Antiprotozoal Diterpenes from Perovskia abrotanoides

Abstract

As part of a screening for new antiparasitic natural products from Iranian plants, -hexane and ethyl acetate extracts from the aerial parts of were found to exhibit strong inhibitory activity against and. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1: -17: ), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5,10)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2: ), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6: ), and 12-methoxybarbatusol (9: ) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against , and. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7-ethoxyrosmanol (4: ) with an IC of 0.8 µM against (SI 14.9) and an IC of 1.8 µM (SI 6.9) against , ferruginol (8: ) with an IC of 2.9 µM (SI 19.2) against , and miltiodiol (10: ) with an IC of 0.5 µM (SI 10.5) against . None of the compounds exhibited selective toxicity against (SI ≤ 1.6).

Norditerpenoids with Selective Anti-Cholinesterase Activity from the Roots of Perovskia atriplicifolia Benth.

“…Therefore, some of its pharmacological properties could also be related to another phytochemical class of completely unrelated biosynthetic origin, namely anthraquinoids. This is the first record of a compound with a linear tricyclic skeleton in P. atriplicifolia, confirming this plant as a valuable source of unique diterpenoids, in addition to the previously isolated perovskatones and many other substituted variations of the abietane core [22,28]. By now, this type of structurally unique compound seems to be limited to some species of the extended Salvia genus and the knowledge on their pharmacological properties is scarce [29].…”

Discovery of Highly Oxidized Abietane Diterpenoids from the Roots of Euphorbia fischeriana with Anti‐tumor Activities

“…Among them, ent ‐abietane diterpenoids (eABDs) were widely reported in Euphorbia fischeriana , except nor‐eABDs. Although 6‐nor‐, [ 4 ] 12‐nor‐, [ 5 ] 18‐nor‐, [ 6‐7 ] 19‐nor‐, [ 8 ] 20‐nor‐, [ 9 ] 16,17‐dinor‐, [ 10 ] 19,20‐dinor‐, [ 11 ] and 16,17,20‐trinor‐ABDs [ 12 ] were ever isolated from different sources, 17‐nor‐ABDs have never been found in nature. And meanwhile, 12,16‐epoxy‐ and 2,3‐seco‐ABDs were also rarely reported.…”

Antiprotozoal Germacranolide Sesquiterpene Lactones from Tanacetum sonbolii

“…In contrast, nonvolatile constituents of the species have not been studied so far. In a continued effort to discover new bioactive secondary metabolites from endemic Iranian plants [14][15][16], we here report on the isolation, structure elucidation, and in vitro antitrypanosomal activity of 7 new germacranolide sesquiterpene lactones from the aerial parts and flowers of T. sonbolii.…”