41 cells induced by chemical carcinogens (EGF, TPA) or ionizing radiation (X-rays and UVB). Moreover, compounds 1 and 4 at the non-toxic concentration of 0.1 µM possessed the highest inhibiting activity on colony formation among the investigated compounds and decreased the colonies number of SK-MEL-2 cells by 64% and 70%, respectively. Thus, triterpene glycosides 1 and 4 can be considered as prospective cancer-preventive and anticancer-compound leaders. 相似文献
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Early ripening sweet cherry cvs ‘Burlat’, ‘Earlise’, ‘Samba’, ‘Souvenir des Charmes’ and clone M, which are all characterised by large fruit size and dark red fruit, on GiSelA 5 rootstock were forced – by closing a polytunnel from 24 March to 20 April 2006 – at Klein-Altendorf research station of Bonn University. A portable gas heater was used for automated frost protection in April. An adjacent uncovered planting at the same spacing of 3.8?m?×?1.75?m served as control. Forcing resulted in a 16–18 days earlier flowering in April relative to the 12–16 days earlier harvest at the beginning of June, resulting in a 2–4 days longer fruit development and retarded ripening. PAR was reduced in the polytunnel by 40% on sunny and 30% on overcast days with a concurrent drop in the humidity to 30% on sunny and 40% on overcast days and nearly 100% relative humidity at night. Polytunnel air temperatures on sunny days were increased – during ventilation – by up to 6?°C relative to the outside, e.g. 33?°C versus 27?°C outside. Forced cherries saved one spray application against aphids compared to those outside. Fully-grown cherry leaves contained 40–60?mg chlorophyll/g FM sufficient for photosynthesis with commensurate chlorophyll contents when grown in the polytunnel compared with those outside, and were deficient in calcium (0.5% DM) and magnesium (0.2% DM), but with a surplus in both nitrogen (3.5% DM) and phosphorus (0.42% DM). The surplus leaf nitrogen was due to excessive nitrogen mineralization in the rich soil under the higher temperatures in the polytunnel which caused the vigorous vegetative growth despite the dwarfing rootstock. Great fluctuations in fertilisation – despite strong flowering and sufficient pollination with honey bees – of between 4–71% may be due to the combination of S-alleles of the cherry varieties, infrequent water supply, nutrient imbalance and microclimate. Trees of cv. ‘Burlat’, ‘Earlise’ and clone M in their fourth leaf yielded an average of 2.5–7.5?kg fruit with 15?kg/tree in one case. Fruit of forced cvs. ‘Burlat’, ‘Souvenir’ and ‘Samba’ were larger compared with those of cv. ‘Earlise’ and clone M, which were smaller as a result of increased fruit load on the tree than those from uncovered control trees. For all five cvs tested, except forced cv. ‘Earlise’, a fruit mass of between 10?g (28?mm ) and 12?g (30?mm) and a sugar content of 12–17% with sugar:acid ratios of 20–37:1 made their fruit suitable for marketing as superior or premium fruit at higher farm-gate prices of 4.5–8?€/kg. Fruits were sufficiently dark red or black and firm for short distance transport and rapid sale. An economic evaluation showed financial gains, when yields exceed 8?kg fruit per tree per year at a farm-gate price of 4.50?€/kg. 相似文献
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Olesya I. Zhuravleva Alexandr S. Antonov Vo Thi Dieu Trang Mikhail V. Pivkin Yuliya V. Khudyakova Vladimir A. Denisenko Roman S. Popov Natalya Y. Kim Ekaterina A. Yurchenko Andrey V. Gerasimenko Anatoly A. Udovenko Gunhild von Amsberg Sergey A. Dyshlovoy Shamil S. Afiyatullov 《Marine drugs》2021,19(1)
Seven new deoxyisoaustamide derivatives (1–7) together with known compounds (8–10) were isolated from the coral-derived fungus Penicillium dimorphosporum KMM 4689. Their structures were established using spectroscopic methods, X-ray diffraction analysis and by comparison with related known compounds. The absolute configurations of some alkaloids were determined based on CD and NOESY data as well as biogenetic considerations. The cytotoxic and neuroprotective activities of some of the isolated compounds were examined and structure-activity relationships were pointed out. New deoxyisoaustamides 4–6 at concentration of 1 µM revealed a statistical increase of PQ(paraquat)-treated Neuro-2a cell viability by 30–39%. 相似文献
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Timofey V. Malyarenko Olesya S. Malyarenko Natalia V. Ivanchina Anatoly I. Kalinovsky Roman S. Popov Alla A. Kicha 《Marine drugs》2015,13(7):4418-4435
Three new sulfated steroid monoglycosides, leptaochotensosides A–C (1–3), and a new sulfated polyhydroxylated steroid (4) were isolated from the alcoholic extract of the Far Eastern starfish Leptasterias ochotensis. The structures of compounds 1–4 were established by extensive nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS) analyses and chemical transformations. Although the isolated compounds did not show any apparent cytotoxicity against melanoma RPMI-7951 and breast cancer T-47D cell lines, leptaochotensoside A (1) demonstrated inhibition of T-47D cell colony formation in a soft agar clonogenic assay at nontoxic doses. In addition, this compound decreased the epidermal growth factor (EGF)-induced colony formation of mouse epidermal JB6 Cl41 cells. The cancer preventive action of 1 is realized through regulation of mitogen-activated protein kinase (MAPK) signaling pathway. 相似文献
5.
Alla A. Kicha Anatoly I. Kalinovsky Timofey V. Malyarenko Olesya S. Malyarenko Svetlana P. Ermakova Roman S. Popov Valentin A. Stonik Natalia V. Ivanchina 《Marine drugs》2022,20(3)
New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS techniques as well as by chemical transformations. Steroids 2 and 3 have an oxo-group in the tetracyclic nucleus at position C-7 and differ from each other by the presence of the 5(6)-double bond. The Δ24-22-sulfoxycholestane side chain of the steroid 5 has not been found previously in the starfish or ophiuroid steroids. The cytotoxic activities of 1, 4, 5, and the mixture of 2 and 3 were determined on the models of 2D and 3D cultures of human epithelial kidney cells (HEK293), melanoma cells (SK-MEL-28), small intestine carcinoma cells (HuTu80), and breast carcinoma cells (ZR-75-1). The mixture of 2 and 3 revealed a significant inhibitory effect on the cell viability of human breast carcinoma ZR-75-1 cells, but other tested compounds were less effective. 相似文献
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Andreé Hamm Jürgen Lorenz Dete Papendieck Olesya Dekova Michael Blanke 《Erwerbs-Obstbau》2007,49(3):85-92
The objective of the present work was to study ways of additional foraging of honey bees in a sustainable production of forced sweet cherries in a polytunnel in order to reduce any loss of bees and to substitute the annual re-introduction of new bumble bees (Bombus terrestris L.) which are lost after use. Three honey bee (Apis mellifera L.) hives were employed during the three weeks flowering in April 2006 in a closed, unheated polytunnel to pollinate sweet cherry cvs ‘Burlat’, ‘Earlise’, ‘Samba’, ‘Souvenir des Charmes’ and an unnamed clone on dwarfing GiSelA 5 rootstock at Klein Altendorf research station near Bonn, Germany. The central position of hive A allowed the honey bees to collect pollen and nectar exclusively from the flowering sweet cherries in the tunnel. Hive B also inside the tunnel had apertures inside and outside the tunnel, while hive C outside the tunnel adjacent to its wall, had inside and outside apertures; honey bees from the latter two hives were allowed to forage both inside the tunnel or outside. Differences in air temperatures between the inside and outside the tunnel were no more than 5?°C due to effective ventilation. A portable gas heater for automated frost protection maintained the night temperature in the polytunnel in April above 0?°C. Measurements of the flight activity showed a close correlation with the ambient temperature at the respective hive location. The two bee hives A and B within the tunnel showed larger flight activities of an averaged 540 bees per hour compared with 180 bees per hour outside due to low spring temperatures. Honey bee population A in the centre of the tunnel declined after three weeks pollination to ca. 9,200 individuals and produced only 46?kg honey due to shortage in food reserves and intense flight activity. The outdoor bee population C with ca. 15,000 individuals yielded also only 49?kg honey due to lack of flight activity during the cold April 2006 compared with 68?kg honey from population B with ca. 16,000 individuals but continuous flight activity within the tunnel and additional foraging outside. Control bee hives D and E with ca. 22,000 individuals each, which had remained at the institute at Bonn, produced 82–93?kg honey during the same time. Cherry forcing resulted in a 12–18 days earlier flowering in April 2006 relative to the 12–16 days earlier harvest in June 2006. Large fluctuations in yield of 0.3–15.4?kg/tree were due to commensurate S-alleles causing intersterility, insufficient fertilisation and location of the cherry cultivars relative to each other and the bee hive. 相似文献
9.
Schepetkin IA Khlebnikov AI Ah SY Woo SB Jeong CS Klubachuk ON Kwon BS 《Journal of agricultural and food chemistry》2003,51(18):5245-5254
Mumie, a semihard black resin formed by long-term humification, is believed to have therapeutic properties. Although mumie has been used in folk medicine since ancient times, there is little information available concerning the physicochemical properties of its constituents and the mechanisms of its therapeutic efficacy. For this study crude mumie was fractionated into fulvic acid (FA), humic acid (HA), humin, hymatomelanic acid, and two low molecular weight fractions (LMW1 and LMW2). The FA fraction was divided into five subfractions, FA1-FA5. The mumie fractions were characterized by IR, UV-vis, and fluorescence spectroscopy. Total carbohydrate content in the fractions was analyzed using the phenol reaction method. The relative content of polar groups and nonpolar hydrocarbon fragments in the mumie fractions correlated well with solubility in an aqueous medium. Biological characterization was performed using only the FA fractions. FA1 and FA2 enhanced the production of reactive oxygen species (ROS) and nitric oxide in murine peritoneal macrophages, as determined with the use of 2',7'-dichlorofluorescin diacetate and Griess reagent, respectively. The enchancement of ROS and nitric oxide production correlated with the level of total carbohydrates in the fractions. Murine splenic lymphocytes treated with FA1 showed a dose-dependent increase in [(3)H]thymidine uptake. These findings suggest that FA derived from mumie has immunomodulatory activity. 相似文献
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Olesya S. Malyarenko Timofey V. Malyarenko Roza V. Usoltseva Valerii V. Surits Alla A. Kicha Natalia V. Ivanchina Svetlana P. Ermakova 《Marine drugs》2021,19(10)
Colorectal cancer is one of the most frequent types of malignancy in the world. The search for new approaches of increasing the efficacy of cancer therapy is relevant. This work was aimed to study individual, combined anticancer effects, and molecular mechanism of action of sulfated laminaran AaLs of the brown alga Alaria angusta and protolinckiosides A (PL1), B (PL2), and linckoside L1 (L1) of the starfish Protoreaster lincki using a 3D cell culture model. The 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS), soft agar, 3D spheroids invasion, and Western blotting assays were performed to determine the effect and mechanism of the action of investigated compounds or their combinations on proliferation, colony formation, and the invasion of 3D HCT 116 spheroids. AaLs, PL1, PL2, and L1 individually inhibited viability, colony growth, and the invasion of 3D HCT 116 spheroids in a variable degree with greater activity of linckoside L1. AaLs in combination with L1 exerted synergism of a combined anticancer effect through the inactivation of protein kinase B (AKT) kinase and, consequently, the induction of apoptosis via the regulation of proapoptotic/antiapoptotic proteins balance. The obtained data about the efficacy of the combined anticancer effect of a laminaran derivative of brown algae and polyhydroxysteroid glycosides of starfish open up prospects for the development of new therapeutic approaches for colorectal cancer treatment. 相似文献