ALKALOIDS OF PLANTS OF BERBERIS TURKOMANIKA KAR

The alkaloid composition of the leaves and young shoots of Berberis turkomanika Kar was studied. The alkaloids glaucine, isocoridine, talicmidine, oxyacanthine, armepavine, berberine, coripalline, as well as the bases turkomanidine and turkamine were isolated from the leaves and young shoots by chromatography. The structure of the alkaloids turcomanidine, turkamine, and the neutral compound cyclotriveratrilene was determined by studying the spectral data and chemical transformations. Turkomanidine, turkamine, and the neutral compound cyclotriveratrilene, were first isolated from a plant of the genus Berberis

Quantitative Content Parameter in the Standardization of Veratrum Aqua, Veratrum Lobelianum Bernh. Based Drug

Introduction. According to the XIV Edition of the Russian Federation State Pharmacopoeia, the quality control of the «Veratrum Lobelianum rhizome and roots» herbal substance is carried out through the determination of the alkaloid sum by means of the titration-based method. There are no selective and sensitive instrumental methods for the quantitative analysis of veratrum aqua active ingredients either. Veratrum aqua is produced from the mentioned above herbal substance. Therefore, the study of veratrum aqua alkaloid composition is relevant, as well as the development of a modern analytical method for individual alkaloid determination that can be implemented in veratrum aqua standardization.Aim. To develop an approach to the quantitative analysis in Veratrum Aqua standardization.Materials and methods. Two analytical methods were developed: one for the veratrum alkaloid determination in veratrum aqua samples by means of high performance liquid chromatography coupled with tandem mass-spectrometry (HPLC-MS/MS), another – for jervine, the main veratrum aqua alkaloid, quantitation by means of HPLC with diode-array detector (HPLC-DAD).Results and discussion. Three main alkaloids, namely jervine, protoveratrine A and protoveratrine B, were identified in veratrum aqua. Jervine was found to be the most abundant one, hence it was chosen for the further development of a more affordable HPLC-DAD method. This method was validated for specificity, linearity, accuracy and precision. Jervine concentrations were measured in seven veratrum aqua samples produced by different manufacturers.Conclusion. The highest jervine concentration among the examined samples was found to be 170 µg/ml, the lowest – 136 µg/ml. It is proposed to implement the following quantitative content parameter in veratrum aqua standardization: «Quantitative test. Jervine content should be not lessthan 136 µg/ml». This parameter is to be determined by HPLC-DAD.

Diterpenoid alkaloids from Aconitum and Delphinum species

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

Native V. californicum Alkaloid Combinations Induce Differential Inhibition of Sonic Hedgehog Signaling

Veratrum californicum is a rich source of steroidal alkaloids such as cyclopamine, a known inhibitor of the Hedgehog (Hh) signaling pathway. Here we provide a detailed analysis of the alkaloid composition of V. californicum by plant part through quantitative analysis of cyclopamine, veratramine, muldamine and isorubijervine in the leaf, stem and root/rhizome of the plant. To determine whether additional alkaloids in the extracts contribute to Hh signaling inhibition, the concentrations of these four alkaloids present in extracts were replicated using commercially available standards, followed by comparison of extracts to alkaloid standard mixtures for inhibition of Hh signaling using Shh-Light II cells. Alkaloid combinations enhanced Hh signaling pathway antagonism compared to cyclopamine alone, and significant differences were observed in the Hh pathway inhibition between the stem and root/rhizome extracts and their corresponding alkaloid standard mixtures, indicating that additional alkaloids present in these extracts are capable of inhibiting Hh signaling.

Native V. Californicum Alkaloid Combinations Induce Differential Inhibition of Sonic Hedgehog Signaling

Veratrum californicum is a rich source of steroidal alkaloids such as cyclopamine, a known inhibitor of the Hedgehog (Hh) signaling pathway. Here we provide a detailed analysis of the alkaloid composition of V. californicum by plant part through quantitative analysis of cyclopamine, veratramine, muldamine and isorubijervine in the leaf, stem and root/rhizome of the plant. To determine if additional alkaloids in the extracts contribute to Hh signaling inhibition, we replicated the concentrations of these alkaloids observed in extracts using commercially available standards and compared the inhibitory potential of the extracts to alkaloid standard mixtures using Shh-Light II cells. Alkaloid combinations enhanced Hh signaling pathway antagonism compared to cyclopamine alone, and significant differences were observed in the Hh pathway inhibition between the stem and root/rhizome extracts and their corresponding alkaloid standard mixtures, indicating that additional alkaloids present in these extracts contribute to Hh signaling inhibition.