Acyl-Homoserine Lactone from Plant-Associated Pseudomonas sp. Influences Solanum lycopersicum Germination and Root Growth.

It is known that plant and associated bacteria coevolved, but just now the roles of chemical signaling compounds in these intricate relationships have been systematically studied. Many Gram-negative bacteria produce N-acyl-L-homoserine lactones (AHL), chemical signals used in quorum-sensing bacterial communications mechanisms. In recent years, it has been shown that these compounds may also influence the development of plants, acting as allelochemicals, in still not well understood eukaryot-prokaryot interactions. In the present work, a quorum-sensing molecule produced by the tomato associated bacterium Pseudomonas sp. was characterized and its effects on germination and growth of tomato seedlings were accessed. The chemical study of the bacterium extract led to the identification of N-3-oxo-dodecanoyl-L-homoserine lactone (1), using gas chromatography coupled to electron impact mass spectrometry (GC-MS), and ultra-high resolution Qq-time-of-flight mass spectrometry (UHR-QqTOF-MS) equipped with an electrospray ionization source (ESI). The synthetic compound was tested at different concentrations in tomato to evaluate its effects on seed germination and seedlings root growth. Inhibition of tomato seed germination and root growth were observed in the presence of micromolar concentrations of the compound 1. Scanning electron microscopy evidenced morphological alterations on roots in the presence of the compound, with reduction of growth, impaired root hairs development and cracks in the rhizodermis.

Acyl-homoserine Lactone from Saccharum × officinarum with Stereochemistry-Dependent Growth Regulatory Activity.

Acyl-homoserine lactones (AHLs) are a class of compounds produced by Gram-negative bacteria that are used in a process of chemical communication called quorum sensing. Much is known about how bacteria use these chemical compounds to control the expression of important factors; however, there have been few reports about the presence and effects of AHLs in plants. In this study, the phytochemical study of leaves and culms of sugar cane (Saccharum × officinarum) led to the identification of N-(3-oxo-octanoyl)homoserine lactone. Since the absolute configuration of the natural product could not be determined, both R and S enantiomers of N-(3-oxo-octanoyl)homoserine lactone were synthesized and tested in sugar cane culms. The enantiomers caused changes in the mass and length of buds and roots when used at micromolar concentrations. Using the sugar cane RB96-6928 variety, the S enantiomer increased sprouting of roots more effectively than the R enantiomer. Furthermore, scanning electron microscopy showed that both the R and S enantiomers led to more stretched root cells compared with the control.

Phenolic compounds and anticancer activity of commercial sugarcane cultivated in Brazil.

The cultivation of sugarcane hybrids (X Saccharum officinarum L.) is an important revenue source for the Brazilian economy. Herein it is reported the evaluation of the cytotoxic activity of mid-polarity sugarcane extracts against human cancer cell lines, as well as the isolation of steroids sitosterol, stigmasterol and campesterol, phenolic acids p-hydroxybenzoic, p-hydroxycinnamic, vanillic and ferulic acid, terpenoids α-tocopherol and ß-carotene and a novel substance in sugarcane, the flavonoid aglycone tricin (5,7,4-trihydroxy-3,5-dimethoxyflavone). The presence of large amounts of phenolic acids and the flavonoid tricin may explain the cytostatic activity observed for the mid-polarity crude extract and filtrates.

Bioguided identification of antifungal and antiproliferative compounds from the Brazilian orchid Miltonia flavescens Lindl.

The Orchidaceae family is appreciated worldwide for the beauty of its flowers, and hundreds of species of this family occur in Brazil. Yet little is known about the potential of orchids for therapeutic application. We have investigated bioactive compounds produced by the South Brazilian orchid Miltonia flavescens Lindl. Bioguided studies with the fungus Cladosporium herbarum allowed the identification of hydrocinnamic acid as the active antifungal compound. In addition, the chloroform fraction exhibited an interesting activity against human cancer cells, and 5,7-dihydroxy-6,4'-dimethoxyflavone isolated from this fraction was found to be active against seven human cancer cell lines, including NCI/ADR-RES ovary sarcoma, with an IC50 value of 2.6 microg/mL. This is the first report on the cytostatic activity of this flavone against human ovary sarcoma.

Crispoic acid, a new compound from Laelia marginata (Orchidaceae), and biological evaluations against parasites, human cancer cell lines and Zika virus.

The phytochemical study of Laelia marginata (Lindl.) L. O. Williams (Orchidaceae) led to the isolation of a new natural product named crispoic acid (1), together with six other known compounds (2-7). The new natural product was identified as a dimer of eucomic acid and was structurally characterised based upon 1D and 2D NMR and HRMS data. Biological assays with plant crude extract, fractions and isolated compounds were performed against two human cancer cell lines (Hela and Siha), and the tropical parasites Trypanosoma cruzi and Leishmania (Leishmania) amazonensis. The phenantrenoid 9,10-dihydro-4-methoxyphenanthren-2,7-diol 2 was active against Hela and Siha cells (CC50 5.86 ± 0.19 and 20.78 ± 2.72 µg/mL, respectively). Sub-lethal concentrations of the flavone rhamnazin 4 were not able to rescue the viability of the Vero cells infected by Zika virus.