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Antioxidant properties and application information
Published in Roger L. McMullen, Antioxidants and the Skin, 2018
Nordihydroguaiaretic acid occurs naturally in the creosote bush (Larrea tridentata), which is native to Mexico and the Southwestern region of the U.S. Nordihydroguaiaretic acid has various pharmacological properties, and for this reason it is often utilized in folk medicine. In addition, it is a potent antioxidant and also inhibits lipoxygenase (enzyme responsible for the formation of lipid hydroperoxide) and cycloxygenase (enzyme responsible for the conversion of arachidonic acid to prostaglandin H2) pathways. Up until the 1960s, it was used extensively as a food preservative until it was withdrawn for toxicity reasons. It was determined that the toxicity was a result of the formation of alpha-quinone during nordihydroguaiaretic acid metabolism. Nowadays, some naturopathic practitioners use chaparral (leaves and flowers from the creosote bush); however, it is not recommended by the FDA. Consumers are warned of possible hepatoxicity and renal complications due to chronic use.
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Important as the dominant vegetation on large areas, serving as an efficient soil protector and stabilizer. Unfortunately, it is nearly worthless for forage. Material soaked in 0.1 normal solution of NaOH for 2 hr, then washed to remove the resin, was quite palatable, as is or ensiled, with crude protein running around 18%. The reddish-brown resin deposited by scale insects was used by the Pima Indians for mending pottery, cementing arrowheads, and coating baskets. Bark contains a reddish dyestuff. Wood favored for smoking game. Contains the antibiotic nordihydroguaiaretic acid (NDGA) active against skin bacteria. Tierra28 classes chaparral as one of the best herbal antibiotics, being used against bacteria, viruses, and other parasites — internally and externally. NDCA is a powerful antioxidant used to preserve fats and oils, once important in the baking industry, approved as a food additive both nationally and internationally.63
Secretion, Alveolar Processing, and Turnover of Pulmonary Surfactant
Published in Jacques R. Bourbon, Pulmonary Surfactant: Biochemical, Functional, Regulatory, and Clinical Concepts, 2019
Other studies have addressed the question of the direct effect of prostaglandins on type II pneumocytes and of the production of prostaglandins and other lipid mediators by these lung cells. Some81 reported a stimulating effect of prostaglandin F2α, while others82 found that the type II cell responded poorly to exogenous prostaglandins. On the other hand, type II cells have been reported to synthesize various lipid mediators from arachidonic acid.81–83 Fetal type II cells appear to produce predominantly prostaglandin E2, while adult cells would rather produce prostacyclin.82 They also synthesize products of the lipoxygenase pathway like hydroxy-eicosa-tetraenoic acid.83 Gilfillan and Rooney84 reappraised the problem in studying the effects of arachidonic acid itself on phosphatidylcholine secretion by type II pneumocytes in primary culture and the consequences of the simultaneous addition of different inhibitors of arachidonic acid metabolism. Arachidonic acid was shown to stimulate secretion in a dose-dependent manner in the range of 1 to 8 µM. The authors tested the effects of nordihydroguaiaretic acid, an inhibitor of the conversion of arachidonic acid to various metabolites, including leukotrienes, through the lipoxygenase pathway, and of various inhibitors of the conversion of arachidonic acid to prostaglandins, thromboxans, and prostacyclin through the cyclooxygenase pathway. Nordihydroguaiaretic acid inhibited arachidonic acid effects at a concentration severalfold less than did indomethacin, while other cyclooxygenase inhibitors were not inhibitory. This strongly suggested that arachidonic acid derivates synthesized through the lipoxygenase pathway were implicated in the surfactant secretion process. More recently, the same investigators demonstrated that leukotrienes E4, D4, and C4 (decreasing order of potency) were stimulatory agents of PC secretion by cultured type II pneumocytes.85 A leukotriene antagonist abolished their effects and reduced those of arachidonic acid.85 The latter study confirms that the stimulatory effect of arachidonic acid on surfactant phospholipid secretion is mediated at least in part by leukotrienes. This is consistent with reports of the presence of receptors specific for leukotrienes in the guinea pig86,87 or the rat88 lung.
Bioactivation of herbal constituents: mechanisms and toxicological relevance
Published in Drug Metabolism Reviews, 2019
Nordihydroguaiaretic Acid (NDGA), a major lignan isolated from the leaves of the evergreen desert shrub Larrea tridentata (Creosote bush) in the southwest United States, has been used in folk medicine for treatment of multiple diseases including cardiovascular diseases, neurological disorders and cancers (Lü et al. 2010). NDGA has a wide range of pharmacological activities including radical-scavenging, antioxidant, cytoprotective, and antitumoral activities (Hernández-Damián et al. 2014). As a lipophilic antioxidant, NDGA was used as a preservative in food industry and was later withdrawn due to its nephrotoxicity and hepatotoxicity in animals (Grice et al. 1968; Lambert et al. 2002). NDGA is the active ingredient in the herbal medicine Chaparral prepared from the creosote bush, and chronic use has been associated with hepatotoxicity in humans (Sheikh et al. 1997). It has been shown that NDGA, a di-catechol lignan, was oxidized to ortho-quinones to form mono- and di-GSH-NDGA adducts (Jeong et al. 2017) (Figure 11(e)). A toxicological mechanism involving ortho-quinone formation has been suggested to elicit liver and kidney toxicities of NGDA (Billinsky et al. 2007). On the other hand, autoxidation of NGDA to ortho-quinones likely contributed to its pharmacological properties including lipoxygenase inhibition and modulation of Keap1/Nrf2/ARE redox signaling system (Hernández-Damián et al. 2014).
New flavonoid – N,N-dibenzyl(N-methyl)amine hybrids: Multi-target-directed agents for Alzheimer´s disease endowed with neurogenic properties
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2019
Martín Estrada-Valencia, Clara Herrera-Arozamena, Concepción Pérez, Dolores Viña, José A. Morales-García, Ana Pérez-Castillo, Eva Ramos, Alejandro Romero, Erik Laurini, Sabrina Pricl, María Isabel Rodríguez-Franco
A selection of new hybrids covering different structural motifs was assayed as inhibitors of hLOX-5, followed the method described by Pufahl et al.55. Two well-known inhibitors, namely (R,S)-zileuton and nordihydroguaiaretic acid (NDGA), were used as internal references and results are gathered in Table 2. Tested compounds were modest hLOX-5 inhibitors, the majority of them with IC50 values in the two-digit micromolar range.