Total reactive antioxidant potential (TRAP) of resinous exudates from Heliotropium species was evaluated by measuring the bleaching of stable free radicals. The antioxidant capacity of the resinous exudates in Trolox equivalents, evaluated from the bleaching of ABTS derived radical cations, ranged from 2.0 M (H. huascoense) to 5.2 M (H. stenophyllum), indicating a very high concentration of phenolic compounds. Considerably smaller values were obtained by measuring the bleaching of DPPH radicals. The ratio between the values obtained employing ABTS derived radicals and DPPH, ranged from 37 (H. megalanthum) to 4.5 (H. chenopodiaceum variety typica). The magnitude of the difference can be considered as an indication of the relative reactivity of the antioxidants present in the exudates. Similar ratios were observed when stoichiometric coefficients were evaluated for representative purified flavonoids obtained from the resinous exudates.

An analysis of the antibacterial activities of 15 terpenoids, eleven of which were previously described by us and four were extracted from the literature, suggested two structural requirements for activity of these and related compounds: a hydrophobic moiety, consisting of a substituted decalin skeleton, and a hydrophilic region possessing one hydrogen-bond-donor group. These structural requirements are responsible for an optimal insertion of these and related compounds into cell membranes, as suggested by the results of docking some of these compounds into a model phospholipid bilayer.

In this study, we tested eight naturally-occurring flavonoids—three flavanones and five flavones—for their possible antibacterial properties against four Gram-positive and four Gram-negative bacteria. Flavonoids are known for their antimicrobial properties, and due their structural diversity; these plant-derived compounds are a good model to study potential novel antibacterial mechanisms. The lipophilicity and the interaction of antibacterial compounds with the cell membrane define the success or failure to access its target. Therefore, through the determination of partition coefficients in a non-polar/aqueous phase, lipophilicity estimation and the quantification of the antibacterial activity of different flavonoids, flavanones, and flavones, a relationship between these parameters was assessed. Active flavonoids presented diffusion coefficients between 9.4 × 10−10 and 12.3 × 10−10 m2/s and lipophilicity range between 2.0 to 3.3. Active flavonoids against Gram-negative bacteria showed a narrower range of lipophilicity values, compared to active flavonoids against Gram-positive bacteria, which showed a wide range of lipophilicity and cell lysis. Galangin was the most active flavonoid, whose structural features are the presence of two hydroxyl groups located strategically on ring A and the absence of polar groups on ring B. Methylation of one hydroxyl group decreases the activity in 3-O-methylgalangin, and methylation of both hydroxyl groups caused inactivation, as shown for 3,7-O-dimethylgalangin. In conclusion, the amphipathic features of flavonoids play a crucial role in the antibacterial activity. In these compounds, hydrophilic and hydrophobic moieties must be present and could be predicted by lipophilicity analysis.

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The compositions of 12 essential oils (EOs) obtained by hydrodistillation of edible fruits and herbs were analyzed by gas chromatography/mass spectroscopy (GC/MS). The insecticidal activity of each oil against the house fly Musca domestica was evaluated by placing flies in a glass jar with a screw cap that held a piece of EO-treated cotton yarn. The dose necessary to kill 50% of flies (LC50) in 30 min was determined at 26 ± 1°C. Twelve EOs and 17 individual terpenes were assayed against M. domestica, showing LC50 values ranging from 3.9 to 85.2 and from 3.3 to >100 mg/dm3, respectively. EO from Citrus sinensis was the most potent insecticide (LC50 = 3.9 mg/dm3), followed by EOs from C. aurantium (LC50 = 4.8 mg/dm3) and Eucalyptus cinerea (LC50 = 5.5 mg/dm3). According to GC/MS analysis, limonene (92.47%), linalool (1.43%), and β-myrcene (0.88%) were the principal components of C. sinensis EO. Limonene was also the principal constituent (94.07%) of C. aurantium, while 1,8-cineole (56.86%) was the major constituent of E. cinerea EO. 1,8-Cineole was most active against M. domestica (LC50 = 3.3 mg/dm3), while (4R)(+)-limonene, was moderately active (LC50 = 6.2 mg/dm3). Dimethyl 2,2-dichlorovinyl phosphate (DDVP) selected as a positive control, showed an LC50 of 0.5 mg/dm3. EOs from C. sinensis, C. aurantium, and E. cinerea show promise as natural insecticides against houseflies.

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Kaurenoic acid is a diterpene with selective antibacterial activity against Gram-positive bacteria. The compound is bacteriolytic for Bacillus cereus. This activity was only partially affected by the composition and pH of the culture medium. Loss of the ability to retain the Gram stain and morphological alterations were produced in B. cereus cells exposed to kaurenoic acid. On the other hand, LPS mutants of Salmonella typhi were resistant to the compound, but spheroplasts of Escherichia coli became more sensitive to kaurenoic acid.

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