Nervisides I–J: Unconventional Side-Chain-Bearing Cycloartane Glycosides from Nervilia concolor

Two new cycloartane glycosides, nervisides I–J, were isolated from Nervilia concolor whole plants. Their structures were unambiguously established by interpretation of their HRESIMS and 1D and 2D NMR data. These cycloartanes comprised a stereogenic center at C-24, the R configuration of which was assigned based on DFT-NMR calculations and the subsequent DP4 probability score. These compounds were tested for cytotoxicity against K562 and MCF-7 tumor cell lines, revealing mild cytotoxic activity.

Spectroscopic Characterization and Cytotoxicity Assessment towards Human Colon Cancer Cell Lines of Acylated Cycloartane Glycosides from Astragalus boeticus L.

In several European countries, especially in Sweden, the seeds of the species Astragalus boeticus L. were widely used as coffee substitutes during the 19th century. Nonetheless, data regarding the phytochemistry and the pharmacological properties of this species are currently extremely limited. Conversely, other species belonging to the Astragalus genus have already been extensively investigated, as they were used for millennia for treating various diseases, including cancer. The current work was addressed to characterize cycloartane glycosides from A. boeticus, and to evaluate their cytotoxicity towards human colorectal cancer (CRC) cell lines. The isolation of the metabolites was performed by using different chromatographic techniques, while their chemical structures were elucidated by nuclear magnetic resonance (NMR) (1D and 2D techniques) and electrospray-ionization quadrupole time-of-flight (ESI-QTOF) mass spectrometry. The cytotoxic assessment was performed in vitro by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays in Caco-2, HT-29 and HCT-116 CRC cells. As a result, the targeted phytochemical study of A. boeticus enabled the isolation of three new cycloartane glycosides, 6-O-acetyl-3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (1), 3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (2), 6-O-acetyl-25-O-β-d-glucopyranosyl-3-O-β-d-xylopyranosylcycloastragenol (3) along with two known compounds, 6-O-acetyl-3-O-β-d-xylopyranosylcycloastragenol (4) and 3-O-β-d-xylopyranosylcycloastragenol (5). Importantly, this work demonstrated that the acetylated cycloartane glycosides 1 and 4 might preferentially inhibit cell growth in the CRC cell model resistant to epidermal growth factor receptor (EGFR) inhibitors.

Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

Review analysis on phytochemical and biological activity studies on plants of Aquilegia L.

About 60-70 species of the Aquilegia L. genus used in Western and Eastern traditional medicine grown in the England, Scotland, Wales, Siberia and Canada. The Aquilegia L. genus is used to treat a variety of diseases, in particular, digestive organs dysfunctions as stomach ulcer, liver disease, as well as cancer, lung disease and rheumatic diseases.The phytochemical studies of Aquilegia L. genus have been started since the 1960s and currently 57 natural compounds isolated from 16 plant species. These include labdane diterpene - 2 (3.5%), cycloartane - 13 (22.8%), flavonoids - 22 (38.5%), alkaloids and nitrogen-containing compounds - 10 (17.5%) and phenolic acids, fatty acids. From these 19 new natural compounds belonging to cycloartane glycosides, labdane diterpene, flavoalkaloids and nitrile nitrogen compound have been identified. The presence of fla-voalkaloid can consider a specific characterization of Aqiulegia species.Antioxidative, hepatoprotective, antibacterial and anti-cancer activities of various extracts and some isolated pure compounds of few species have been studied.In Mongolia, there are five species of plants including A.sibirica Lam, A.viridiflora Pall, A.glandulosa Fisch, A.ganboldii Kamelin & Gubanov, A.turczaninovii Kamelin & Gubanov and their phytochemical and biological activity have not been studied yet. Удвалын (Aquilegia L.) төрлийн ургамлуудын химийн бүрдэл ба биологийн идэвхийн судалгааны тойм Хураангуй: Өрнө, дорнын анагаах ухаанд хэрэглэгддэг Удвалын төрлийн 60-70 орчим зүйл ургамал манай дэлхийн ихэвчлэн Англи, Шотланд, Уэльс, Сибирь, Канадын сэрүүн бүс нутгаар тархан ургадаг. Удвалын төрлийн ургамлууд нь олон төрлийн өвчнийг анагаахад ач тустай хэмээн уламжлалт анагаах ухаанд ходоодны шархлаа, хорт хавдар, элэгний өвчин, уушигны өвчин, хэрэх өвчний үед хэрэглэдэг.Удвалын төрлийн ургамлуудын фитохимийн судалгаа 1960-аад оны үеэс хийгдэж эхэлсэн бөгөөд одоогоор 16 зүйл ургамлаас 57 бага молекулт нэгдлийг ялгасан ба тэдгээрээс лабданы дитерпен - 2 (3.5%), циклоартанен - 13 (22.8%), флавоноид - 22 (38.5%), алкалоид ба нитрилийн уламжлалын нэгдэл - 10 (17.5%) болон фенолын хүчил, тосны хүчлийн ангиллын нэгдлүүд байна. Эдгээр нэгдлээс тритерпений ангиллын циклоартанений гликозидууд, лабданы дитерпен, нитрилийн уламжлалын азот агуулсан нэгдэл, флавоалкалоид зэрэг 19 байгалийн шинэ нэгдлийг ялгаж бүтэц байгууламжийг тогтоосон бөгөөд Удвалын зүйл ургамалд флавоалкалоид агуулагддаг онцлогтой.Мөн Удвалын зарим зүйл ургамлын төрөл бүрийн ханд, цэвэр нэгдлүүдийн антиоксидант, элэг хамгаалах, бактерийн эсрэг, хорт хавдрын эсрэг зэрэг биологийн идэвх судлагдсан байна.Манай оронд Удвалын төрлийн ургамлуудаас Сибирь удвал, Ногоон удвал, Шүүсэвчит удвал, Ганболдын удвал, Турчаниновын удвал зэрэг 5 зүйл ургамал ургадаг бөгөөд тэдгээрийн фитохими, биологийн идэвхийн судалгаа хараахан хийгдээгүй. Түлхүүр үгс: Удвал, флавоалкалоид, тритерпеноид, флавонол, биологийн идэвх