Perillaldehyde Research Articles

Perilaldehyde activates AMP-activated protein kinase to suppress the growth of gastric cancer via induction of autophagy.

Perillaldehyde (PAH), one of the major oil components in Perilla frutescens, is very critical to health maintenance, for a wide range of human chronic diseases, including cancers. AMP-activated protein kinase (AMPK) has been implicated in the activation of autophagy in distinct tissues. This study was designed to explore whether PAH prevents gastric cancer growth and to investigate the molecular mechanism. In cultured mouse gastric cancer cell line MFCs and human gastric cancer cell lines GC9811-P, PAH activated AMPK by increasing the Thr172 phosphorylation and activity in a time-/concentration-dependent manner. Furthermore, incubation of MFCs with PAH also increased autophagy as determined by monodansylcadaverine (MDC) staining, which was reversed by AMPK inhibitor compound C. PAH further decreased MFCs cell survival, which was abolished by compound C or autophagy inhibitor 3-Methyladenine (3-MA). In vivo studies indicated that 4-week administration of PAH (100 mg/kg/day) suppressed the growth of gastric cancer and increased the levels of autophagy-related proteins, including beclin-1, LC3-II, cathepsin, caspase-3, p53, and cathepsin in tumors isolated from the xenograft model of gastric cancer in mice. Moreover, these anticancer effects produced by PAH were abolished by coadministration of compound C or 3-MA in vivo. PAH increases AMPK phosphorylation and activity to induce gastric cancer cell autophagy to inhibit the growth of gastric cancer. In perspective, therapy of PAH should be applied to treat patients with gastric cancer.

Induced cell death in Ceratocystis fimbriata by pro‐apoptotic activity of a natural organic compound, perillaldehyde, through Ca2+ overload and accumulation of reactive oxygen species

Black rot caused by the fungus Ceratocystis fimbriata causes notable losses in sweet potato production. Perillaldehyde (PAE), a secondary metabolite in perilla, was studied to determine its antifungal effects on mycelial growth and spore germination of C. fimbriata. The effects of PAE on cell wall integrity and cell membrane permeability were also investigated. To elucidate the possible mechanisms of cell death triggered by PAE, sensitivity of C. fimbriata to PAE toxicity was determined by cytoplasmic and mitochondrial calcium ion concentrations ([Ca2+]c and [Ca2+]m), reactive oxygen species (ROS), mitochondrial membrane potential (MMP), cytochrome c (cyt c) release, metacaspase activation, phosphatidylserine (PS) externalization and DNA fragmentation. The results suggest that mycelial growth and spore germination were inhibited by PAE in a dose‐dependent manner. Ceratocystis fimbriata spores treated with PAE experienced dramatic Ca2+ overload and elevated ROS production. Compared to untreated controls, the proportion of fluorescent cells stained with the ROS indicator DCFH‐DA and treated with a range of PAE concentrations from 0.0625 to 0.50 μL mL−1 increased by 2.9 ± 0.79% to 27.1 ± 0.38%. Ca2+ overload and ROS accumulation induced depolarization of the MMP, contributing to mitochondrial dysfunction. Cyt c was released from the mitochondria to the cytosol, triggering metacaspase activation. The significant antifungal activity of PAE on C. fimbriata was demonstrated by these studies, suggesting that PAE has the potential for wide application to postharvest management of tuber crops, in addition to the application to above‐ground fruit and vegetables that have been previously investigated.

Perillaldehyde prevents the formations of atherosclerotic plaques through recoupling endothelial nitric oxide synthase

Nitric oxide (NO) produced by endothelial NO synthase (eNOS) is essential for cardiovascular homeostasis owing to its anti-inflammatory, antithrombotic, antiproliferative, and antioxidant effects. Perillaldehyde (PAH), one of the major oil components in Perilla frutescens, has anti-inflammatory effects. This study was designed to explore whether PAH prevents atherosclerosis through normalizing eNOS functions. The model of atherosclerosis was induced by feeding rats and mice with high-fat diet or plus balloon injury. Oil red and hematoxylin-eosin (HE) stainings were used to assess the atherosclerotic plaque. Pretreatment of PAH for 30 minutes concentration-dependently increased tetrahydrobiopterin (BH4) levels, NO generations, and improved cell viabilities in cultured human umbilicus vessel endothelial cells (HUVEC) incubated with oxidized (OX) low-density lipoprotein (LDL), in which all protective effects of PAH were abolished by guanosinetriphosphate (GTP) cyclohydrolase 1 inhibitor 2,4-Diamino-6-hydroxypyrimidine (DAHP) or eNOS inhibitor L-NAME in those cells. In rats, high-fat diet plus balloon injury induced the formation of atherosclerotic plaque in carotid arteries. Administration of PAH or lovastatin reduced the size of atherosclerotic plaque in rats and improved the responses of aortic rings to acetylcholine isolated from rats, accompanied with increased BH4 content and NO generations. In Apoe -/- mice feeding with normal diet or high-fat diet, PAH (150 mg/kg) reduced the size of atherosclerotic plaque in aortic arteries, prevented endothelial dysfunctions, and increased both BH4 and NO generations in carotid arteries. PAH prevents the growth of atherosclerosis through increasing BH4 generation and subsequent eNOS recouping. Clinically, PAH should be considered as a new medicine to treat patients with atherosclerosis.

Perillaldehyde Controls Postharvest Black Rot Caused by Ceratocystis fimbriata in Sweet Potatoes.

Black rot caused by Ceratocystis fimbriata is the most damaging postharvest disease among sweet potatoes. Black rot can be controlled by synthetic fungicides, but these synthetic fungicides also have several negative effects. Perillaldehyde (PAE), a major component of the herb perilla, is an effective and eco-friendly method of controlling this disease. The antifungal activity of PAE on the mycelial growth in C. fimbriata was evaluated in vitro. Sweet potatoes at the postharvest stage were surfaced-disinfected with 75% ethanol. Artificially created wounds were inoculated with a C. fimbriata cell suspension, and then, the PAE was spontaneously volatilized inside the residual airspace of the containers at 28°C. Samples were collected at 0, 3, 6, 9, 12, 15, 18, and 21 days from each group, and the tissues around the wounds of the sweet potatoes were collected using a sterilized knife and then homogenized to determine their defense-related enzyme activity and quality parameters. In vitro assays showed that the mycelial growth of C. fimbriata was inhibited by PAE in a dose-dependent manner. An in vivo test demonstrated that 25, 50, and 100 μl/l PAE doses, when applied to sweet potatoes inoculated with C. fimbriata, could remarkable lower lesion diameter as compared to the control. Even though the storage time was prolonged, PAE vapor treatment still drastically inhibited sweet potato decay during storage at 28°C. These PAE vapor treatments also enhanced the activities of superoxide dismutase (SOD), catalase (CAT), ascorbate peroxidase (APX), peroxidase (POD), polyphenol oxidase (PPO), and phenylalanine ammonia-lyase (PAL). These treatments remarkably decreased weight loss rates and had minor effects on other fruit quality parameters, such as anthocyanin content and vitamin C content. In our study, the results suggested that the effects of PAE on postharvest sweet potatoes may be attributed to the maintenance of enzymatic activity and fruit quality. In sum, PAE may be a promising approach to controlling C. fimbriata in sweet potatoes.

Perilla aldehyde attenuates CUMS-induced depressive-like behaviors via regulating TXNIP/TRX/NLRP3 pathway in rats

BackgroundCurrent evidence supports that inflammatory reaction in the hippocampus is a potential cause of major depressive disorder (MDD). Perilla aldehyde (PAH), a major constituent from Perilla frutescens, has been reported to have anti-inflammatory and anti-oxidant activity. The aim of this study is to explore the antidepressant-like effect and the underlying mechanism of PAH on the rats model induced by chronic unpredictable mild stress (CUMS). MethodsCUMS rats model was built to tested their depressive-like behaviors. The levels of pro-inflammatory cytokines were tested. Proteins were analyzed by Western blot and Immunohistochemistry. ResultsWe found that treatment with PAH (20, 40 mg/kg) and fluoxetine (FLU, 10 mg/kg) significantly improved the sucrose consumption, immobility time in forced swim test (FST), as well as locomotor activity in open-field test (OFT). The levels of pro-inflammatory cytokines in hippocampus were also suppressed effectively by PAH and FLU administration. Western blot analysis showed the up-regulated levels of TXNIP, NLRP3, Cleaved caspase-1 and p-NF-κB p65 in the hippocampus in rats exposed to CUMS paradigm, while different degrees of down-regulation in their expression were detected after PAH (20, 40 mg/kg) and FLU (10 mg/kg) treatment respectively. The results from histopathological examination further demonstrated that PAH (20, 40 mg/kg) and FLU (10 mg/kg) treatment reversed the alteration of TRX, NLRP3 and Cleaved caspase-1 induced by CUMS procedure. ConclusionsOur results demonstrated that PAH exhibited antidepressant-like effect in CUMS-induced rats model of depression, which might be mediated by TXNIP/TRX/NLRP3 pathway.

Chemical profile and bioactive properties of the essential oil isolated from Ammodaucus leucotrichus fruits growing in Sahara and its evaluation as a cosmeceutical ingredient

Ammodaucus leucotrichus is a medicinal plant commonly used in Algeria by the indigenous populations, especially due to its therapeutic effects. In this context, the aim of the present study was to chemically characterize the essential oil of A. leucotrichus fruits (EOALF) growing in Algerian Sahara, and to evaluate its bioactive properties (antimicrobial, antioxidant and anti-inflammatory). Considering the interest of the cosmetic industry for natural ingredients, and taking into account the obtained biological properties, the essential oil was also evaluated by incorporation in a base cosmetic (cream). The essential oil was extracted with a yield of 2.58 ± 0.17%, being perilla aldehyde identified as the main component, accounting for 85.6% of the total composition. Concerning the tested bioactivities, EOALF presented antioxidant potential, a strong anti-inflammatory activity, and was effective against the tested microbial strains (Staphylococcus aureus, Eschericia coli and Pseudomonas aeruginosa), being S. aureus the most sensitive bacteria. After incorporation in a base cosmetic, the developed formulation was able to preserve the EOALF bioactivities along 28 days under storage. The obtained results, with relevance for the strong-anti-inflammatory activity, pointed out the interest to exploit this essential oil as a cosmeceutical ingredient in the cosmetic industry.

Intestinal Anti-Inflammatory Activity of Perillaldehyde.

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-α 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-κB p65. The half maximal inhibitory concentration for decreased expression levels of TNF-α mRNA was 171.7 μM. We discuss the in vivo function of PA in amelioration of intestinal inflammation via JNK-mediated cytokine regulation.

A Comparative Evaluation of the Cytotoxic and Antioxidant Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone, and Analogues on Human Glioblastoma.

Cancer is a major public health problem around the globe. This disorder is affected by alterations in multiple physiological processes, and oxidative stress has been etiologically implicated in its pathogenesis. Glioblastoma (GBM) is considered the most common and aggressive brain tumor with poor prognosis despite recent improvements in surgical, radiation, and chemotherapy-based treatment approaches. The purpose of this study was to evaluate antitumor activity from Mentha crispa essential oil (MCEO), its major constituent rotundifolone (ROT), and a series of six analogues on the human U87MG glioblastoma cell line. Cytotoxic effects of the compounds on the human U87MG-GBM cell line were assessed using in vitro cell viability and oxidative and molecular genetic assays. In addition, biosafety assessment tests were performed on cultured human blood cells. Our findings revealed that MCEO, 1,2-perillaldehyde epoxide (EPER1), and perillaldehyde (PALD) were the most cytotoxic compounds against U87MG cells, with IC50 values of 16.263, 15.087, and 14.888 μg/mL, respectively. Further, these compounds increased the expressions of BRAF, EGFR, KRAS, NFκB1, NFκB1A, NFκB2, PIK3CA, PIK3R, PTEN, and TP53 genes at different degrees and decreased the expression of some genes such as AKT1, AKT2, FOS, and RAF1. Finally, treatment with MCEO, EPER1, and PALD did not lead to genotoxic damage in blood cells. Taken together, our findings reveal antiproliferative potential of MCEO, its major component ROT, and its tested analogues. Some of these chemical analogues may be useful as prototypes for the development of novel chemotherapeutic agents for treating human brain cancer and/or other cancers due to their promising activities as well as nonmutagenic property and safety.

Calcium and oxidative stress mediate perillaldehyde-induced apoptosis in Candida albicans.

New anti-Candida albicans drugs are needed due to the emergence of resistant cases in recent years. Perillaldehyde (PAE) is a natural monoterpenoid compound derived from Perilla frutescens. The minimum inhibitory concentration of PAE against C. albicans was 0.4μL/mL. We aimed to elucidate the antifungal mode of action of PAE against C. albicans. The antifungal activity of PAE against C. albicans was found to correlate with an elevation in intracellular Ca2+ and accumulation of ROS. Several downstream apoptosis events such as the disruption of mitochondrial membrane potential, phosphatidylserine externalization, cytochrome c release, and metacaspase activation were observed in PAE-treated cells. DNA damage and nuclear fragmentation assays also revealed apoptosis of C. albicans cells. In summary, by means of fluorescent microscopy, flow cytometer analysis, and Western blot, our data uncovered that PAE exerts its antifungal activity through Ca2+ and oxidative stress-mediated apoptosis mechanisms. This study deciphered the mode of action of PAE, which will be useful in the design of improved antifungal therapies.

Anti-mycotoxin Effect and Antifungal Properties of Essential Oil from Ammodaucus leucotrichus Coss. & Dur. on Aspergillus flavus and Aspergillus ochraceus

The essential oil of Ammodaucus leucotrichus Coss. & Dur. seeds growing wild in SouthWest of Algeria were obtained by hydrodistillation and analysed by GC and GC-MS. Other parameters such as density, refractive index, optical rotation, freezing point, solubility in ethanol, acid value and ester index are also measured. The antifungal properties of the essential oil were conducted using biomass technique on liquid medium, mycotoxigenic test, mycelial growth, determination of minimum inhibitory concentration (MIC), sporulation and germination spores’. The essential oil was found to be active against Aspergillus flavus MTTC 2799 (Microbial Type Culture Collection and Gene Bank) and Aspergillus ochraceus CECT 2092 (Spanish Type Culture Collection). The GC and GC-MS data showed a total of 19 compounds were identified in the hydrodistilled oil. The oil was dominated by oxygenated monoteprenes represented by perilla aldehyde (81.62%).

Active Volatile Constituents in Perilla frutescens Essential Oils and Improvement of Antimicrobial and Anti-Inflammatory Bioactivity by Fractionation

Perilla frutescens (L.) Britt Labiatae (Pl), known as “Zi-So” and widely grown in China (red cultivar, Rpl) and Japan (green cultivar, Gpl), is frequently served on “Sa-Shi-Mi” dishes. Considering whether the perilla leaves substantially possess antimicrobial activity, we prepared the essential oils (EO: EOr and EOg), the pentane and ether [E: E(rp) and E(gp)] subfractions, the aqueous [Rpl(w) and Gpl(w)] and ethanolic extracts [pl(E), Rpl(E) and Gpl(E)] to compare their biological activities. Results indicated Gpl(E) and Rpl(E) contained huge amount (in mg/100 g) of polyphenoilcs (1472±1.0 vs. 1269.8±1.7), rutin (20.8±0.8 vs. 11.4±0.6), quercetin (29.8±0.9 vs. 13.6±0.6), and lutein (13.9±0.7 vs. 14.2±0.8). The total number of volatile constituents present in EOr and EOg were 27 in each but different phytochemicals. The top five major constituents (in %) in EOr were perilla aldehyde (54.35%), limonene (23.81%), trans-caryophyllene (7.2%), cis,trans-α-farnescene (7.02%), and linalool (2.40%); that in EOg were perilla aldehyde (65.26%), limonene (12.49%), cis,trans-α-farnescene (7.31%), trans- caryophyllene (5.91%), and linalool (2.75%); The top two constituents in E(rp) were perilla aldehyde (93.19%) and linalool (4.02%); that of E(gp) were perilla aldehyde (84.40%) and linalool (5.03%). EO and E showed moderate DPPH free radical scavenging-, ferrous ion chelating-, superoxide anion- and H2O2 -scavenging capabilities. At 1.0 mg/mL the Es always revealed to be superior to EOs against E. coli, S. aureus, V. parahemolyticus, and T. mentagrophytes. Amazingly, E was stronger than perilla aldehyde against S. typhimurium,. The cytotoxicity test indicated Gpl(E) was more toxic than Rpl(E) and the pl(E)s were more toxic than pl(w)s. Conversely, the pl(w)s showed stronger TNF-α suppressing activity than pl(E)s. The pentane subfractions were entirely ineffective. Conclusively, the Perilla EOs contain huge amount of polyphenoilcs, the Es exhibit the rather good antimicrobial and cytotoxic effects, while the pl(w)s possess rather promising anti-inflammatory effect, underlying the promising antimicrobial and antiinflammtory effects of perilla leaves.

Perillaldehyde, a Promising Antifungal Agent Used in Food Preservation, Triggers Apoptosis through a Metacaspase-Dependent Pathway in Aspergillus flavus.

In the present study, we provide detailed insights into perillaldehyde (PAE)'s mechanisms of action on Aspergillus flavus and offer evidence in favor of the induction of an apoptosis-like phenotype. Specifically, PAE's antifungal mode of action was investigated through the detection of mitochondrial membrane potential (MtΔψ) and phosphatidylserine (PS) exposure, as well as intracellular Ca2+ level, reactive oxygen species accumulation, and metacaspase activation. This was done by way of fluorometry, measuring DNA fragmentation, and condensation by fluorescent microscopy. Furthermore, we searched for phenotypic changes characteristic of apoptosis by transmission electron microscopy and flow cytometry, determining the amount of cytochrome c released using Western blotting. Results indicated that cultivation of A. flavus in the presence of PAE caused depolarization of MtΔψ, rapid DNA condensation, large-scale DNA fragmentation, and an elevation of intracellular Ca2+ level. The percentage of early apoptotic cells with exposure of PS were 27.4% and 48.7%, respectively, after 9 h incubations with 0.25 and 0.5 μL/mL of PAE. The percentage of stained cells with activated intracellular metacaspases exposed to PAE at concentrations of 0.25 and 0.5 μL/mL compared with control subjects were increased by 28.4 ± 3.25% and 37.9 ± 4.24%, respectively. The above results has revealed that PAE induces fungal apoptosis through a caspase-dependent mitochondrial pathway. In all, our findings provide a novel mechanism for exploring a possible antifungal agent used in food preservation.

Tissue distribution and enhanced in vivo anti-hyperlipidemic-antioxidant effects of perillaldehyde-loaded liposomal nanoformulation against Poloxamer 407-induced hyperlipidemia

An optimized perillaldehyde-loaded liposomal nanoformulation (PAH-LNF) was successfully applied to improve the pharmacological effect of perillaldehyde (PAH) in poloxamer 407-induced hyperlipidemia. Oral administration of PAH-LNF (240mg/kg per body weight) in rats significantly enhanced solubility and relative bioavailability (270.7%) compared to the free PAH with about 2.7-, 1.5-, 1.3-, 1.3- and 1.5-fold increase in AUC, T1/2, MRT, Cmax and Tmax, respectively. Tissue distribution study also revealed the accumulation of PAH in the liver, lungs, spleen, kidney, brain and heart in order of decreasing affinity. Moreover, a significant decrease in serum total cholesterol (TC), triglyceride (TG) and low-density lipoprotein cholesterol (LDL-C) with simultaneous increase in high-density lipoprotein cholesterol (HDL-C) level was observed in the chemically-induced hyperlipidemic mice which further confirmed PAH’s anti-hyperlipidemic properties. Additionally, PAH-LNF also significantly increased the activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) with a concurrent decrease in malondialdehyde (MDA) to affirm the antioxidant and hepatoprotective effects of PAH. Thus, liposomal nanoformulation promises to be a useful drug delivery system for the development of PAH.

Comparison of five Perilla frutescens (L.) Britt. genotypes in Hungary

In our research work five Perilla frutescens (L.) Britt. accessions (GB, J3, JTD3, PS3, 588P) of different origin were evaluated in an open-filed experiment in 2014. Fresh biomass, number of glandular hairs, essential oil content and composition were studied. The dried herb was hydrodistilled and the oil analysed by GC-MS. The components were identified by MS libraries and their LRIs. Highest fresh biomass was produced by the accession JTD3 (864 g·plant -1 ) while the lowest fresh weight was measured in the population of 588P (396 g·plant -1 ). The highest dlandular hair density (1130 hairs·100 mm -2 ) and essential oil content (1.4 ml·100 g -1 d.w.) was detected in the population 588P while the lowest result were detected in J3 (22 hairs·100 mm -2 , 0.14 ml·100 g d.w. -1 ). Based on the essential oil composition the investigated populations represent different chempotypes. In PS3 and GB the main components of the essential oil was s-dehydro- elsholtzia ketone (54-76 %), they are belong to the elsholtzia ketone (EK) chemotype. The main components of the essential oil in J3, JTD3, 588P population were perilla aldehyde (60-78%), limonene (6-15%) and s-caryophyllene (5-6%) (PA – perillaaldehyde chemotype).

Insecticidal and acetylcholinesterase inhibitory activities of Lamiaceae plant essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae)

Drosophila suzukii is recognized as an economically important pest in North America and Europe as well as Asia. Assessments were made of fumigant and contact toxicities of 12 Lamiaceae plant essential oils (EOs) and their components. The possible mode of action of the major components of the active EOs was pursued by evaluating their activities against acetylcholinesterase (AChE) of D. suzukii. Among the EOs tested, effective fumigant activity was observed with EOs of Mentha piperita and Perilla frutescens. Menthone and menthol, and perilla aldehyde were identified as major components of M. piperita and P. frutescens, respectively. LD50 (mg/L) values of M. piperita, P. frutescens, menthone, menthol and perilla aldehyde was 3.87, 2.44, 5.76, 1.88, and 0.99 against males and 4.10, 3.31, 5.13, 1.94, and 1.15 against females, respectively. EOs of Satureja montana and Thymus zygis showed effective contact toxicity. Thymol, carvacrol, and p-cymene were the most major components of these two EOs. LD50 (μg/fly) values for contact toxicity of S. montana, T. zygis, thymol, and carvacrol were 2.95, 2.93, 1.63, and 1.30 for male, and 4.59, 5.09, 2.68 and 2.60 for female, respectively. p-Cymene was not effective in contact toxicity. Fumigant and contact toxicities of the effective EOs and their major compounds were compared with those of two commercial insecticides. Among the 6 major components which showed fumigant and contact toxicity, perilla aldehyde showed most active inhibition against AChE of both sexes of SWD. Our result indicated that Lamiaceae plant EOs and their components can be used as alternatives to conventional insecticides.

Characterization of the Aldehydes and Their Transformations Induced by UV Irradiation and Air Exposure of White Guanxi Honey Pummelo (Citrus Grandis (L.) Osbeck) Essential Oil.

Aldehydes are key aroma contributors of citrus essential oils. White Guanxi honey pummelo essential oil (WPEO) was investigated in its aldehyde constituents and their transformations induced by UV irradiation and air exposure by GC-MS, GC-O, and sensory evaluation. Nine aldehydes, i.e., octanal, nonanal, citronellal, decanal, trans-citral, cis-citral, perilla aldehyde, dodecanal, and dodecenal, were detected in WPEO. After treatment, the content of citronellal increased, but the concentrations of other aldehydes decreased. The aliphatic aldehydes were transformed to organic acids. Citral was transformed to neric acid, geranic acid, and cyclocitral. Aldehyde transformation caused a remarkable decrease in the minty, herbaceous, and lemon notes of WPEO. In fresh WPEO, β-myrcene, d-limonene, octanal, decanal, cis-citral, trans-citral, and dodecenal had the highest odor dilution folds. After the treatment, the dilution folds of decanal, cis-citral, trans-citral, and dodecenal decreased dramatically. This result provides information for the production and storage of aldehyde-containing products.

Isolation and Identification of a New Phenylpropanoid Derivative from the Fruits of Pimpinella Haussknechtii Rech. f. & Riedl and GC-MS Analysis of the Essential Oil.

The chemical composition of the essential oil of fruits of Pimpinella haussknechtii. was studied by GC-MS. After GC-MS analysis, one unknown component (56.7%) was observed, which was not characterized in the GC-MS library. The essential oil of P.haussknechtii was injected to HPLC using YMC-Pak-Sil column (250 × 20 mm) with gradient system of hexane (A), and hexane: ethyl acetate, 9:1 (B) to yield the interested compound as a new phenylpropanoid derivative. Its structure was elucidated as 4-(prop-2-enyl)-phenyl-3'-methylbutanoate based on (13)C- and (1)H-NMR as well as 2D-NMR, IR and different MS spectra. In the essential oil analysis, thirty-six components, comprising 94.9% of the total oil, were identified. 4-(2-propenyl)-phenyl 3'-methylbutyrate (56.7%), bicyclogermacrene (8.9%), germacrene D (7.6%), perilla aldehyde (3.5%) and β-caryophyllene (2.9%) were found to be the major constituents of the oil. The oil of the fruits of P. haussknechtii consisted of eight monoterpene hydrocarbons (1.7%), two oxygenated monoterpenes (3.9%), sixteen sesquiterpene hydrocarbons (26.8%), two oxygenated sesquiterpenes (2.1%) and five phenylpropanoids (58.7%). Three other nonterpenic compounds also comprised 1.7% of the oil.

Advances in research of volatile oil and its different chemotypes in leaves of Perilla frutescens

The volatile oil is the main component in the leaves of Perilla frutescens. According to the main types of monoterpenoids or aromatic compounds, it can be divided into different chemotypes and the main chemotypes of Chinese producing Perilla are PA type (mainly containing Perilla aldehyde and limonene), PK type (mainly containing perillaketone) and PP type (subdivided as PP-a type, with apiole as its main component; PP-m type, with myristicin as its main component; PP-e type, with elemicin as main component; PP-as type, with asarone as main component). Based on the biosynthetic pathways analysis, we also found that the formation of the particular chemotype is usually controlled by a single gene or a few genes, and different types have different pharmacological effects. In this paper, the classification under the species P. frutescens, main chemotypes of the volatile oil, and their biogenesis and regulation, pharmacological effect and influence factors are summarized and reviewed.

Efficacy and possible mechanisms of perillaldehyde in control of Aspergillus niger causing grape decay

A variety of plant products have been recognized for their antifungal activity and recently have attracted food industry attention for their efficacy in controlling postharvest fungal decay of fruits. The antifungal activity of perillaldehyde (PAE) was evaluated against Aspergillus niger, a known cause of grape spoilage, and possible mechanisms were explored. PAE showed notable antifungal activity against A. niger, with a minimum inhibitory concentration (MIC) and a minimum fungicidal concentration (MFC) of 0.25 and 1μl/ml, respectively. The accumulation of mycelial biomass was also inhibited by PAE in a dose-dependent manner, completely inhibiting mycelial growth at 1μl/ml. In vivo data confirmed that the vapour treatment of grapes with various concentrations of PAE markedly improved control of A. niger and suppressed natural decay. Concentrations of PAE of 0.075μl/ml air showed the greatest inhibition of fungal growth compared to the controls. Further experiments indicated that PAE activated a membrane-active mechanism that inhibits ergosterol synthesis, increases membrane permeability (as evidenced by extracellular pH and conductivity measurements), and disrupts membrane integrity, leading to cell death. Our findings suggest that this membrane-active mechanism makes PAE a promising potential antifungal agent for postharvest control of grape spoilage.

Essential oils of green and red Perilla frutescens as potential sources of compounds for mosquito management

Dengue fever is a mosquito-borne disease transmitted by Aedes aegypti producing high rates of human morbidity and mortality. In order to find new and effective compounds against A. aegypti with low mammalian and less environmental toxic products, green and red Perilla frutescens (L.) Britt. (perilla) essential oils were investigated for their deterrent and larvicidal activity. Green perilla oil showed more promising deterrent and larvicidal activity than red perilla oil. Therefore, we focused on the principle compounds in green perilla oil and, in addition, perilla alcohol and perillic acid were included for the activity relationship on the allylic methyl groups on carbon 7. Chemical composition of green and red perilla essential oils was compared using gas-chromatography–flame ionization detection (GC–FID) and gas chromatography–mass spectrometry (GC–MS). In biting deterrent bioassays, biting deterrence index (BDI) values for compounds methyl perillate (0.73), perillic acid (0.71), perilla alcohol (0.69), perilla aldehyde (0.62), caryophyllene oxide (0.60), and limonene (0.52) indicated good biting deterrent activity but the activity was significantly lower (proportion not biting (PNB) value 0.84) than the positive control N,N-diethyl-3-methylbenzamide (DEET) at 25nmol/cm2. In larval bioassays, methyl perillate was the most toxic compound with LC50 of 16.0ppm. Methyl perillate was the most active compound against A. aegypti larvae and this compound may offer a new biodegradable mosquito control agent.