Since 1986 we started investigating diterpene alkaloids from Aconitum and Delphinum species in Mongolia. Alkaloid composition of some 12 species of Aconitum and Delphinum of Ranunculaceae family and 63 individual compounds were isolated and identified. Among them 9 were newly found naturally-occurring compounds and structure of these alkaloids were elucidated completely. High resolution Mass-spectrometry, 1H and 13C NMR, 2D NMR techniques such as COSY, HMQC, HMBC were employed to elucidate structure of new compounds. Structure of altaconitine was elucidated and confirmed by applying X-ray crystallographic analysis in addition to above- mentioned techniques. As a result of our long-term chemical in-vestigation of plant species of Mongolia, we have observed and established that secondary metabolites such as alkaloids, coumarins, lignans and xanthones accumulate in more oxidized form in plant species grown in Mongolia. This principle is also demonstrated in the structure of diterpenoid alkaloids isolated from plants of Ranunculaceae family grown in Mongolia. As can be seen from alkaloids 11-acetyl-1, 19-epoxydenudatine and turpelline each contain 4 oxygen atoms, which is more oxygen atoms than in commonly-occurring C-20 diterpenoid alkaloids. Except turpelline no other C-20 alkaloid containing four hydroxyl groups was found in nature. Altaconitine is a newly discovered alkaloid which contains functional groups with highest number of oxygen atoms among C-19 diterpenoid alkaloids. Ring “A” in altaconitine structure is substituted at C-1, C-2 and C-3 positions with 2, 3-transdiol system, making altaconitine a unique structure found in nature. Хорс ба Гэзэг цэцгийн төрлийн ургамлын дитерпений алкалоид Хураангуй: Дэлхий дахинаа Aconitum, Astagne, Consolida, Delphinum ба Inula-гийн төрлийн ургамлууд нь дитерпений алкалоидын баялаг эх сурвалж бөгөөд манай оронд тэдгээрээс Хорс ба Гэзэг цэцэгийн төрлийн ургамлууд элбэг тохиолддог. Холтсон цэцгийн овгийн Хорс ба Гэзэг цэцэгийн төрөлд хамаарагдах 12 зүйл ургамалд дитерпений алкалоидын судалгаа явуулж, дээрхи ургамлуудаас С-19, С-20 дитерпений алкалоидод хамаарагдах 63 бодисыг химийн цэвэр байдлаар ялгаж, тэдгээрийн бүтцийг таньж тодорхойлсоны дотор 9 дитерпений шинэ алкалоидыг анх удаа байгалиас олсон. Эдгээрийн дотроос бүтцийн хувьд нилээд сонирхолтой нь альтаконитин бөгөөд тэр нь 6 хираль нүүрстөрөгчийн атом агуулсан цууны ба бензоины хүчлээр ацилжсан, үндсэн цагиргийн 10 нүүрстөрөгчийн атом нь хүчилтөрөгч бүхий халагч бүлэгтэй ба ялангуяа “А” цагиргийн 2 ба 3-р байрлалд буй гидроксил бүлгүүд нь транс диол систем бүхий рекорд исэлдсэн хэлбэртэй, өвөрмөц бүтэц бүхий байгалийн шинэ алкалоид юм. Түүнчлэн турпеллин алкалоид нь үндсэн цагиргийн 4 нүүрстөрөгчийн атом нь хүчилтөрөгч бүхий халагч бүлэгтэй байгаа нь тус алкалоид бүтцийн хувьд рекорд исэлдсэн напеллины төрлийн цорын ганц нэгдэл болж бүртгэгдээд байна. Түлхүүр үгс: Хорс, Гэзэг цэцэг, дитерпений алкалоид

The diterpenoid alkaloids, with an intriguing chemistry and numerous varied bioactivities, constitute the largest and most complicated group of terpenoid alkaloids. The diterpenoid alkaloids, isolated mainly from Aconitum and Delphinium species (Ranunculaceae), have been of great interest since the early 1800 because of their pharmacological properties. Extracts of Aconitum species were used in ancient times for treatment of gout, hypertension, neuralgia, rheumatism, and even toothache. Extracts have also been used as arrow poisons. Some Delphinium species are extremely toxic and constitute a serious threat to livestock. Delphinium extracts also manifest insecticidal properties. In the past 30 to 40 years, interest in the diterpenoid alkaloids has increased because of the complex structures and interesting chemistry involved. In this review, we summarize recent progress on the chemical transformations of diterpenoid alkaloids. Дитерпений алкалоидын химийн хувиралт Хураангуй: Дитерпений алкалоидууд нь олон төрлийн биологийн идэвхийг үзүүлдэг тул химичдийн анхаарлыг ихэд татдаг. Тэдгээр нь терпеноид алкалоидын үлэмж нарийн бүтэцтэй томоохон бүлэг нэгдлүүд юм. Өвөрмөц фармакологийн шинж чанартай Холтсон цэцэгтний (Ranunculaceae) овгийн Гэзэг цэцэг (Aconitum) ба Хорсны (Delphinium) зүйлүүдийг судлах сонирхол бүр 1800 оноос эхлэлтэй гэж үздэг. Хорсны зүйлүүдийн хандыг эрт дээр үеэс хэрлэг тулуй, цусны даралт ихсэх, мэдрэлийн гаралтай өвчин, ревматизм, шүдний өвчнийг анагаахад хэрэглэж байв. Мөн нум сумны зэвний хор болгон ашиглаж байсан байна. Гэзэг цэцэгний зарим зүйл маш хортой тул гэрийн тэжээвэр амьтныг хордуулдаг байна. Гэзэг цэцэгний хандыг хортон шавжийг усгах зорилгоор ашигладаг. Сүүлийн 30-40 жилд химийн нарийн бүтэцтэй, фармакологийн өндөр идэвхтэй дитерпений алкалоидыг судлах сонирхол улам бүр ихсэж байна. Энэхүү тойм өгүүлэлд бид дитерпений алкалоидуудын химийн хувиралтын талаарх материалыг нэгтгэн дүгнэх оролдлого хийсэн болно. Түлхүүр үгс: дитерпений алкалоид, химийн хувиралт, Холтсон цэцэг, Гэзэг цэцэг, Хорс, Өндөр гэзэг цэцэг

We have isolated and structurally elucidated by spectroscopic methods the monoterpenoid iridoid glucosides mussaenoside and euphroside from the aerial parts of the Mongolian medicinal plant Pedicularis flava Pall. Euphroside and mussaenoside have been isolated for the first time from this natural source.

Lagotis integrifolia (Willd.) Schischk is an ingredient of the many traditional prescriptions andused for the treatment of fever, blood disorder, vitals disorder, diphtheria, anthrax, and pneumonia in Mongolian traditional medicine. A compound was isolated by column chromatography and HPLC methods. Molecular structures of them were elucidated by MS, 1H, 13С, HSQC, HMBC and 1Н-1Н COSY NMR method. We purified and identified as 7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl) chromen-4-one (diosmetin) from the aerial parts of Lagotis integrifolia (Willd.)Schischk. Diosmetin has been obtained from this species for the first time

The catalytic properties of acid-modified montmorillonite, kaolinite (Mongolia) and illite (Belarus) clays, as well as a commercial aluminosilicate catalyst AS-36 were studied in the liquid-phase isomerization of a-pinene and 3-carene. The largest conversion of alpha-pinene (100% after 6 h) was observed in the presence of illite clay treated with 10% HCI at 90 degrees C. The presence of only weak and medium acidic sites in the clays resulted in the formation of camphene (50.1-54.3%) as the main reaction product. Conversion of 3-carene increases with an increase of the total catalyst acidity. The reaction products were 2-carene (11.9-15.0%), mentadienes (35.5-48.5%), menthenes (7.9-17.1%) and cymenes (10,1-20.4%). The amount of mentadienes in the reaction mixture decreased while the opposite was observed for menthenes and cymenes with increase of concentration and strength of the acid sites. The kinetic model for 3-carene transformations was developed. (C) 2017 Elsevier B.V. All rights reserved.

The results of development of multi-layer ceramic membranes on the basis of natural quartz raw material from Mongolia are presented. The influence of the phase composition and temperature of calcination on the porosity, morphology and mechanical strength of large-porous ceramic support obtained by the method of isostatic pressing was studied. It was established that multi-layer ceramic membranes obtained by the application of water suspension of high-disperse quartz sand of Mongolia and alumosilicate binder with the addition of 15–35wt% of quartz are characterized by optimal properties. The developed tubular ceramic membranes with the average pore size 5.3µm, coefficient of air permeability (4.17–4.41)×10−13m2, productivity by water 46.3–48.0m3/(h×m2×bar) and mechanical strength 2.27–2.53MPa are perspective for wide use in microfiltration processes.

The method of obtaining hybrid organic biocidal structures through the interaction of the guanidine base with alumophosphates and copper hydroxy carbonate has been described. It is established that the reaction products consist of tripolyphosphates and pyrophosphates of aluminum forming ionic bonds with polyhexamethylene guanidine ions and copper (II). It is shown that when applied to the surface of a ceramic filter element at a temperature of 170 °C, a biocidal composite is fixed on them, on average, amounting to 50.0 wt. % of a product that provides the protection of filters from biofouling.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Overdose of the analgesic and anti-pyretic acetaminophen causes a potentially fatal hepatic necrosis due to a high toxicity and depletion of cellular defense mechanisms. In the present work, the potential hepatoprotective effect of the fruit extract of Paeonia anomala against acetaminophen induced cell damages was evaluated in cultured HepG2 cells and compared to the root extract. The fruit extract showed a potent protection against acetaminophen induced cell death, while the root extract showed a weak protection. Particularly, the pre-treatment of lower doses of the fruit extract, 10 μg/ mL and 20 μg/mL, significantly enhanced cell viability. The level of total glutathione in HepG2 cells treated with the fruit extract prior to the treatment of 40 mM acetaminophen was enhanced, however, the root extract failed for this activity. In addition, activities of quinone reductase, glutathione peroxidase and glutathione reductase were increased and protein levels of glutathione peroxidase 1 and superoxide dismutase 1 were enhanced in the cells treated with 10-20 μg/mL of the fruit extract. Furthermore, the protein level of Nrf2, a crucial regulator for detoxifying and antioxidant systems, was increased by the fruit extract treatment. These results suggest that the fruit extract of P. anomala exerts protective effects against acetaminophen-induced toxicity through activation of key antioxidant systems.DOI: http://dx.doi.org/10.5564/mjc.v14i0.190 Mongolian Journal of Chemistry 14 (40), 2013, p.5-11

A new isoquinoline alkaloid, along with other known 4 bioactive compounds (1 isoquinoline alkaloid, 2 flavonoids, 1 coumarin), were isolated from the ethanol extract of aerial parts of Carduus crispus L. Crispine А N-oxide was newly isolated compound, two of them (quercetin and rutin) were compounds isolated for the first time from indicated plant. The structures of these compounds were elucidated and confirmed with spectroscopic methods e.g. 1H-NMR, 13C-NMR, EI-MS, COSY, HSQC, HMBC, and by comparison with literature data.DOI: http://dx.doi.org/10.5564/mjc.v12i0.178 Mongolian Journal of Chemistry Vol.12 2011: 85-87

DOI: http://dx.doi.org/10.5564/mjc.v13i0.155 Mongolian Journal of Chemistry Vol.13 2012: 23-27

From the aerial parts of four Delphinium species 11 known and 3 new norditerpenoid alkaloids have been isolated: from D. dissectum Huth: delavaine A/B, deoxylycoctonine, methyllycaconitine; new: 10-hydroxymethyllycaconitine; from D. excelsum Reichenb.: delcaroline, delectinine, delterine, methyllycaconitine; new: 10-hydroxymethyllycaconitine, 18-O-methyldelterine and 10-hydroxynudicaulidine; from D. grandiflorum L.: delcosine, deltatsine, grandiflorine, methyllycaconitine; from D. triste Fisch.: delcosine, macrocentridine, 14-dehydrodelcosine. The structures of the new alkaloids were established on the basis of MS, 1H, 13C, DEPT, homonuclear COSY, HMQC and HMBC NMR spectroscopic techniques.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Reduction of elatidal oxime and imines based on methylamine, ethanolamine, tyramine, and S - and (±)-alaninols gave rise to the 18-amino-18-deoxy derivatives of elatidine.

We have investigated the alkaloidal constituents of Aconitum barbatum, A. kusnezoffii, A. volubile, and Delphinium cheilanthum collected in Mongolia. Seven norditerpenoid and seven diterpenoid alkaloids were isolated and identified from these plants. 1H Decoupled 13C, 2D 1H phase sensitive COSY, ROESY, TOCSY, HMQC-TOCSY and HMBC NMR spectral studies were carried out on denudatine and lepenine to make definitive assignments for the carbon atoms of these alkaloids.

From the epigeal part ofOxytropis muricata growing on Mongolian territory we have isolated the new alkaloid muricatide, the known alkaloids N-benzoyl-2-hydroxyphenethylamine and N-nicotinoyl-2-hydroxyphenethylamine, and the flavonoids robinin and kaempferol. On the basis of spectral characteristics, the structure of muricatide has been established as N-benzoyl-2-acetoxyphenethylamine, and this has been confirmed by partial synthesis. Muricatide was known previously as a synthetic compound but this is the first time that it has been found in Nature.

The coumarin composition of the epigeal part ofStellera chamaejasme has been studied. Together with the known coumarins daphnoretin, daphnetin, daphnin, and daphnorin, we have isolated the new bicoumarin glycoside chamaejasmoside and have established its structure by chemical transformations and a study of its spectral properties. Of the known coumarins, this is the first time that daphnorin and daphnin have been isolated from this plant.

In the course of a further study of the alkaloids of the epigeal part of Aconitum turczaninowiia new alkaloid has been isolated, which has been named turpelline. A structure for turpelline has been proposed on the basis of a study of its IR, mass, PMR,13C NMR, and 2D COSY spectra.