Meliaceae and Rutaceae families are known for the high diversity of their secondary metabolites, which include many groups that represent a rich source of structural diversity, and are good candidates as sources of allelochemicals that could be useful in agriculture. In the work described here the bioactivity profiles were evaluated for 3 alkaloids (1-3), 12 coumarins (4-15), 2 phenylpropanoic acid derivatives (16 and 17) and 14 flavonoids (18-31) from 11 species belonging to the Meliaceae and Rutaceae families. All compounds were tested in the wheat coleoptile bioassay and those that showed the highest activities were tested on the STS (Standard Target Species) Lepidium sativum (cress), Lactuca sativa (lettuce), Lycopersicon esculentum (tomato), and Allium cepa (onion). Most of the isolated compounds showed phytotoxic activity and graveoline (3), psoralen (8), and flavone (18) were the most active, with bioactivity levels similar to that of the commercial herbicide Logran 1. The results indicate that these compounds could be involved as semiochemicals in the allelopathic interactions of these plant species.
Citrus sinensis grafted on C. limonia produces a considerable number of compounds that are not common in both plants developed from germination of seeds. The chemical profile of scion and rootstock differ notably for absence in the form of flavonoids and coumarins containing C5 prenyl groups attached to the carbon atoms of aromatic and heterocyclic systems or to oxygen. Only linear pyranocoumarins xanthyletin and xanthoxyletin were found in scion. This observation indicates that the prenylated compounds once biosynthesized in the roots could have been translocated to other organs. Xylella fastidiosa colonizes the xylem of plants causing diseases on several economically important crops such as citrus variegated chlorosis (CVC). A number of flavonoids, coumarins, alkaloids, dihydrocinnamic acid derivative, anacardic acid, triterpenes, and limonoids were tested for in vitro activity on the growth of Xylella fastidiosa. Azadirachtin A was the most active. Hesperidin, which occurs in great amounts in cells of the mesophyll of the affected leaves with CVC, showed a moderate activity suggesting that it can act as a good barrier for small-size colonies from X. fastidiosa.
Six triterpenes and eight limonoids were evaluated for their capacity to inhibit the growth of three human tumour cell lines, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and melanoma (A375-C5). The mechanisms involved in the observed cell growth arrest of the four most potent compounds were carried out by studying their effect in cell cycle profile and programmed cell death. The results showed that one triterpene (odoratol) and two limonoids (gedunin and cedrelone) caused cell cycle arrest while only the limonoids gedunin and cedrelone were found to be very potent inducers of apoptosis.
Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2-6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete (1)H and (13)C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.
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