Pyrrolizidine alkaloids and fatty acids from the endemic plant species Rindera umbellata and the effect of lindelofine-N-oxide on tubulin polymerization

• Published in: Molecules (Basel, Switzerland) Switzerland), 2013-09, Vol.18 (9), p.10694-10706
• Main Authors: Mandić, Boris M, Simić, Milena R, Vučković, Ivan M, Vujisić, Ljubodrag V, Novaković, Miroslav M, Trifunović, Snežana S, Nikolić-Mandić, Snežana D, Tešević, Vele V, Vajs, Vlatka V, Milosavljević, Slobodan M
• Format: Article
• Language: English
• Subjects: Animals; Antineoplastic Agents - chemistry; Boraginaceae - chemistry; Cattle; Cell cycle; Electronic mail systems; Fatty acids; Fatty Acids - chemistry; Fatty Acids - isolation & purification; Flowers & plants; Metabolites; Natural products; Pharmacy; Phytochemicals; Plant Components, Aerial - chemistry; Plant Extracts - chemistry; Plant Roots - chemistry; Polymerization; Protein Multimerization - drug effects; pyrrolizidine alkaloids; Pyrrolizidine Alkaloids - chemistry; Pyrrolizidine Alkaloids - isolation & purification; Rindera umbellata; Seeds; Seeds - chemistry; Toxicity; Tubulin - chemistry; Tubulin Modulators - chemistry; tubulin polymerization
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules180910694

The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (¹H- and ¹³C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.