Crotofoligandrin, a new endoperoxide crotofolane-type diterpenoid from the twigs of Croton oligandrus Pierre ex. Hutch (Euphorbiaceae).

Crotofoligandrin (1), a new endoperoxide crotofolane-type diterpenoid was isolated from the dichloromethane/methanol (1:1) extract of the twigs of Croton oligandrus Pierre Ex Hutch along with thirteen known secondary metabolites including 1-nonacosanol (2), lupenone (3), friedelin (4), ß-sitosterol (5), taraxerol (6), (-)-hardwickiic acid (7), apigenin (8), acetyl aleuritolic acid (9), betulinic acid (10), fokihodgin C 3-acetate (11), D-mannitol (12), scopoletin (13) and quercetin (14). The structures of the isolated compounds were determined based on their spectroscopic data. The crude extract and the isolated compounds were assessed in vitro for their antioxidant, lipoxygenase, butyrylcholinesterase (BChE), urease and glucosidase inhibitory potentials. Compounds 1-3, and 10 displayed activities on all the performed bioassays. All the tested samples showed strong to significant antioxidant activity with compound 1 being the most potent (IC50 39.4 µM).

Bioactive Arylnaphthalide Lignans from Justicia depauperata.

Eleven previously undescribed arylnaphthalide lignans (1-11) together with seven known compounds were isolated from the whole plant of Justicia depauperata. The structures of 1-11 were elucidated by spectroscopic analysis and mass spectrometry. Compounds 6 (IC50 = 4.1 µM) and 9 (IC50 = 9.5 µM) displayed cytotoxic activity against the KB-3-1 cervical carcinoma cell line. This report provides an insight into the conformational equilibria occurring in the arylnaphthalide lignan constituents of this plant.

Bioguided isolation of antiplasmodial secondary metabolites from Persea americana Mill. (Lauraceae).

The antiplasmodium assay-guided investigation of the roots, stem bark, and leaves of Persea americana Mill. led to the isolation of a new fatty alcohol, perseatriol (1), along with six known compounds (2-7). Their structures were elucidated based on the analysis of their NMR and MS data. All crude extracts and fractions exhibited good antiplasmodial activity on Plasmoduim falciparum 3D7 with IC50 values ranging from 0.76 to 10.5 µg/mL; they also displayed cytotoxicity against HeLa cells with low selectivity indexes (SIs). A preliminary Plasmodium lactate dehydrogenase (pLDH) assay was also performed on the isolated compounds. 9,9'-Di-O-feruloyl-5,5'-dimethoxysecoisolariciresinol (4) turned out to be non-toxic and displayed the best activities on P. falciparum with an IC50 value of 0.05 µM, comparable to the reference drug chloroquine with an IC50 value of 0.03 µM. Furthermore, besides compound 4, this work reports the first isolation of lutein (2) and scopoletin (3) from P. americana. The crude extracts of roots, stem bark, and leaves of P. americana, their fractions and compounds completely suppressed the growth of P. falciparum. The observed activity supports the use of P. americana in folk medicine for the treatment of malaria.

Constituents from Nauclea latifolia with Anti-Haemophilus influenzae Type b Inhibitory Activities.

Three previously undescribed indole alkaloids, named latifolianine A (1) and latifoliaindoles A and B (2 and 3), along with 10 known compounds (4-13), were isolated from the heartwood of Nauclea latifolia. Their structures were elucidated based on the analysis of their NMR and MS data. Latifolianine A (1) represents an unusual and unprecedented monoterpene indole alkaloid unit condensed with an ursane-type pentacyclic triterpenoid moiety. Plausible biogenetic routes toward latifolianine A (1) and latifoliaindoles A and B (2 and 3) were proposed. All the isolates were assessed in vitro for their inhibitory effects on Haemophilus influenzae. Naucleidinal (7) exhibited potent antibacterial activity (MIC value of 3.1 µg/mL) as compared to a reference drug, ciprofloxacin (MIC value of 1.6 µg/mL).