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Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Toxicity — Perilla ketone is a potent pulmonary edemagenic agent for lab animals and livestock. Perilla ketone, egomaketone, and isoegonaketone are chemically closely related to the toxic ipomeanols of moldy sweet potatoes; intravenous doses of the compounds generally resulted in illness or death, while intraruminal injections had no effect. All resulted in pleural effusion and edema.252,253 Okazaki et al.254 report dermatitis on the hands of 20 to 50% of long-time workers with the plant. Patch tests were performed with results suggesting that this skin disease is associated with 1-perillaldehyde and perillalcohol contained in shiso oil. Patients responded negatively to patch tests, with perillic acid detected on cotton gloves once used by them. Guinea pig maximization tests were carried out with these shiso oil components. The experimental animals became sensitized with perillaldehyde and not with perillalcohol or perillic acid.
Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Yoshiaki Noma, Yoshinori Asakawa
Limonene is the most widely distributed terpene in nature after α-pinene (4) (Krasnobajew, 1984). (4R)-(+)-Limonene (68) is present in citrus peel oils at a concentration of over 90%; a low concentration of the (4S)-(−)-limonene (68′) is found in oils from the Mentha species and conifers (Bauer et al., 1990). The first microbial biotransformation on limonene was carried out by using a soil Pseudomonad. The microorganism was isolated by the enrichment culture technique on limonene as the sole source of carbon (Dhavalikar and Bhattacharyya, 1966). The microorganism was also capable of growing on α-pinene (4), β-pinene (1), 1-p-menthene (62), and p-cymene (178). The optimal level of limonene for growth was 0.3%–0.6% (v/v) although no toxicity was observed at 2% levels. Fermentation of limonene (68) by this bacterium in a mineral salt medium resulted in the formation of a large number of neutral and acidic products such as dihydrocarvone (64), carvone (61), carveol (60), 8-p-menthene-1,2-cis-diol (65b), 8-p-menthen-1-ol-2-one (66), 8-p-menthene-1,2-trans-diol (65a), and 1-p-menthene-6,9-diol (62). Perillic acid (69), β-isopropenyl pimaric acid (72), 2-hydroxy-8-p-menthen-7-oic acid (70), and 4,9-dihydroxy-1-p-menthen-7-oic acid (73) were isolated and identified as acidic compounds. Based on these data, three distinct pathways for the catabolism of limonene (68) by the soil Pseudomonad were proposed by Dhavalikar et al. (1966), involving allylic oxygenation (pathway 1), oxygenation of the 1,2-double bond (pathway 2), and progressive oxidation of the 7-methyl group to perillic acid (82) (pathway 3) (Figure 22.27) (Krasnobajew, 1984). Pathway 2 yields (+)-dihydrocarvone (101) via intermediate limonene epoxide (69) and 8-p-menthen-1-ol-2- one (72) as oxidation product of limonene-1,2-diol (71). The third and main pathway leads to perillyl alcohol (74), perillaldehyde (78), perillic acid (82), constituents of various essential oils and used in the flavor and fragrance industry (Fenaroli, 1975), 2-oxo-8-p-menthen-7-oic acid (85), β-isopropenyl pimaric acid (86), and 4,9-dihydroxy-1-p-menthene-7-oic acid (83).
Perillaldehyde Protects Against Aspergillus fumigatus Keratitis by Reducing Fungal Load and Inhibiting Inflammatory Cytokines and LOX-1
Published in Current Eye Research, 2022
Mengting He, Jia You, Xing Liu, Xudong Peng, Cui Li, Shanshan Yang, Qiang Xu, Jing Lin, Guiqiu Zhao
Perillaldehyde (PAE) is the main component of essential oil derived from perilla plant (Perilla frutescens), which has valued us due to its extensive antifungal, anti-inflammatory functions in fighting against infectious diseases.6 Both fungal virulence factors and excessive inflammation can lead to corneal tissue damage.7 Fungal infections include the adhesion to host cells, the growth of hyphae, and the formation of biofilm, which lead to the invasion of fungi and the aggravation of diseases.8–10 Researches revealed that PAE was able to inhibit the growth of Candida albicans (C. albicans) in vitro and it could also interfere with ergosterol biosynthesis, which can lead to the destruction of biofilm of Aspergillus niger.11–13 Our previous studies also verified that PAE had an inhibitory effect on the growth of A. fumigatus14. In addition, the excessive secretion of inflammatory cytokines in FK can exacerbate corneal damage.15 In latest studies, PAE was confirmed to decrease the number of immune cells like neutrophils and macrophages in mice infected with C. albicans and alleviate the overexpression of inflammatory factors in cerebral ischemia–reperfusion injury.16,17
Inhibition of TRIM14 protects cerebral ischemia/reperfusion injury through regulating NF-κB/NLRP3 pathway-mediated inflammation and apoptosis
Published in Journal of Receptors and Signal Transduction, 2022
Xianlong Xie, Fan Wang, Xiujuan Li
Zhang et al. indicated that Tenacissoside H could protect mice against I/R-induced neurological impairments via modulating inflammation and oxidative stress [37]. The anti-apoptotic, anti-oxidant, and anti-inflammatory effects of thalidomide on cerebral I/R injury in rats have been also reported [38]. Xu et al. indicated that Perillaldehyde attenuates cerebral I/R injury in the rat brain cortex, and suggest its neuroprotective effect is related to regulating the inflammatory response [39]. Other medicines, including polysaccharides of the Euphoria longan (Lour.) [40], Buyang Huanwu Decoction fraction [41], and Methionine [42], are also reported to exert protective roles in I/R injury. Whether TRIM14 was involved in the underlying mechanism needs further investigations. Considering the results from the present study, agents for inhibiting TRIM14 are also potential factors for the treatment of cerebral I/R. In conclusion, this study confirmed that TRIM14 knockdown could inhibit the apoptosis of neurons and the inflammatory response after I/R and thus protected the brain. This study provides a new idea for further study on the mechanism of cerebral I/R injury and provides a new therapy for cerebral vascular diseases.