Antiparasitic, nematicidal and antifouling constituents from Juniperus berries

Abstract

A bioassay-guided fractionation of Juniperus procera berries yielded antiparasitic, nematicidal and antifouling constituents, including a wide range of known abietane, pimarane and labdane diterpenes. Among these, abieta-7,13-diene (1) demonstrated in vitro antimalarial activity against Plasmodium falciparum D6 and W2 strains (IC(50) = 1.9 and 2.0 microg/mL, respectively), while totarol (6), ferruginol (7) and 7beta-hydroxyabieta-8,13-diene-11,12-dione (8) inhibited Leishmania donovani promastigotes with IC(50) values of 3.5-4.6 microg/mL. In addition, totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina at a concentration of 80 microg/mL and 1 microg/mL, respectively. The resinous exudate of J. virginiana afforded known antibacterial E-communic acid (4) and 4-epi-abietic acid (5), while the volatile oil from its trunk wood revealed large quantities of cedrol (9). Using GC/MS, the two known abietanes totarol (6) and ferruginol (7) were identified from the berries of J. procera, J. excelsa and J. phoenicea.

In vitro evaluation of new terpenoid derivatives against Leishmania infantum and Leishmania braziliensis

“…Totarol, ferruginol and 7β-hydroxyabieta-8,13-diene-11,12-dione have shown potent antileishmanial activity (IC 50 values of 3.5-4.6 µg/mL vs. 1.3 µg/mL for pentamidine) against Leishmania donovani promastigotes (Samoylenko et al 2008). Abietane derivatives have also shown appreciable in vitro antileishmanial activity against the intracellular amastigote forms of L. donovani and Leishmania major in other studies (Tan et al 2002).…”

Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group

“…15 In 2008, Muhammad and co-workers reported antimalarial activity against D6 (chloroquine-sensitive, IC 50 = 4.2 lg/mL) and W2 (chloroquine-resistant, IC 50 = 3.5 lg/mL) strains of P. falciparum for ferruginol (1). 10 Recently, an additional report confirmed significant antimalarial activity against K1 strain (chloroquine-resistant, IC 50 = 0.9 lM), showing moderate selectivity index (SI = 15.6 (in L6 cells)). 16 To further explore the potential of ferruginol (1) as antimalarial candidate, and in continuation of our research programs to discover bioactive terpenoids and new scaffolds as potential antimalarial agents, 17,18 we developed a focused compound library based on (+)-ferruginol (1) using a short, and efficient synthetic strategy from commercially available (+)-dehydroabietylamine (DHAA) (Scheme 1).…”

Secondary Metabolites with Antinematodal Activity from Higher Plants

“…8α-Hydroxyelemol (72) from the berries of Juniperus sp. (Cupressaceae) showed moderate nematicidal activity at 80µg/ml against C. elegans [69].…”

“…Totarol (or named 14-isopropyl podocarpa-8,11,13-trien-13-ol, 82) and ferruginol (or named 13-isopropyl podocarpa-8,11,13-trien-12-ol, 83) were isolated from the berries of three cupressaceous plants Juniperus procera, J. excelsa, and J. phoenicea. Totarol (82) showed strong nematicidal activity at 80µg/ml against C. elegans, and ferruginol (83) exhibited moderate nematicidal activity at 80µg/ml [69]. Three diterpenoids: 20 (86), were isolated from the roots of Euphorbia kansui (Euphorbiaceae) under the bioassay-guided method.…”