Saturated and unsaturated pyrrolizidine alkaloids (PAs) are present in more than 6000 plant species growing in countries all over the world. They have a typical heterocyclic structure in common, but differ in their potential toxicity, depending on the presence or absence of a double bond between C1 and C2. Fortunately, most plants contain saturated PAs without this double bond and are therefore not toxic for consumption by humans or animals. In a minority of plants, however, PAs with this double bond between C1 and C2 exhibit strong hepatotoxic, genotoxic, cytotoxic, neurotoxic, and tumorigenic potentials. If consumed in error and in large emouns, plants with 1,2-unsaturated PAs induce metabolic breaking-off of the double bonds of the unsaturated PAs, generating PA radicals that may trigger severe liver injury through a process involving microsomal P450 (CYP), with preference of its isoforms CYP 2A6, CYP 3A4, and CYP 3A5. This toxifying CYP-dependent conversion occurs primarily in the endoplasmic reticulum of the hepatocytes equivalent to the microsomal fraction. Toxified PAs injure the protein membranes of hepatocytes, and after passing their plasma membranes, more so the liver sinusoidal endothelial cells (LSECs), leading to life-threatening hepatic sinusoidal obstruction syndrome (HSOS). This injury is easily diagnosed by blood pyrrolizidine protein adducts, which are perfect diagnostic biomarkers, supporting causality evaluation using the updated RUCAM (Roussel Uclaf Causality Assessment Method). HSOS is clinically characterized by weight gain due to fluid accumulation (ascites, pleural effusion, and edema), and may lead to acute liver failure, liver transplantation, or death. In conclusion, plant-derived PAs with a double bond between C1 and C2 are potentially hepatotoxic after metabolic removal of the double bond, and may cause PA-HSOS with a potential lethal outcome, even if PA consumption is stopped.

This study analyzed chemical components and investigated the antioxidant and antimicrobial activities of fourteen vegetable edible oils marketed in Japan. High-performance liquid chromatography (HPLC) was used to identify and quantify principal phenolic acids and flavonoids. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, sunflower, safflower, canola, soybean, Inca inchi, sesame, and rice bran showed markedly greater activity, whilst the percentage of lipid peroxidation inhibition (LPI%) in sunflower, canola, cotton, grape, flax, perilla, Inca inchi, perillartine, and rice bran were significantly higher than other oils. Maximum total phenol content (TPC) was recorded in flax, followed by perillartine, rice bran, and perilla, whereas total flavonoid content (TFC) was the greatest in Inca inchi and sesame. Benzoic acid was the most common constituent, followed by vanillic acid, p-hydroxybenzoic acid, ferulic acid, and p-coumaric acid. On the other hand, luteolin was the most abundant flavonoid, followed by esculetin, myricetin, isoquercetin, and kaempferol, while fisetin was detected only in sunflower. In general, all of the edible oils showed antimicrobial activity, but the growth inhibition of Staphylococcus aureus and Escherichia coli of cotton, grape, chia, sesame, and rice bran were greater than other oils.

In this study, we evaluated antioxidant, antihyperuricemic, and herbicidal activities of essential oils (EOs) from Piper cubeba Bojer and Piper nigrum L.; two pepper species widely distributed in tropics, and examined their chemical compositions. Dried berries of P. cubeba and P. nigrum were hydro-distilled to yield essential oil (EO) of 1.23 and 1.11% dry weight, respectively. In the antioxidant assay, the radical scavenging capacities of P. cubeba EO against DPPH and ABTS free radicals were 28.69 and 24.13% greater than P. nigrum, respectively. In the antihyperuricemic activity, P. cubeba EO also exhibited stronger inhibitory effects on xanthine oxidase (IC50 = 54.87 µg/mL) than P. nigrum EO (IC50 = 77.11 µg/mL). In the herbicidal activity, P. cubeba EO showed greater inhibition on germination and growth of Bidens pilosa and Echinochloa crus-galli than P. nigrum EO. Besides, P. cubeba EO decreased 15.98–73.00% of photosynthesis pigments of B. pilosa and E. crus-galli, while electrolyte leakages, lipid peroxidations, prolines, phenolics, and flavonoids contents were increased 10.82–80.82% at 1.93 mg/mL dose. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analyses revealed that P. nigrum and P. cubeba EOs principally possessed complex mixtures of monoterpenes and sesquiterpenes. Terpinen-4-ol (42.41%), α-copaene (20.04%), and γ-elemene (17.68%) were the major components of P. cubeba EO, whereas β-caryophyllene (51.12%) and β-thujene (20.58%) were the dominant components of P. nigrum EO. Findings of this study suggest both P. cubeba and P. nigrum EOs were potential to treat antioxidative stress and antihyperuricemic related diseases. In addition, the EOs of the two plants may be useful to control B. pilosa and E. crus-galli, the two invasive and problematic weeds in agriculture practice.

There is currently much interest in finding new phytochemicals among plants and fungi as nature-based alternatives to replace problematic herbicides such as glyphosate, which are preferentially used in agricultural production n. We discovered striking herbicidal potency in Cordyceps militaris (L.) and identified cordycepin as its principal plant growth inhibitor. Cordycepin obtained as an ethyl acetate extract was subjected to column chromatography and evaluated for its bioassay-guided phytotoxic capacity against Raphanus sativus (radish), showing a maximum inhibition on germination and growth of radish (IC50 = 0.052–0.078 mg/mL). Gas chromatography-mass spectrometry (GC-MS) (m/z: 251.2) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) ([M + Na]+ m/z: 274.1; [M + H]+ m/z: 252.1) analyses confirmed cordycepin as the major component of the tested column fraction (55.38%). At 0.04 mg/mL, cordycepin showed 3.8–5.9- and 3.3–3.7-fold greater inhibition of the germination and growth of radish than benzoic acid (BA) and glyphosate, respectively. Compared with BA, isolated cordycepin reduced plant chlorophyll and carotenoid contents (2.0–9.5 -fold), while proline, total phenolic and total flavonoid contents were increased 1.2–1.8-fold. Finally, cordycepin promoted electrolyte leakage and malondialdehyde accumulation in radish aerial parts. Thus, cordycepin successfully isolated from Cordyceps militaris is a highly potent plant growth inhibitor with pending worldwide patent and may become a potential plant-based novel alternative to the disputed glyphosate.