Allelopathic potential and an allelopathic substance in mango leaves

The present study was aimed to determine the allelopathic potential of mango (Mangifera indica L.) leaves and to identify allelopathic substances in the leaves. The aqueous methanol extracts of mango leaves inhibited seedling growth of garden cress, radish, rapeseed, foxtail fescue and crabgrass, and the inhibitory effects increased with the increasing extract concentration, suggesting that mango leaves may contain allelopathic substances. The extract was then purified by several chromatographic runs through a bioassay-directed fractionation, and an growth inhibitory substance was isolated and identified by spectral data as methyl-3,4,5-trihydroxybenzoate (methyl gallate). Methyl gallate at the concentration of 10 mM inhibited 98.6% and 99.8% of root and shoot growth of garden cress relative to the control, respectively, and 94.4% and 49.3% of those of foxtail fescue, respectively. The concentrations of methyl gallate required for 50% growth inhibition (I₅₀) on garden cress roots and shoots were 3.9 and 3.3 mM, and those on foxtail fescue roots and shoots were 1.5 and 9.5 mM, respectively. It is the first report of an allelopathic substance in mango leaves and allelopathic activity of methyl gallate. Therefore, the mango leaves may have potential as a soil additive material for the weed management options.     

Two potent allelopathic substances in cucumber plants

Since cucumber plants are mostly discarded as large waste after crop harvesting, allelopathy of cucumber plants was investigated for possible weed management options and utilization of the waste. Two potent growth inhibitory substances were isolated from an aqueous methanol extract of cucumber (Cucumis sativus L. cv. Phung Tuong) plants. These substances were determined as 9-hydroxy-4,7-megastigmadien-9-one (HMO) and (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one (THMO) by the analysis of MS, ¹H NMR spectra and optical rotation. HMO inhibited the growth of cress (Lepidium sativum L.) and Echinochloa crus-galli (L.) Beauv seedlings at concentrations greater than 0.3 and 1 μM, respectively. THMO inhibited the growth of cress and E. crus-galli seedlings at concentrations greater than 1 and 3 μM, respectively. The concentrations required for 50% growth inhibition on roots and shoots of cress and E. crus-galli were 2.4–29.3 μM for HMO and 8.1–52.2 μM for THMO. The endogenous levels of HMO and THMO in cucumber plants were 31.8 and 43.5 μg g⁻¹ dry weight, respectively. These results suggest that HMO and THMO may be the causal factors for the growth inhibitory effect of cucumber plants. Therefore, cucumber plants may be potentially useful for weed management options in an agricultural setting, such as a cover crop and soil admixture, which should be investigated further in the field.     

Evaluation of phytotoxic potential and identification of phytotoxic substances in Cassia alata Linn. leaves

Cassia alata (Caesalpiniaceae) is a large perennial shrub native to tropical America. It is an important medicinal and ornamental plant and has been reported to possess several pharmacological properties. However, phytotoxic substances from C. alata have not yet been documented in the literature. Therefore, this study seeks to evaluate the phytotoxic potential of C. alata leaves and to identify inhibitory substances for the purpose of eco-friendly weed management. The effect of aqueous methanol extracts of C. alata on the seedling growth of alfalfa, cress, lettuce, rapeseed, barnyard grass, foxtail fescue, Italian ryegrass, and timothy was examined. The level of inhibition of the extracts corresponded to concentration. Several chromatographic steps were performed to separate the extracts, and through spectroscopic analysis, two active substances were isolated and characterised as rutin and syringone. These two active substances significantly inhibited the seedling growth of cress and foxtail fescue. The range of I₅₀ values (required concentration for 50% growth inhibition) of rutin and syringone for the seedling growth of cress and foxtail fescue were 129.5–417.8 and 160.1–466.5?µM, respectively. These results indicate that the two identified active phytotoxic substances from C. alata may be responsible for its growth inhibitory properties.     

Two allelopathic substances from Paspalum commersonii Lam.

Paspalum commersonii (Poaceae) is a herbaceous perennial weed distributed in the tropics and subtropics regions and grows mainly in the moist, or even flooded soil. It often appears in the rice field as a competitive weed and difficult to manage. Its strong competitive nature indicates possible allelopathic potential of P. commersonii. However, no studies have been found yet on the allelopathic activity of P. commersonii. Thus, we investigated the allelopathic potential of this weed and determined its allelopathic substances. Aqueous methanol extracts of P. commersonii showed concentration-dependent inhibitory activity on the seedling growth of cress, alfalfa, rapeseed, lettuce, barnyard grass, foxtail fescue, Italian ryegrass, and timothy. Two substances were isolated through bioassay-guided fractionation and their structures were determined through spectral data as dehydrovomifoliol and loliolide. Dehydrovomifoliol and loliolide started inhibiting the shoot and root growth of cress at concentrations greater than 3 and 0.03?mM, respectively. The concentrations required for 50% inhibition (I₅₀) of cress shoot and root growth were 3.34 and >3.50?mM for dehydrovomifoliol and 0.04 and 0.05?mM for loliolide, respectively. These results indicate that both substances may affect the inhibitory activity of P. commersonii.     

Isolation and identification of two phytotoxic compounds from the medicinal plant Cassia alata L.

Cassia alata (Caesalpiniaceae), an ornamental shrub, has many biological properties such as antifungal and antibacterial activities. Several bioactive and phytotoxic compounds have already been isolated from C. alata. Phytotoxic substances from plants have drawn attention as an alternative biological approach to control weeds. Thus, we conducted this research to explore other phytotoxic compounds in C. alata leaves. Aqueous methanol extracts of C. alata leaves strongly inhibited the seedling growth of broccoli, cabbage, cress, radish and rapeseed, in which the level of inhibition correlated with concentration. Two active compounds were isolated through chromatographies and identified using spectral data as (S)‐4‐(3‐hydroxybutyl)phenol [(+)‐rhododendrol] and (E)‐4‐((1R,4R)‐4‐hydroxy‐2,6,6‐trimethylcyclohex‐2‐en‐1‐yl)but‐3‐en‐2‐one [3‐hydroxy‐α‐ionone]. These two active compounds inhibited the growth of cress seedlings in a concentration‐dependent manner. The required concentrations for 50% growth inhibition (I₅₀ value) of cress seedlings were 192.0–296.1 μM for (+)‐rhododendrol and 132.4–195.3 μM for 3‐hydroxy‐α‐ionone. These results indicate that the two phytotoxic compounds play a part in the phytotoxic activity of C. alata leaves.     

Phytotoxic potential of Chrysopogon aciculatus (Retz.) Trin. (Poaceae)

The creeping weed, Chrysopogon aciculatus (Retz.) Trin., is widely known for its use as folk medicine, while its phytotoxic potential has not been examined. Therefore, we carried out an investigation into the phytotoxic potential of C. aciculatus to identify phytotoxic substances. C. aciculatus extracts showed inhibitory effects on shoot and root growth of cress, lettuce, rapeseed, and Italian ryegrass. Inhibition was both species‐dependent and concentration‐dependent. Two substances, (9S,10E,12Z)‐9‐hydroxyoctadeca‐10,12‐dienoic acid (9‐HO‐ODDEA) and rhizopycnin A, were isolated using chromatographies and characterized by spectral analysis. 9‐HO‐ODDEA retarded shoot and root growth of cress at concentrations higher than 1.0 and 0.3 mM, respectively, while on cress seedling by rhizopycnin A, the inhibition began from 1.0 mM. The concentrations needed for 50% inhibition of the shoot and root growth of test plants ranged from 1.71–2.31, and 0.71–0.72 mM for 9‐HO‐ODDEA and rhizopycnin A, respectively. These results indicate that these substances may contribute, to a certain extent, to the phytotoxic activity of C. aciculatus.     

Phytotoxic activity of Chinese violet (Asystasia gangetica (L.) T. Anderson) and two phytotoxic substances

Chinese violet (Asystasia gangetica (L.) T. Anderson) is a perennial invasive weed belonging to Acanthaceae. Leaves of this weed have been suggested to possess phytotoxic activity. However, phytotoxic substances in this weed have not yet been reported. Therefore, the present study investigated phytotoxic activity of Chinese violet extracts and phytotoxic substances. The extracts of Chinese violet leaves inhibited the root and shoot growth of cress, lettuce, alfalfa, barnyard grass, ryegrass, and timothy, where the level of inhibition increased with increasing extract concentrations. Bioassay‐guided separations of the extracts led to isolation of two phytotoxic substances, indole‐3‐carboxaldehyde and (6R,9S)‐3‐oxo‐α‐ionol. Indole‐3‐carboxaldehyde significantly inhibited the root and shoot growth of cress at concentrations ≥100 and 30 μmol L^?1, respectively, and concentrations of the substance required for 50% growth inhibition were 210 and 127 μmol L^?1 for cress roots and shoots, respectively. The other substance, (6R,9S)‐3‐oxo‐α‐ionol, was reported to have strongly inhibited cress roots and shoots. The present results suggest that Chinese violet contains two phytotoxic substances indole‐3‐carboxaldehyde and (6R,9S)‐3‐oxo‐α‐ionol, and those substances may play an important role in the phytotoxic activity of Chinese violet.     

Metabolomic Characterization of a cf. Neolyngbya Cyanobacterium from the South China Sea Reveals Wenchangamide A,a Lipopeptide with In Vitro Apoptotic Potential in Colon Cancer Cells

Metabolomics can be used to study complex mixtures of natural products, or secondary metabolites, for many different purposes. One productive application of metabolomics that has emerged in recent years is the guiding direction for isolating molecules with structural novelty through analysis of untargeted LC-MS/MS data. The metabolomics-driven investigation and bioassay-guided fractionation of a biomass assemblage from the South China Sea dominated by a marine filamentous cyanobacteria, cf. Neolyngbya sp., has led to the discovery of a natural product in this study, wenchangamide A (1). Wenchangamide A was found to concentration-dependently cause fast-onset apoptosis in HCT116 human colon cancer cells in vitro (24 h IC₅₀ = 38 μM). Untargeted metabolomics, by way of MS/MS molecular networking, was used further to generate a structural proposal for a new natural product analogue of 1, here coined wenchangamide B, which was present in the organic extract and bioactive sub-fractions of the biomass examined. The wenchangamides are of interest for anticancer drug discovery, and the characterization of these molecules will facilitate the future discovery of related natural products and development of synthetic analogues.