Perillaldehyde

Anti-Leishmania and cytotoxic activities of perillaldehyde epoxide synthetic positional isomers.[Pubmed:29533085]

Nat Prod Res. 2018 Mar 13:1-5.

Leishmaniasis belongs to a complex of zoonotic disease caused by protozoa of the genus Leishmania and is considered a major public health problem. Several essential oil chemical components have inhibitory effect against protozoa, including Leishmania donovani. Thus, the aim of this study was to evaluate for the first time the anti-Leishmania activity of two p-menthane monoterpene isomers (EPER-1: Perillaldehyde 1,2-epoxide and EPER-2: Perillaldehyde 8,9-epoxide) against L. donovani promastigotes as well as evaluating cytotoxic effect on mononuclear peripheral blood cells. Results of anti-Leishmania assay revealed that EPER-2 (IC50 = 3.8 mug.mL(-1)) was 16-fold more potent than its isomer EPER-1 (IC50 = 64.6 mug.mL(-1)). In contrast to PBMC cells, EPER-2 was not cytotoxic (IC50 > 400 mug.mL(-1)) when compared to positive control. These data suggest that the disposition of epoxide group into the p-menthane skeleton affects the anti-Leishmania activity, being that the presence of the exocyclic epoxide group considerably increased potency. Thus, it was possible to observe that the location of the epoxide group into the p-menthane skeleton resulted in different potencies.

[Research on effects of chemotype and components of Perilla frutescens leaf volatile oil I: different phenological periods].[Pubmed:28959842]

Zhongguo Zhong Yao Za Zhi. 2017 Feb;42(4):712-718.

This experiment researched on three kinds of Perilla frutescens including the widespread PK, PA and rare PL chemotype. The Perilla samples were the mature leaves collected in nutrition, flowering and frutescence three different phenological periods, and at 7 am, 12 pm and 6 pm three day time. The volatile oil was extracted by steam distillationand analyzed by GC-MS, as a result, the three chemotype samples'volatile oil yield was between 0.08% and 0.96%; volatile oil yield of different growth period was as follow: nutrition>flowering>fructescence, and the volatile oil yield of nutrition period: PA type>PK type>PL type. Each chemotype was not affected by the growth and development, indicating that the chemotype is determined by genetic factors. Characteristic and main components of PA and PK type are relatively stable, and the characteristic components of PL type are significantly decreased with the growth. There are still a large number of upstream metabolism components, and the chemical type may have their primitiveness and changeability. The relative content of Perillaldehyde, characteristic components of PA type, is basically decreased from morning to night, in all the period. The relative content of perillaketone, characteristic components of PK type, in nutrition and flowering period, when samples were collected at 12 noon is relatively higher than that at 7 am and 6 pm, and contrary to samples collected in frutescence period. The relative content of perillene, characteristic components of PL type, in nutrition and frutescence period are highest at 12 noon, while in flowering period is highest at 6 pm. According to the volatile oil yield and relative content of maincomponents, the best harvest time of PA type is in the morning of the nutrition period; the best harvest time of PK type is in the morning of all the period; and the best harvest time of PL type is at dusk of the nutrition period.

Monoterpenes induce the heat shock response in Arabidopsis.[Pubmed:29197862]

Z Naturforsch C. 2018 Apr 25;73(5-6):177-184.

Monoterpenes are common constituents of essential oils produced by plants. Although it has been reported that monoterpenes enhanced the heat tolerance of plants, the mechanism has not been elucidated. Here, we tested whether 13 monoterpenes promoted the heat shock response (HSR) in Arabidopsis. To assess the HSR-inducing activity of monoterpenes, we produced transgenic Arabidopsis, which has the beta-glucuronidase gene driven by the promoter of a small heat shock protein (HSP17.6C-CI) gene. Results indicated that two monocyclic and four bicyclic monoterpenes showed HSR-inducing activities using the reporter gene system. In particular, (-)-Perillaldehyde, which is a monocyclic monoterpene, demonstrated the most potent HSR-inducing activity. (-)-Perillaldehyde significantly inhibited the reduction of chlorophyll content by heat shock in Arabidopsis seedlings. Our previous study indicated that chemical HSR inducers such as geldanamycin and sanguinarine inhibited the activity of plant chaperones in vitro. (-)-Perillaldehyde also inhibited chaperone activity, indicating that it might promote the expression of heat shock protein genes by inhibiting chaperones in the plant cell.

Comparison of the production and chemical constituents of five Perilla frutescens (L.) Britt. accessions.[Pubmed:29262704]

Acta Biol Hung. 2017 Dec;68(4):453-465.

An open field experiment was carried out with five purple Perilla frutescens accessions (588P, GB, J3, JTD3, PS3) in 2014 and 2015. Morphological traits, production, total phenolic content (TPC), essential oil content (EOC) and composition as well as the antioxidant capacity (AOC) were investigated. Highest biomass was produced by JTD3 in both years. The antioxidant capacity and total phenolic content in the stems was lower than in the leaves in all accessions. Leaves of accession GB produced the highest AOC values (215.594 +/- 1.437 in 2014 and 86.609 +/- 3.602 mg AAE g(-1) in 2015, respectively) while the strain 588P showed the lowest values (139.544 +/- 1.934 in 2014 and 38.966 +/- 4.569 mg AAE g(-1) in 2015, respectively). The highest TPC values were measured by PS3 in 2014 (204.320 +/- 1.822 mg GAE g(-1)) and GB in 2015 (136.450 +/- mg GAE g(-1)). The 588P produced the highest essential oil content (1.432 ml 100 g(-1) DM) while J3 had the lowest (0.144 ml 100 g(-1) DM) in both years. Strong positive correlation was found between the density of glandular hairs and the essential oil content. Three accessions (588P, J3, JTD3) belong to the Perillaldehyde chemotype while GB and PS3 to the dehydro elsholtzia ketone chemotype. All studied accessions can be cultivated in Hungary. For the biomass production the JTD3, while for the essential oil production the 588P can be recommended.

Perillaldehyde Inhibits AHR Signaling and Activates NRF2 Antioxidant Pathway in Human Keratinocytes.[Pubmed:29643980]

Oxid Med Cell Longev. 2018 Feb 14;2018:9524657.

The skin covers the outer surface of the body, so the epidermal keratinocytes within it are susceptible to reactive oxygen species (ROS) generated by environmental pollutants such as benzo(a)pyrene (BaP), a potent activator of aryl hydrocarbon receptor (AHR). Antioxidant activity is generally mediated by the nuclear factor-erythroid 2-related factor-2 (NRF2) and heme oxygenase-1 (HO1) axis in human keratinocytes. Perillaldehyde is the main component of Perilla frutescens, which is a medicinal antioxidant herb traditionally consumed in East Asia. However, the effect of Perillaldehyde on the AHR/ROS and/or NRF2/HO1 pathways remains unknown. In human keratinocytes, we found that Perillaldehyde (1) inhibited BaP-induced AHR activation and ROS production, (2) inhibited BaP/AHR-mediated release of the CCL2 chemokine, and (3) activated the NRF2/HO1 antioxidant pathway. Perillaldehyde is thus potentially useful for managing inflammatory skin diseases or disorders related to oxidative stress.

Growth and Accumulation of Secondary Metabolites in Perilla as Affected by Photosynthetic Photon Flux Density and Electrical Conductivity of the Nutrient Solution.[Pubmed:28523012]

Front Plant Sci. 2017 May 4;8:708.

The global demand for medicinal plants is increasing. The quality of plants grown outdoors, however, is difficult to control. Myriad environmental factors influence plant growth and directly impact biosynthetic pathways, thus affecting the secondary metabolism of bioactive compounds. Plant factories use artificial lighting to increase the quality of medicinal plants and stabilize production. Photosynthetic photon flux density (PPFD) and electrical conductivity (EC) of nutrient solutions are two important factors that substantially influence perilla (Perilla frutescens, Labiatae) plant growth and quality. To identify suitable levels of PPFD and EC for perilla plants grown in a plant factory, the growth, photosynthesis, and accumulation of secondary metabolites in red and green perilla plants were measured at PPFD values of 100, 200, and 300 mumol m(-2) s(-1) in nutrient solutions with EC values of 1.0, 2.0, and 3.0 dS m(-1). The results showed significant interactive effects between PPFD and EC for both the fresh and dry weights of green perilla, but not for red perilla. The fresh and dry weights of shoots and leafy areas were affected more by EC than by PPFD in green perilla, whereas they were affected more by PPFD than by EC in red perilla. Leaf net photosynthetic rates were increased as PPFD increased in both perilla varieties, regardless of EC. The Perillaldehyde concentration (mg g(-1)) in red perilla was unaffected by the treatments, but accumulation in plants (mg per plant) was significantly enhanced as the weight of dry leaves increased. Perillaldehyde concentrations in green perilla showed significant differences between combinations of the highest PPFD with the highest EC and the lowest PPFD with the lowest EC. Rosmarinic acid concentration (mg g(-1)) was increased in a combination of low EC and high PPFD conditions. Optimal cultivation conditions of red and green perilla in plant factory will be discussed in terms of plant growth and contents of medicinal ingredients.

Intestinal Anti-Inflammatory Activity of Perillaldehyde.[Pubmed:29533613]

J Agric Food Chem. 2018 Apr 4;66(13):3443-3448.

Monoterpenoid Perillaldehyde (PA) is the major component in Perilla frutescens leaf essential oil, but its function regarding anti-inflammatory effect is unclear. We explored the anti-inflammatory activity of PA in a dextran sulfate sodium (DSS)-induced colitis mouse model using relief of bodyweight loss (avg. 49.2% mitigation; P = 0.094) and colon damage (avg. 35.3% mitigation; P < 0.05) by administration of PA at a 100 mg/kg dosage. The PA administration resulted in suppression of DSS-induced expression of pro-inflammatory cytokine genes and matrix metalloproteinase-9 in the colon (e.g., avg. 60.6% mitigation for TNF-alpha mRNA levels; P < 0.05). These effects were confirmed in macrophage RAW264.7 cells stimulated with lipopolysaccharide (LPS). Application of PA induced cell suppression of LPS-induced expressions of genes and proteins of pro-inflammatory cytokines and induced activation of c-Jun N-terminal kinases (JNKs, p54 and p46; P < 0.05) but not nuclear factor-kappaB p65. The half maximal inhibitory concentration for decreased expression levels of TNF-alpha mRNA was 171.7 muM. We discuss the in vivo function of PA in amelioration of intestinal inflammation via JNK-mediated cytokine regulation.