eudesmanolide and germacranolide

In continuation of a search for new antiprotozoal agents from plants of the family Asteraceae, Tarchonanthus camphoratus and Schkuhria pinnata have been investigated. By following the promising in vitro activity of the dichloromethane extracts from their aerial parts, bioassay-guided chromatographic isolation yielded two known sesquiterpene lactones (1 and 2) from T. camphoratus and 20 known compounds of this type from S. pinnata. From the latter, a new eudesmanolide, (1R*,5S*,6R*,7R*,8R*,10R*)-1-hydroxy-8-[5″-hydroxy-4'-(2″-hydroxyisovaleroyloxy)tigloyloxy]-3-oxoeudesma-11(13)-en-6,12-olide (3), and two new germacranolides, 3β-(2″-hydroxyisovaleroyloxy)-8β-(3-furoyloxy)costunolide (14) and 1(10)-epoxy-3β-hydroxy-8β-[5'-hydroxy-4'-(2″-hydroxyisovaleroyloxy)tigloyloxy]costunolide (16), were obtained. Additionally, the flavonoid pectolinarigenin (24) and 3-hydroxy-4,5-dimethoxybenzenepropanol (25) were also isolated from S. pinnata. The compounds were characterized by analysis of 1D and 2D NMR spectroscopic and HR/MS data. In vitro antitrypanosomal activity and cytotoxicity against mammalian cells (L6 cell line) were evaluated for all the compounds. Santhemoidin A (13) and 3β-(2″-hydroxyisovaleroyloxy)-8β-(3-furoyloxy)costunolide (14) were the most active compounds found in this study, with IC

Topics: Animals; Antiprotozoal Agents; Asteraceae; Cell Line; Lactones; Leishmania donovani; Plant Extracts; Plasmodium falciparum; Sesquiterpenes; Sesquiterpenes, Germacrane; Trypanocidal Agents; Trypanosoma brucei rhodesiense

Leishmaniases are neglected infectious diseases caused by parasites of the 'protozoan' genus

Topics: Animals; Antiprotozoal Agents; Bridged-Ring Compounds; Cells, Cultured; Drug Evaluation, Preclinical; Furans; Inhibitory Concentration 50; Lactones; Leishmania infantum; Leishmaniasis, Visceral; Macrophages, Peritoneal; Mice, Inbred BALB C; Nitric Oxide; Sesquiterpenes; Sesquiterpenes, Germacrane; Sesquiterpenes, Guaiane; Sesterterpenes

The extract of Artemisia asiatica herb with antiproliferative activity against four human tumor cell lines (A2780, A431, HeLa, and MCF7) was analyzed by the MTT assay, and bioassay-directed fractionation was carried out in order to identify the compounds responsible for the cytotoxic activity. Guaianolide (1-4), seco-guianolide (5), germacranolide (6) and eudesmanolide sesquiterpenes (7), monoterpenes (8, 9), including the new compound artemisia alcohol glucoside (8), and flavonoids (10-16) were isolated as a result of a multistep chromatographic procedure (CC, CPC, PLC, and gel filtration). The compounds were identified by means of UV, MS, and NMR spectroscopy, including (1)H-and (13)C-NMR, (1)H-(1)H COSY, NOESY, HSQC, and HMBC experiments. The isolated compounds 1-16 were evaluated for their tumor cell growth-inhibitory activities on a panel of four adherent cancer cell lines, and different types of secondary metabolites were found to be responsible for the cytotoxic effects of the extract. Especially cirsilineol (13), 3β-chloro-4α,10α-dihydroxy-1α,2α-epoxy-5α,7αH-guai-11(13)-en-12,6α-olide (3), and iso-seco-tanapartholide 3-O-methyl ester (5) exerted marked cytotoxic effects against the investigated cell lines, while jaceosidin (12), 6-methoxytricin (15), artecanin (2), and 5,7,4',5'-tetrahydroxy-6,3'-dimethoxyflavone (14) were moderately active. All the sesquiterpenes and monoterpenes are reported here for the first time from this species, and in the case of artecanin (2), 3α-chloro-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αH-guai-11(13)-en-12,6α-olide (4), ridentin (6), and ridentin B (7), previously unreported NMR spectroscopic data were determined.

Topics: Antineoplastic Agents, Phytogenic; Artemisia; Cell Line, Tumor; Drug Screening Assays, Antitumor; Flavones; Flavonoids; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Sesquiterpenes; Sesquiterpenes, Germacrane

Phytochemical investigation of the aerial parts of Inula hupehensis Ling. led to the isolation and identification of 27 sesquiterpene lactones (1-27), including three new eudesmanolides (3-5), three new germacranolides (9-11), one new xanthanolide (16), two new carabrone derivatives (25-26), and 18 known sesquiterpene lactones. The structures were elucidated by extensive spectroscopic methods and comparison to previously reported spectroscopic data. All compounds were evaluated for their inhibitory effects against LPS-induced nitric oxide production in RAW264.7 macrophages, and compound 5 showed the strongest activity with the IC₅₀ value of 3.2 ± 0.4 µM.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cell Line; Cell Survival; Inhibitory Concentration 50; Inula; Lactones; Lipopolysaccharides; Macrophages; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; Nitric Oxide; Plant Components, Aerial; Sesquiterpenes; Sesquiterpenes, Germacrane; Structure-Activity Relationship